amaranzoles B-F，来自海洋海绵 Phorbas amaranthus 的咪唑-2-羧酸甾体。来自不同氧化生物合成的 C24-N-和 C24-O 类似物。
Amaranzoles B-F, imidazole-2-carboxy steroids from the marine sponge Phorbas amaranthus. C24-N- and C24-O-analogues from a divergent oxidative biosynthesis.
机构信息
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0358, USA.
出版信息
J Org Chem. 2010 Apr 16;75(8):2453-60. doi: 10.1021/jo1000324.
Abstract
Five new steroidal imidazoles, amaranzoles B-F, were isolated from extracts of the marine sponge Phorbas amaranthus along with the known amaranzole A. The C24-N-(4-p-hydroxyphenyl)imidazol-5-yl constitution found in amaranzoles A, C, and D is replaced by a C24-O-(4-p-hydroxyphenyl)imidazole-2-carboxylate motif in amaranzoles B, E, and F. The structures were elucidated by interpretation of spectroscopic data. The C24 side chain configuration was assigned by synthesis of a model ester followed by chiroptical comparisons of its CD spectrum with that of an amaranzole B derivative.
摘要
从海洋海绵 Phorbas amaranthus 的提取物中分离出了五种新型甾体咪唑，分别为 amaranzoles B-F，同时还分离出了已知的 amaranzole A。在 amaranzoles A、C 和 D 中发现的 C24-N-(4-对羟基苯基)咪唑-5-基结构被 amaranzoles B、E 和 F 中的 C24-O-(4-对羟基苯基)咪唑-2-羧酸酯取代。通过光谱数据的解释阐明了这些结构。通过合成模型酯并比较其圆二色光谱与 amaranzole B 衍生物的圆二色光谱，确定了 C24 侧链的构型。
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本文引用的文献
1
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2
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3
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J Phys Chem A. 2008 Sep 18;112(37):8775-84. doi: 10.1021/jp8030286. Epub 2008 Aug 20.
5
Exciton coupling circular dichroism of an allylic N-imidazolyl group in amaranzole A, a marine natural product from Phorbas amaranthus.
Chirality. 2008 Sep;20(9):1066-70. doi: 10.1002/chir.20636.
6
Lipid-lowering effects of ethyl 2-phenacyl-3-aryl-1H-pyrrole- 4-carboxylates in rodents.
Molecules. 2004 Feb 28;9(3):134-57. doi: 10.3390/90300134.
7
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Org Lett. 2007 Dec 6;9(25):5219-22. doi: 10.1021/ol702325e. Epub 2007 Nov 9.
8
Hamigerols A and B, unprecedented polysulfate sterol dimers from the Mediterranean sponge Hamigera hamigera.
J Nat Prod. 2007 Jul;70(7):1195-9. doi: 10.1021/np070027x. Epub 2007 Jun 20.
9
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J Am Chem Soc. 2005 Oct 26;127(42):14668-74. doi: 10.1021/ja051291k.
10
Phorbasterones A-D, cytotoxic nor-ring A steroids from the sponge Phorbas amaranthus.
J Nat Prod. 2004 Apr;67(4):731-3. doi: 10.1021/np034037j.
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