Biotransformation of β-Mangostin by an Endophytic Fungus of Garcinia mangostana to Furnish Xanthenes with an Unprecedented Heterocyclic Skeleton

Panarat Arunrattiyakorn, Mayuso Kuno, Thammarat Aree, Surat Laphookhieo, Teerayut Sriyatep, Hiroshi Kanzaki, Miguel Angel Garcia Chavez, Yan Alexander Wang, Raymond J. Andersen

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Abstract

Biotransformation of β-mangostin (1) by the endophytic fungus Xylaria feejeensis GM06 afforded hexacyclic ring-fused xanthenes with an unprecedented hexacyclic heterocylic skeleton. β-Mangostin (1) was transformed to two diastereomeric pairs of enantiomers, mangostafeejin A [(-)-2a/(+)-2b)] and mangostafeejin B [(-)-3a/(+)-3b)]. The chemical structures of the transformation products were elucidated by analysis of NMR and MS data, and the structure of mangostafeejin A [(-)-2a/(+)-2b)] was confirmed by single-crystal X-ray diffraction analysis. The absolute configurations of 3a and 3b were established on the basis of calculated and measured ECD data using the ECD spectra of 2a and 2b as models. The fungal biotransformation described herein provides an effective method to convert an abundant achiral plant natural product scaffold into new chiral heterocyclic scaffolds representing expanded chemical diversity for biological activity screening.

Original languageEnglish
Pages (from-to)2244-2250
Number of pages7
JournalJournal of Natural Products
Volume81
Issue number10
DOIs
Publication statusPublished - Oct 26 2018

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Arunrattiyakorn, P., Kuno, M., Aree, T., Laphookhieo, S., Sriyatep, T., Kanzaki, H., Garcia Chavez, M. A., Wang, Y. A., & Andersen, R. J. (2018). Biotransformation of β-Mangostin by an Endophytic Fungus of Garcinia mangostana to Furnish Xanthenes with an Unprecedented Heterocyclic Skeleton. Journal of Natural Products, 81(10), 2244-2250. https://doi.org/10.1021/acs.jnatprod.8b00519