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Planta Med 2009; 75(12): 1344-1348
DOI: 10.1055/s-0029-1185560
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Terpenoids from Roots of Chloranthus henryi

Xianwen Gan1 , Lei Ma2 , Qigang Chen1 , Qiuqun Chen1 , Qiang Yu1 , Lihong Hu1 , 2
  • 1Shanghai Research Center for Modernization of Traditional Chinese Medicine, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, P. R. China
  • 2School of Pharmacy, East China University of Science and Technology, Shanghai, P. R. China
Further Information

Publication History

received Sept. 22, 2008 revised February 18, 2009

accepted March 9, 2009

Publication Date:
02 April 2009 (online)

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Abstract

Six new terpenoids, including three diterpenoids (1–3), one norditerpenoid (4) and two sesquiterpenoids (11 and 12), were isolated from the roots of Chloranthus henryi. The structures were elucidated mainly by 1D, and 2D NMR and MS experiments, and their relative configurations were determined by NOE techniques.

Key words

Chloranthus henryi - Chloranthaceae - terpenoids - norditerpenoids - sesquiterpenoids

References

  • 1 [no authors listed]. Chinese herbal medicine, Vol. 3. Shanghai; Shanghai Science and Technology Publishing Co. 1997: 1594-1595
    Google Scholar
  • 2 Zhang Y N, Zhong X G, Zheng Z P, Hu X D, Zuo J P, Hu L H. Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.  Bioorg Med Chem. 2007;  15 988-996
    CrossrefPubMedGoogle Scholar
  • 3 [no authors listed]. Chinese herbal medicine, Vol. 3. Shanghai; Shanghai Science and Technology Publishing Co. 1997: 450-451
    Google Scholar
  • 4 Li C J, Zhang D M, Luo Y M. Studies on the chemical constituents from the roots of Chloranthus henryi.  Acta Pharmacol Sin. 2005;  40 525-528
    PubMedGoogle Scholar
  • 5 Wu B, He S, Wu X D, Pan Y J. Bioactive terpenes from the roots of Chloranthus henryi.  Planta Med. 2006;  72 1334-1338
    Article in Thieme ConnectPubMedGoogle Scholar
  • 6 Wu B, He S, Pan Y J. Sesquiterpenoid with new skeleton from Chloranthus henryi.  Tetrahedron Lett. 2007;  48 453-456
    CrossrefPubMedGoogle Scholar
  • 7 Wu B, He S, Wu X D, Wu D K, Pan Y J. Cadinane and eudesmane sesquiterpenoids from Chloranthus henryi.  Helv Chim Acta. 2007;  90 1586-1592
    CrossrefPubMedGoogle Scholar
  • 8 Garcia-Granados A, Linan E, Martinez A, Rivas F, Arias J. Preparation of polyoxygenated ent-13-epi-manoyl oxides by chemical-microbiological semisyntheses.  Phytochemistry. 1995;  38 1237-1244
    CrossrefPubMedGoogle Scholar
  • 9 Karplus M. Vicinal proton coupling in nuclear magnetic resonance.  J Am Chem Soc. 1963;  85 2870-2871
    CrossrefPubMedGoogle Scholar
  • 10 Zhou L, Fuentes E R, Hoffmann J J, Timmermann B N. Diterpenoids from Grindelia tarapacana.  Phytochemistry. 1995;  40 1201-1207
    CrossrefPubMedGoogle Scholar
  • 11 Fraga B M, González P, Guillermo R, Hernández M G. The biotransformation of manoyl oxide derivatives by Gibberella fujikuroi: the fungal epimerization of an alcohol group.  Tetrahedron. 1998;  54 6159-6168
    CrossrefPubMedGoogle Scholar
  • 12 Wang Y Z, Tang C P, Ke C Q, Weiss H C, Gesing E R, Ye Y. Diterpenoids from the pericarp of Platycladus orientalis.  Phytochemistry. 2008;  69 518-526
    CrossrefPubMedGoogle Scholar
  • 13 Li C J, Zhang D M, Luo Y M, Yu S S, Li Y, Lu Y. Bis-sesquiterpenes and diterpenes from Chloranthus henryi.  Phytochemistry. 2008;  69 2867-2874
    CrossrefPubMedGoogle Scholar
  • 14 Bell R A, Gravestock M B, Taguchi V Y. Synthesis of methyl 12S- and 12R-hydroxyllabd-8(17)-en-19-oates.  Can J Chem. 1975;  53 2869-2873
    CrossrefPubMedGoogle Scholar
  • 15 Inoue M, Hasegawa S, Hirose Y. Terpenoids from the seed of Platycladus orientalis.  Phytochemistry. 1985;  24 1602-1604
    CrossrefPubMedGoogle Scholar
  • 16 Hsieh Y L, Fang J M, Cheng Y S. Terpenoids and flavonoids from Pseudotsuga wilsoniana.  Phytochemistry. 1998;  47 845-850
    CrossrefPubMedGoogle Scholar
  • 17 Kobayashi M, Ishida K, Terabayashi S, Mitsuhashi H. 10-Hydroxypheophytins and a new norlabdane diterpene from the leaves of Cupressus funebris Endl.  Chem Pharm Bull. 1991;  39 3348-3349
    CrossrefPubMedGoogle Scholar
  • 18 Hikina H, Sakurai Y, Takemoto T. Structure of curcolone.  Chem Pharm Bull. 1967;  15 1065-1066
    PubMedGoogle Scholar
  • 19 Hikina H, Sakurai Y, Takemoto T. Structure and absolute configuration of curcolone.  Chem Pharm Bull. 1968;  5 827-831
    PubMedGoogle Scholar
  • 20 Su W C, Fang J M, Cheng Y S. Labdanes from Cryptomeria japonica.  Phytochemistry. 1994;  37 1109-1114
    CrossrefPubMedGoogle Scholar
  • 21 Fang J M, Sou Y C, Chiu Y H, Cheng Y S. Diterpenes from the bark of Juniperus chinensis.  Phytochemistry. 1993;  34 1581-1584
    CrossrefPubMedGoogle Scholar
  • 22 Fujimoto Y, Kakimuna K, Eguchi T, Ikekawa N, Hirayama N, Mbarushimana A, Ntahomvukiye D. 12,15-Dihydroxylabda-8(17),13-dien-19-oic acid from Guizotia scabra.  Phytochemistry. 1990;  29 319-321
    CrossrefPubMedGoogle Scholar
  • 23 Wang H X, Liu C M, Liu Q, Gao K. Three types of sesquiterpenes from rhizomes of Atractylodes lancea.  Phytochemstry. 2008;  69 2088-2094
    CrossrefPubMedGoogle Scholar
  • 24 Syu W J, Shen C C, Don M J, Ou J C, Lee G H, Sun C M. Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria. .  J Nat Prod. 1998;  61 1531-1534
    CrossrefPubMedGoogle Scholar

Prof. Dr. Lihong Hu

Shanghai Research Center for Modernization of Traditional Chinese Medicine
Shanghai Institute of Materia Medica
Chinese Academy of Sciences

199 Guoshoujing Road

Shanghai 201203

People's Republic of China

Phone: + 86 21 50 27 22 21

Fax: + 86 21 50 27 22 21

Email: simmhulh@mail.shcnc.ac.cn