Cytotoxic bromotyrosine derivatives from a two-sponge association of Jaspis sp. and Poecillastra sp.
Bioassay-guided chemical investigation of the lipophilic extract of a two-sponge association (Jaspis sp. and Poecillastra sp.) led to the isolation of two new bromotyrosine derivatives (1 and 2), along with known derivatives (3-12). Cyclobispsammaplin A (1) is a cyclic derivative of the previously reported bispsammaplin A (13), while psammaplin M (2) is composed of beta-alanine (or aspartic acid) unit. Compounds 3, 4, 6, 10, and 12 are isolated for the first time from a sponge belonging to the subclass Tetractinomorpha. Structure elucidation was performed by a combination of high resolution mass and 2D NMR (principally COSY, HMBC, HSQC, and NOESY) spectroscopy. Compounds 1-4, 6, 10, and 12 were evaluated for cytotoxicity against a small panel of five human solid tumor cell lines and their activity was compared in relevance to their structure.
Shinde
Pramod B
PB
College of Pharmacy, Pusan National University, Geumjung-ku, Busan 609-735, Republic of Korea.
Lee
Yoon Mi
YM
Dang
Hung The
HT
Hong
Jongki
J
Lee
Chong-O
CO
Jung
Jee H
JH
D000818:Animals; D045744:Cell Line, Tumor; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor / Q000379:methods*; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D011161:Porifera; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
C475724:bromotyrosine; D014443:Tyrosine; D000432:Methanol