Bioactive sesterterpenoids from a Korean sponge Monanchora sp.
Chemical investigation of a Korean marine sponge, Monanchora sp., yielded nine new sesterterpenoids (1-9) along with phorbaketals A-C (10-12). The planar structures were established on the basis of NMR and MS analysis, and the absolute configurations of 1-9 were defined using the modified Mosher's method and CD spectroscopic data analysis. Compounds 1-8, designated as phorbaketals D-K, possess a spiroketal-modified benzopyran moiety such as phorbaketal A, and their structural variations are due to oxidation and/or reduction of the tricyclic core or the side chain. Compound 9, designated as phorbin A, has a monocyclic structure and is proposed to be a possible biogenetic precursor of the phorbaketals. Compounds 1-9 were evaluated for cytotoxicity against four human cancer cell lines (A498, ACHN, MIA-paca, and PANC-1), and a few of them were found to exhibit cytotoxic activity.
Center for Marine Natural Products and Drug Discovery, School of Earth and Environmental Sciences, Seoul National University, Seoul, Korea.
Weihong
W
Wang
Bora
B
Mun
Yehee
Y
Lee
Mallepally
M
Venkat Reddy
Youngmin
Y
Park
Jihye
J
Lee
Hiyoung
H
Kim
Dongyup
D
Hahn
Jungwook
J
Chin
Merrick
M
Ekins
Sang-Jip
SJ
Nam
Heonjoong
H
Kang
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification; D006801:Humans; D007723:Korea; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D054830:Sesterterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D005663:Furans; D054830:Sesterterpenes; D013141:Spiro Compounds; C520774:spiroketal