Aplysiasecosterols B and C: two new 9,11-secosteroids with a cis-fused 1,4-quinone structure from the sea hare Aplysia kurodai

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• 作者：Masaki Kita ; ^{mkita@chem.tsukuba.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Atsushi Kawamura ; Hideo Kigoshi ; ^{kigoshi@chem.tsukuba.ac.jp" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Marine natural products ; Secosteroid ; Isolation and structure ; Biosynthesis
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：24 February 2016
• 年：2016
• 卷：57
• 期：8
• 页码：858-860
• 全文大小：747 K

文摘

Two new 9,11-secosteroids with a cis-fused 3β,5β-dihydroxy-1,4-quinone structure, aplysiasecosterols B and C, were isolated from the sea hare Aplysia kurodai. Their structures were determined by 1D- and 2D-NMR spectroscopic analysis, molecular modeling studies, and a modified Mosher’s method. Aplysiasecosterol B might be the biosynthetic precursor of aplysiasecosterol A, another 9,11-secosteroid with a tricyclic γ-diketone structure from A. kurodai, via two α-ketol rearrangements and intramolecular acetalization.