5-EPI-ILIMIQUINONE, A METABOLITE OF THE SPONGE FENESTRASPONGIA SP
5-EPI-ILIMIQUINONE, A METABOLITE OF THE SPONGE FENESTRASPONGIA SP
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DOI：
10.1021/jo00215a039
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发表时间：
1985-01-01
影响因子：
3.6
通讯作者：
FAULKNER, DJ
中科院分区：
文献类型：
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作者：
CARTE, B;ROSE, CB;FAULKNER, DJ
图I暂时鉴定为Fenestraspongia 1种的海绵提取物在受精海胆卵试验中表现出体外抗菌活性和抑制细胞分裂。海绵材料的提取物含有非活性代谢物呋刺洛菌素-1（l）2和活性代谢物伊利马醌（2）3和5-七-伊利马醌（3）。本文报道了5-epi-ilimaquinone（3）的结构解析（图一）。在帕劳的Rekthapel岛附近采集了窗孔珊瑚属物种的标本，并冷冻储存直至需要。在Sephadex LH-20上使用1：1二氯甲烷-甲醇作为洗脱剂的甲醇提取物的色谱法将主要的非活性代谢物呋刺奴洛辛-1（1，0.4%干重）与6：4的冬青醌（2）和5-表-冬青醌（3）（2.1%干重）的混合物分离。我们以前遇到过许多来自帕劳的海绵样品，它们含有与10-20%异海绵醌（4）混合的伊利马醌（2），4-5，但来自这种海绵的活性混合物含有两种都具有环外亚甲基的化合物。NMR谱包含在5.86（s，1H）、4.45（s，1H）、4.45（s，1H）和4.45（s，1H）处的对伊里马醌（2）预期的信号。1H NMR（400MHz，DMS0-d6）δ：4.43 1H NMR（400 MHz，DMS 0-d 6）和3.87（s，3 H）处的信号，以及在5.87（s，1H）、4.70（s，1H）和3.87（s，3 H）处的另外一组信号。在低场区域中，具有4.67（br s，1H）、4.67（br s，1H）和3.88（s，3 H）的平均值。这些数据表明：（1）该海绵的鉴定条件异常差，但具有窗海绵属的基本特征。(2)Cimino，G.; De Stefano，S.;米纳莱湖Tetrahedron 1972，28，1315.步行者，RP; Thompson，JE; Faulkner，DJ J. Org. Chem. 1980，45，4976.
Chart I extracts of a sponge tentatively identified as a species of Fenestraspongia1 exhibited in vitro antimicrobial activity and inhibited cell division in thefertilized sea urchin egg assay. Extracts of the sponge material contained the in-active metabolite furospinulosin-1 (l) 2 and the active metabolites ilimaquinone (2) 3 and 5-ept-ilimaquinone (3). In this note we report the structural elucidation of 5-epi-ilimaquinone (3)(Chart I). Specimens of Fenestraspongia sp. were collected near Urukthapel Island, Palau, and were stored frozen until required. Chromatography of a methanolic extract on Sephadex LH-20 using 1: 1 dichloromethane-methanol as eluant separated the major inactive metabolite furospinulosin-1 (1, 0.4% dry weight) from a 6: 4 mixture of ili-maquinone (2) and 5-epi-ilimaquinone (3)(2.1% dry weight). We had previously encountered a number of sponge samples from Palau that contained ilimaquinone (2) mixed with 10-20% isospongiaquinone (4), 4-5 but the active mixture from this sponge contained two compounds both having an exocyclic methylene group. The NMR spectrum contained the signals expected for ilimaquinone (2) at 5.86 (s, 1 H), 4.45 (br s, 1 H), 4.43 (br s, 1 H), and 3.87 (s, 3 H) together with an additional set of signals at 5.87 (s, 1 H), 4.70 (br s, 1 H), 4.67 (br s, 1 H), and 3.88 (s, 3 H) in the low-field region. These data suggested that (1) The sponge was in an unusually poor condition for identification but has the basic characteristics of the genus Fenestraspongia Bergquist.(2) Cimino, G.; De Stefano, S.; Mínale, L. Tetrahedron 1972, 28, 1315. Walker, RP; Thompson, JE; Faulkner, DJ J. Org. Chem. 1980, 45, 4976.