Xylomolones A-D from the Thai Mangrove Xylocarpus moluccensis: Assignment of Absolute Stereostructures and Unveiling a Convergent Strategy for Limonoid Biosynthesis

Wan Shan Li, Attila Mándi, Jun Jun Liu, Li Shen, T. Kurtán, Jun Wu

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Two new 9,10-seco limonoids with a central 3,4-dihydro-2H-pyran motif, named xylomolones A and B (1 and 2, respectively), possessing identical absolute configurations but reversed alignments of ring A, compared to the tricyclic core of rings B-D, were obtained from seeds of the Thai mangrove Xylocarpus moluccensis, together with a highly modified 1,2-seco limonoid, named xylomolone C (3), containing a novel 3-oxabicyclo[3.2.1]octane-2,7-dione motif, and a new C 11 -terpenic acid methyl ester (4). The relative and absolute configurations of 1-4 were evidenced by extensive nuclear magnetic resonance (NMR) investigations combined with density functional theory and time-dependent density functional theory calculations of electronic circular dichroism, specific optical rotation, and 13 C NMR data. The co-isolation of 1-4 allowed us to propose a novel convergent strategy for limonoid biosynthesis for the first time. This study demonstrates that mangroves of the genus Xylocarpus harbor new limonoid biosynthetic routes.

Original languageEnglish
Pages (from-to)2596-2606
Number of pages11
JournalJournal of Organic Chemistry
Volume84
Issue number5
DOIs
Publication statusPublished - Mar 1 2019

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Xylomolones A-D from the Thai Mangrove Xylocarpus moluccensis: Assignment of Absolute Stereostructures and Unveiling a Convergent Strategy for Limonoid Biosynthesis'. Together they form a unique fingerprint.

  • Cite this