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Grayanoids from the Ericaceae family: structures, biological activities and mechanism of action

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Abstract

Grayanoids, occurring exclusively in Ericaceae plants, are well-known highly toxic components from the genera Rhododendron, Pieris, Leucothoe, Craibiodendron, Lyonia, Kalmia, etc. Grayanoids have been the topic of research in many phytochemical and pharmacological laboratories due to their complex structures and fascinating bioactivities. This review, citing 100 references, summarises their chemistry, including the total synthesis and bioactivity of grayanoids isolated from the Ericaceae family in the last five decades, to illustrate the chemo-diversity and biological significance of these diterpenoids.

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References

  • Bao GH, Wang LQ, Cheng KF, Qin GW (2002) One new diterpene glucoside from the roots of Rhododendron molle. Chin Chem Lett 13:955–956

    CAS  Google Scholar 

  • Bao GH, Wang LQ, Cheng KF, Feng YH, Li XY, Qin GW (2003) Diterpenoid and phenolic glycosides from the roots of Rhododendron molle. Planta Med 69:434–439

    Article  PubMed  CAS  Google Scholar 

  • Borrelly S, Paquette LA (1996) Studies directed to the synthesis of the unusual cardiotoxic agent kalmanol. Enantioselective construction of the advanced tetracyclic 7-oxy-5,6-dideoxy congener. J Am Chem Soc 118:727–740

    Article  CAS  Google Scholar 

  • Burke JW, Doskotch RW (1990) High field 1H- and 13C-NMR assignments of grayanotoxins I, IV, and XIV isolated from Kalmia angustifolia. J Nat Prod 53:131–137

    Article  PubMed  CAS  Google Scholar 

  • Burke JW, Doskotch RW, Ni CZ, Clardy J (1989) Kalmanol, a pharmacologically active diterpenoid with a new ring skeleton from Kalmia angustifolia L. J Am Chem Soc 111:5831–5833

    Article  CAS  Google Scholar 

  • Chen JS, Zheng S (1987) Chinese poisonous plants. Science Press, Beijing

    Google Scholar 

  • Chen SN, Zhang HP, Wang LQ, Bao GH, Qin GW (2004) Diterpenoids from the flowers of Rhododendron molle. J Nat Prod 67:1903–1906

    Article  PubMed  CAS  Google Scholar 

  • El-Naggar SF, Doskotch RW (1980) Antifeedant diterpenes for the gypsy moth larvae from Kalmia latifolia: isolation and characterization of ten grayanoids. J Nat Prod 43:617–631

    Article  CAS  Google Scholar 

  • Fukuyama K, Tsukihara T, Katsube Y, Katai M, Meguri H (1976) A structure analysis of pieristoxin G by the X-ray diffraction method. Chem Pharm Bull 24:2775–2780

    Article  CAS  Google Scholar 

  • Furusaki A, Hamanaka N, Miyakoshi H (1972) Leucothol A, an anthraditerpenoid from Leucothoe grayana Max. Chem Lett 1:783–786

    Article  Google Scholar 

  • Furusaki A, Gasa S, Hamanaka N, Ikeda R, Matsumoto T (1979) Grayathol A, a new diterpene from Leucothoe grayana Max. Chem Lett 8:665–666

    Article  Google Scholar 

  • Furusaki A, Gasa S, Ikeda R, Matsumoto T (1981a) The crystal and molecular structure of grayanotoxin XIX. A new minor diterpene from Leucothoe grayana Max. Bull Chem Soc Jpn 54:1622–1626

    Article  CAS  Google Scholar 

  • Furusaki A, Gasa S, Ikeda R, Matsumoto T, Yasuoka N, Matsuura Y (1981b) The crystal and molecular structure of grayanotoxin XVIII. A new minor diterpene from Leucothoe grayana Max. Bull Chem Soc Jpn 54:657–660

    Article  CAS  Google Scholar 

  • Fushiya S, Hikino H, Takemoto T (1974) Stereostructure of grayanol A and B, diterpenoids of Leucothoe grayana. Tetrahedron Lett 15:183–186

    Article  Google Scholar 

  • Gasa S, Ikeda R, Hamanaka N, Matsumoto T (1976) New A-nor-B-homo-ent-kauranoids (Grayanotoxin XVI and XVII) from Leucothoe Grayana Max. Bull Chem Soc Jpn 49:835–836

    Article  CAS  Google Scholar 

  • Gunduz A, Turedi S, Uzun H, Topbas M (2006) Mad honey poisoning. Am J Emerg Med 24:595–598

    Article  PubMed  Google Scholar 

  • Gunduz A, Turedi S, Russell RM, Ayaz FA (2008) Clinical review of grayanotoxin/mad honey poisoning past and present. Clinical toxicology 46:437–442

    Article  PubMed  CAS  Google Scholar 

  • Hamanaka N, Miyakoshi H, Furusaki A, Matsumoto T (1972a) Isolation and characterization of two new diterpenoids from Leucothoe grayana Max. Chem Lett 1:779–782

    Article  Google Scholar 

  • Hamanaka N, Miyakoshi H, Furusaki A, Matsumoto T (1972b) Leucothol B and C, further examples of anthraditerpenoids from Leucothoe grayana Max. Chem Lett 1:787–790

    Article  Google Scholar 

  • Hegnauer R (1966) Chemotaxonomie der pflanzen: band 4: dicotyledoneae: daphniphyllaceae bis lythraceae. Birkhäuser, Basel

    Google Scholar 

  • Hikino H, Ito K, Takemoto T (1969a) Stereostructure of asebotoxin I and II, toxin of Pieris japonica. Chem Pharm Bull 17:854–855

    Article  PubMed  CAS  Google Scholar 

  • Hikino H, Ito K, Ohta T, Takemoto T (1969b) Stereostructure of rhodojaponin I, II, III, toxins of Rhododendron japonicum, and of asebotoxin III, toxin of Pieris japonica. Chem Pharm Bull 17:1078–1079

    Article  PubMed  CAS  Google Scholar 

  • Hikino H, Ogura M, Ohta T, Takemoto T (1970a) Stereochemistry of grayanotoxins, asebotoxins and rhodojaponins, toxins of Ericaceae. Chem Pharm Bull 18:1071–1073

    Article  CAS  Google Scholar 

  • Hikino H, Shoji N, Koriyama S, Ohta T, Hikino Y, Takemoto T (1970b) Stereostructure of rhodojaponin IV, toxin of Rhododendron japonicum, and of grayanotoxin V, VI, and VII, toxins of Leucothoe grayana. Chem Pharm Bull 18:2357–2359

    CAS  Google Scholar 

  • Hikino H, Hikino Y, Takemoto T, Takahashi S (1970c) Stereostructure of lyoniatoxin, toxin of Lyonia ovalifolia var. elliptica. Chem Pharm Bull 18:852–854

    Article  CAS  Google Scholar 

  • Hikino H, Ohta T, Koriyama S, Hikino Y, Takemoto T (1971a) Stereostructure of Grayanotoxin VIII, IX, X, and XI. Toxins of Leucothoe grayana. Chem Pharm Bull 19:1289–1291

    Article  CAS  Google Scholar 

  • Hikino H, Ogura M, Fuzita M, Ito K, Takemoto T (1971b) Stereostructure of asebotoxin IV and V, toxins of Pieris japonica. Chem Pharm Bull 19:856–857

    Article  CAS  Google Scholar 

  • Hikino H, Ogura M, Takemoto T (1971c) Stereostructure of asebotoxin VII, toxin of Pieris japonica. Chem Pharm Bull 19:1980–1981

    Article  CAS  Google Scholar 

  • Hikino H, Koriyama S, Ohta T, Takemoto T (1972a) Stereostructure of grayanotoxin XII and XIII, toxins of Leucothoe grayana. Chem Pharm Bull 20:422–423

    Article  CAS  Google Scholar 

  • Hikino H, Ohta T, Hikino Y, Takemoto T (1972b) Stereostructure of rhodojaponin V and VII, toxins of Rhododendron japonicum. Chem Pharm Bull 20:1090–1092

    Article  CAS  Google Scholar 

  • Hikino H, Koriyama S, Takemoto T (1972c) Stereostructure of leucothol B and D, diterpenoids of Leucothoe grayana. Tetrahedron Lett 13:3831–3834

    Article  Google Scholar 

  • Hikino H, Ogura M, Fushiya S, Konno C, Takemoto T (1977) Stereostructure of asebotoxin VI, VIII, and IX, toxin of Pieris japonica. Chem Pharm Bull 25:523–524

    Article  CAS  Google Scholar 

  • Huang XZ, Wang YH, Yu SS, Fu GM, Hu YC, Liu Y, Fan LH (2005) Iridoid glycosides and grayanane diterpenoids from the roots of Craibiodendron henryi. J Nat Prod 68:1646–1650

    Article  PubMed  CAS  Google Scholar 

  • Huang XZ, Huang R, Du G, Yin Y, Dai Y, Yu MQ (2008) Grayanane diterpenoids from the barks of Craibiodendron henryi. Heterocycles 75:3043–3049

    Article  CAS  Google Scholar 

  • Iriye R, Sasakura M (1977) Transformation of 6β-bromo-4,4-dimethyl-1α,2α-epoxy-3α,5α- oxido-cholestane into 6β-bromo-4,4-dimethyl-3α,5α-oxido-5(10 → 1βH)abeo-10(19)- cholesten-2α-ol. Agric Biol Chem 41:2109–2110

    Article  CAS  Google Scholar 

  • Iriye R, Tomide I (1972) New constituents of Rhododendron japonicum Suringer, rhodojaponin V and VI. Tetrahedron Lett 15:1381–1382

    Article  Google Scholar 

  • Ishii H, Kinoshita E, Kimura T, Yakehiro M, Yamaoka K, Imoto K, Mori Y, Seyama I (1999) Point-mutations related to the loss of batrachotoxin binding abolish the grayanotoxin effect in Na+ channel isoforms. Jpn J Physiol 49:457–461

    Article  PubMed  CAS  Google Scholar 

  • Iwasa J, Kumazawa Z, Nakajima M (1961) Studies on the active principles of Leucothoe grayana Max. The structure of grayanotoxin-II. Part 1. Agric Biol Chem 25:782–792

    CAS  Google Scholar 

  • Jansen SA, Kleerekooper I, Hofman ZLM, Kappen IFPM, Stary-Weinzinger A, van der Heyden MAG (2012) Grayanotoxin poisoning: “mad honey disease” and beyond. Cardiovasc Toxicol 12:208–215

    Article  PubMed  CAS  Google Scholar 

  • Kaiya T, Sakakibara J (1982) Diterpenoids from Ericaceous plants. Nagoya Shiritsu Daigaku Yakugakubu Kenkyu Nenpo 30:1–34

    Google Scholar 

  • Kaiya T, Sakakibara J (1985) Occurrence of pieroside C, a grayanotox-9-ene derivative, in Pieris japonica. Chem Pharm Bull 33:4637–4639

    Article  CAS  Google Scholar 

  • Kaiya T, Shirai N, Sakakibara J (1979) One-step synthesis of the diterpenoid leucothol D from grayanotoxin-II. J Chem Soc, Chem Commun 9:431–432

    Article  Google Scholar 

  • Kaiya T, Shirai N, Sakakibara J (1981) Synthesis of the diterpenoid grayanol B from grayanotoxin II. J Chem Soc, Chem Commun 1:22

    Article  Google Scholar 

  • Kakisawa H, Kurono M, Takahashi S, Hirata Y (1961) Structure of grayanotoxin I and III. Tetrahedron Lett 588:59–67

    Article  Google Scholar 

  • Kakisawa H, Kozima T, Yanai M, Nakanishi K (1965) Stereochemistry of grayanotoxins. Tetrahedron 21:3091–3104

    Article  CAS  Google Scholar 

  • Kan T, Hosokawa S, Nara S, Oikawa M (1994) Total synthesis of (−)-grayanotoxin III. J Org Chem 59:5532–5534

    Article  CAS  Google Scholar 

  • Katai M, Meguri H (1986) A new diterpenoid from the leaves of Leucothoe grayana Max. J Chem Soc Japan 8:1122–1126

    Google Scholar 

  • Katai M, Matsushima T, Terai T, Meguri H (1975) Studies on the constituents of the leaves of Pieris japonica D. Don. IV. The isolation and the structure of pieristoxin F, pieristoxin G and several toxic components. Yakugaku Zasshi 95:778–783

    PubMed  CAS  Google Scholar 

  • Katai M, Fujiwara M, Terai T, Meguri H (1980) Studies on the constituents of the leaves of Pieris japonica D. Don. Chem Pharm Bull 28:3124–3126

    Article  CAS  Google Scholar 

  • Katakawa J, Tetsumi T, Terai T, Katai M (2000) Crystal and molecular structure of grayanotoxin VII. J Chem Crystallogr 30:573–576

    Article  CAS  Google Scholar 

  • Khodorov BI (1985) Batrachotoxin as a tool to study voltage-sensitive sodium channels of excitable membranes. Prog Biophys Mol Biol 45:57–148

    Article  PubMed  CAS  Google Scholar 

  • Kim SE, Shin MC, Akaike N, Kim CJ (2010) Presynaptic effects of grayanotoxin III on excitatory and inhibitory nerve terminals in rat ventromedial hypothalamic neurons. Neurotoxicology 31:230–238

    Article  PubMed  Google Scholar 

  • Kimura T, Kinoshita E, Yamaoka K, Yuki T, Yakehiro M, Seyama I (2000) On site of action of grayanotoxin in domain 4 segment 6 of rat skeletal muscle sodium channel. FEBS Lett 465:18–22

    Article  PubMed  CAS  Google Scholar 

  • Kimura T, Yamaoka K, Kinoshita E, Maejima H, Yuki T, Yakehiro M, Seyama I (2001) Novel site on sodium channel alpha-subunit responsible for the differential sensitivity of grayanotoxin in skeletal and cardiac muscle. Mol Pharmacol 60:865–872

    PubMed  CAS  Google Scholar 

  • Klocke JA, Hu MY, Chiu SF, Kubo I (1991) Grayanoid diterpene insect antifeedants and insecticides from Rhododendron molle. Phytochemistry 30:1797–1800

    Article  CAS  Google Scholar 

  • Kohanawa M (1956) Pharmacological studies on “rhodotoxin” isolated from Rhododendron hymenanthes and andromedotoxin isolated from Andromeda japonica Thunberg. Jpn J Pharmacol 6:46–56

    Article  PubMed  CAS  Google Scholar 

  • Li CJ, Wang LQ, Chen SN, Qin GW (2000) Diterpenoids from the fruits of Rhododendron molle. J Nat Prod 63:1214–1217

    Article  PubMed  CAS  Google Scholar 

  • Li CJ, Liu H, Wang LQ, Jin MW, Chen SN, Bao GH, Qin GW (2003) Diterpenoids from the fruits of Rhododendron molle. Acta Chim Sinica 61:1153–1156

    CAS  Google Scholar 

  • Li CH, Niu XM, Luo Q, Xie MJ, Luo SH, Zhou YY, Li SH (2010) Novel polyesterified 3,4-seco-grayanane diterpenoids as antifeedants from Pieris formosa. Org Lett 12:2426–2429

    Article  PubMed  CAS  Google Scholar 

  • Liu ZG, Pan XF (1989) Studies on the chemical constituents of Chinese azalea. Acta Chim Sinica 7:235–239

    Article  Google Scholar 

  • Liu ZG, Pan XF, Chen CY, Chen JS (1990) Studies on the chemical constituents of Rhododendron molle G. Don. Acta Pharmaceutica Sinica 25:830–833

    CAS  Google Scholar 

  • Maejima H, Kinoshita E, Seyama I, Yamaoka K (2003) Distinct sites regulating grayanotoxin binding and unbinding to D4S6 of Na(v)1.4 sodium channel as revealed by improved estimation of toxin sensitivity. J Biol Chem 278:9464–9471

    Article  PubMed  CAS  Google Scholar 

  • Masutani T, Hamada M, Kawano E, Iwasa J, Kumazawa Z, Ueda H (1981a) Biosynthesis of grayanotoxins in Leucothoe grayana Max. Incorporation of mevalonic acid and (−)-kaurene into grayanotoxin-III. Agric Biol Chem 45:1281–1282

    Article  CAS  Google Scholar 

  • Masutani T, Seyama I, Narahashi T, Iwasa J (1981b) Structure-activity relationship for grayanotoxin derivatives in frog skeletal muscle. J Pharmacol Exp Ther 217:812–819

    PubMed  CAS  Google Scholar 

  • Meguri H (1959) Isolation of desacetylandromedotoxin (grayanotoxin III) and pieristoxin C from the leaves of Pieris japonica. Yakugaku Zasshi 79:1057–1059

    CAS  Google Scholar 

  • Narayanan P, Rohrl M, Zechmeister K, Hoppe W (1970) Crystal and molecular structure of grayanotoxin-I. Tetrahedron Lett 11:3943–3944

    Article  Google Scholar 

  • Nishida R, Fukami H, Iriye R, Kumazawa Z (1990) Accumulation of highly toxic Ericaceous diterpenoids by the geometrid moth, Arichanna gaschkevitchii. Agric Biol Chem 54:2347–2352

    Article  CAS  Google Scholar 

  • Ohta T, Hikino H (1981) Revised structure of lyoniatoxin, toxin of Lyonia ovalifolia var. elliptica. Chem Pharm Bull 29:280–282

    Article  CAS  Google Scholar 

  • Okuno T, Hamanaka N, Miyakoshi H, Matsumoto T (1970) New A-nor-B-homo-(−)-kauranoids from Leucothoe grayana max. Tetrahedron 26:4765–4769

    Article  PubMed  CAS  Google Scholar 

  • Onat FY, Yegen BC, Lawrence R, Oktay A, Oktay S (1991a) Site of action of grayanotoxins in mad honey in rats. J Appl Toxicol 11:199–201

    Article  PubMed  CAS  Google Scholar 

  • Onat FY, Yegen BC, Lawrence R, Oktay A, Oktay S (1991b) Mad honey poisoning in man and rat. Rev Environ Health 9:3–9

    Article  PubMed  CAS  Google Scholar 

  • Sakakibara J, Shirai N (1980) Grayanoside D, a diterpene glucoside from Leucothoe grayana. Phytochemistry 19:2159–2162

    Article  CAS  Google Scholar 

  • Sakakibara J, Ikai K, Yasue M (1974) Studies on the constituents of Lyonia ovalifolia Drude var. elliptica Hand.-Mazz. XVIII. Structure of diterpenoid, lyoniol-D and correlation of lyoniol-A (lyoniatoxin) with grayanotoxin-I. Yakugaku Zasshi 94:1534–1540

    PubMed  CAS  Google Scholar 

  • Sakakibara J, Shirai N, Kaiya T, Nakata H (1978) Grayanoside A, a new diterpene glucoside from Leucothoe grayana. Phytochemistry 17:1672–1673

    Article  CAS  Google Scholar 

  • Sakakibara J, Shirai N, Kaiya T, Nakata H (1979) Grayanotoxin-XVIII and grayanoside B, a new A-nor-B-homo-ent-kaurene and its glucoside from Leucothoe grayana. Phytochemistry 18:135–137

    Article  CAS  Google Scholar 

  • Sakakibara J, Kaiya T, Shirai N (1980a) Studies on the constituents of Pieris japonica. Isolation and structural elucidation of a new diterpene, asebotoxin X and a new diterpene glucoside, pieroside A. Yakugaku Zasshi 100:540–545

    CAS  Google Scholar 

  • Sakakibara J, Shirai N, Kaiya T, Iitaka Y (1980b) Grayanoside C, a new diterpene glucoside from Leucothoe grayana. Phytochemistry 19:1495–1497

    CAS  Google Scholar 

  • Sakakibara J, Shirai N, Kaiya T (1981) Diterpene glycosides from Pieris japonica. Phytochemistry 20:1744–1745

    Article  CAS  Google Scholar 

  • Seyama I, Yamaoka K, Yakehiro M, Yoshioka Y, Morihara K (1985) Is the site of action of grayanotoxin the sodium channel gating of squid axon? Jpn J Physiol 35:401–410

    Article  PubMed  CAS  Google Scholar 

  • Tallent WH, Riethof ML, Horning EC (1954) Studies on the occurrence and structure of acetylandromedol (andromedotoxin). J Am Chem Soc 79:4548–4554

    Article  Google Scholar 

  • Tsuji K, Kawanishi T, Handa S, Kamano H, Iwasa J, Seyama I (1991) Effect of structural modification of several groups on the D-ring of grayanotoxin on its depolarization potency in squid giant axon. J Pharmacol Exp Ther 257:788–794

    PubMed  CAS  Google Scholar 

  • Wang LQ, Qin GW (1997) Progress of grayanoids in Ericaceae on chemistry and bioactivity. Nat Prod Res Dev 9:82–90

    CAS  Google Scholar 

  • Wang SY, Wang GK (1999) Batrachotoxin-resistant Na + channels derived from point mutations in transmembrane segment D4–S6. Biophys J 76:3141–3149

    Article  PubMed  CAS  Google Scholar 

  • Wang LQ, Ding BY, Qin GW, Lin G (1998a) Grayanoids from Pieris formosa. Phytochemistry 49:2045–2048

    Article  CAS  Google Scholar 

  • Wang LQ, Chen SN, Qin GW, Cheng K (1998b) Grayanane diterpenoids from Pieris formosa. J Nat Prod 61:1473–1475

    Article  PubMed  CAS  Google Scholar 

  • Wang LQ, Ding BY, Zhao WM, Qin GW (1998c) Grayanane diterpenoids from Pieris formosa. Chin Chem Lett 9:465–467

    CAS  Google Scholar 

  • Wang LQ, Chen SN, Cheng KF, Li CJ, Qin GW (2000) Diterpene glucosides from Pieris formosa. Phytochemistry 54:847–852

    Article  PubMed  CAS  Google Scholar 

  • Wang LQ, Qin GW, Chen SN, Li CJ (2001) Three diterpene glucosides and a diphenylamine derivative from Pieris formosa. Fitoterapia 72:779–787

    Article  PubMed  CAS  Google Scholar 

  • Wang SJ, Lin S, Zhu CG, Yang YC, Li S, Zhang JJ, Chen XG, Shi JG (2010a) Highly acylated diterpenoids with a new 3,4-secograyanane skeleton from the flower buds of Rhododendron molle. Org Lett 12:1560–1563

    Article  PubMed  CAS  Google Scholar 

  • Wang WG, Li HM, Li HZ, Wu ZY, Li RT (2010b) New grayanol diterpenoid and new phenolic glucoside from the flowers of Pieris formosa. J Asian Nat Prod Res 12:70–75

    Article  PubMed  Google Scholar 

  • Wu ZY, Li YD, Wu GS, Luo HR, Li HM, Li RT (2011a) Three new highly acylated 3,4-seco-grayanane diterpenoids from the fruits of Pieris formosa. Chem Pharm Bull 59:492–495

    Article  PubMed  CAS  Google Scholar 

  • Wu ZY, Li HZ, Wang WG, Li HM, Chen R, Li RT, Luo HR (2011b) Lyonin A, a new 9,10-secograyanotoxin from Lyonia ovalifolia. Chem Biodivers 8:1182–1187

    Article  PubMed  CAS  Google Scholar 

  • Wu ZY, Li HZ, Wang WG, Li XL, Li RT (2012) Secopieristoxins A and B, two unusual diterpenoids with a new 9,10-secograyanane skeleton from the fruits of Pieris formosa. Phytochem Lett 5:87–90

    Article  CAS  Google Scholar 

  • Yakehiro M, Yamamoto S, Baba N, Nakajima S, Iwasa J, Seyama I (1993) Structure-activity relationship for D-ring derivatives of grayanotoxin in the squid giant axon. J Pharmacol Exp Ther 265:1328–1332

    PubMed  CAS  Google Scholar 

  • Yao GM, Zhai H, Wang LQ, Qin GW (2006) Research progress in chemical constituents and biological activities of Pieris plants (Ericaceae). Science paper online 1:13–19

    Google Scholar 

  • Yasue M, Kato Y, Kishida T, Ota H (1961) Isolation of lyoniol-A, B and C, the toxic principles of Lyonia ovalifolia var. elliptica. Chem Pharm Bull 9:171

    Article  CAS  Google Scholar 

  • Zhang HP, Wang LQ, Qin GW (2005a) Grayanane diterpenoids from the leaves of Craiobiodendron yunnanense. Bioorg Med Chem 13:5289–5298

    Article  PubMed  CAS  Google Scholar 

  • Zhang HP, Wang HB, Wang LQ, Bao GH, Qin GW (2005b) A new 1,5-seco grayanotoxin from Rhododendron decorum. J Asian Nat Prod Res 7:87–90

    Article  PubMed  CAS  Google Scholar 

  • Zhang WD, Jin HZ, Chen G, Li XF, Yan SK, Zhang L, Shen YH, Yang M (2008) A new grayanane diterpenoid from Rhododendron decorum. Fitoterapia 79:602–604

    Article  PubMed  CAS  Google Scholar 

  • Zhong GH, Hu MY, Wei XY, Weng QF, Xie JJ, Liu JX, Wang WX (2005) Grayanane diterpenoids from the flowers of Rhododendron molle with cytotoxic activity against a Spodoptera frugiperda cell line. J Nat Prod 68:924–926

    Article  PubMed  CAS  Google Scholar 

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Acknowledgments

This project was supported by the Natural Science Foundation of China (No. 21132009) and the National Science and Technology Project of China (No. 2012ZX09301002-002).

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  1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, No. 1 Xian Nong Tan Street, Beijing, 100050, People’s Republic of China

    Yong Li, Yun-Bao Liu & Shi-Shan Yu

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Li, Y., Liu, YB. & Yu, SS. Grayanoids from the Ericaceae family: structures, biological activities and mechanism of action. Phytochem Rev 12, 305–325 (2013). https://doi.org/10.1007/s11101-013-9299-z

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