Variation in cytostatic constituents of a sponge-derived Gymnascella dankaliensis by manipulating the carbon source.
The Halichondria sponge-derived fungus, Gymnacella dankaliensis, was cultured in two different media conditions. A modified malt extract medium containing soluble starch instead of glucose resulted in two extremely unusual steroids, dankasterones A (2) and B (3), while four additional unusual steroids, gymnasterones A (4), B (5), C (6), and D (7), were isolated from the original malt extract medium. Their stereostructures have been established on the basis of spectroscopic analyses along with X-ray crystal structure analyses, modified Mosher's method, CD exciton method, and a chemical transformation. All the steroids except for 4 exhibited significant growth inhibition against the murine P388 cancer cell line. Dankasterone A (2) also exhibited potent growth inhibition against human cancer cell lines.
Amagata
Taro
T
Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan. amagata@chemistry.ucsc.edu
Tanaka
Makoto
M
Yamada
Takeshi
T
Doi
Mitsunobu
M
Minoura
Katsuhiko
K
Ohishi
Hirofumi
H
Yamori
Takao
T
Numata
Atsushi
A
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D002244:Carbon / Q000737:chemistry; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007564:Japan; D007941:Leukemia P388; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D011161:Porifera / Q000382:microbiology*; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
D000970:Antineoplastic Agents; D013256:Steroids; D002244:Carbon