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Planta Med 2009; 75(6): 641-646
DOI: 10.1055/s-0029-1185378
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

ent-Abietane and ent-Kaurane Diterpenoids from the Roots of Suregada glomerulata

Su-li He1 , Ren-yi Yan1 , Li Zuo1 , Ruo-yun Chen1
  • 1Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, P. R. China
Further Information

Publication History

received Sept. 6, 2008 revised January 3, 2009

accepted January 9, 2009

Publication Date:
23 February 2009 (online)

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Abstract

Twelve ent-abietane and ent-kaurane type diterpenoids, 1–12, including five new compounds 1–5, were isolated from the roots of Suregada glomerulata. The structures of the new compounds were elucidated on the basis of 1D and 2D NMR and other spectroscopic studies, and the structures of 1 and 2 were confirmed by X‐ray crystallography. Cytotoxic activities against five human tumor cell lines were evaluated.

Key words

Euphorbiaceae - Suregada glomerulata - diterpenoids - ent‐abietanes - ent‐kauranes

References

  • 1 Parween N, Khan N U. Luteolin 7, 4′-dimethyl ether 3′-glucoside from Gelonium multiflorum.  Phytochemistry. 1987;  26 2130-2131
    CrossrefPubMedSearch in Google Scholar
  • 2 Das B, Chakravarty A K. Three flavone glycosidases from Gelonium multiflorum.  Phytochemistry. 1993;  33 493-496
    CrossrefPubMedSearch in Google Scholar
  • 3 Sengupta P, Khastigir H N. Terpenoids and related compounds-III: bauerenol and multiflorenol from Gelonium multiflorum A. Juss. The structure of multiflorenol.  Tetrahedron. 1963;  19 123-132
    PubMedSearch in Google Scholar
  • 4 Venkatesan M, Viswanathan M B, Ramesh N, Lakshmanaperumalsamy P. Antibacterial potential from Indian Suregada angustifolia. .  J Ethnopharmacol. 2005;  99 349-352
    CrossrefPubMedSearch in Google Scholar
  • 5 Talapatra S K, Das G, Talapatra B. Sterostructures and molecular conformations of six deterpene lactones from Gelonium multiflorum.  Phytochemistry. 1989;  28 1181-1185
    CrossrefPubMedSearch in Google Scholar
  • 6 Talapatra B, Das G, Das A K, Biswas K, Talapatra S K. Sterostructures and conformations of four deterpene lactones from Gelonium multiflorum.  Phytochemistry. 1998;  49 1353-1359
    CrossrefPubMedSearch in Google Scholar
  • 7 Das B, Charkravarty A K, Masuda K, Suzuki H, Ageta H A. Diterpenoid from roots of Gelonium multiflorum.  Phytochemistry. 1994;  37 1363-1366
    CrossrefPubMedSearch in Google Scholar
  • 8 Charkravarty A K, Pal B C, Guitter E, Ahond A. Structure of a new diterpene lactone from Gelonium multiflorum by 2D NMR.  Indian J Chem. 1991;  30 B 3-6
    PubMedSearch in Google Scholar
  • 9 Jahan I A, Nahar N, Zaman M M, Shaheen F, Parween Z, Atta-ur-Rahman, Choudhary M I. Novel diterpene lactones from Suregada multiflora. .  J Nat Prod. 2002;  65 932-934
    CrossrefPubMedSearch in Google Scholar
  • 10 Jahan I A, Nahar N, Zaman M M, Shaheen F, Parween Z, Atta-ur-Rahman, Choudhary M I. Six new diterpenoids from Suregada multiflora. .  J Nat Prod. 2004;  67 1789-1795
    CrossrefPubMedSearch in Google Scholar
  • 11 Choudhary M I, Gondal H Y, Abbaskhan A, Jahan I A, Parvez M, Nahar N, Atta-ur-Rahman. Revisiting diterpene lactones of Suregada multiflora.  Tetrahedron. 2004;  60 7933-7941
    CrossrefPubMedSearch in Google Scholar
  • 12 Cheenpracha S, Yodsaoue O, Karalai C, Ponglimanont C, Subhadhirasakul S, Tewtrakul S, Kanjana-opas A. Potential anti-allergic ent-kaurene diterpenes from the bark of Suregada multiflora. .  Phytochemistry. 2006;  67 2630-2634
    CrossrefPubMedSearch in Google Scholar
  • 13 Lee C L, Chang F R, Hsieh P W, Chiang M Y, Wu C C, Huang Z Y, Lan Y H, Chen M, Lee K H, Yen H F, Hung W C, Wu Y C. Cytotoxic ent-abietane diterpenes from Gelonium aequoreum. .  Phytochemistry. 2008;  69 276-287
    CrossrefPubMedSearch in Google Scholar
  • 14 He S L, Chen R Y. A new diterpene from Suregada glomerulata (BL.) Baill. .  Chin Chem Lett. 2005;  16 786-788
    PubMedSearch in Google Scholar
  • 15 He S L, Chen R Y. Studies on chemical constituents of Suregada glomerulata (BL.) Baill. .  Zhongcaoyao. 2005;  36 662-663
    PubMedSearch in Google Scholar
  • 16 Yan R Y, Chen R Y. Studies on chemical constituents of Suregada glomerulata (BL.) Baill. (II).  Zhongguozhongyao. 2007;  32 1653-1655
    PubMedSearch in Google Scholar
  • 17 Yan R Y, Tan Y X, Cui X Q, Chen R Y, Yu D Q. Diterpenoids from the roots of Suregada glomerulata.  J Nat Prod. 2008;  71 195-198
    CrossrefPubMedSearch in Google Scholar
  • 18 Crespi-Perellino N, Garofano L, Arlandini E, Pinciroli V, Minghetti A, Vincieri F F, Danieli B. Identification of new ditrepenoids from Euphorbia calyptrata cell cultures.  J Nat Prod. 1996;  59 773-776
    CrossrefPubMedSearch in Google Scholar
  • 19 Duan H Q, Takaishi Y, Momota H, Ohmoto Y, Taki T, Jia Y F, Li D. Immunosupressive diterpenoids from Tripterygium wilfordii. .  J Nat Prod. 1999;  62 1522-1525
    CrossrefPubMedSearch in Google Scholar
  • 20 Jeske F, Jakupovic J, Berendsohn W. Diterpenes from Euphorbia seguieriana.  Phytochemistry. 1995;  40 1743-1750
    CrossrefPubMedSearch in Google Scholar
  • 21 Kitajima J, Komori T, Kawasaki T. Studies on the constituents of the crude drug “Fritillariae Bulbus.”III On the diterpenoids constituents of fresh bulbs of Fritillaria thunbergii Miq.  Chem Pharm Bull. 1982;  30 3912-3921
    CrossrefPubMedSearch in Google Scholar
  • 22 Nascimento I R, Lopes L MX. Diterpene esters of aristolochic acids from Aristolochia pubescens.  Phytochemistry. 2003;  63 953-957
    CrossrefPubMedSearch in Google Scholar
  • 23 Jia Z J, Shi J G, Yang L. ent-Kaurane diterpenoids from Euphorbia wangii.  J Nat Prod. 1994;  57 811-816
    CrossrefPubMedSearch in Google Scholar
  • 24 Elliger C A, Wong R Y, Benson M, Gaffield W, Waiss Jr A C. Diterpenes of Calibrachoa parviflora.  J Nat Prod. 1992;  55 1477-1487
    CrossrefPubMedSearch in Google Scholar
  • 25 Tinto W F, Blyden G, Reynolds W F, McLean S. Diterpene and anthraquinone constituents of Glycydendron amazonicum. .  J Nat Prod. 1991;  54 1127-1130
    CrossrefPubMedSearch in Google Scholar
  • 26 Li X, Zhang D Z, Onda M, Konda Y, Iguchi M, Harigaya Y. ent-Kauranoid diterpenes from Artemisia sacrorum.  J Nat Prod. 1990;  53 657-661
    CrossrefPubMedSearch in Google Scholar
  • 27 Zhang P C, Wang S, Wu Y, Chen R Y, Yu D Q. Five new diprenylated flavonols from the leaves of Broussonetia kazinoki.  J Nat Prod. 2001;  64 1206-1209
    CrossrefPubMedSearch in Google Scholar

Prof. Ruo-yun Chen

Institute of Materia Medica
Chinese Academy of Medical Sciences and Peking Union Medical College

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