Sesquiterpene Lactone Glycosides, Eudesmanolides, and Other Constituents from Carpesium macrocephalum

 

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Abstract

Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2α-O-β-D-glucopyranosyl-5α, 11αH-eudesma-4(15)-en-12,8β-olide (1), 2α-O-β-D-glucopyranosyl-5αH-eudesma-4(15),11(13)-dien-12,8β-olide (2), 2α-acetoxy-5α-hydroxy-11αH-eudesma-4(15)-en-12,8β-olide (3) and 2α,5α-dihydroxy-11αH-eudesma-4(15)-en-12,8β-olide (4) by spectroscopic methods including 2D NMR techniques (¹H-¹H COSY, ¹H-¹H NOESY, HMQC, HMBC) and chemical transformations. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibacterial activity, while compound 4 showed appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell).

References

• 1 Maruyama M, Shibata F. Stereochemistry of granilin isolated from Carpesium abrotanoides .  Phytochemistry. 1975;  14 2247-8
  CrossrefPubMedSearch in Google Scholar
• 2 Maruyama M, Omura S. Carpesiolin from Carpesium abrotanoides .  Phytochemistry. 1977;  16 782-3
  CrossrefPubMedSearch in Google Scholar
• 3 Maruyama M, Karube A. Sesquiterpene lactone from Carpesium abrotanoides .  Phytochemistry. 1983;  22 2773-4
  CrossrefPubMedSearch in Google Scholar
• 4 Dong Y F, Ding Y M. Sesquiterpene lactone from Carpesium abrotanoides .  Acta Botanica Sinica. 1988;  30 71-5
  PubMedSearch in Google Scholar
• 5 Maruyama M. Sesquiterpene lactone from Carpesium divaricatum .  Phytochemistry. 1990;  29 547-50
  CrossrefPubMedSearch in Google Scholar
• 6 Maruyama M, Watanabe K, Kwakami T, Nozoe S, Ohta T. Ineupatorolides from Carpesium glossophyllum .  Planta Medica. 1995;  61 388-9
  PubMedSearch in Google Scholar
• 7 Lin Y L, Ou J C, Kuo Y H, Lin J K, Lee K H. Nepalolides A-D, four new sesquiterpene lactones from Carpesium nepalense. J. Nat.  Prod.. 1996;  59 991-3
  PubMedSearch in Google Scholar
• 8 Kim D K, Baek N I, Choi S U, Lee K R, Zee O P. Four new cytotoxic germacranolides from Carpesium divaricatum. J. Nat.  Prod.. 1997;  60 1199-202
  PubMedSearch in Google Scholar
• 9 Shi Y P, Guo W, Jia Z J. Germacranolides from Carpesium lipskyi .  Planta Medica. 1999;  65 94-6
  PubMedSearch in Google Scholar
• 10 Xue Z W, Yu Y Q. ZhongGuo ZhongChaoYao MingJia. People's Health Press Beijing; 1996: 756
  Search in Google Scholar
• 11 Topcu G, Öksüz S, Shieh H L, Cordell G A. Cytotoxic and antibacterial sesquiterpenes from Inula graveolens .  Phytochemistry. 1993;  33 407-10
  CrossrefPubMedSearch in Google Scholar
• 12 Marshall J A, Cohen N. The structure of alantolactone. J. Org.  Chem.. 1964;  29 3727-9
  PubMedSearch in Google Scholar
• 13 Bohlmann F, Mahanta P K, Jakupovic J, Rastogi R C, Natu A A. New sesquiterpene lactones from Inula species.  Phytochemistry. 1978;  17 1165-72
  CrossrefPubMedSearch in Google Scholar
• 14 Abyshev A Z, Zmeikov V P. ¹³C-NMR spectra and structure of bungeidiol and its transformation products.  Chemistry of Natural Compounds. 1982;  18 270-6
  PubMedSearch in Google Scholar
• 15 Batterham T J, Highet R J. Nuclear magnetic resonance spectra of flavonoids. Aust. J.  Chem.. 1964;  17 428-39
  PubMedSearch in Google Scholar
• 16 Zdero C, Bohlmann F, King R M. Eudesmane derivatives and other constituents from Apalochlamys spectabilis and Cassinia species.  Phytochemistry. 1990;  29 3201-6
  CrossrefPubMedSearch in Google Scholar

Prof. Zhong-Jian Jia

Department of Chemistry

Lanzhou University

Lanzhou, Gansu 730000


Peoples Republic of China

Email: Zhengrl@lzu.edu.cn

Fax: + 86-0931-8 912 582