Asterolaurins A-F, xenicane diterpenoids from the Taiwanese soft coral Asterospicularia laurae.
Six new xenicane-type diterpenoids, designated as asterolaurins A-F (1-6), have been isolated from the organic extract of the soft coral Asterospicularia laurae, collected in southern Taiwan. Compounds 1-4 possess a xenicin skeleton with a 2-oxabicyclo[7.4.0]tridecane ring system, while 5 and 6 are xeniolide A-type compounds. The structures of the new secondary metabolites, including their configurations, were established on the basis of an extensive spectroscopic analysis, including 1D and 2D NMR (1H-1H COSY, HMQC, HMBC, and NOESY), and by comparison of their NMR data with those of the related compounds. The structure of asterolaurin A (1) was confirmed by X-ray diffraction analysis, and its absolute configuration was determined using the modified Mosher's method. Asterolaurin A (1) exhibited moderate cytotoxicity against HepG2 cells with an IC50 of 8.9 microM, while asterolaurin D (4) showed potent inhibition of elastase release and superoxide anion generation in vitro.
School of Pharmacy, College of Medicine, National Taiwan University, Taipei 100, Taiwan, Republic of China.
Yu-Chi
YC
Lin
Mohamed H
MH
Abd El-Razek
Tsong-Long
TL
Hwang
Michael Y
MY
Chiang
Yao-Haur
YH
Kuo
Chang-Feng
CF
Dai
Ya-Ching
YC
Shen
D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010196:Pancreatic Elastase / Q000187:drug effects* / Q000378:metabolism; D013624:Taiwan
D000970:Antineoplastic Agents; D004224:Diterpenes; C545290:asterolaurin A; C545291:asterolaurin D; D010196:Pancreatic Elastase