Aciculitins A-C: Cytotoxic and antifungal cyclic peptides from the lithistid sponge Aciculites orientalis

Aciculitins A-C: Cytotoxic and antifungal cyclic peptides from the lithistid sponge Aciculites orientalis
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DOI:
10.1021/ja953628w
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发表时间:
1996-05-08
影响因子:
15
通讯作者:
Faulkner, DJ
Faulkner, DJ
中科院分区:
化学1区
文献类型:
--
作者:
Bewley, CA;He, HY;Faulkner, DJ

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石海绵Aciculites orientalis含有三个环肽,aciculitins A-C(1-3),除了同源的脂质残基外,它们是相同的。通过光谱数据的解释阐明了主要肽Aciculitin B(2)的结构。针状肽由一个含有不寻常的组氨酸-酪氨酸桥的双环肽组成。与双环肽连接的是在3位带有D-来苏糖的C-13-C-15 2,3-二羟基-4,6-二烯酸。还提供了Aciculitamides A(4)和B(5)的结构,它们是早先从这种海绵中获得的人工产物。Aciculitins 1- 3抑制白色念珠菌的生长,并对HCT-116细胞株具有细胞毒性。
The lithistid sponge Aciculites orientalis contains three cyclic peptides, aciculitins A-C (1-3), that are identical except for homologous lipid residues. The structure of the major peptide, aciculitin B (2), was elucidated by interpretation of spectroscopic data. The aciculitins consist of a bicyclic peptide that contains an unusual histidino-tyrosine bridge. Attached to the bicyclic peptide are C-13-C-15 2,3-dihydroxy-4,6-dienoic acids bearing D-lyxose at the 3-position. The structures of aciculitamides A (4) and B (5), which are artifacts obtained earlier from this sponge, are also presented. The aciculitins 1--3 inhibited the growth of Candida albicans and were cytotoxic toward the HCT-116 cell line.