Skip to main content
Log in

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

  • Articles
  • Published:


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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others



column chromatography


dimethyl disulfide


electron impact-mass spectrometry


fast atom bombardment-mass spectrometry


gas chromatography-mass spectrometry


hydroperoxyoctadecadienoic acid




linoleic acid




mass spectrometry


nuclear magnetic resonance


oleic acid


  1. Hawksworth, D.L., Kirk, P.M., Sutton, B.C., and Pegler, D.N. (1995) Truffle, Dictionary of the Fungi, pp. 467–469, University Press, Cambridge.

    Google Scholar 

  2. Gao, J.-M., Hu, L., and Liu, J.-K. (2001) A Novel Sterol from Chinese Truffle Tuber indicum, Steroids 66, 771–775.

    Article  Google Scholar 

  3. Harki, E., Klaebe, A., Talou, T., and Dargent, R. (1996) Identification and Quantification of Tuber melanosporum Vitt. Sterols, Steroids 61, 609–612.

    Article  PubMed  CAS  Google Scholar 

  4. Pelusio, F., Nilsson, T., Montanarella, L., Tilio, R., Larsen, B., Facchetti, S., and Madsen, J. (1995) Headspace Solid-Phase Microextraction Analysis of Volatile Organic Sulfur Compounds in Black and White Truffle Aroma, J. Agric. Food Chem. 43, 2138–2143.

    Article  CAS  Google Scholar 

  5. Claus, R., Hoppen, H.O., and Karg, H. (1981) The Secret of Truffles: A Steroidal Pheromone?, Experientia 37, 1178–1179.

    Article  CAS  Google Scholar 

  6. Mau, J.L., Beelman, R.B., Ziegler, G.R., and Royse, D.J. (1991) Effect of Nutrient Supplementation on Flavor, Quality, and Shelf Life of the Cultivated Mushroom, Agaricus bisporus, Mycologia 83, 142–149.

    CAS  Google Scholar 

  7. Li, H.Z., Huang, D.X., Xu, X.P., Zhang, D.C., Shi, Q.Q., and Wu, S.G. (1998) Studies on the Chemical Compositions in Russula vinosa, Mycosystema 17, 68–74.

    Google Scholar 

  8. Bonzom, P.M.A., Nicolaou, A., Zloh, M., Baldeo, W., and Gibbons, W.A. (1999) NMR Lipid Profile of Agaricus bisporus, Phytochemistry 50, 1311–1321.

    Article  CAS  Google Scholar 

  9. Kawagishi, H., Ando, M., Mizuno, T., Yokota, H., and Konishi, S. (1990) A Novel Fatty Acid from the Mushroom Hericium erinaceum, Agric. Biol. Chem. 54, 1329–1331.

    CAS  Google Scholar 

  10. Anke, H., Morales, P., and Sterner, O. (1996) Assays of the Biological Activities of Two Fatty Acid Derivatives Formed in the Edible Mushrooms Cantharellus cibarius and C. tubaeformis as a Response to Injury, Planta Med. 62, 181–183.

    PubMed  CAS  Google Scholar 

  11. Stadler, M., Mayer, A., Anke, H., and Sterner, O. (1994) Fatty Acids and Other Compounds with Nematicidal Activity from Cultures of Basidiomycetes, Planta Med. 60, 128–132.

    PubMed  CAS  Google Scholar 

  12. Shgarma, S., and Mehta, B.K. (1998) Isolation and Characterization of a Novel Amide from Michelia champaka, Indian J. Chem. 37B, 1219–1220.

    Google Scholar 

  13. Gao, J.-M., Dong, Z.-J., and Liu, J.-K., (2001) A New Ceramide from the Basidiomycete Russula cyanoxantha, Lipids 36, 175–180.

    PubMed  CAS  Google Scholar 

  14. Crombie, L., Morgan, D.O., and Smith, E.H. (1991) An Isotopic Study (2H and 18O) of the Enzymic Conversion of Linoleic Acid into Colneleic Acid with Carbon Chain Fracture: The Origin of Shorter Chain Aldehydes, J. Chem. Soc. Perkin Trans. 1, 567–575.

    Article  Google Scholar 

  15. Gao, J.-M., Hu, L., Dong, Z.-J., and Liu, J.-K. (2001) New Glycosphingolipid Containing an Unusual Sphingoid Base from the Basidiomycete Polyporus ellisii, Lipids 36, 521–527.

    PubMed  CAS  Google Scholar 

  16. Herz, W., and Kulanthaivel, P. (1985) Trinydroxy-C18-acids and a Labdane from Rudbeckia fulgida, Phytochemistry 24, 89–91.

    Article  CAS  Google Scholar 

  17. Graveland, A. (1973) Enzymic Oxidation of Linoleic Acid in Aqueous Wheat Flour Suspensions, Lipids 8, 606–611.

    PubMed  CAS  Google Scholar 

  18. Kato, T., Yamaguchi, Y., Abe, N., Uyehara, T., Namai, T., Kodama, M., and Shiobara, Y. (1985) Structure and Synthesis of Unsaturated Trihydroxy C18 Fatty Acids in Rice Plant Suffering from Rice Blast Disease, Tetrahedron Lett. 26, 2357–2360.

    Article  CAS  Google Scholar 

  19. Hermann, E., and Erwin, S. (1977) Isomeric Trihydroxyoctadecenoic Acids in Bee: Evidence for Their Presence and Quantitative Determination, Z. Lebensm. Unters. Forsch. 164, 255–259.

    Article  Google Scholar 

  20. Wang, J.-Z., and Wang, F.-B. (1996) Studies on Chemical Constituents of Codonopsis pilosula, Nat. Prot. Res. Dev. 8, 8–12.

    CAS  Google Scholar 

  21. Dilika, F., Bremner, P.D., Meyer, J.J.M. (2000) Antibacterial Activity of Linoleic Acid and Oleic Acid Isolated from Helichrysum pedunculatum: A Plant Used During Circumcision Rites, Fitoterapia 71, 450–452.

    Article  PubMed  CAS  Google Scholar 

  22. Stadler, M., and Sterner, O. (1998) Production of Bioactive Secondary Metabolites in the Fruit Bodies of Macrofungi as a Response to Injury, Phytochemistry 49, 1013–1019.

    Article  CAS  Google Scholar 

  23. Mizushina, Y., Watanabe, I., Togashi, H., Hanashima, L., Takemura, M., Ohta, K., Sugawara, F., Koshino, H., Esumi, Y., Uzawa, J., et al. (1998) An Ergosterol Peroxide, a Natural Product That Selectively Enhances the Inhibitory Effect of Linoleic Acid on DNA Polymerase β, Biol. Pharm. Bull. 21, 444–448.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to Jin-Ming Gao.

About this article

Cite this article

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).

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: