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

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).

Key words

Carpesium macrocephalum - Compositae - eudesmanolide - sesquiterpene lactone glycosides - antibacterial activity - cytotoxic activity

References

• 1 Maruyama M, Shibata F. Stereochemistry of granilin isolated from Carpesium abrotanoides .  Phytochemistry. 1975;  14 2247-8
• 2 Maruyama M, Omura S. Carpesiolin from Carpesium abrotanoides .  Phytochemistry. 1977;  16 782-3
• 3 Maruyama M, Karube A. Sesquiterpene lactone from Carpesium abrotanoides .  Phytochemistry. 1983;  22 2773-4
• 4 Dong Y F, Ding Y M. Sesquiterpene lactone from Carpesium abrotanoides .  Acta Botanica Sinica. 1988;  30 71-5
• 5 Maruyama M. Sesquiterpene lactone from Carpesium divaricatum .  Phytochemistry. 1990;  29 547-50
• 6 Maruyama M, Watanabe K, Kwakami T, Nozoe S, Ohta T. Ineupatorolides from Carpesium glossophyllum .  Planta Medica. 1995;  61 388-9
• 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
• 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
• 9 Shi Y P, Guo W, Jia Z J. Germacranolides from Carpesium lipskyi .  Planta Medica. 1999;  65 94-6
• 10 Xue Z W, Yu Y Q. ZhongGuo ZhongChaoYao MingJia. People's Health Press Beijing; 1996: 756
• 11 Topcu G, Öksüz S, Shieh H L, Cordell G A. Cytotoxic and antibacterial sesquiterpenes from Inula graveolens .  Phytochemistry. 1993;  33 407-10
• 12 Marshall J A, Cohen N. The structure of alantolactone. J. Org.  Chem.. 1964;  29 3727-9
• 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
• 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
• 15 Batterham T J, Highet R J. Nuclear magnetic resonance spectra of flavonoids. Aust. J.  Chem.. 1964;  17 428-39
• 16 Zdero C, Bohlmann F, King R M. Eudesmane derivatives and other constituents from Apalochlamys spectabilis and Cassinia species.  Phytochemistry. 1990;  29 3201-6