Phytochemistry Reviews

, Volume 12, Issue 4, pp 603–651 | Cite as

Synthetic approaches to polycyclic semiochemicals and their derivatives: combinatorial methods towards phytochemicals

Article

Abstract

Semiochemicals are natural products occurring in plants, bacteria or animals which function as carriers of a special message. Depending on the mode of function of the semiochemicals, they are divided into pheromones that trigger a response in members of the same species and allelochemicals (kairomones, allomones) that act between individuals of different species. Semiochemicals are very important compounds that influence the behavior of plants and animals and their adaption to a changing environment. As their importance for plants, animals and the ecological system itself is huge, the synthetic access to these chemicals, their precursors and derivatives is of high interest. Beyond novel strategies for the construction of semiochemical skeletons, combinatorial methods have been implemented to synthesize medium-sized and large-sized libraries that enable diverse modifications of the active compounds. These combinatorial approaches allow the screening for more active compounds and they elucidate the mode of action of the semiochemical or of the biological target. This review summarizes the state of the art procedures for the synthesis of important skeletons appearing in semiochemicals and gives special synthetic procedures for selected examples if the procedure is suitable for a general transfer to the synthesis of derivatives. The synthetic examples are given in the context of known active phytochemicals and their function that allows an evaluation of the given procedures with respect to the fulfillment of the common structural requirements (the structural diversity and flexibility) and the importance for the regulation of biological systems. Parts of this review were given in a lecture at the BioCom 12 in Cadiz, 2012.

Keywords

Combinatorial synthesis Indole alkaloids Natural products Oxygen heterocycles Solid-phase synthesis 

Abbreviations

DMF

Dimethylformamide

n-BuLi

n-Butyl lithium

TMEDA

Tetramethylethylenediamine

CB1

Cannabinoid receptor 1

CB2

Cannabinoid receptor 2

cAMP

Cyclic adenosine monophosphate

THC

9–Tetrahydrocannabinol

4-HSA

4-Hydroxysalicylaldehyde

HAL

Hypersensitive acid-labile

BAP

6-Benzyl aminopurine

Boc

Di-tert-butyl dicarbonate

BOA

2-Benzoxazolinone

BOMBA

4-Benzyloxy-2-methoxybenzylamine

BINAP

2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl

COD

Cyclooctadiene

DMAD

Dimethyl acetylenedicarboxylate

DDQ

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

DHP

3,4-Dihydro-2H-pyran

DIBOA

2,4-Dihydroxy-1,4-benzoxa-zin-3-one

DIMBOA

2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one

DIPEA

N,N-diisopropylethylamine

DNA

Desoxyribonucleic acid

DOMA

Domino oxa-Michael-aldol

dppp

1,3-Bis(diphenylphosphino)propane

eq./equiv.

Equivalents

Fmoc

Fluorenylmethyloxycarbonyl

GA

Gibberellin

Glc

Glucose

LDA

Lithium diisopropylamide

LiHMDS

Lithium bis(trimethylsilyl)amide

mCPBA

Meta-chloroperoxybenzoic acid

Mes

Mesityl

MW

Microwave irradiation

NMO

N-methylmorpholine-N-oxide

Ph

Phenyl

PG

Protecting group

PPTS

p-Toluenesulfonate

SNAr

Nucleophilic aromatic substitution

TBDAS

Tert-butyldiarylsilyl

TBDMS

Tert-butyldimethylsilyl

TFA

Trifluoroacetic acid

THF

Tetrahydrofuran

TPAP

Tetrapropylammonium perruthenate

TRIAL

Tumor necrosis factor (TNF)-related apoptosis-inducing ligand

tRNA

Transfer ribonucleic acid

rt

Room temperature

References

  1. Abd El-Aziz T, Mohamed R et al (2012) Catechin protects against oxidative stress and inflammatory-mediated cardiotoxicity in adriamycin-treated rats. Clin Exp Med 12(4):233–240PubMedGoogle Scholar
  2. Abdala LR (1999) Flavonoids of the aerial parts from Tagetes lucida (Asteraceae). Biochem Syst Ecol 27(7):753–754Google Scholar
  3. Abdel Hafez OM, Amin KM et al (2009) Synthesis and antitumor activity of some new xanthotoxin derivatives. Eur J Med Chem 44(7):2967–2974PubMedGoogle Scholar
  4. Abenavoli MR, Cacco G et al (2006) The inhibitory effects of coumarin on the germination of durum wheat (Triticum turgidum ssp. durum, cv. Simeto) seeds. J Chem Ecol 32(2):489–506PubMedGoogle Scholar
  5. Abenavoli MR, Sorgona A et al (2003) Coumarin inhibits the growth of carrot (Daucus carota L. cv. Saint Valery) cells in suspension culture. J Plant Physiol 160(3):227–237PubMedGoogle Scholar
  6. Acebedo SL, Alonso F et al (2011) Synthesis and biological activity of ring-A difluorinated brassinosteroids. Steroids 76(10–11):1016–1020PubMedGoogle Scholar
  7. Acebedo SL, Ramirez JA et al (2009) Synthesis and biological activity of brassinosteroids fluorinated at C-2. Steroids 74(4–5):435–440PubMedGoogle Scholar
  8. Adler MJ, Baldwin SW (2009) Direct, regioselective synthesis of 2,2-dimethyl-2H-chromenes. Total syntheses of octandrenolone and precocenes I and II. Tetrahedron Lett 50(36):5075–5079Google Scholar
  9. Aghoramurthy K, Seshadri TR (1954) Nuclear oxidation in flavones and related compounds. Part XLVII. A new synthesis of fraxetin and a synthesis of 4-methylfraxetin. J Chem Soc (Resumed)(0):3065–3067Google Scholar
  10. Ahmad A, Misra LN (1997) Isolation of herniarin and other constituents from Matricaria chamomilla flowers. Pharm Biol 35(2):121–125Google Scholar
  11. Ahmadabadi M, Ruf S et al (2007) A leaf-based regeneration and transformation system for maize (Zea mays L.). Transgenic Res 16(4):437–448PubMedGoogle Scholar
  12. Ahrabi F, Enteshari S et al (2011) Allelopathic potential of para-hydroxybenzoic acid and coumarin on canola: Talaieh cultivar. J Med Plants Res 5(20):5104–5109Google Scholar
  13. Akiyama K, Matsuzaki K-i et al (2005) Plant sesquiterpenes induce hyphal branching in arbuscular mycorrhizal fungi. Nature 435(7043):824–827PubMedGoogle Scholar
  14. Akiyama K, Ogasawara S et al (2010) Structural requirements of strigolactones for hyphal branching in AM fungi. Plant Cell Physiol 51(7):1104–1117PubMedGoogle Scholar
  15. Al-Tawaha AM, Seguin P et al (2007) Irrigation level affects isoflavone concentrations of early maturing soya bean cultivars. J Agron Crop Sci 193(4):238–246Google Scholar
  16. Aldrich JR, Avery JW et al (1996) Semiochemistry of cabbage bugs (Heteroptera: Pentatomidae: Eurydema and Murgantia). J Entomol Sci 31(2):172–182Google Scholar
  17. Amelot MEA, Avendano M et al (2003) Repellency and feeding deterrence activity of Ageratum conyzoides against the stored grain pests Tribolium castaneum and Sitophilus oryzae. Active plant parts and composition. Ciencia (Maracaibo, Venez.) 11(1):61–76Google Scholar
  18. Anastasia M, Ciuffreda P et al (1983) A new synthesis of brassino steroids: plant growth promoting steroids. J Chem Soc Perkin Trans 1(2):379–382Google Scholar
  19. Aparicio D, Attanasi OA et al (2006) Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions. J Org Chem 71(16):5897–5905PubMedGoogle Scholar
  20. Appendino G, Hoflack J et al (1988) Intramolecular Diels–Alder reaction with furan-diene. Comparison of reactivity and stereoselectivity within a set of structurally related substrates of potential use in gibberellin total synthesis. Tetrahedron 44:4605–4618Google Scholar
  21. Arai MA, Sato M et al (2008) Efficient synthesis of chromone and flavonoid derivatives with diverse heterocyclic units. Chem Asian J 3(12):2056–2064PubMedGoogle Scholar
  22. Arite T, Kameoka H et al (2012) Strigolactone positively controls crown root elongation in rice. J Plant Growth Regul 31(2):165–172Google Scholar
  23. Atmaca M, Bilgin H et al (2011) The hepatoprotective effect of coumarin and coumarin derivates on carbon tetrachloride-induced hepatic injury by antioxidative activities in rats. J Physiol Biochem 67(4):569–576PubMedGoogle Scholar
  24. Auer CA (1997) Cytokinin conjugation: recent advances and patterns in plant evolution. Plant Growth Regul 23:17–32Google Scholar
  25. Austin RE, Okonya JF et al (2002) Microwave-assisted solid-phase synthesis (MASS) of 2, 6, 9-trisubstituted purines. Tetrahedron Lett 43:6169–6171Google Scholar
  26. Bai X, Bu C et al (2012) Antifungal activity of umbelliferone to plant pathogenic fungi. Zhiwu Baohu 38(2):42–45Google Scholar
  27. Baizer MM, Clark JR et al (1956) A new synthesis of kinetin and its analogs. J Org Chem 21:1276–1277Google Scholar
  28. Bajguz A (1999) The effect of brassinosteroids on the growth and development of plants. Kosmos (Krakow) 48(1):75–85Google Scholar
  29. Bajguz A, Czerpak R (1996) Effect of brassinosteroids on growth and proton extrusion in the alga Chlorella vulgaris Beijerinck (Chlorophyceae). J Plant Growth Regul 15(3):153–156Google Scholar
  30. Bakthavatsalam N, Tandon PL (2005) Interactions between plant chemicals and the entomophages. Pestology 29(11):17–31Google Scholar
  31. Barbercheck ME, Herbert DA et al (1995) Evaluation of semiochemical baits for management of southern corn-rootworm (Coleoptera, Chrysomelidae) in peanuts. J Econ Entomol 88(6):1754–1763Google Scholar
  32. Barciszewski J, Massino F et al (2007) Kinetin—a multiactive molecule. Int J Biol Macromol 40:182–192PubMedGoogle Scholar
  33. Baxter CA, Cleator E et al (2010) A novel approach to 3-methylindoles by a Heck/cyclization/isomerization process. Org Lett 12(4):668–671PubMedGoogle Scholar
  34. Beck JJ, Higbee BS et al (2012) Hull split and damaged almond volatiles attract male and female navel orangeworm moths. J Agric Food Chem 60(33):8090–8096PubMedGoogle Scholar
  35. Beckett JS, Beckett JD, Hofferberth JE (2010) A divergent approach to the diastereoselective synthesis of several ant-associated iridoids. Org Lett 12(7):1408–1411Google Scholar
  36. Beehler JW, Millar JG et al (1994) Field-evaluation of synthetic compounds mediating oviposition in Culex Mosquitos (Diptera, Culicidae). J Chem Ecol 20(2):281–291Google Scholar
  37. Behrenswerth A, Volz N et al (2009) Synthesis and pharmacological evaluation of coumarin derivatives as cannabinoid receptor antagonists and inverse agonists. Bioorg Med Chem 17(7):2842–2851PubMedGoogle Scholar
  38. Belliotti TR, Wustrow DJ et al (1999) A series of 6- and 7-piperazinyl- and -piperidinylmethylbenzoxazinones with dopamine D4 antagonist activity: discovery of a potential atypical antipsychotic agent. J Med Chem 42(25):5181–5187PubMedGoogle Scholar
  39. Beran F, Mewis I et al (2011) Male Phyllotreta striolata (F.) produce an aggregation pheromone: identification of male-specific compounds and interaction with host plant volatiles. J Chem Ecol 37(1):85–97Google Scholar
  40. Berlage U, Schmidt J et al (1987) A formal total synthesis of (±)-strigol. Tetrahedron Lett 28(27):3091–3094Google Scholar
  41. Berube M, Delagoutte F et al (2010) Preparation of 6beta-estradiol derivative libraries as bisubstrate inhibitors of 7beta-hydroxysteroid dehydrogenase type using the multidetachable sulfamate linker. Molecules 15(3):1590–1631PubMedGoogle Scholar
  42. Bestmann HJ, Übler E et al (1997) First biosynthetic studies on trail pheromones in ants. Angew Chem Int Ed Engl 36(4):395–397Google Scholar
  43. Beveridge THJ, Li TSC et al (2002) Phytosterol content in American ginseng seed oil. J Agric Food Chem 50(4):744–750PubMedGoogle Scholar
  44. Bhat AS, Whetstone JL et al (2000) A method for the rapid synthesis of benzopyrone libraries employing a resin capture strategy. J Comb Chem 2(6):597–599PubMedGoogle Scholar
  45. Birkett MA, Campbell CAM et al (2000) New roles for cis-jasmone as an insect semiochemical and in plant defense. Proc Natl Acad Sci USA 97(16):9329–9334PubMedGoogle Scholar
  46. Blum MS, Jones TH et al (1982) Biochemistry of termite defenses: Coptotermes, rhinotermes and Cornitermes species. Comp Biochem Physiol B 71(4):731–733Google Scholar
  47. Boehm TL, Showalter HDH (1996) Development of a novel silyl ether linker for solid-phase organic synthesis. J Org Chem 61(19):6498–6499PubMedGoogle Scholar
  48. Bohlmann F, Stöhr F-M (1980) Synthese natürlich vorkommender p-hydroxyacetophenon-derivate, III. Liebigs Ann Chem 1980(2):185–191Google Scholar
  49. Bohman B, Jeffares L et al (2012) The discovery of 2-hydroxymethyl-3-(3-methylbutyl)-5-methylpyrazine: a semiochemical in orchid pollination. Org Lett 14(10):2576–2578Google Scholar
  50. Borradaile N, Carroll K et al (1999) Regulation of HepG2 cell apolipoprotein B metabolism by the citrus flavanones hesperetin and naringenin. Lipids 34(6):591–598PubMedGoogle Scholar
  51. Boulogne I, Petit P et al (2012) Insecticidal and antifungal chemicals produced by plants: a review. Environ Chem Lett 10(4):325–347Google Scholar
  52. Bowers W, Ohta T et al (1976) Discovery of insect anti-juvenile hormones in plants? 2U. Science 193(4253):542–547PubMedGoogle Scholar
  53. Boyer FD, de Saint Germain A et al (2012) Structure-activity relationship studies of strigolactone-related molecules for branching inhibition in garden pea: molecule design for shoot branching. Plant Physiol 159(4):1524–1544PubMedGoogle Scholar
  54. Bräse S, Dahmen S (2002) Linkers for solid-phase synthesis, vol 1. Wiley-VCH Verlag GmbH & Co., KGaA, Weinheim, Germany, pp 59–169Google Scholar
  55. Bräse S, Gil C et al (2002) The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles. Bioorg Med Chem 10(8):2415–2437PubMedGoogle Scholar
  56. Bräse S, Köbberling J et al (1999) Triazenes as robust and simple linkers for amines in solid-phase organic synthesis. Tetrahedron Lett 40(11):2105–2108Google Scholar
  57. Brattsten LB, Evans CK et al (1984) Induction by carrot allelochemicals of insecticide-metabolising enzymes in the southern armyworm (Spodoptera eridania). Comp Biochem Physiol C 77(1):29–37PubMedGoogle Scholar
  58. Brill WKD, Riva-Toniolo C (2001) Solid-phase synthesis of 2, 6, 8-trisubstituted purines. Tetrahedron Lett 42(37):6515–6518Google Scholar
  59. Brill WKD, Riva-Toniolo C et al (2001) Catalysis of 2- and 6- substitution reactions of purines on solid phase. Synlett (7):1097–1100Google Scholar
  60. Bröhmer MC, Volz N et al (2009) Microwave-assisted rhodium-catalyzed decarbonylation of functionalized 3-formyl-2H-chromenes: a sequence for functionalized chromenes like deoxycordiachromene (pg 1383, 2009). Synlett (10):1694–1694Google Scholar
  61. Brosa C, Capdevila JM et al (1996) Brassinosteroids: a new way to define the structural requirements. Tetrahedron 52(7):2435–2448Google Scholar
  62. Brosa C, Nusimovich S et al (1994) Synthesis of new brassinosteroids with potential activity as antiecdysteroids. Steroids 59(8):463–467PubMedGoogle Scholar
  63. Brown BH, Crozier A, Sandberg G (1986) Catabolism of indole-3-acetic acid in chloroplast fractions from light-grown Pisum sativum L. seedlings. Plant Cell Environ 9(7):527–534.Google Scholar
  64. Brown N, Luo DH et al (2009) New synthesis of (±)-cis-trikentrin A via tandem indole aryne cycloaddition/Negishi reaction. Applications to library development. Tetrahedron Lett 50(51):7113–7115PubMedGoogle Scholar
  65. Brown PM, Krishnamoorthy V et al (1970) Naturally occurring quinones. Part XVII. Synthesis of lambertellin. J Chem Soc C Organ (1):109–110Google Scholar
  66. Buchbauer G, Klein CT et al (2000) Threshold-based structure—activity relationships of pyrazines with bell-pepper flavor. J Agric Food Chem 48(9):4273–4278PubMedGoogle Scholar
  67. Burns Kraft TF, Dey M et al (2008) Phytochemical composition and metabolic performance-enhancing activity of dietary berries traditionally used by native North Americans. J Agric Food Chem 56(3):654–660PubMedGoogle Scholar
  68. Byers JA (1992) Attraction of bark beetles, Tomicus piniperda, Hylurgops palliatus, and Trypodendron domesticum and other insects to short-chain alcohols and monoterpenes. J Chem Ecol 18(12):2385–2402Google Scholar
  69. Byers JA (1993) Avoidance of competition by spruce bark beetles, Ips typographus and Pityogenes chalcographus. Experientia 49(3):272–275Google Scholar
  70. Cabezas R, El-Bachá RS et al (2012) Mitochondrial functions in astrocytes: neuroprotective implications from oxidative damage by rotenone. Neurosci Res 74(2):80–90PubMedGoogle Scholar
  71. Caliendo G, Perissutti E et al (2004) Synthesis by microwave irradiation of a substituted benzoxazine parallel library with preferential relaxant activity for guinea pig trachealis. Eur J Med Chem 39(10):815–826PubMedGoogle Scholar
  72. Cao J, Tang E et al (2006) Polymer-support selenium-induced electrophilic cyclization. Solid-phase synthesis of flavonoids. Chin Chem Lett 17(7):857–858Google Scholar
  73. Casaschi A, Rubio BK et al (2004) Inhibitory activity of diacylglycerol acyltransferase (DGAT) and microsomal triglyceride transfer protein (MTP) by the flavonoid, taxifolin, in HepG2 cells: potential role in the regulation of apolipoprotein B secretion. Atherosclerosis 176(2):247–253PubMedGoogle Scholar
  74. Castillo L, Rossini C (2010) Bignoniaceae metabolites as semiochemicals. Molecules 15(10):7090–7105PubMedGoogle Scholar
  75. Cechinel Filho V, Schlemper V et al (1998) Isolation and identification of active compounds from Drimys winteri barks. J Ethnopharmacol 62(3):223–227PubMedGoogle Scholar
  76. Cerana R, Spelta M et al (1985) On the effects of cholesterol on hydrogen ion extrusion and on growth in maize root segments: comparison with brassinosteroid. Plant Sci (Limerick, Irel) 38(2):99–105Google Scholar
  77. Chakraborti PC, Ghosh S et al (1979) Stereocontrolled total synthesis of dl-1α-carboxy-7-methoxy-1β, 4aα-dimethyl-1, 2, 3, 4, 4a, 9aα-hexahydrofluorene and related hydrofluorene synthons towards gibberellin A12. Indian J Chem, Sect B 18B:183–185Google Scholar
  78. Chandra S, Shahi AK et al (1996) Essential oil composition of Ageratum houstonianum Mill. from Jammu Region of India. J Essent Oil Res 8(2):129–134Google Scholar
  79. Chao EY, Minick DJ et al (2002) A novel method for the generation of nitrile oxides on solid phase: application to the synthesis of substituted benzopyranoisoxazoles. Org Lett 4(3):323–326PubMedGoogle Scholar
  80. Chapman E, Best MD et al (2004) Sulfotransferases: structure, mechanism, biological activity, inhibition, and synthetic utility. Angew Chem Int Ed 43(27):3526–3548Google Scholar
  81. Chen CM (1997) Cytokinin biosynthesis and interconversion. Physiol Plant 101(4):665–673Google Scholar
  82. Chunyan C, Bo S et al (2008) Isolation and purification of psoralen and bergapten from Ficus carica L. leaves by high-speed countercurrent chromatography. J Liq Chromatogr Relat Technol 32(1):136–143Google Scholar
  83. Cianfrogna JA, Zangerl AR et al (2002) Effects of furanocoumarins on feeding behavior of parsnip webworms: Depressaria pastinacella. J Chem Ecol 28(7):1365–1375PubMedGoogle Scholar
  84. Clement S, Tasinato A et al (1997) The effect of alpha-tocopherol on the synthesis, phosphorylation and activity of protein kinase C in smooth muscle cells after phorbol 12-myristate 13-acetate down-regulation. Eur J Biochem 246(3):745–749PubMedGoogle Scholar
  85. Clouse SD (2008) The molecular intersection of brassinosteroid-regulated growth and flowering in Arabidopsis. Proc Natl Acad Sci USA 105(21):7345–7346PubMedGoogle Scholar
  86. Corey EJ, Danheiser RL et al (1978) Stereospecific total synthesis of gibberellic acid. A key tricyclic intermediate. J Am Chem Soc 100:8031Google Scholar
  87. Corey EJ, Guzman-Perez A et al (1994) demonstration of the synthetic power of oxazaborolidine-catalyzed enantioselective Diels–Alder reactions by very efficient routes to cassiol and gibberellic acid. J Am Chem Soc 116(8):3611–3612Google Scholar
  88. Cornelius P, Lee E et al (2009) Design, synthesis, and pharmacology of fluorescent-labeled analogs of serotonin: application to screening of the 5-HT2c receptor. J Biomol Screen 14(4):360–370PubMedGoogle Scholar
  89. Cossey AL, Lombardo L et al (1980) Total synthesis of gibberellin A4. Tetrahedron Lett 21:4383–4386Google Scholar
  90. Craig D, Robson MJ et al (1998) Traceless linkers for solid-phase synthesis. Homo- and hetero-Diels-Alder reactions of o-quinodimethanes. Synlett (12):1381–1383Google Scholar
  91. Cronin DA, Stanton P (1976) 2-methoxy-3-sec-butylpyrazine—an important contributor to carrot aroma. J Sci Food Agric 27(2):145–151Google Scholar
  92. Dahmen S, Bräse S (2000) Nitrogen-based linkers, part 8. The first stable diazonium ion on solid support-investigations on stability and usage as linker and scavenger in solid-phase organic synthesis. Angew Chem Int Ed 39(20):3681–3683Google Scholar
  93. Danheiser RL, Trova MP (1995) Synthesis of linear furocoumarins via a photochemical aromatic annulation strategy. An efficient total synthesis of Bergapten. Synlett 1995(Sup. I):573–574Google Scholar
  94. Dapkevicius A, van Beek TA et al (2002) Isolation and structure elucidation of radical scavengers from Thymus vulgaris leaves. J Nat Prod 65(6):892–896PubMedGoogle Scholar
  95. De SI, Voss U et al (2011) Unraveling the evolution of auxin signaling. Plant Physiol 155(1):209–221Google Scholar
  96. de Werra P, Huser A et al (2011) Plant- and microbe-derived compounds affect the expression of genes encoding antifungal compounds in a pseudomonad with biocontrol activity. Appl Environ Microbiol 77(8):2807–2812PubMedGoogle Scholar
  97. Degen T, Buser H-R et al (1999) Patterns of oviposition stimulants for carrot fly in leaves of various host plants. J Chem Ecol 25(1):67–87Google Scholar
  98. Delis C, Krokida A et al (2011) Role of lupeol synthase in Lotus japonicus nodule formation. New Phytol 189(1):335–346PubMedGoogle Scholar
  99. Derksen S, Chatterton M et al (2007) Semiochemical-mediated oviposition behavior by female peachtree borer, Synanthedon exitiosa. Entomol Exp Appl 123(2):101–108Google Scholar
  100. Deulofeu V, Schopflocher N (1953) The flavonic glucosides of Ombu (Phytolacca dioica). III. The synthesis of ombuin and of other flavonic derivatives of the isovanillic series. Gazz Chim Ital 83:449–453Google Scholar
  101. Ding S, Gray NS et al (2001) A concise and traceless linker strategy toward combinatorial libraries of 2, 6, 9-substituted purines. J Org Chem 66:8273–8276PubMedGoogle Scholar
  102. Dobbs A (2001) Total synthesis of indoles from Tricholoma species via Bartoli/heteroaryl radical methodologies. J Org Chem 66(2):638–641PubMedGoogle Scholar
  103. Dobbs AP, Voyle M et al (1999) Synthesis of novel indole derivatives: variations in the Bartoli reaction. Synlett (10): 1594–1596Google Scholar
  104. Dobler S (2001) Evolutionary aspects of defense by recycled plant compounds in herbivorous insects. Basic Appl Ecol 2(1):15–26Google Scholar
  105. Dobson DR, Gilmore J et al (1992) Synthesis of 7-formylindole using the Bartoli indole methodology. Synlett (1):79–80Google Scholar
  106. Dudley DA, Bunker AM et al (2000) Rational design, synthesis, and biological activity of benzoxazinones as novel factor Xa inhibitors. J Med Chem 43(22):4063–4070PubMedGoogle Scholar
  107. Edwards KG, Stoker JR (1968) Biosynthesis of herniarin: the isomerization stage. Phytochemistry 7(1):73–77Google Scholar
  108. Eifler-Lima VL, Graebin CS et al (2010) Highlights in the solid-phase organic synthesis of natural products and analogues. J Braz Chem Soc 21(8):1401–1423Google Scholar
  109. Ekiert H, Gomolka E (2000) Furanocoumarins in Pastinaca sativa L. in vitro culture. Pharmazie 55(8):618–620PubMedGoogle Scholar
  110. Ellington E, Bastida J et al (2003) Occurrence of colchicine derivatives in plants of the genus Androcymbium. Biochem Syst Ecol 31(7):715–722Google Scholar
  111. Erdal S, Dumlupinar R (2010) Progesterone and β-estradiol stimulate seed germination in chickpea by causing important changes in biochemical parameters. Z Naturforsch C J Biosci 65(3/4):239–244Google Scholar
  112. Ferraro GE, Coussio JD (1973) Flavonoids from Eupatorium subhastatum. Phytochemistry 12(7):1825Google Scholar
  113. Flekhter OB, Karachurina LT et al (2000) The synthesis and hepatoprotective activity of esters of the lupane group triterpenoids. Russ J Bioorg Chem 26(3):192–200Google Scholar
  114. Fletcher S (2010) Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction. Tetrahedron Lett 51(22):2948–2950Google Scholar
  115. Fomsgaard IS (2006) Chemical ecology in wheat plant-pest interactions. How the use of modern techniques and a multidisciplinary approach can throw new light on a well-known phenomenon: allelopathy. J Agric Food Chem 54(4):987–990PubMedGoogle Scholar
  116. Francisco DOA, Pasqual M et al (2003) Rootings of semi-woody cuttings of olive tree under effects of collection time, substrate, and concentrations of indole-3-butyric acid (IBA). Cienc Agrotecnol 27(1):117–125Google Scholar
  117. Friebe A (2001) Role of benzoxazinones in cereals. J Crop Prod 4(2):379–400Google Scholar
  118. Friedrich A, Bräse S et al (2009) Synthesis of 4-, 5-, 6-, and 7-azidotryptamines. Tetrahedron Lett 50(1):75–76PubMedGoogle Scholar
  119. Friedrich A, Jainta et al M (2008) Synthesis of hexahydroindole carboxylic acids by intramolecular Diels–Alder reaction. Synlett (4):589–591Google Scholar
  120. Galindo JCG, Macias FA et al (2004) Chemistry of host-parasite interactions. CRC Press LLCGoogle Scholar
  121. Gao J, Li X et al (2011) Efficient synthesis of trisaccharide saponins and their tumor cell killing effects through oncotic necrosis. Bioorg Med Chem Lett 21(2):622–627PubMedGoogle Scholar
  122. Gapper NE, Coupe SA et al (2005) Regulation of harvest-induced senescence in Broccoli (Brassica oleracea var. italica) by cytokinin, ethylene, and sucrose. J Plant Growth Regul 24:153–165Google Scholar
  123. Gauthier C, Legault J et al (2011) Advances in the synthesis and pharmacological activity of lupane-type triterpenoid saponins. Phytochem Rev 10(4):521–544Google Scholar
  124. Geen GR, Evans JM et al (1996) Pyrans and their benzo derivatives: applications. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, pp 469–500Google Scholar
  125. Ghosh P, Das J et al (2012) Oxidation with selenium dioxide: the first report of solvent-selective steroidal aromatization, efficient access to 4β,7α-dihydroxy steroids, and syntheses of natural diaromatic ergosterols. Tetrahedron 68(32):6485–6491Google Scholar
  126. Gil C, Bräse S (2004) Traceless and multifunctional linkers for the generation of small molecules on solid supports. Curr Opin Chem Biol 8(3):230–237PubMedGoogle Scholar
  127. Gil C, Bräse S (2005) Efficient solid-phase synthesis of highly functionalized 1, 4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-Wittig reactions. Chem A Eur J 11:2680–2688Google Scholar
  128. González AG, Aguiar ZE et al (1991) Chromenes from Ageratum conyzoides. Phytochemistry 30(4):1137–1139Google Scholar
  129. Gordeev MF (1998) Combinatorial approaches to pharmacophoric heterocycles: a solid-phase synthesis of 3,1-benzoxazine-4-ones. Biotechnol Bioeng 61(1):13–16PubMedGoogle Scholar
  130. Graves AD, Holsten EH et al (2008) Protection of spruce from colonization by the bark beetle, Ips perturbatus, in Alaska. For Ecol Manage 256(11):1825–1839Google Scholar
  131. Gray NS, Kwon S et al (1997) Combinatorial synthesis of 2, 9-substituted purines. Tetrahedron Lett 38:1161–1164Google Scholar
  132. Gross U, Gross PJ et al (2011) Catalytic synthesis of coumarins via direct annulations of alpha, beta-unsaturated aldehydes and salicylaldehydes. Synlett (5):635–638Google Scholar
  133. Gutierrez CK, Matsui GY et al (2009) Production of the phytohormone indole-3-acetic acid by estuarine species of the genus Vibrio. Appl Environ Microbiol 75(8):2253–2258PubMedGoogle Scholar
  134. Habtemariam S, Dagne E (2010) Comparative antioxidant, prooxidant and cytotoxic activity of sigmoidin A and eriodictyol. Planta Med 76(EFirst):589–594PubMedGoogle Scholar
  135. Harel D, Khalid SA et al (2011) Encecalol angelate, an unstable chromene from Ageratum conyzoides L.: total synthesis and investigation of its antiprotozoal activity. J Ethnopharmacol 137(1):620–625PubMedGoogle Scholar
  136. Harikrishnan LS, Showalter HDH (2000) A novel synthesis of 2, 3-disubstituted benzopyran-4-ones and application to the solid phase. Tetrahedron 56(4):515–519Google Scholar
  137. Harrison TL, Zangerl AR et al (2001) Developmental variation in cytochrome P450 expression in Papilio polyxenes in response to xanthotoxin, a hostplant allelochemical. Arch Insect Biochem Physiol 48(4):179–189PubMedGoogle Scholar
  138. Hashem HA, Bassuony FM et al (2011) Stigmasterol seed treatment alleviates the drastic effect of NaCl and improves quality and yield in flax plants. Aust J Crop Sci 5(13):1858–1867Google Scholar
  139. Hashem HA, Bassuony FM et al (2012) Role of stigmasterol in alleviating the drastic effect of NaCl and improving the yield quantity and quality of flax plants. J Environ Sci (Mansoura Egypt) 41(1):89–115Google Scholar
  140. Hauer H, Ritter T et al (1995) An improved and large scale synthesis of the natural coumarin scopoletin. Arch Pharm 328(10):737–738Google Scholar
  141. Havelkova M, Dvorak D et al (2001) The Suzuki-Miyaura cross-coupling reactions of 2-, 6-or 8-halopurines with boronic acids leading to 2-, 6-or 8-aryl- and -alkenylpurine derivatives. Synth Stuttg (11):1704–1710Google Scholar
  142. Hedin PA, McCarty JC Jr (1991) Effects of kinetin formulations on allelochemicals and agronomic traits of cotton. J Agric Food Chem 39:549–553Google Scholar
  143. Hempel J, Pforte H et al (1999) Flavonols and flavones of parsley cell suspension culture change the antioxidative capacity of plasma in rats. Food/Nahrung 43(3):201–204Google Scholar
  144. Hepworth JD, Gabbutt CD et al (1996) Pyrans and their benzo derivatives: synthesis. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, pp 351–468Google Scholar
  145. Heydorn WE, Creed GJ et al (1986) Effect of 5,7-dihydroxytryptamine on the concentration of individual proteins in different areas of the rat brain. Brain Res 368(1):193–196PubMedGoogle Scholar
  146. Higa S, Hirano T et al (2003) Fisetin, a flavonol, inhibits TH2-type cytokine production by activated human basophils. J Allergy Clin Immunol 111(6):1299–1306PubMedGoogle Scholar
  147. Higashi E, Nakajima M et al (2007) Inhibitory effects of neurotransmitters and steroids on human CYP2A6. Drug Metab Dispos 35(4):508–514PubMedGoogle Scholar
  148. Hirano T, Higa S et al (2006) Luteolin, a flavonoid, inhibits AP-1 activation by basophils. Biochem Biophys Res Commun 340(1):1–7PubMedGoogle Scholar
  149. Hirayama K, Mori K (1999) Synthesis of (+)-strigol and (+)-orobanchol, the germination stimulants, and their stereoisomers by employing lipase-catalyzed asymmetric acetylation as the key step. Eur J Org Chem 1999(9):2211–2217Google Scholar
  150. Hoefnagel AJ, Gunnewegh EA et al (1995) Synthesis of 7-hydroxycoumarins catalysed by solid acid catalysts. J Chem Soc Chem Commun (2):225–226Google Scholar
  151. Hogetsu T, Shibaoka H et al (1974) Involvement of cellulose synthesis in actions of gibberellin and kinetin on cell expansion. Gibberellin-coumarin and kinetin-coumarin interactions on stem elongation. Plant Cell Physiol 15(2):265–272Google Scholar
  152. Hook JM, Mander LN et al (1984) Studies on gibberellin synthesis: the total synthesis of gibberellic acid from hydrofluorenone intermediates. J Org Chem 49:3250–3260Google Scholar
  153. Huang Q, Wu L-J et al (2005a) (+)-Catechin, an ingredient of green tea, protects murine microglia From oxidative stress-induced DNA damage and cell cycle arrest. J Pharmacol Sci 98(1):16–24PubMedGoogle Scholar
  154. Huang X, Tang E, Xu WM, Cao J (2005b) Lewis acid catalyzed solid-phase synthesis of flavonoids using selenium-bound resin. J Comb Chem 7(6):802–805PubMedGoogle Scholar
  155. Hwang JY, Choi HS et al (2006) Method for the solid-phase parallel synthesis of a 6-alkylamino-2-(functionalized-aminomethyl)-2H-1-benzopyran library. J Comb Chem 8(6):897–906PubMedGoogle Scholar
  156. Ishiwata N (2011) Functional compounds from soybeans: focus on phytochemicals. Shokuhin to Kagaku 53(5):63–67Google Scholar
  157. Ismaili J, Boisvert M et al (2012) Brassinosteroids and analogs as neuroprotectors: synthesis and structure-activity relationships. Steroids 77(1–2):91–99PubMedGoogle Scholar
  158. Iverson CD, Zahid S et al (2010) Glutathione S-transferase inhibitory, free radical scavenging, and anti-leishmanial activities of chemical constituents of Artocarpus nobilis and Matricaria chamomilla. Phytochem Lett 3(4):207–211Google Scholar
  159. Ivkovic A, Matovic R et al (2004) Ring-closing metathesis/fragmentation route to geometrically defined medium-ring cycloalkenes: total synthesis of (±)-periplanone C. Org Lett 6(8):1221–1224PubMedGoogle Scholar
  160. Janoueix-Lerosey I, Schleiermacher G et al (2009) Overall genomic pattern is a predictor of outcome in neuroblastoma. J Clin Oncol 27(7):1026–1033PubMedGoogle Scholar
  161. Jenny TF, Previsani N et al (1991) Carbocyclic analogs of nucleosides via modified Mitsunobu reactions. Tetrahedron Lett 32(48):7029–7032Google Scholar
  162. Jung N, Wiehn M et al (2007) Multifunctional linkers for combinatorial solid phase synthesis. In: Bräse S (ed) Combinatorial chemistry on solid supports, vol 278. Springer, Berlin, pp 1–88Google Scholar
  163. Kähkönen MP, Heinämäki J et al (2003) Berry anthocyanins: isolation, identification and antioxidant activities. J Sci Food Agric 83(14):1403–1411Google Scholar
  164. Kang K, Kang S et al (2008) Enzymatic features of serotonin biosynthetic enzymes and serotonin biosynthesis in plants. Plant Signal Behav 3(6):389–390PubMedGoogle Scholar
  165. Kapeller DC, Bräse S (2011) Towards a library of chromene cannabinoids: a combinatorial approach on solid supports. Synlett (2):161–164Google Scholar
  166. Kapeller DC, Bräse S (2011b) Versatile solid-phase synthesis of chromenes resembling classical cannabinoids. ACS Comb Sci 13(5):554–561PubMedGoogle Scholar
  167. Karvela E, Makris DP et al (2012) Implementation of response surface methodology to assess the antiradical behaviour in mixtures of ascorbic acid and α-tocopherol with grape (Vitis vinifera) stem extracts. Food Chem 132(1):351–359Google Scholar
  168. Katkevičs M, Kontijevskis A et al (2007) Microwave-promoted automated synthesis of a coumarin library. Chem Heterocycl Compd 43(2):151–159Google Scholar
  169. Katsuyama Y, Miyahisa I et al (2007) One-pot synthesis of genistein from tyrosine by coincubation of genetically engineered Escherichia coli and Saccharomyces cerevisiae cells. Appl Microbiol Biotechnol 73(5):1143–1149PubMedGoogle Scholar
  170. Kaval N, Appukkuttan P et al (2006) The chemistry of 2-(1H)-pyrazinone drivsatives in solution and on solid support. Top Heterocycl Chem 1:267–304Google Scholar
  171. Kern F, Klein R et al (1997) Mellein, a trail pheromone component of the ant Lasius fuliginosus. J Chem Ecol 23(3):779–792Google Scholar
  172. Kiehlmann E, Slade PW (2003) Methylation of dihydroquercetin acetates: synthesis of 5-O-methyldihydroquercetin. J Nat Prod 66(12):1562–1566PubMedGoogle Scholar
  173. Kim BH, Jacobs PB et al (1988) A general synthetic approach to optically active iridoid aglycons. The total syntheses of β-ethyl decarbomethoxyverbenalol, ethyl catalpol, and (−)-specionin. Tetrahedron 44(11):3079–3092Google Scholar
  174. King GR, Mander LN et al (1997) A new and efficient strategy for the total synthesis of polycyclic diterpenoids: the preparation of gibberellins (±)-GA103 and (±)-GA73. J Am Chem Soc 119:3828–3829Google Scholar
  175. Kitamura T, Tatemoto K et al (2012) Cascade synthesis of 3-alkenylcoumarins by palladium-catalyzed reaction of phenols and ethyl propiolate. Chem Lett 41(7):705–707Google Scholar
  176. Knepper K, Bräse S (2003) Bartoli indole synthesis on solid supports. Org Lett 5(16):2829–2832PubMedGoogle Scholar
  177. Knepper K, Vanderheiden S et al (2012) Synthesis of diverse indole libraries on polystyrene resin—scope and limitations of an organometallic reaction on solid supports. Beilstein J Org Chem 8:1191–1199PubMedGoogle Scholar
  178. Knypl JS (1970) Control of chlorophyll synthesis by coumarin and plant growth retarding chemicals. Acta Soc Bot Pol 39(2):321–332Google Scholar
  179. Koh YH, Landesman MB et al (2004) Synthesis of nucleoside libraries on solid support. II. 2,6,8-trisubstituted purine nucleosides using 8-bromoguanosine as precursor. Nucleosides Nucleotides Nucleic Acids 23(1–2):501–507PubMedGoogle Scholar
  180. Kokontis J, Ruddat M (1986) Promotion of hyphal growth in Ustilago violacea by host factors from Silene alba. Arch Microbiol 144(3):302–306Google Scholar
  181. Kong C, Hu F et al (2002) Allelopathic potential and chemical constituents of volatiles from Ageratum conyzoides under stress. J Chem Ecol 28(6):1173–1182PubMedGoogle Scholar
  182. Kostova I (1992) Hydroxycoumarins from Fraxinus ornus bark. Planta Med 58(05):484PubMedGoogle Scholar
  183. Kretzschmar T, Kohlen W et al (2012) A petunia ABC protein controls strigolactone-dependent symbiotic signalling and branching. Nature 483(Copyright (C) 2013 U.S. National Library of Medicine.):341–344Google Scholar
  184. Kuhnle GGC, Dell’Aquila C et al (2008) Phytoestrogen content of beverages, nuts, seeds, and oils. J Agric Food Chem 56(16):7311–7315PubMedGoogle Scholar
  185. Kumar N, Kiuchi M et al (2005) Small-molecule diversity using a skeletal transformation strategy. Org Lett 7(13):2535–2538PubMedGoogle Scholar
  186. Laghari AH, Memon S et al (2011) Alhagi maurorum: a convenient source of lupeol. Ind Crops Prod 34(1):1141–1145Google Scholar
  187. Lampert EC, Dyer LA et al (2011) Chemical defense across three trophic levels: Catalpa bignonioides, the Caterpillar Ceratomia catalpae, and its Endoparasitoid Cotesia congregata. J Chem Ecol 37(10):1063–1070PubMedGoogle Scholar
  188. Lazny R, Poplawski J et al (1999) Triazenes: a useful protecting strategy for sensitive secondary amines. Synlett (8):1304–1306Google Scholar
  189. Lazny R, Sienkiewicz M et al (2001) Application of triazenes for protection of secondary amines. Tetrahedron 57(27):5825–5832Google Scholar
  190. Lee CL, Chan KP et al (2001) Solid-phase combinatorial synthesis of 1,4-benzoxazin-3(4H)-one and 1,4-benzothiazin-3(4H)-one derivatives. Tetrahedron Lett 42(6):1167–1169Google Scholar
  191. Lee JM, Yu E-A et al (2009) Solid-phase synthesis of 7-aryl-benzo[b][1,4]oxazin-3(4H)-one derivatives on a BOMBA resin utilizing the smiles rearrangement. Bull Korean Chem Soc 30(6):1325–1330Google Scholar
  192. Lee M-H, Jeong J-H et al (2004) Enhanced triterpene and phytosterol biosynthesis in Panax ginseng overexpressing squalene synthase gene. Plant Cell Physiol 45(8):976–984PubMedGoogle Scholar
  193. Lee SB, Cha KH et al (2007) The chemopreventive effect of taxifolin is exerted through ARE-dependent gene regulation. Biol Pharm Bull 30(6):1074–1079PubMedGoogle Scholar
  194. Lee ST, Davis TZ et al (2010) Tremetone and structurally related compounds in white snakeroot (Ageratina altissima): a plant associated with trembles and milk sickness. J Agric Food Chem 58(15):8560–8565PubMedGoogle Scholar
  195. Lee T, Gong Y-D (2012) Solid-phase parallel synthesis of drug-like artificial 2H-benzopyran libraries. Molecules 17:5467–5496PubMedGoogle Scholar
  196. Legraverend M (2008) Recent advances in the synthesis of purine derivatives and their precursors. Tetrahedron 64(37):8585–8603Google Scholar
  197. Legraverend M, Ludwig O et al (2001) Synthesis of a new series of purine derivatives and their anti-cyclin-dependent kinase activities. J Heterocycl Chem 38(1):299–303Google Scholar
  198. Li H, Deng Z et al (2012a) Highly pigmented vegetables: anthocyanin compositions and their role in antioxidant activities. Food Res Int 46(1):250–259Google Scholar
  199. Li S, Tian M et al (2012b) Optimization of mobile phase condition by using HCI program for extracting luteolin and apigenin from celery. Asia-Pac J Chem Eng 7(3):337–342Google Scholar
  200. Li X, Berenbaum MR et al (2000) Molecular cloning and expression of CYP6B8: a xanthotoxin-inducible cytochrome P450 cDNA from Helicoverpa zea. Insect Biochem Mol Biol 30(1):75–84PubMedGoogle Scholar
  201. Lindh JM, Kaennaste A et al (2008) Oviposition responses of Anopheles gambiae s.s. (Diptera: culicidae) and identification of volatiles from bacteria-containing solutions. J Med Entomol 45(6):1039–1049PubMedGoogle Scholar
  202. Litkei G, Gulácsi K et al (1995) Cyclodehydrogenation of 2′-hydroxychalcones with hypervalent iodine reagent: a new synthesis of flavones. Liebigs Ann 1995(9):1711–1715Google Scholar
  203. Liu G-L, Hao B et al (2012) Synthesis and anthelmintic activity of osthol analogs against Dactylogyrus intermedius in goldfish. Eur J Med Chem 54:582–590PubMedGoogle Scholar
  204. Liu Y, Li X et al (2008) Synthesis of catechins via thiourea/AuCl3-catalyzed cycloalkylation of aryl epoxides. J Organ Chem 73(12):4625–4629Google Scholar
  205. Lloyd HA, Evans SL et al (1978) 8-Hydroxyisocoumarin and 3,4-dihydro-8-hydroxyisocoumarin in the defensive secretion of the tenebrionid beetle, Apsena pubescens. Insect Biochem 8(5):333–336Google Scholar
  206. Loewenthal HJE, Schatzmiller S (1975) Synthesis of compounds related to gibberellic acid. IV. Construction of a tetracyclic system containing functional elements of rings A, C, and D. J Chem Soc Perkin Trans 1:2149–2157Google Scholar
  207. Lombardo L, Mander LN (1983) A new strategy for C20 gibberellin synthesis: total synthesis of (±)-gibberellin A38 methyl ester. J Org Chem 48:2298–2300Google Scholar
  208. Lombardo L, Mander LN et al (1980) General strategy for gibberellin synthesis: total syntheses of (±)-gibberellin A1 and gibberellic acid. J Am Chem Soc 102:6626–6628Google Scholar
  209. Looker JH, Holm MJ et al (1964) Imidazole-catalyzed hydrolysis of acetoxyflavones physical and chemical properties of hydroxyflavones. III. J Heterocycl Chem 1(5):253–256Google Scholar
  210. Lopez-Raez JA, Matusova R et al (2009) Strigolactones: ecological significance and use as a target for parasitic plant control. Pest Manag Sci 65(5):471–477PubMedGoogle Scholar
  211. Lou H, Jing X et al (2012) Eriodictyol protects against H2O2-induced neuron-like PC12 cell death through activation of Nrf2/ARE signaling pathway. Neurochem Int 61(2):251–257PubMedGoogle Scholar
  212. Lupini A, Sorgona A et al (2010) Short-term effects of coumarin along the maize primary root axis. Plant Signal Behav 5(11):1395–1400PubMedGoogle Scholar
  213. Lykakis IN, Efe C et al (2011) Ph3PAuNTf2 as a superior catalyst for the selective synthesis of 2H-chromenes: application to the concise synthesis of benzopyran natural products. Eur J Org Chem 2011(12):2334–2338Google Scholar
  214. Macias FA, Marin D et al (2006) Isolation and synthesis of allelochemicals from gramineae: benzoxazinones and related compounds. J Agric Food Chem 54(4):991–1000PubMedGoogle Scholar
  215. Macias FA, Marin D et al (2009) Rediscovering the bioactivity and ecological role of 1,4-benzoxazinones. Nat Prod Rep 26(4):478–489PubMedGoogle Scholar
  216. Macias FA, Oliveros-Bastidas A et al (2007) Plant biocommunicators: their phytotoxicity, degradation studies and potential use as herbicide models. Phytochem Rev 7(1):179–194Google Scholar
  217. MacMillan J (2001) Occurrence of gibberellins in vascular plants, fungi, and bacteria. J Plant Growth Regul 20(4):387–442PubMedGoogle Scholar
  218. MacMillan J (2002) Occurrence of gibberellins in vascular plants, fungi, and bacteria (vol 20, pg 387, 2002). J Plant Growth Regul 21(3):242–243Google Scholar
  219. Majetich G, Grove JL (2012) Synthesis of 8-hydroxyisochromenes and 8-hydroxyisocoumarins from 3-ethoxycyclohex-2-en-1-one. Heterocycles 84(2):983–1012Google Scholar
  220. Mali RS, Jagtap PG et al (1992) Novel AlCl3 catalysed syntheses of naturally occurring (±) 8-hydroxy-3-methyl-3,4-dihydroisocoumarins. J Chem Soc Chem Commun (12):883–884Google Scholar
  221. Maltais R, Tremblay MR et al (2000) Solid-phase synthesis of hydroxysteroid derivatives using the diethylsilyloxy linker. J Comb Chem 2(6):604–614PubMedGoogle Scholar
  222. Mander LN (1982) The total synthesis of gibberellins. Search 13:188–193Google Scholar
  223. Mander LN, Patrick GL (1990) A general procedure for the preparation of 11β-hydroxygibberellins: synthesis of the methyl esters of GA35 and 11β-hydroxy-GA7. Tetrahedron Lett 31:423–426Google Scholar
  224. Mander LN, Pyne SG (1981) Studies on gibberellin synthesis. Assembly of an ethanophenanthrenoid lactone and conversion into a gibbane derivative. Aust J Chem 34:1899–1911Google Scholar
  225. Marriott K-SC, Bartee R et al (2012) Expedited synthesis of benzofuran-2-carboxylic acids via microwave-assisted Perkin rearrangement reaction. Tetrahedron Lett 53(26):3319–3321PubMedGoogle Scholar
  226. Masters KS, Wallesch M et al (2011) Ortho-bromo(propa-1,2-dien-1-yl)arenes: substrates for domino reactions. J Org Chem 76(21):9060–9067PubMedGoogle Scholar
  227. Matin A, Gavande N et al (2009) 7-Hydroxy-benzopyran-4-one derivatives: a novel pharmacophore of peroxisome proliferator-activated receptor α and -γ (PPARα and γ) dual agonists. J Med Chem 52(21):6835–6850PubMedGoogle Scholar
  228. Matsushita H, Lee SH et al (2004) N-H insertion reactions of boc-amino acid amides: solution- and solid-phase synthesis of pyrazinones and pyrazines. Org Lett 6(24):4627–4629PubMedGoogle Scholar
  229. Meredith FI, Thomas CA et al (1986) Isolation of coumarin in snap beans and its effect on uredospore germination. J Agric Food Chem 34(3):456–458Google Scholar
  230. Mignet N, Seguin J et al (2012) Development of a liposomal formulation of the natural flavonoid fisetin. Int J Pharm 423(1):69–76PubMedGoogle Scholar
  231. Mik V, Szuecova L et al (2011) N9-Substituted N6-[(3-methylbut-2-en-1-yl)amino]purine derivatives and their biological activity in selected cytokinin bioassays. Bioorg Med Chem 19:7244–7251PubMedGoogle Scholar
  232. Ming LG, Zhou J et al (2011) Osthol, a coumarin isolated from common cnidium fruit, enhances the differentiation and maturation of osteoblasts in vitro. Pharmacology 88(1–2):33–43PubMedGoogle Scholar
  233. Miyano M (1965) Rotenoids. XX.1 Total synthesis of rotenone. J Am Chem Soc 87(17):3958–3962PubMedGoogle Scholar
  234. Mok DWS, Mok MC (2001) Cytokinin metabolism and action. Annu Rev Plant Physiol Plant Mol Biol 52:89–118PubMedGoogle Scholar
  235. Mori K (2010) Chemical synthesis of hormones, pheromones, and other bioregulators. Wiley, ChichesterGoogle Scholar
  236. Mori K, Matsui M (1966) Recent topics in the total synthesis of diterpenoids. Kagaku No Ryoiki 20:829–840Google Scholar
  237. Mori K, Takemoto I et al (1976) Synthesis of substances related to gibberellins. XXVI. A total synthesis of (±)-gibberellin A12 via methyl (±)-7, 16-dioxo-17-norkauran-19-oate. Tetrahedron 32:1497–1502Google Scholar
  238. Morozova EV, Kats VV (1982) Effect of coumarin on the initial stage of cucumber seed germination and phytohormone activity, Mosk. Obl. Pedagog. InstGoogle Scholar
  239. Moura-Letts G, DiBlasi CM et al (2011) Solid-phase synthesis and chemical space analysis of a 190-membered alkaloid/terpenoid-like library. Proc Natl Acad Sci USA 108(17):6745–6750PubMedGoogle Scholar
  240. Murakami S, Robinson R (1928) CCII.—a synthesis of pyrylium salts of anthocyanidin type. Part XVII. The synthesis of peonidin chloride by means of O-benzoylphloroglucinaldehyde. J Chem Soc (Resumed) 1537–1541Google Scholar
  241. Murakami T, Takada N et al (2007) Stimulation of the biosynthesis of the antibiotics lambertellols by the mycoparasitic fungus Lambertella corni-maris under the acidic conditions produced by its host fungus in vitro. Biosci Biotechnol Biochem 71(5):1230–1235PubMedGoogle Scholar
  242. Murch SJ, Hall BA et al (2010) Changes in the levels of indoleamine phytochemicals during veraison and ripening of wine grapes. J Pineal Res 49(1):95–100PubMedGoogle Scholar
  243. Musthapa I, Juliawaty L et al (2009) An oxepinoflavone from Artocarpus elasticus with cytotoxic activity against P-388 cells. Arch Pharmacal Res 32(2):191–194Google Scholar
  244. Mwakaboko AS, Zwanenburg B (2011) Single step synthesis of strigolactone analogues from cyclic keto enols, germination stimulants for seeds of parasitic weeds. Bioorg Med Chem 19(16):5006–5011PubMedGoogle Scholar
  245. Nagaoka H, Shimano M et al (1988) Total synthesis of (±)-gibberellin A3. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 30:431–438Google Scholar
  246. Nagata W, Wakabayashi T et al (1971) Stereocontrolled total synthesis of dl-gibberellin A15. J Am Chem Soc 93:5740–5758Google Scholar
  247. Nakata T, Tahara A (1976) Synthesis of gibberellin A12 from 1-abietic acid. Tetrahedron Lett (18):1515–1518Google Scholar
  248. Nalliah RE, Phillips JS et al (2009) Experimental in vitro arterial reactivity and tissue culture solutions alter the time-dependent stability of anthocyanins from elderberry, chokeberry, and bilberry extracts. Int J Food Sci Nutr 60(s1):209–219PubMedGoogle Scholar
  249. Namdaung U, Aroonrerk N et al (2006) Bioactive constituents of the root bark of Artocarpus rigidus subsp. rigidus. Chem Pharm Bull 54(10):1433–1436PubMedGoogle Scholar
  250. Ngandeu F, Bezabih M et al (2008) Rotenoid derivatives and other constituents of the twigs of Millettia duchesnei. Phytochemistry 69(1):258–263PubMedGoogle Scholar
  251. Nguyen VT, Nguyen VH et al (2007) Synthesis of lupeol derivatives and their antimicrobial activity. Tap Chi Hoa Hoc 45(1):37–41Google Scholar
  252. Niassy B, Lobstein A et al (2005) Flavonoids from Tephrosia deflexa and T. albifoliolis. Biochem Syst Ecol 33(3):309–312Google Scholar
  253. Nicolaou KC, Evans RM et al (2003) Discovery and optimization of non-steroidal FXR agonists from natural product-like libraries. Org Biomol Chem 1(6):908–920PubMedGoogle Scholar
  254. Nicolaou KC, Pfefferkorn JA et al (2000a) Natural product-like combinatorial libraries based on privileged structures. 3. The “libraries from libraries” principle for diversity enhancement of benzopyran libraries. J Am Chem Soc 122(41):9968–9976Google Scholar
  255. Nicolaou KC, Pfefferkorn JA et al (2000b) Natural product-like combinatorial libraries based on privileged structures. 2. Construction of a 10 000-membered benzopyran library by directed split-and-pool chemistry using NanoKans and optical encoding. J Am Chem Soc 122(41):9954–9967Google Scholar
  256. Nicolaou KC, Pfefferkorn JA et al (2000c) Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans. J Am Chem Soc 122(41):9939–9953Google Scholar
  257. Nicolaou KC, Pfefferkorn JA et al (2000d) Combinatorial synthesis of novel and potent inhibitors of NADH : ubiquinone oxidoreductase. Chem Biol 7(12):979–992PubMedGoogle Scholar
  258. Nicolaou KC, Roecker AJ et al (2001) Discovery of novel antibacterial agents active against methicillin-resistant Staphylococcus aureus from combinatorial benzopyran libraries. ChemBioChem 2(6):460–465PubMedGoogle Scholar
  259. Nicolaou KC, Sasmal PK et al (2004) Biomimetically inspired total synthesis and structure activity relationships of 1-O-methyllateriflorone. 6 pi electrocyclizations in organic synthesis. J Am Chem Soc 126(17):5493–5501PubMedGoogle Scholar
  260. Nigg HN, Mallory LL et al (1994) Caribbean fruit fly, Anastrepha suspensa (Loew), attraction to host fruit and host kairomones. J Chem Ecol 20(3):727–743Google Scholar
  261. Nishida R, Schulz S et al (1996) Male sex pheromone of a giant danaine butterfly, Idea leuconoe. J Chem Ecol 22(5):949–972Google Scholar
  262. Nishijima T (2007) Cytokinin has enlarging effect on petunia flowers. Nogyo oyobi Engei 82:867–872Google Scholar
  263. Niu G, Pollock HS et al (2012) Effects of a naturally occurring and a synthetic synergist on toxicity of three insecticides and a phytochemical to navel orangeworm (Lepidoptera: Pyralidae). J Econ Entomol 105(2):410–417PubMedGoogle Scholar
  264. Nogueira JHC, Gonçalez E et al (2010) Ageratum conyzoides essential oil as aflatoxin suppressor of Aspergillus flavus. Int J Food Microbiol 137(1):55–60PubMedGoogle Scholar
  265. Nugiel DA, Cornelius LAM et al (1997) Facile preparation of 2, 6-disubstituted purines using solid-phase chemistry. J Org Chem 62:201–203PubMedGoogle Scholar
  266. Nuyttens F, Appendino G et al (1991) The intramolecular Diels–Alder reaction with furan-diene: a novel route to (±)-gibberellin A5. Synlett (7):526–528Google Scholar
  267. O’Donnell F, Ramachandran VN et al (2009) An investigation of bioactive phytochemicals in the leaves of Melicope vitiflora by electrospray ionisation ion trap mass spectrometry. Anal Chim Acta 634(1):115–120PubMedGoogle Scholar
  268. O’Keefe BM, Simmons N et al (2011) Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin. Tetrahedron 67(24):4344–4351PubMedGoogle Scholar
  269. Ogawa S (2002) Growth regulators for higher plants. Idemitsu Giho 45:233–238Google Scholar
  270. Oh S, Jang HJ et al (2010) Construction of a polyheterocyclic benzopyran library with diverse core skeletons through diversity-oriented synthesis pathway. J Comb Chem 12(4):548–558PubMedGoogle Scholar
  271. Parast BM, Chetri SK et al (2011) In vitro isolation, elicitation of psoralen in callus cultures of Psoralea corylifolia and cloning of psoralen synthase gene. Plant Physiol Biochem 49(10):1138–1146PubMedGoogle Scholar
  272. Pare PW, Lewis WJ et al (1999) Induced plant volatiles: biochemistry and effects on parasitoids. American Phytopathological Society, St. Paul, Minnesota, USAGoogle Scholar
  273. Pare PW, Tumlinson JH (1998) Cotton volatiles synthesized and released distal to the site of insect damage. Phytochemistry 47(4):521–526Google Scholar
  274. Patil RP, Nimbalkar MS et al (2010) Antiaflatoxigenic and antioxidant activity of an essential oil from Ageratum conyzoides L. J Sci Food Agric 90(4):608–614PubMedGoogle Scholar
  275. Peralta MA, Ortega MaG et al (2011) Prenylated flavanones with anti-tyrosinase activity from Dalea boliviana. J Nat Prod 74(2):158–162PubMedGoogle Scholar
  276. Pereyra PC, Bowers MD (1988) Iridoid glycosides as oviposition stimulants for the buckeye butterfly, Junonia coenia (Nymphalidae). J Chem Ecol 14(3):917–928Google Scholar
  277. Plet J, Wasson A et al (2011) MtCRE1-dependent cytokinin signaling integrates bacterial and plant cues to coordinate symbiotic nodule organogenesis in Medicago truncatula. Plant J 65(4):622–633PubMedGoogle Scholar
  278. Poulton GA, Bushnell GW et al (1992) Lambertellin, a metabolite of Ciboriagordonii Funk. Can J Chem 70(10):2688–2692Google Scholar
  279. Pour M, King GR et al (1998) Synthetic and structural studies on novel gibberellins. Pure Appl Chem 70:351–354Google Scholar
  280. Prusakova LD, Chizova SI (1996) Role of brassinosteroids in growth, resistance and productivity of plants. Agrokhimiya (11):137–150Google Scholar
  281. Pszczolkowski MA, Durden K et al (2012) Effects of ginkgo biloba constituents on fruit-infesting behavior of codling moth (Cydia pomonella) in apples. J Agric Food Chem 59(20):10879–10886Google Scholar
  282. Pudelova N, Krchnak V (2009) Multiplicity of diverse heterocycles from polymer-supported alpha-acylamino ketones. J Comb Chem 11(5):851–859PubMedGoogle Scholar
  283. Qu GR, Zhang ZG et al (2007a) Microwave-assisted rapid and regioselective synthesis of N-(alkoxycarbonylmethyl) nucleobases in water. J Braz Chem Soc 18(5):1061–1067Google Scholar
  284. Qu L-p, Fan G-r et al (2007b) Isolation of six isoflavones from Semen sojae praeparatum by preparative HPLC. Fitoterapia 78(3):200–204PubMedGoogle Scholar
  285. Quintero C, Bowers MD (2011) Plant induced defenses depend more on plant age than previous history of damage: implications for plant-herbivore interactions. J Chem Ecol 37(9):992–1001PubMedGoogle Scholar
  286. Rajesh BK, Vijaya KK et al (2012) A novel solid-supported synthesis of flavones. Int J Pharm Technol 4(1):3943–3950Google Scholar
  287. Ramachandran L, Manu KA et al (2012) Isorhamnetin inhibits proliferation and invasion and induces apoptosis through the modulation of peroxisome proliferator-activated receptor γ activation pathway in gastric cancer. J Biol Chem 287(45):38028–38040PubMedGoogle Scholar
  288. Ramani A, Chanda BM et al (1999) One-pot synthesis of coumarins. Catalysis by the solid base, calcined Mg-Al hydrotalcite. Green Chem 1(3):163–165Google Scholar
  289. Rao HSP, Sivakumar S (2006) Condensation of alpha-aroylketene dithioacetals and 2-hydroxyarylaldehydes results in facile synthesis of a combinatorial library of 3-aroylcoumarins. J Org Chem 71(23):8715–8723PubMedGoogle Scholar
  290. Rappaport NG, Owen DR et al (2001) Interruption of semiochemical-mediated attraction of Dendroctonus valens (Coleoptera: Scolytidae) and selected nontarget insects by verbenone. Environ Entomol 30(5):837–841Google Scholar
  291. Ravindra PV, Narayan MS (2003) Antioxidant activity of the anthocyanin from carrot (Daucus carota) callus culture. Int J Food Sci Nutr 54(5):349–355PubMedGoogle Scholar
  292. Reiter E, Jiang Q et al (2007) Anti-inflammatory properties of α- and γ-tocopherol. Mol Aspects Med 28(5–6):668–691PubMedGoogle Scholar
  293. Reiter RJ, Tan DX et al (2001) Melatonin in plants. Nutr Rev 59(9):286–290PubMedGoogle Scholar
  294. Rempel V, Volz N et al (2012) 7-Alkyl-3-benzylcoumarins: a versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists. J Med Chem 55(18):7967–7977PubMedGoogle Scholar
  295. Repčák M, Šmajda B et al (2009) Circadian rhythm of (Z)- and (E)-2-β-d-glucopyranosyloxy-4-methoxy cinnamic acids and herniarin in leaves of Matricaria chamomilla. Plant Cell Rep 28(7):1137–1143PubMedGoogle Scholar
  296. Ribeiro VLS, dos Santos JC et al (2011) Acaricidal properties of the essential oil and precocene II obtained from Calea serrata (Asteraceae) on the cattle tick Rhipicephalus (Boophilus) microplus (Acari: Ixodidae). Vet Parasitol 179(1–3):195–198PubMedGoogle Scholar
  297. Romero-Avila M, de Dios-Bravo G et al (2007) Synthesis and biological activity of furostanic analogues of brassinosteroids bearing the 5alpha-hydroxy-6-oxo moiety. Steroids 72(14):955–959PubMedGoogle Scholar
  298. Romon P, Iturrondobeitia JC et al (2007) Quantitative association of bark beetles with pitch canker fungus and effects of verbenone on their semiochemical communication in monterey pine forests in Northern Spain. Environ Entomol 36(4):743–750PubMedGoogle Scholar
  299. Rosenbaum C, Katzka C et al (2003) Traceless Fischer indole synthesis on the solid phase. Chem Commun (15):1822–1823Google Scholar
  300. Rosenbaum C, Rohrs S et al (2005) Modulation of MRP-1-mediated multidrug resistance by indomethacin analogues. J Med Chem 48(4):1179–1187PubMedGoogle Scholar
  301. Ruddat M, Kokontis J et al (1991) Interactions of Microbotryum violaceum (ustilago violacea) with its host plant Silene alba. Plant Sci 80(1–2):157–165Google Scholar
  302. Ruff BM, Zhong S et al (2011) A combined vinylogous Mannich/Diels–Alder approach for the stereoselective synthesis of highly functionalized hexahydroindoles. Eur J Organ Chem 2011(32):6558–6566Google Scholar
  303. Sakakibara H (2005) Cytokinin biosynthesis and regulation. Vitam Horm (San Diego, CA) 72:271–287Google Scholar
  304. Sakurai K, Ikeda K, Mori K (1988) Both (4aS, 7S, 7aR)-(+)-nepetalactone and its antipode are powerful attractants for cats. Agric Biol Chem 52(9):2369–2371Google Scholar
  305. Salinthone S, Kerns AR et al (2013) α-Tocopherol (vitamin E) stimulates cyclic AMP production in human peripheral mononuclear cells and alters immune function. Mol Immunol 53(3):173–178PubMedGoogle Scholar
  306. Salom SM, Carlson JA et al (1994) Laboratory evaluation of biologically-based compounds as antifeedants for the pales weevil, Hylobius pales (Herbst) (Coleoptera, Curculionidae). J Entomol Sci 29(3):407–419Google Scholar
  307. Sancheti S, Sancheti S et al (2013) Ameliorative effects of 7-methylcoumarin and 7-methoxycoumarin against CCl4-induced hepatotoxicity in rats. Drug Chem Toxicol 36(1):42–47PubMedGoogle Scholar
  308. Sandberg G (1984) Biosynthesis and metabolism of indole-3-ethanol and indole-3-acetic-acid by Pinus sylvestris L needles. Planta 161(5):398–403Google Scholar
  309. Sang A, X-l He et al (2012) Synthesis of novel 3-methylindole derivatives. Huaxue Shiji 34(2):173–176,192Google Scholar
  310. Sarkar FH, Li Y (2003) Soy isoflavones and cancer prevention. Cancer Invest 21(5):744–757PubMedGoogle Scholar
  311. Sato N (1996) Pyrazines and their benzo derivatives. In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II. Pergamon, Oxford, pp 233–278Google Scholar
  312. Savic B, Tomic S et al (2009) Auxin amidohydrolases from Brassica rapa cleave the alanine conjugate of indolepropionic acid as a preferable substrate: a biochemical and modeling approach. Plant Cell Physiol 50(9):1587–1599PubMedGoogle Scholar
  313. Schaller H (2003) The role of sterols in plant growth and development. Prog Lipid Res 42(3):163–175PubMedGoogle Scholar
  314. Schiedel MS, Briehn CA, Bauerle P (2002) C-C Cross-coupling reactions for the combinatorial synthesis of novel organic materials. J Organomet Chem 653(1):200–208Google Scholar
  315. Schiestl FP, Roubik DW (2003) Odor compound detection in male euglossine bees. J Chem Ecol 29(1):253–257PubMedGoogle Scholar
  316. Schmarr HG, Sang W et al (2011) New insights into the synthesis and characterization of 2-methoxy-3-alkylpyrazines and their deuterated isotopologues. J Labelled Compd Radiopharm 54(8):438–440Google Scholar
  317. Selepe MA, Drewes SE et al (2010) Total synthesis of the pyranoisoflavone kraussianone 1 and related isoflavones. J Nat Prod 73(10):1680–1685Google Scholar
  318. Shaabani A, Ghadari R et al (2009) Novel one-pot three- and pseudo-five-component reactions: synthesis of functionalized benzo[g]- and dihydropyrano[2,3-g]chromene derivatives. J Comb Chem 11(6):956–959PubMedGoogle Scholar
  319. Shahwar D, Raza MA et al (2013) Identification of flavonoids with trypsin inhibitory activity extracted from orange peel and green tea leaves. J Sci Food Agric 93(6):1420–1426Google Scholar
  320. Shamaun S, Rahmani M et al (2010) Prenylated flavones from Artocarpus altilis. J Nat Med 64(4):478–481PubMedGoogle Scholar
  321. Shimizu Y, Imayoshi Y et al (2011) New eudesmane-type sesquiterpenoids and other volatile constituents from the roots of Gynura bicolor DC. Flavour Fragr J 26(1):55–64Google Scholar
  322. Shin E, Choi K-M et al (2010) Inhibitory effects of coumarins from the stem barks of Fraxinus rhynchophylla on adipocyte differentiation in 3T3-L1 cells. Biol Pharm Bull 33(9):1610–1614PubMedGoogle Scholar
  323. Shoji M, Suzuki E et al (2009) Total synthesis of (±)-5-deoxystrigol via reductive carbon−carbon bond formation. J Org Chem 74(10):3966–3969Google Scholar
  324. Shore LS, Kapulnik Y et al (1992) Effects of estrone and 17β-estradiol on vegetative growth of Medicago sativa. Physiol Plant 84(2):217–222Google Scholar
  325. Sicker D, Frey M et al (2000) Role of natural benzoxazinones in the survival strategy of plants. Int Rev Cytol 198:319–346PubMedGoogle Scholar
  326. Sicker D, Schulz M (2002) Benzoxazinones in plants: occurrence, synthetic access, and biological activity. Stud Nat Prod Chem 27(Bioactive Natural Products (Part H)):185–232Google Scholar
  327. Sidorov V, Gilbertson L et al (2006) Agrobacterium-mediated transformation of seedling-derived maize callus. Plant Cell Rep 25(4):320–328PubMedGoogle Scholar
  328. Silva LF, Craveiro MV (2008) A diastereoselective total synthesis of trans-trikentrin A: a ring contraction approach. Org Lett 10(23):5417–5420PubMedGoogle Scholar
  329. Singh R, Singh B et al (2010) Umbelliferone—an antioxidant isolated from Acacia nilotica (L.) Willd. Ex. Del. Food Chem 120(3):825–830Google Scholar
  330. Skemiene K, Rakauskaite G et al (2013) Anthocyanins block ischemia-induced apoptosis in the perfused heart and support mitochondrial respiration potentially by reducing cytosolic cytochrome c. Int J Biochem Cell Biol 45(1):23–29PubMedGoogle Scholar
  331. Slavikova B, Kohout L et al (2008) Brassinosteroids: synthesis and activity of some fluoro analogues. J Med Chem 51(13):3979–3984PubMedGoogle Scholar
  332. Snyder JC, Guo ZH et al (1993) 2,3-Dihydrofarnesoic acid, a unique terpene from trichomes of lycopersicon hirsutum, repels spider-mites. J Chem Ecol 19(12):2981–2997Google Scholar
  333. Sondhia S, Duke SO et al (2012) Phytotoxic furanocoumarins from the shoots of Semenovia transiliensis. Nat Prod Commun 7(10):1327–1330PubMedGoogle Scholar
  334. St. Denis JD, Gordon JS IV et al (2010) Novel synthesis of the isoflavone Genistein. Synthesis (10):1590–1592Google Scholar
  335. Stallknecht GF, Farnsworth S (1982) General characteristics of coumarin-induced tuberization of axillary shoots of Solanum tuberosum L. cultured in vitro. Am Potato J 59(1):17–32Google Scholar
  336. Stock AJ, Borden JH et al (1994) Containment and concentration of infestations of the western balsam bark beetle, Dryocoetes confusus (Coleoptera, Scolytidae), using the aggregation pheromone exo-brevicomin. Can J For Res 24(3):483–492Google Scholar
  337. Sugawara S, Hishiyama S et al (2009) Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis. Proc Natl Acad Sci USA 106(13):5430–5435PubMedGoogle Scholar
  338. Sugino T, Tanaka K (2001) Solvent-free coumarin synthesis. Chem Lett 30(2):110–111Google Scholar
  339. Takemoto I, Mori K et al (1976) A total synthesis of (+-)-gibberellin A12 via methyl (+-)-7, 16-dioxo-17-norkauran-19-oate. Agric Biol Chem 40:251–253Google Scholar
  340. Takikawa H, Imaishi H et al (2010) Synthesis of optically active strigolactones: enzymatic resolution and asymmetric hydroxylation. Tetrahedron Asymmetry 21(9–10):1166–1168Google Scholar
  341. Talbot A, Maltais R et al (2012) New diethylsilylacetylenic linker for parallel solid-phase synthesis of libraries of hydroxy acetylenic steroid derivatives with improved metabolic stability. ACS Comb Sci 14(6):347–351Google Scholar
  342. Tan G, Gyllenhaal C et al (2006) Biodiversity as a source of anticancer drugs. Curr Drug Targets 7(3):265–277PubMedGoogle Scholar
  343. Tanaka J, Nakanishi T et al (2010) Purple rice extract and anthocyanidins of the constituents protect against light-induced retinal damage in vitro and in vivo. J Agric Food Chem 59(2):528–536PubMedGoogle Scholar
  344. Tararov VI, Kolyachkina SV et al (2011) N6-acetyl-2′,3′,5′-tri-O-acetyladenosine; a convenient, “missed out” substrate for regioselective N6-alkylations. Synthesis (15):2483–2489Google Scholar
  345. Thompson MJ, Meudt WJ et al (1982) Synthesis of brassinosteroids and relationship of structure to plant growth-promoting effects. Steroids 39(1):89–105PubMedGoogle Scholar
  346. Tomasch R, Wagner KH et al (2001) Antioxidative power of plant oils in humans: the influence of α- and γ-tocopherol. Ann Nutr Metab 45(3):110–115PubMedGoogle Scholar
  347. Toräng J, Vanderheiden S et al (2007) Synthesis of 3-alkylcoumarins from salicylaldehydes and alpha,beta-unsaturated aldehydes utilizing nucleophilic carbenes: a new umpoled domino reaction. Eur J Organ Chem (6):943–952Google Scholar
  348. Toyota M, Odashima T et al (2000a) Application of palladium-catalyzed cycloalkenylation reaction to C20 gibberellin synthesis: formal syntheses of GA12, GA111, and GA112. J Am Chem Soc 122:9036–9037Google Scholar
  349. Toyota M, Wada T et al (1998) Total synthesis of (±)-methyl atis-16-en-19-oate via homoallyl-homoallyl radical rearrangement. J Am Chem Soc 120(20):4916–4925Google Scholar
  350. Toyota M, Wada T et al (1995) Simple design for the construction of complex gibberellin framework—stereoselective synthesis of a possible key intermediate to GA12 via Pd2+-promoted cycloalkenylation reaction. Tetrahedron 51(25):6927–6940Google Scholar
  351. Toyota M, Yokota M et al (2001) Remarkable control of radical cyclization processes of cyclic enyne: total syntheses of (±)-methyl gummiferolate, (±)-methyl 7β-hydroxykaurenoate, and (±)-methyl 7-oxokaurenoate and formal synthesis of (±)-gibberellin A12 from a common synthetic precursor. J Am Chem Soc 123:1856–1861PubMedGoogle Scholar
  352. Toyota M, Yokota M et al (2000b) Total syntheses of plant growth regulators GA12, GA111 and GA112. Tennen Yuki Kagobutsu Toronkai Koen Yoshishu 42nd:241–246Google Scholar
  353. Tremblay MR, Poirier D (1999) Solid-phase synthesis of phenolic steroids: towards combinatorial libraries of estradiol derivatives. Tetrahedron Lett 40:1277–1280Google Scholar
  354. Tsui K-H, Chung L-C et al (2012) Upregulation of prostate-derived Ets factor by luteolin causes inhibition of cell proliferation and cell invasion in prostate carcinoma cells. Int J Cancer 130(12):2812–2823PubMedGoogle Scholar
  355. Ueno K, Fujiwara M et al (2011) Structural requirements of strigolactones for germination induction of Striga gesnerioides seeds. J Agric Food Chem 59(17):9226–9231PubMedGoogle Scholar
  356. Ueno K, Hanada A et al (2010) Preparation of multideuterated 5-deoxystrigol for use as an internal standard for quantitative LC/MS. J Label Compd Radiopharm 53(13):763–766Google Scholar
  357. Uesusuki S, Watanabe B et al (2004) Synthesis of brassinosteroids of varying acyl side chains and evaluation of their brassinolide-like activity. Biosci Biotechnol Biochem 68(5):1097–1105PubMedGoogle Scholar
  358. von Pechmann H (1884) Neue bildungsweise der cumarine. Synthese des daphnetins. I. Ber Dtsch Chem Ges 17(1):929–936Google Scholar
  359. Vadassery J, Ritter C et al (2008) The role of auxins and cytokinins in the mutualistic interaction between Arabidopsis and Piriformospora indica. Mol Plant Microbe Interact 21(10):1371–1383PubMedGoogle Scholar
  360. Vankova B, Krchnak V et al (2011) Direct C-H arylation of purine on solid phase and its use for chemical libraries synthesis. ACS Comb Sci 13:496–500PubMedGoogle Scholar
  361. Vicker N, Lawrence HR et al (2006) Focused libraries of 16-substituted estrone derivatives and modified E-ring steroids: inhibitors of 17 beta-hydroxysteroid dehydrogenase type 1. ChemMedChem 1(4):464–481PubMedGoogle Scholar
  362. Voegtle H, Jones T et al (2008) E-2-ethylhexenal, E-2-ethyl-2-hexenol, mellein, and 4-hydroxymellein in Camponotus species from Brunei. J Chem Ecol 34(2):215–219PubMedGoogle Scholar
  363. Volz N, Bröhmer MC et al (2009) Adventures in heterocycle chemistry: the oxa-Michael cascade for the synthesis of complex natural products and highly functionalized bioactive compounds. Indian J Chem Sect B Organ Chem Incl Med Chem 48(12):1699–1703Google Scholar
  364. Wagner R, Czerny M et al (1999) Structure-odour-activity relationships of alkylpyrazines. Zeitschrift für Lebensmitteluntersuchung und -Forschung A 208(5–6):308–316Google Scholar
  365. Wan Z-K, Wacharasindhu S et al (2006) An efficient direct amination of cyclic amides and cyclic ureas. Org Lett 8:2425–2428PubMedGoogle Scholar
  366. Wan Z-K, Wacharasindhu S et al (2007) The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas. J Org Chem 72:10194–10210PubMedGoogle Scholar
  367. Wang J, Yan X et al (2005) Relationship between adventitious root formation and plant hormones. Zhiwu Shenglixue Tongxun 41:133–142Google Scholar
  368. Wang R, Sun Y et al (2012) Effects of six plant secondary metabolites on activities of detoxification enzymes in Spodoptera litura. Shengtai Xuebao 32(16):5191–5198Google Scholar
  369. Wang Y, Huang TN (1998) Solid-phase synthesis of heterocycles via palladium-catalyzed annulation. Tetrahedron Lett 39(52):9605–9608Google Scholar
  370. Watson BT, Christiansen GE (1998) Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation. Tetrahedron Lett 39(33):6087–6090Google Scholar
  371. Weir TL, Bais HP et al (2003) Intraspecific and interspecific interactions mediated by a phytotoxin, (−)-catechin, secreted by the roots of Centaurea maculosa (spotted knapweed). J Chem Ecol 29:2397–2412PubMedGoogle Scholar
  372. Welzel P, Rohrig S et al (1999) Strigol-type germination stimulants: the C-2′ configuration problem. Chem Commun (Cambridge)(20):2017–2022Google Scholar
  373. Wheeler GS, Slansky F Jr et al (2001) Food consumption, utilization and detoxification enzyme activity of larvae of three polyphagous noctuid moth species when fed the botanical insecticide rotenone. Entomol Exp Appl 98:225–239Google Scholar
  374. Wurm G, Geres U (1982) Eine neue eriodictyolsynthese. Arch Pharm 315(2):183–185Google Scholar
  375. Wuyts N, Swennen R et al (2006) Effects of plant phenylpropanoid pathway products and selected terpenoids and alkaloids on the behavior of the plant-parasitic nematodes Radopholus similis, Pratylenchus penetrans and Meloidogyne incognita. Nematology 8(1):89–101Google Scholar
  376. Xia Y, Yang ZY et al (1999) Asymmetric solid-phase synthesis of (3 ‘ R,4 ‘ R)-Di-O-cis-acyl 3-carboxyl khellactones. Org Lett 1(13):2113–2115PubMedGoogle Scholar
  377. Xie X, Yoneyama K et al (2007) Isolation and identification of alectrol as (+)-orobanchyl acetate, a germination stimulant for root parasitic plants. Phytochemistry 69(2):427–431Google Scholar
  378. Xu F, Wang C et al (2012) Ruthenium-catalyzed [2 + 2 + 2] cycloaddition of diynes with nitriles in pure water. ChemSusChem 5(5):854–857PubMedGoogle Scholar
  379. Yaguchi A, Yoshinari T et al (2009) Isolation and identification of precocenes and piperitone from essential oils as specific inhibitors of trichothecene production by Fusarium graminearum. J Agric Food Chem 57(3):846–851PubMedGoogle Scholar
  380. Yang D, Yang J et al (2011) Scoparone potentiates transactivation of the bile salt export pump gene and this effect is enhanced by cytochrome P450 metabolism but abolished by a PKC inhibitor. Br J Pharmacol 164(5):1547–1557PubMedGoogle Scholar
  381. Yoneyama K, Xie X et al (2007) Nitrogen deficiency as well as phosphorus deficiency in sorghum promotes the production and exudation of 5-deoxystrigol, the host recognition signal for arbuscular mycorrhizal fungi and root parasites. Planta 227(1):125–132Google Scholar
  382. Young H, Letham DS et al (1990) Synthesis of radioactive zeatin riboside and related compounds by alkylation of purine moieties. Phytochemistry 29:385–386Google Scholar
  383. Yu SJ, Abo-Elghar GE (2000) Allelochemicals as inhibitors of glutathione S-transferases in the fall armyworm. Pestic Biochem Physiol 68(3):173–183Google Scholar
  384. Yuan Y, Liu G et al (2007) Synthesis of diverse benzo[1,4]oxazin-3-one-based compounds using 1,5-difluoro-2,4-dinitrobenzene. J Comb Chem 9(1):158–170PubMedGoogle Scholar
  385. Zangerl AR, Berenbaum MR (2004) Genetic variation in primary metabolites of Pastinaca sativa; can herbivores act as selective agents? J Chem Ecol 30(10):1985–2002PubMedGoogle Scholar
  386. Zhang BL, Wang FD et al (2007) Concise and efficient synthesis of linear furocoumarins: psoralen and 4-methylpsoralen. Synth Commun 37(1):63–70Google Scholar
  387. Zhang Q-H, Chauhan KR et al (2004) Semiochemistry of the goldeneyed lacewing Chrysopa oculata: attraction of males to a male-produced pheromone. J Chem Ecol 30(9):1849–1870PubMedGoogle Scholar
  388. Zhang QH, Schlyter F (2003) Redundancy, synergism, and active inhibitory range of non-host volatiles in reducing pheromone attraction in European spruce bark beetle Ips typographus. Oikos 101(2):299–310Google Scholar
  389. Zhang QH, Schlyter F (2004) Olfactory recognition and behavioural avoidance of angiosperm nonhost volatiles by conifer-inhabiting bark beetles. Agric For Entomol 6(1):1–19Google Scholar
  390. Zhou F, Zhong W et al (2012) Reduction of rat cardiac hypertrophy by osthol is related to regulation of cardiac oxidative stress and lipid metabolism. Lipids 47(10):987–994PubMedGoogle Scholar
  391. Zhuravel IO, Kovalenko SM et al (2005) Solution-phase synthesis of a combinatorial library of 3-[4-(Coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides. Molecules 10(2):444–456PubMedGoogle Scholar
  392. Zwanenburg B, Thuring JWJF (1997) Synthesis of strigolactones and analogs: a molecular approach to the witchweed problem. Pure Appl Chem 69(3):651–654Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Nicole Jung
    • 1
    • 2
  • Franziska Gläser
    • 1
  • Stefan Bräse
    • 1
    • 2
  1. 1.Institute of Organic ChemistryKarlsruhe Institute of Technology (KIT)KarlsruheGermany
  2. 2.Institute of Toxicology and GeneticsKarlsruhe Institute of Technology (KIT)Eggenstein-LeopoldshafenGermany

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