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

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Issued Date

2018

Resource Type

Article

File Type

application/pdf

ISSN

1633864

DOI

10.1021/acs.jnatprod.8b00519

Other identifier(s)

2-s2.0-85055189576

Rights Holder(s)

มหาวิทยาลัยศรีนครินทรวิโรฒ

Bibliographic Citation

Journal of Natural Products. Vol 81, No.10 (2018), p.2244-2250

Suggested Citation

Arunrattiyakorn P., Kuno M., Aree T., Laphookhieo S., Sriyatep T., Kanzaki H., Garcia Chavez M.A., Wang Y.A., Andersen R.J. Biotransformation of β-Mangostin by an Endophytic Fungus of Garcinia mangostana to Furnish Xanthenes with an Unprecedented Heterocyclic Skeleton. Journal of Natural Products. Vol 81, No.10 (2018), p.2244-2250. doi:10.1021/acs.jnatprod.8b00519 Retrieved from: https://hdl.handle.net/20.500.14740/5811

Title

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

Author(s)

Arunrattiyakorn P.
 Kuno M.
 Aree T.
 Laphookhieo S.
 Sriyatep T.
 Kanzaki H.
 Garcia Chavez M.A.
 Wang Y.A.
 Andersen R.J.

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. © 2018 American Chemical Society and American Society of Pharmacognosy.

Subject(s)

Beta mangostin
 Herbaceous agent
 Mangostafeejin A
 Mangostafeejin B
 Natural product
 Unclassified drug
 Xanthene derivative
 Heterocyclic carboxylic acid
 Mangostin
 Xanthene derivative
 Xanthone derivative
 Article
 Biotransformation
 Carbon nuclear magnetic resonance
 Comparative study
 Diastereoisomer
 Drug isolation
 Drug structure
 Enantiomer
 Endophytic fungus
 Garcinia mangostana
 High performance liquid chromatography
 Hydrogen bond
 Nonhuman
 Reversed phase high performance liquid chromatography
 X ray diffraction
 Xylaria feejeensis
 Biotransformation
 Chemical structure
 Circular dichroism
 Garcinia mangostana
 Mass spectrometry
 Metabolism
 Microbiology
 Nuclear magnetic resonance spectroscopy
 Stereoisomerism
 Synthesis
 Xylariales
 Acids, Heterocyclic
 Biotransformation
 Circular Dichroism
 Garcinia mangostana
 Magnetic Resonance Spectroscopy
 Mass Spectrometry
 Molecular Structure
 Stereoisomerism
 X-Ray Diffraction
 Xanthenes
 Xanthones
 Xylariales

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URI

https://hdl.handle.net/20.500.14740/5811

Collections

Scopus: Year 1983-2021

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