Ecdysteroids from the Antarctic tunicate Synoicum adareanum.
Five new ecdysteroids, hyousterones A-D (2-5) and abeohyousterone (6), have been isolated from the Antarctic tunicate Synoicum adareanum along with the known ecdysteroid diaulusterol B (1). Hyousterones B (3) and D (5) are unusual ecdysteroids in bearing the 14beta-hydroxyl group, and abeohyousterone incorporates the 13(14-->8) abeo steroid skeleton, reflecting a rearrangement of the steroid C/D ring system. Abeohyousterone has moderate cytotoxicity toward several cancer cell lines. Hyousterones bearing the 14alpha-hydroxy group (2 and 4) were weakly cytotoxic, while the 14beta-hydroxy hyousterones (3 and 5) were devoid of cytotoxicity. The 14beta-hydroxy function may be a thermodynamic pathway to the 13(14-->8) abeo steroid skeleton. Hyousterones, abeohyousterone, and diaulusterol B are the first ecdysteroids reported from tunicates.
Department of Chemistry and Center for Molecular Diversity in Drug Design, Discovery, and Delivery, University of South Florida, Tampa, FL 33620, USA.
Yoshinari
Y
Miyata
Thushara
T
Diyabalanage
Charles D
CD
Amsler
James B
JB
McClintock
Frederick A
FA
Valeriote
Bill J
BJ
Baker
D000818:Animals; D000864:Antarctic Regions; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D026461:Ecdysteroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D014561:Urochordata / Q000737:chemistry*
D000970:Antineoplastic Agents; D026461:Ecdysteroids