Exploration of possible biosynthetic origin of 1/8/9-orthoester moiety in phragmalins

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• 作者：Sheng-Mou Hu ; Jun Luo ; Lei Yang ; Ling-Yi Kong
• 关键词：NJDSYFZABUKFPR-WJBCSJKLSA-N ; QVTYQLVAVXYHAF-YRQKUAAESA-N ; UPQNRCUDTCJVHO-QMRSJGSNSA-N ; HAYDDYJJUDSCRM-QTGYDEOYSA-N ; SZIDSIGOGROVCU-LPCXZXSUSA-N
• 刊名：Tetrahedron Letters
• 出版年：22 January, 2014
• 年：2014
• 卷：55
• 期：4
• 页码：815-817
• 全文大小：712 K

文摘

The orthoester, a functional group that features three alkoxy groups attaching to a single carbon atom, was an important structural subunit discovered in plant resource. Diverse phragmalin-type limonoids with different orthoester moiety and connected locations have been isolated from the Meliaceae family. Under the guidance of plausible biosynthetic pathway, phragmalin-type 1/8/9-orthoesters were effectively synthesized from its phragmalin mother nuclear through a key intermediate with an esterfunction at C-1. These interesting findings indicated that natural phragmalin-type 1/8/9-orthoesters were derived from phragmalins with esterified substituent at C-1 and hydroxyl groups at C-8 and C-9.