Skip to main content

Sesquiterpene coumarins

Abstract

Plants have a long history as therapeutic tools in the treatment of human diseases and have been used as a source of medicines for ages. In search of new biologically active natural products, many plants and herbs used in traditional medicine are screened for natural products with pharmacological activity. In this paper, we present a group of natural products, the sesquiterpene coumarins isolated from plants, and describe their wide range of biological activity. Sesquiterpene coumarins are found in some plants of the families Apiaceae (Umbelliferae), Asteraceae (Compositae) and Rutaceae. The coumarin moiety is often umbelliferone (7-hydroxycoumarin) but scopoletin (7-hydroxy-6-methoxycoumarin) and isofraxidin (7-hydroxy-6,8-dimethoxycoumarin) are also found. These coumarins are linked to a C15 terpene moiety through an ether linkage. Another group of sesquiterpene coumarins is the prenylated 4-hydroxycoumarins where the link between the coumarin and the C15 terpene moiety is a C–C-bond at carbon 3 of the coumarin moiety. Finally, the prenyl-furocoumarin-type sesquiterpenoids are a separate group of sesquiterpene coumarins based on the suggested biosynthetic pathway. Our relatively limited knowledge on the biosynthesis of sesquiterpene coumarins is reviewed.

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Fig. 3

Abbreviations

AChE:

Acetylcholinesterase

BIS:

Bisphenyl synthase

CPE:

Cytopathic effect

F6′H1:

Fe(II)- and 2-oxoglutarate-dependent dioxygenase

FDP:

Farnesyl diphosphate

FDU7T:

Farnesyl diphosphate umbelliferone transferase

HRV:

Human rhinoviruses

INH:

Isonicotinic acid hydrazide

M4Beu:

Human metastatic pigmented malignant melanoma cells

MDR:

Multidrug resistance

MIC:

Minimum inhibitory concentration

NDP:

Nerolidyl diphosphate

SHC:

Squalene-hopene cyclase

SQE:

Squalene epoxidase

VEGF:

Vascular endothelial growth factor

UPE:

Umbelliprenin epoxidase

References

  1. Abd El-Razek MH, Ohta S, Ahmed AA, Hirata T (2001) Sesquiterpene coumarins from the roots of Ferula assa-foetida. Phytochemistry 58:1289–1295

    PubMed  Article  CAS  Google Scholar 

  2. Abd El-Razek MH, Y-Ch Wu, Chang F-R (2007) Sesquiterpene coumarins from Ferula foetida. J Chin Chem Soc 54:235–238

    CAS  Google Scholar 

  3. Ahmed AA (1999) Sesquiterpene coumarins and sesquiterpenes from Ferula sinaica. Phytochemistry 50:109–112

    Article  CAS  Google Scholar 

  4. Ahmed AA, Bishr MM, El-Shanawany MA, Attia EZ, Ross SA, Paré PW (2005) Rare trisubstituted sesquiterpenes daucanes from the wild Daucus carot. Phytochemistry 66:1680–1684

    PubMed  Article  CAS  Google Scholar 

  5. Ahmed AA, Hegazy M-EF, Zellagui A, Rhouati S, Mohamed TA, Sayed AA, Abdella MA, Ohta S, Hirata T (2007) Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry 68:680–686

    PubMed  Article  CAS  Google Scholar 

  6. Al-Yahya MA, Muhammad I, Mirza HH, El-Feraly FS (1998) Antibacterial constituents from the rhizomers of Ferula communis. Phytoter Res 12:335–339

    Article  CAS  Google Scholar 

  7. Appendino G, Tagliapietra S, Gariboldi P, Nano GM, Picci V (1988) ω-Oxygenated prenylated coumarins from Ferula communis. Phytochemistry 27:3619–3624

    Article  CAS  Google Scholar 

  8. Appendino G, Nano GM, Viterbo D, De Munno G, Cisero M, Palmisano G, Aragno M (1991) Ammodoremin, an epimeric mixture of prenylated chromandiones from Ammoniacum. Helv Chim Acta 74:495–500

    Article  CAS  Google Scholar 

  9. Appendino G, Őzen HC, Nano GN, Cisero M (1992) Sesquiterpene coumarin ethers from the genus Heptaptera. Phytochemistry 31:4223–4226

    Article  CAS  Google Scholar 

  10. Appendino G, Tagliapietra S, Nano GM, Jakupovic J (1994) Sesquiterpene coumarin ethers from asafetida. Phytochemistry 35:183–186

    Article  CAS  Google Scholar 

  11. Appendino G, Jakupovic J, Alloatti S, Ballero M (1997) Daucane esters from Ferula arrigonii. Phytochemistry 45:1639–1643

    Article  CAS  Google Scholar 

  12. Appendino G, Mercalli E, Fuzzati N, Arnoldi L, Stavri M, Gibbons S, Ballero M, Maxia A (2004) Antimycobacterial coumarins from the Sardinian Giant Fennel (Ferula communis). J Nat Prod 67:2108–2110

    PubMed  Article  CAS  Google Scholar 

  13. Appendino G, Maxia L, Bascope M, Houghton PJ, Sanchez-Duffhues G, Munoz E, Sterner O (2006) A meroterpenoid NF-κB inhibitor and drimane sesquiterpenoids from asafetida. J Nat Prod 69:1101–1104

    PubMed  Article  CAS  Google Scholar 

  14. Bandyopadhyay D, Basak B, Chatterjee A, Lai TK, Banerji A, Banerji J, Neuman A, Prangé T (2006) Saradaferin, a new sesquiterpenoid coumarin from Ferula assafoetida. Nat Prod Res 20:961–965

    PubMed  Article  CAS  Google Scholar 

  15. Barthomeuf C, Demeule M, Grassi J, Saidkhodjaev A, Beliveau R (2006) Conferone from Ferula schtschurowskiana enhances vinblastine cytotoxicity in MDCK-MDR1 cells by competitively inhibiting P-glycoprotein transport. Planta Med 72:634–639

    PubMed  Article  CAS  Google Scholar 

  16. Barthomeuf C, Lim S, Iranshahi M, Chollet P (2008) Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu metastatic pigmented malignant melanoma cells through cell-cycle arrest in G1 and induction of caspase-dependent apoptosis. Phytomedicine 15:103–111

    PubMed  Article  CAS  Google Scholar 

  17. Bocca C, Gabriel L, Bozzo F, Miglietta A (2002) Microtubule-interacting activity and cytotoxicity of the prenylated coumarin ferulenol. Planta Med 68:1135–1137

    PubMed  Article  CAS  Google Scholar 

  18. Bourgaud F, Hehn A, Larbat R, Doerper S, Gontier E, Kellner S, Matern U (2006) Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes. Phytochem Rev 5:293–308

    Article  CAS  Google Scholar 

  19. Bouvier F, Rahier A, Camara B (2005) Biogenesis, molecular regulation and function of plant isoprenoids. Prog Lip Res 44:357–429

    Article  CAS  Google Scholar 

  20. Brandt W, Bräuer L, Günnewich N, Kufka J, Rausch F, Schulze D, Schulze E, Weber R, Zakharova S, Wessjohann L (2009) Molecular and structural basis of metabolic diversity mediated by prenyldiphosphate converting enzymes. Phytochemistry 70:1758–1775

    PubMed  Article  CAS  Google Scholar 

  21. Caglioti L, Naef H, Arigoni D, Jeger O (1959) Zur Kenntnis der Sesquiterpene und Azulene. 127. Mitteilung. Über die Inhaltsstoffe der Asa foetida II. Farnesiferol B und C. Helv Chim Acta 42:2557

  22. Cha MR, Choi YH, Choi CW, Kim YS, Kim YK, Ryu SY, Kim YH, Choi SU (2011) Galbanic acid, a cytotoxic sesquiterpene from the gum resin of Ferula asafoetida, blocks protein farnesyltransferase. Planta Med 77:52–54

    PubMed  Article  CAS  Google Scholar 

  23. Choudhary MI, Baig I, Nur-e-Alam M, Shahzad-ul-Hussan S, Öndognii P, Bunderya M, Oyun Z, Atta-ur-Rahman (2001) New α-Glucosidase inhibitors from the Mongolian medicinal plant Ferula mongolic. Helv Chim Acta 84:2409–2416

    Article  CAS  Google Scholar 

  24. Cravotto G, Balliano G, Robaldo B, Oliaro-Bosso S, Chimichi S, Boccalini M (2004) Farnesyloxycoumarins a new class of squalene-hopene cyclase inhibitors. Bioorg Med Chem Lett 14:1931–1934

    PubMed  Article  CAS  Google Scholar 

  25. Dall’Acqua S, Maggi F, Minesso P, Salvagno M, Papa F, Vittori S, Innocenti G (2010) Identification of non-alkaloid acetylcholinesterase inhibitors from Ferulago campestris (Besser) Grecescu (Apiaceae). Fitoterapia 81:1208–1212

    PubMed  Article  Google Scholar 

  26. El-Bassuony AA, Gohar AA, Kabbash AM (2007) Two new sesquiterpene coumarins, ferusinol and samarcandin diastereomer from Ferula sinaica. Iran J Pharm Res 6:217–221

    CAS  Google Scholar 

  27. Fazly Bazzaz BS, Du AR, Iranshhahi M, Naderinasab M, Karamodin MK (2009) Evaluating the potentiating effect of galbanic acid from Ferula szowitsiana on three common antibiotics against resistant hospital isolates of Staphylococcus aureus. Iran J Pharm Res 8:217–221

    Google Scholar 

  28. Filippini R, Piovan A, Innocenti G, Caniato R, Cappelletti EM (1998) Production of coumarin compounds by Haplophyllum patavinum in vivo and in vitro. Phytochemistry 49:2337–2340

    Article  CAS  Google Scholar 

  29. Gohar AA, El-Bassuony AA (2007) Two new sesquiterpene coumarins, ferusinol and samarcandin diastereomer from Ferula sinaica. Saudi Pharm J 15:33–37

    CAS  Google Scholar 

  30. Greger H, Haslinger E, Hofer O (1982a) Albartin–a new sesquiterpene–coumarin ether from Artemisis alb. Monatsh Chem 113:375–379

    Article  CAS  Google Scholar 

  31. Greger H, Hofer O, Nikiforov A (1982b) New sesquiterpene-coumarin ethers from Achillea and Artemisis species. J Nat Prod 45:455–461

    Article  CAS  Google Scholar 

  32. Greger H, Hofer O, Robien W (1983) New sesquiterpene coumarin ethers from Achillea ochroleuca. 13C NMR of isofraxidin-derived open-chain and bicyclic sesquiterpene ethers. J Nat Prod 46:510–516

    Article  CAS  Google Scholar 

  33. Hamerski D, Schmitt D, Matern U (1990) Induction of two prenyltransferases for the accumulation of coumarin phytoalexins in elicitor-treated Ammi majus cell suspension cultures. Phytochemistry 29:1131–1135

    PubMed  Article  CAS  Google Scholar 

  34. Hofer O, Greger H (1984a) Naturally occurring sesquiterpene-coumarin ethers, VI. New sesquiterpene-isofraxidin ethers from Achillea depress. Monatsh Chem 115:477–483

    Article  CAS  Google Scholar 

  35. Hofer O, Greger H (1984b) Scopoletin sesquiterpene ethers from Artemisia persica. Phytochemistry 23:181–182

    Article  CAS  Google Scholar 

  36. Hofer O, Weissensteiner W, Widhalm M (1983) Absolute configurations and circular dichroism of sesquiterpene-coumarin ethers. Monatsh Chem 114:1399–1411

    Article  CAS  Google Scholar 

  37. Iranshahi M, Shahverdi AR, Mirjani R, Amin G, Shafiee A (2004) Umbelliprenin from Ferula persica roots inhibits the red pigment production in Serratia marcescens. Z Naturforsch 59c:506–508

    Google Scholar 

  38. Iranshahi M, Arfa P, Ramezani M, Jaafari MR, Sadeghian H, Bassarello C, Piacente S, Pizza C (2007) Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes. Phytochemistry 68:554–561

    PubMed  Article  CAS  Google Scholar 

  39. Iranshahi M, Kalategi F, Rezaee R et al (2008) Cancer chemopreventive activity of terpenoid coumarins from Ferula species. Planta Med 74:147–150

    PubMed  Article  CAS  Google Scholar 

  40. Iranshahi M, Sahebkar A, Takasaki M et al (2009a) Cancer chemopreventive activity of the prenylated coumarin, umbelliprenin, in vivo. Eur J Cancer Prev 18:412–415

    PubMed  Article  CAS  Google Scholar 

  41. Iranshahi M, Askari M, Sahebkar A, Hadjipavlou-Litina D (2009b) Evaluation of antioxidant, anti-inflammatory and lipoxygenase inhibitory activities of the prenylated coumarin umbelliprenin. Daru 17:99–103

    CAS  Google Scholar 

  42. Iranshahi M, Ghiadi M, Sahebkar A, Rahimi A, Bassarello C, Piacente S, Pizza C (2009c) Badrakemonin, a new eremophilane-type sesquiterpene from the roots of Ferula badrakema Kos.-Pol. Iran J Pharm Res 8:275–279

    CAS  Google Scholar 

  43. Iranshahi M, Masullo M, Asili A, Hamedzadeh A, Jahanbin B, Festa M, Capasso A, Piacente S (2010) Sesquiterpene Coumarins from Ferula gumosa. J Nat Prod 73:1958–1962

    PubMed  Article  CAS  Google Scholar 

  44. Isaka K, Nagatsu A, Ondognii P, Zevgeegiin O, Gombosurengyin P, Davgiin K, Kojima K, Ogihara Y (2001) Sesquiterpenoid derivatives from Ferula ferulioides. V. Chem Pharm Bull 49:1072–11076

    PubMed  Article  CAS  Google Scholar 

  45. Jabrane A, Jannet HB, Mighri Z, Mirjolet J-F, Duchamp O, Harzallah-Skhiri F, Lacaille-Dubois M-A (2010) Two new sesquiterpene derivatives from the Tunisian endemic Ferula tunetana POM. Chem Biodivers 7:392–399

    PubMed  Article  CAS  Google Scholar 

  46. Jandl B, Hofer O, Kalchhauser H, Greger H (1997) Open chain sesquiterpene coumarin ethers and coniferylalcohol-4-O-farnesyl ether from Achillea ochroleuc. Nat Prod Lett 11:17–24

    Article  CAS  Google Scholar 

  47. Kai K, Mizutani M, Kawamura N, Yamamoto R, Tamai M, Yamaguchi H, Sakata K, Shimizu B (2008) Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabisdopsis thaliana. Plant J 55:989–999

    PubMed  Article  CAS  Google Scholar 

  48. Kajimoto T, Yahiro K, Nohara T (1989) Sesquiterpenoid and disulphide derivatives from Ferula assa-foetida. Phytochemistry 28:1761–1763

    Article  CAS  Google Scholar 

  49. Khorramizadeh MR, Esmail-Nazari Z, Zarei-Ghaane Z, Shakibaie M, Mollazadeh-Moghaddam K, Iranshahi M, Shahverdi AR (2010) Umbelliprenin-coated Fe3O4 magnetite nanoparticles: Antiproliferation evaluation on human Fibrosarcoma cell line (HT-1080). Mate Sci Eng C 30:1038–1042

    Article  CAS  Google Scholar 

  50. Kisiel W, Stojakowska A (1997) A sesquiterpene coumarin ether from transformed roots of Tanacetum parthenium. Phytochemistry 46:515–516

    Article  CAS  Google Scholar 

  51. Kojima K, Isaka K, Ondognii P, Zevgeegiin O, Gombosurengyin P, Davgiin K, Mizukami H, Ogihara Y (2000) Sesquiterpenoid derivatives from Ferula ferulioides. IV. Chem Pharm Bull 48:353–356

    PubMed  Article  CAS  Google Scholar 

  52. Lahouel M, Zini R, Zellagui A, Rhouati S, Carrupt P-A, Morin D (2007) Ferulenol specifically inhibits succinate ubiquinone reductase at the level of the ubiquinone cycle. Biochem Biophys Res Comm 355:252–257

    PubMed  Article  CAS  Google Scholar 

  53. Lee Ch-L, Chiang L-Ch, Cheng L-H, Liaw Ch-Ch, Abd El-razek MH, Chang F-R, Wu Y-Ch (2009) Influenza A (H1N1) Antiviral and cytotoxic agents from Ferula assa-foetida. J Nat Prod 72:1568–1572

    PubMed  Article  CAS  Google Scholar 

  54. Lee J-H, Choi S, Lee Y, Lee H-J, Kim K-H, Ahn K-S, Bae H, Lee H-J, Lee E-O, Ahn K-S, Ryu SY, Lü J, Kim S-H (2010) Herbal compound farnesiferol C exerts antiangiogenic and antitumor activity and targets multiple aspects of VEGFR1 (Flt1) or VEGFR2 (Flk1) signaling cascades. Mol Cancer Ther 9:389–399

    PubMed  Article  CAS  Google Scholar 

  55. Liu B, Raeth T, Beuerle T, Beerhues L (2010) A novel 4-hydroxycoumarin biosynthetic pathway. Plant Mol Biol 72:17–25

    PubMed  Article  CAS  Google Scholar 

  56. Madureira AM, Molnar A, Abreu PM, Molnar J, Ferreira MU (2004) A new sesquiterpene coumarin ether and a new abietane diterpene and their effects as inhibitors of p-glycoprotein. Planta Med 70:828–833

    PubMed  Article  CAS  Google Scholar 

  57. Marchi A, Appendino G, Pirisi I, Ballero M, Loi MC (2003) Genetic differentiation of two distinct chemotypes of Ferula communis (Apiaceae) in Sardinia (Italy). Biochem Sys Eco 31:1397–1408

    Article  CAS  Google Scholar 

  58. Mashinchian O, Salehi R, Dehghan G, Aganejad A, Davaran S, Omidi Y (2010) Novel thermosensitive poly (N-isopropylacrylamide-co-vinylprrolidone-co-methacrylic acid) nanosystems for delivery of natural products. Int J Drug Deliv 2:278–286

    Article  CAS  Google Scholar 

  59. Miski M, Ulubelen A (1985) Sesquiterpene-coumarin ethers of Ferula tingitana. J Nat Prod 48:326–327

    PubMed  Article  CAS  Google Scholar 

  60. Monti M, Pinotti M, Appendino G, Dallocchio F, Bellini T, Antognoni F, Poli F, Bernardi F (2007) Characterization of anti-coagulant properties of prenylated coumarin ferulenol. Biochim Biophys Acta 1770:1437–1440

    PubMed  Article  CAS  Google Scholar 

  61. Mossa JS, El-Feraly FS, Muhammad I (2004) Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide. Phytother Res 18:934–937

    PubMed  Article  CAS  Google Scholar 

  62. Motai T, Kitanaka S (2004) Sesquiterpene coumarins from Ferula fukanensis and Nitric Oxide production inhibitory effects (2). Chem Pharm Bull 52:1215–1218

    PubMed  Article  CAS  Google Scholar 

  63. Motai T, Kitanaka S (2006) Sesquiterpenoids from Ferula fukanensis and their inhibitory effects on nitric oxide production. J Nat Med 60:54–57

    Article  CAS  Google Scholar 

  64. Murphy EM, Nahar L, Byres M, Shoeb M, Siakalima M, Rahman MM, Gray AI, Sarker SD (2004) Coumarins from the seeds of Angelica sylvestris (Apiaceae) and their distribution within the genus Angelica. Biochem Syst Ecol 32:203–207

    Article  CAS  Google Scholar 

  65. Murray RDH (2002) The naturally occurring coumarins. Progress in the chemistry of organic natural products, vol 83. Springer, Vienna, p 673

    Google Scholar 

  66. Murray RDH, Méndez J, Brown SA (1982) The natural coumarins: occurrence, chemistry and biochemistry. Wiley, Chichester

    Google Scholar 

  67. Nadkarni KK, Kamat SP, Paknikar SK (1994) Synthesis of (±)-6-hydroxy-3, 4-dihydro-4, 7-dimethylbenzo-1-pyran-2(h)-one, a tetranorsesquiterpenoid. Indian J Chem B 33:432–435

    Google Scholar 

  68. Nagatsu A, Isaka K, Ondognii P, Zevgeegiin O, Gombosurengyin P, Davgiin K, Irfan B, Choudhary MI, Ogihara Y (2002) New sesquiterpenes from Ferula ferulaeoides (STEUD.) KOROVIN. VI. Isolation and identification of three new dihydrofuro [2, 3-b]chromones. Chem Pharm Bull 50:675–677

    PubMed  Article  CAS  Google Scholar 

  69. Oughlissi-Dehak K, Lawton P, Michalet S, Bayet C, Darbour N, Hadj-Mahammed M, Badjah-Hadj-Ahmed YA, Dijoux-Franca M-G, Guilet D (2008) Sesquiterpenes from aerial parts of Ferula vesceritensis. Phytochemistry 69:1933–1938

    PubMed  Article  CAS  Google Scholar 

  70. Paknikar SK, Fondekar KPP (2001) Synthesis of the 7-hydroxy-4-isopropyl-6-methylcoumarin: a bisnorsesquiterpene. J Indian Inst Sci 81:175–179

    CAS  Google Scholar 

  71. Phillips DR, Rasbery JM, Bartel B, Matsuda SPT (2006) Biosynthetic diversity in plant triterpene cyclization. Curr Opin Plant Biol 9:305–314

    PubMed  Article  CAS  Google Scholar 

  72. Pillai SP, Menon SR, Mitscher LA, Pillai CA, Shankel DM (1999) Umbelliferone analogues and their potential to inhibit benzo(a)pyrene- and hydrogen peroxide-induced mutations. J Nat Prod 62:1358–1362

    PubMed  Article  CAS  Google Scholar 

  73. Rasbery JM, Shan H, LeClair RJ, Norman M, Matsuda SPT, Bartel B (2007) Arabidopsis thaliana squalene epoxidase 1 is essential for root and seed development. J Biol Chem 282:17002–17013

    PubMed  Article  CAS  Google Scholar 

  74. Rassouli FB, Matin MM, Iranshahi M, Bahrami AR, Neshati V, Mollazadeh S, Neshati Z (2009) Mogoltacin enhances vincristine cytotoxicity in human transitional cell carcinoma (TCC) cell line. Phytomedicine 16:181–187

    Article  CAS  Google Scholar 

  75. Razdan TK, Qadri B, Qurishi MA, Khuroo MA, Kachroo PK (1989) Sesquiterpene esters and sesquiterpene-coumarin ethers from Ferula jaeskeana. Phytochemistry 28:3389–3393

    Article  CAS  Google Scholar 

  76. Rollinger JM, Hornick A, Langer T, Stuppner H, Prast H (2004) Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. J Med Chem 47:6248–6254

    PubMed  Article  CAS  Google Scholar 

  77. Rollinger JM, Steindl TM, Schuster D, Kirchmair J, Anrain K, Ellmerer EP, Langer T, Stuppner H, Wutzler P, Schmidtke M (2008) Structure-based virtual screening for the discovery of natural inhibitors for human Rhinovirus coat protein. J Med Chem 51:842–851

    PubMed  Article  CAS  Google Scholar 

  78. Rosselli S, Maggio A, Bellone G, Formisano C, Basile A, Cicala C, Alfieri A, Mascolo N, Bruno M (2007) Anitbacterial and anticoagulant activities of coumarins isolated from the flowers of Magydaris tomentosa. Planta Med 73:116–120

    PubMed  Article  CAS  Google Scholar 

  79. Sahebkar A, Iranshahi M (2010) Cancer chemoprevention by 7-prenyloxycoumarins: A role for 5-lipoxygenases inhibition? Integr Cancer Ther 9:259–260

    PubMed  Article  CAS  Google Scholar 

  80. Saleh O, Haagen Y, Seeger K, Heide L (2009) Prenyl transfer to aromatic substrates in the biosynthesis of aminocoumarins, meroterpenoids and phenazines: the ABBA prenyltransferase family. Phytochemistry 70:1728–1738

    PubMed  Article  CAS  Google Scholar 

  81. Sasaki K, Mito K, Ohara K, Yamamoto H, Yazaki K (2008) Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens. Plant Physiol 146:1075–1084

    PubMed  Article  CAS  Google Scholar 

  82. Sayed AAR (2011) Ferulsinaic acid attenuation of advanced glycation end products extends the lifespan of Caenorhabditis elegans. J Pharm Pharmacol 63:423–428

    PubMed  Article  CAS  Google Scholar 

  83. Shahverdi A-R, Iranshahi M, Mirjani R, Jamalifar H, Amin G, Shafiee A (2005) Bioassay-guided isolation and identification of an antibacterial compound from Ferula persica var. persica roots. Daru 13:17–19

    CAS  Google Scholar 

  84. Shahverdi AR, Saadat F, Khorramizadeh MR, Iranshahi M, Khoshayand MR (2006) Two matrix metalloproteinases inhibitors from Ferula persica var. persica. Phytomedicine 13:712–717

    PubMed  Article  CAS  Google Scholar 

  85. Shahverdi AR, Fakhimi A, Zarrini G, Dehghan G, Iranshahi M (2007) Galbanic acid from Ferula szowitsiana enhanced the antibacterial activity of penicillin G and cephalexin against Staphylococcus aureus. Biol Pharm Bull 30:1805–1807

    PubMed  Article  CAS  Google Scholar 

  86. Soltani F, Mosaffa F, Iranshahi M, Karimi G, Malekaneh M, Haghighi F, Behravan J (2009) Evaluation of antigenotoxicity effects of umbelliprenin on human peripheral lymphocytes exposed to oxidative stress. Cell Biol Toxicol 25:291–296

    PubMed  Article  CAS  Google Scholar 

  87. Su B-N, Takaishi Y, Honda G, Itoh M, Takeda Y, Kodzhimatov OK, Ashurmetov O (2000) Sesquiterpene coumarins and related derivatives from Ferula palli. J Nat Prod 63:436–440

    PubMed  Article  CAS  Google Scholar 

  88. Sutthivaiyakit S, Mongkolvisut W, Prabpai S, Kongsaeree P (2009) Diterpenes, sesquiterpenes and a sesquiterpene-coumarin conjugate from Jatropha integerrima. J Nat Prod 72:2024–2027

    PubMed  Article  CAS  Google Scholar 

  89. Tligui N, Ruth GR, Felice LJ (1994) Plasma ferulenol concentration and activity of clotting factors in sheep with Ferula communis variety brevifolia intoxication. Am J Vet Res 55:1564–1569

    PubMed  CAS  Google Scholar 

  90. Valle MG, Appendino G, Nano GM, Picci V (1987) Prenylated coumarins and sesquiterpenoids from Ferula communis. Phytochemistry 26:253–256

    Article  Google Scholar 

  91. Vandyshev VV, Sklyar YuE, Perel’son ME, Moroz MD, Pimenov MG (1972) Conferol—a new coumarin from the roots of Ferula conocaula and F. moschata. Khim Prirodn Soedin 5:670–671

    Google Scholar 

  92. Yang J-R, An Z, Li Z-H, Jing S, Qin H-L (2006) Sesquiterpene coumarins from the roots of Ferula sinkiangensis and Ferula teterrim. Chem Pharm Bull 54:1595–1598

    PubMed  Article  CAS  Google Scholar 

  93. Yazaki K, Kunihisa M, Fujisaki T, Sato F (2002) Geranyl diphosphate:4-hydroxybenzoate geranyl-transferase from Lithospermum erythrorhizon. Cloning and characterization of a key enzyme in shikonin biosynthesis. J Biol Chem 277:6240–6246

    PubMed  Article  CAS  Google Scholar 

  94. Yazaki K, Sasaki K, Tsurumaru Y (2009) Prenylation of aromatic compounds, a key diversification of plant secondary metabolites. Phytochemistry 70:1739–1745

    PubMed  Article  CAS  Google Scholar 

  95. Zhai D-D, Zhong J-J (2010) Simultaneous analysis of three bioactive compounds in Artemisia annua hairy root cultures by reversed-phase high-performance liquid chromatography–diode array detector. Phytochem Anal 21:524–530

    PubMed  Article  CAS  Google Scholar 

  96. Zhao P, Inoue K, Kouno I, Yamamoto H (2003) Characterization of leachianone G 2′′-dimethylallyl-transferase, a novel prenyl side-chain elongation enzyme for the formation of the lavandulyl group of sophoraflavanone G in Sophora flavescens Ait. cell suspension cultures. Plant Physiol 133:1306–1313

    PubMed  Article  CAS  Google Scholar 

  97. Zhong C, Yongxing Z, Xu Z et al (2001) Expression of multidrugassociated protein, P-glycoprotein, P53 and Bcl-2 proteins in bladder cancer and clinical implication. J Tongji Med Univ 21:56–58

    Article  Google Scholar 

  98. Zhou P, Takaishi Y, Duan H, Chen B, Honda G, Itoh M, Takeda Y, Kodzhimatov O, Lee K-H (2000) Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry 53:689–697

    PubMed  Article  CAS  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Peter E. Brodelius.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Gliszczyńska, A., Brodelius, P.E. Sesquiterpene coumarins. Phytochem Rev 11, 77–96 (2012). https://doi.org/10.1007/s11101-011-9220-6

Download citation

Keywords

  • Farnesyldiphosphate
  • 4-Hydroxycoumarin
  • Isofraxidin
  • Prenylated coumarins
  • Prenyl-furocoumarin sesquiterpenenes
  • Scopoletin
  • Sesquiterpene coumarins
  • Umbelliferone