New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium

被引:55
作者
Son, BW [1 ]
Jensen, PR [1 ]
Kauffman, CA [1 ]
Fenical, W [1 ]
机构
[1] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA
来源
NATURAL PRODUCT LETTERS | 1999年 / 13卷 / 03期
基金
美国国家科学基金会; 美国国家卫生研究院; 新加坡国家研究基金会;
关键词
marine fungi; Penicillium sp; cytotoxic dioxopiperazines; epidithio-dioxopiperazine dimers; verticillins;
D O I
10.1080/10575639908048788
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Two new cytotoxic dioxopiperazine dimers, 11,11'-dideoxyverticillin A (1) and 11'-deoxyverticillin A (2), and the previously described verticillin A (3), have been isolated from the mycelium of a marine-derived fungus of the genus Penicillium. An inactive, but new bisdethio-bis(methylthio)-dioxopiperazine 4, was also obtained by extraction of the culture broth. The structures and absolute stereochemistries of the new compounds were assigned on the basis of NMR and CD experiments. Compounds 1 and 2 exhibit potent in vitro cytotoxicity against HCT-116 human colon carcinoma (IC50 = 30 ng/ml).
引用
收藏
页码:213 / 222
页数:10
相关论文
共 24 条
[1]   MELINACIDINS 2 3 AND 4 - STRUCTURAL STUDIES [J].
ARGOUDELIS, AD ;
MIZSAK, SA .
JOURNAL OF ANTIBIOTICS, 1977, 30 (06) :468-473
[2]   OPTICAL ROTATORY PROPERTIES OF DIKETOPIPERAZINES [J].
BALASUBRAMANIAN, D ;
WETLAUFE.DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3449-+
[3]   New cytotoxic sesquiterpenoid nitrobenzoyl esters from a marine isolate of the fungus Aspergillus versicolor [J].
Belofsky, GN ;
Jensen, PR ;
Renner, MK ;
Fenical, W .
TETRAHEDRON, 1998, 54 (09) :1715-1724
[4]   SPORIDESMINS .16. STRUCTURE OF CHETOMIN, A TOXIC METABOLITE OF CHAETOMIUM-COCHLIODES, BY N-15 AND C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].
BREWER, D ;
MCINNES, AG ;
SMITH, DG ;
TAYLOR, A ;
WALTER, JA ;
LOOSLI, HR ;
KIS, ZL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1248-1251
[5]   CIRCULAR DICHROISM AND ABSOLUTE CONFIGURATION OF CHIRAL DISULFIDE GROUP [J].
CARMACK, M ;
NEUBERT, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (26) :7134-+
[6]   Inhibition of c-fos proto-oncogene induction by Sch 52900 and Sch 52901, novel diketopiperazines produced by Gliocladium sp [J].
Chu, M ;
Truumees, I ;
Rothofsky, ML ;
Patel, MG ;
Gentile, F ;
Das, PR ;
Puar, MS ;
Lin, SL .
JOURNAL OF ANTIBIOTICS, 1995, 48 (12) :1440-1445
[7]   Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .2. Physico-chemical properties and structures [J].
Cui, CB ;
Kakeya, H ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1996, 49 (06) :534-540
[8]   OPTICAL ROTATORY DISPERSION STUDIES .78. COMPARATIVE STUDIES OF CIRCULAR DICHROISM AND ROTATORY DISPERSION CURVES - SOME OBSERVATIONS ON SULFUR-CONTAINING CHROMOPHORES [J].
DJERASSI, C ;
BUNNENBERG, E ;
WOLF, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (23) :4552-&
[9]   TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN [J].
FUKUYAMA, T ;
NAKATSUKA, S ;
KISHI, Y .
TETRAHEDRON, 1981, 37 (11) :2045-2078
[10]  
Furuya K, 1985, ANN REP SANKYO RES L, V37, P140