Download PDF
Planta Med 2014; 80(11): 918-924
DOI: 10.1055/s-0034-1382828
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Depside α-Glucosidase Inhibitors from a Culture of the Mushroom Stereum hirsutum

Bo Tao Wang   *
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, P. R. China
2   School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang, P. R. China
,
Qiu Yue Qi   *
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, P. R. China
3   University of Chinese Academy of Sciences, Beijing, P. R. China
,
Ke Ma
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, P. R. China
,
Yun Fei Pei
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, P. R. China
,
Jun Jie Han
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, P. R. China
,
Wei Xu
2   School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University, Shenyang, P. R. China
,
Er Wei Li
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, P. R. China
,
Hong Wei Liu
1   State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, P. R. China
› Author Affiliations
Further Information

Publication History

received 11 March 2014
revised 02 June 2014

accepted 04 June 2014

Publication Date:
16 July 2014 (online)

Also available at
    Permissions and Reprints

Abstract

Nine new isoprenylated depsides, sterenins E–M (1–9), as well as five known compounds (10–14), were isolated from the solid culture of Stereum hirsutum. The structures of the new compounds were elucidated by spectroscopic methods. Their inhibitory activities against yeast α-glucosidase were evaluated in vitro. Compounds 1–4 and 7–14 showed inhibitory activities with IC50 values of 7.62, 3.06, 6.03, 22.70, 36.64, 13.09, 27.52, 25.10, 12.32, 3.31, 23.82, and 14.17 µM, respectively. Compounds 5 and 6 showed no inhibitory activities with IC50 values higher than 50 µM. Therefore, the culture of S. hirsutum and its secondary metabolites could have a potential usage for the development of hypoglycemic drugs.

Key words

Stereum hirsutum - Stereaceae - isoprenylated phenols - structure elucidation - glucosidase inhibition

* These authors contributed equally to this work.


Supporting Information

 

  • References

  • 1 Reid DA. A monograph of the stipitate steroid fungi. Weinheim: Verlag von J. Cramer Press; 1965: 6-8
    Search in Google Scholar
  • 2 Losada L, Ajayi O, Frisvad JC, Yu J, Nierman WC. Effect of competition on the production and activity of secondary metabolites in Aspergillus species. Med Mycol 2009; 47: S88-S96
    CrossrefPubMedSearch in Google Scholar
  • 3 Schulz B, Boyle C, Draeger S, Rommert AK, Krohn K. Endophytic fungi: a source of novel biologically active secondary metabolites. Mycol Res 2002; 106: 996-1004
    CrossrefPubMedSearch in Google Scholar
  • 4 Liu ZN, Zheng SF. Structural correction of the fruiting body for Golden Ears. Edible Fungi 1994; 16: 12-13
    PubMedSearch in Google Scholar
  • 5 Sterry P, Hughes B. Collins complete British mushrooms and toadstools: the essential photograph guide to Britainʼs fungi. London: Collins; 2009: 26-27
    Search in Google Scholar
  • 6 Ito-Kobayashi M, Aoyagi A, Tanaka I, Muramatsu Y, Umetani M, Takatsu T. Sterenin A, B, C and D, novel 11β-hydroxysteroid dehydrogenase type 1 inhibitors from Stereum sp. J Antibiot 2008; 61: 128-135
    CrossrefPubMedSearch in Google Scholar
  • 7 Kurasawa S, Naganawa H, Takeuchi T, Umezawa H. The structure of MS-3-glyoxalase-I inhibitor produced by a mushroom. Agric Biol Chem 1975; 39: 2009-2014
    CrossrefPubMedSearch in Google Scholar
  • 8 Ma K, Bao L, Han J, Jin T, Yang X, Zhao F, Li S, Song F, Liu M, Liu H. New benzoate derivatives and hirsutane type sesquiterpenoids with antimicrobial activity and cytotoxicity from the solid-state fermented rice by the medicinal mushroom Stereum hirsutum . Food Chem 2014; 143: 239-245
    CrossrefPubMedSearch in Google Scholar
  • 9 Dubin GM, Fkyerat A, Tabacchi R. Acetylenic aromatic compounds from Stereum hirsutum . Phytochemistry 2000; 53: 571-574
    CrossrefPubMedSearch in Google Scholar
  • 10 Cateni F, Doljak B, Zacchigna M, Anderluh M, Piltaver A, Scialino G, Banfi E. New biologically active epidioxysterols from Stereum hirsutum . Bioorg Med Chem Lett 2007; 17: 6330-6334
    CrossrefPubMedSearch in Google Scholar
  • 11 Liermann JC, Schüffler A, Wollinsky B, Birnbacher J, Kolshorn H, Anke T, Opatz T. Hirsutane-type sesquiterpenes with uncommon modifications from three Basidiomycetes. J Org Chem 2010; 75: 2955-2961
    CrossrefPubMedSearch in Google Scholar
  • 12 Talontsi FM, Facey P, Tatong MD, Tofazzal Islam M, Frauendorf H, Draeger S, Tiedemann AV, Laatsch H. Zoosporicidal metabolites from an endophytic fungus Cryptosporiopsis sp. of Zanthoxylum leprieurii . Phytochemistry 2012; 83: 87-94
    CrossrefPubMedSearch in Google Scholar
  • 13 Tan C, Wang QX, Luo CH, Chen S, Li QY, Li P. Yeast α-glucosidase inhibitory phenolic compounds isolated from Gynura medica leaf. Int J Mol Sci 2013; 14: 2551-2558
    CrossrefPubMedSearch in Google Scholar
  • 14 Yuan T, Wan CP, Ma H, Seeram NP. New phenolics from the flowers of Punica granatum and their in vitro α-glucosidase inhibitory activities. Planta Med 2013; 79: 1674-1679
    Thieme ConnectPubMedSearch in Google Scholar
  • 15 Escandón-Rivera S, González-Andrade M, Bye R, Linares E, Navarrete A, Mata R. α-Glucosidase inhibitors from Brickellia cavanillesii . J Nat Prod 2012; 75: 968-974
    CrossrefPubMedSearch in Google Scholar
  • 16 Tabopda TK, Ngoupayo J, Awoussong PK, Mitaine-Offer AC, Ali MS, Ngadjui BT, Lacaille-Dubois MA. Triprenylated flavonoids from Dorstenia psilurus and their K-glucosidase inhibition properties. J Nat Prod 2008; 71: 2068-2072
    CrossrefPubMedSearch in Google Scholar
  • 17 Wang YH, Xiang LM, Wang CH, Tang C, He XJ. Antidiabetic and antioxidant effects and phytochemicals of mulberry fruit (Morus alba L.) polyphenol enhanced extract. PLoS One 2013; 8: e71144
    CrossrefPubMedSearch in Google Scholar
  • 18 Ma HY, Gao HY, Sun L, Huang J, Xu XM, Wu LJ. Constituents with a-glucosidase and advanced glycation end-product formation inhibitory activities from Salvia miltiorrhiza Bge. J Nat Med 2011; 65: 37-42
    CrossrefPubMedSearch in Google Scholar
  • 19 Huang GJ, Hsieh WT, Chang HY, Huang SS, Lin YC, Kuo YH. α-Glucosidase and aldose reductase inhibitory activities from the fruiting body of Phellinus merrillii . J Agric Food Chem 2011; 59: 5702-5706
    CrossrefPubMedSearch in Google Scholar
  • 20 Miyazawa M, Takahashi T, Horibe I, Ishikawa R. Two new aromatic compounds and a new D-arabinitol ester from the mushroom Hericium erinaceum . Tetrahedron 2012; 68: 2007-2010
    CrossrefPubMedSearch in Google Scholar
  • 21 Li W, Wei K, Fu HW, Koike K. Structure and absolute configuration of clerodane diterpene glycosides and a rearranged cadinane sesquiterpene glycoside from the stems of Tinospora sinensis . J Nat Prod 2007; 70: 1971-1976
    CrossrefPubMedSearch in Google Scholar