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A new trihydroxy fatty acid from the ascomycete, Chinese truffle Tuber indicum

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Lipids

Abstract

From the chloroform/methanol extract of the fruiting bodies of the ascomycete Chinese truffle Tuber indicum Cooke et Massee, a new trihydroxylated monounsaturated fatty acid (1) has been isolated. The structure of this new linoleic acid-derived metabolite was established as 9,10,11-trihydroxy-(12Z)-12-octadecenoic acid by means of spectroscopic and chemical methods. The fatty acid composition of the chloroform-soluble fraction of this fungus was analyzed by gas chromatography-mass spectrometry. The content of the predominant unsaturated fatty acids (oleic and linoleic acids) is as high as 68%. The use of dimethyl disulfide adduct was effective in the determination of the position of the double bond, and the glycol oxidation fission reaction with sodium metaperiodate supported on silica gel was helpful in establishing the location of the trihydroxylic groups in the new fatty acid.

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Abbreviations

CC:

column chromatography

DMDS:

dimethyl disulfide

EI-MS:

electron impact-mass spectrometry

FAB-MS:

fast atom bombardment-mass spectrometry

GC-MS:

gas chromatography-mass spectrometry

HPODE:

hydroperoxyoctadecadienoic acid

IR:

infrared

LA:

linoleic acid

LOX:

lipoxygenase

MS:

mass spectrometry

NMR:

nuclear magnetic resonance

OA:

oleic acid

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Authors and Affiliations

  1. College of Life Sciences, Northwest Science & Technology University of Agriculture and Forestry, Yangling, 712100, Shaanxi, People’s Republic of China

    Jin-Ming Gao & An-Ling Zhang

  2. Department of Phytochemistry, Kunming Institute of Botany, Chinese Academy of Sciences, 650204, Kunming, People’s Republic of China

    Jin-Ming Gao, Chen-Ying Wang & Ji-Kai Liu

Authors
  1. Jin-Ming Gao
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  2. Chen-Ying Wang
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  3. An-Ling Zhang
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  4. Ji-Kai Liu
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Correspondence to Jin-Ming Gao.

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Gao, JM., Wang, CY., Zhang, AL. et al. A new trihydroxy fatty acid from the ascomycete, Chinese truffle Tuber indicum . Lipids 36, 1365–1370 (2001). https://doi.org/10.1007/s11745-001-0853-y

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  • DOI: https://doi.org/10.1007/s11745-001-0853-y

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