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Planta Med 2009; 75(15): 1602-1607
DOI: 10.1055/s-0029-1185813
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Lanostanes from Phellinus igniarius and Their iNOS Inhibitory Activities

Guei-Jane Wang1 , Tung-Hu Tsai2 , Tun-Tschu Chang3 , Cheng-Jen Chou1 , Lie-Chwen Lin1 , 2 , 4
  • 1National Research Institute of Chinese Medicine, Taipei, Taiwan
  • 2Institute of Traditional Medicine, National Yang-Ming University, Taipei, Taiwan
  • 3Division of Forest Protection, Taiwan Forestry Research Institute, Taipei, Taiwan
  • 4Graduate Institute of Integrated Medicine, China Medical University, Taichung, Taiwan
Further Information

Publication History

received February 28, 2009 revised May 16, 2009

accepted May 20, 2009

Publication Date:
25 June 2009 (online)

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Abstract

Four new lanostanol-type triterpenoids, igniarens A – D (1–4), were isolated from the fruit body of Phellinus igniarius together with two known triterpenoids, and two known ergostanes. These four new compounds were identified by spectroscopic analysis as 22R-hydroxy-24-methylene-29-norlanost-7, 9(11)-dien-3-one (1), 3α,22R-dihydroxy-24-methylene-29-norlanost-7, 9(11)-diene (2), 3α,22R-dihydroxy-24-methylene-29-norlanost-8-ene (3), and 3α,22R-dihydroxy-24-methylenelanost-8-ene (4). Their effects on NO production in lipopolysaccharide (LPS)-activated macrophages were assessed. Compounds 1–8 inhibited NO production in activated RAW 264.7 cells to various degrees. The most potent compound 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β‐ol (7) significantly inhibited LPS-induced NO production in a concentration-dependent manner without affecting the cellular viability, with an IC50 of 37.57 ± 1.38 µM.

Key words

Phellinus igniarius - Hymenochaetaceae - triterpenoids - igniarens - inflammation - macrophages - nitric oxide

References

  • 1 Chou W N, Chang T T. Mushrooms of Taiwan. Taipei; Yuan-Liou Publisher 2005: 325
    Google Scholar
  • 2 Wang Y, Mo S Y, Wang S J, Li S, Yang Y C, Shi J G. A unique highly oxygenated pyrano[4,3-c][2]benzopyran-1,6-dione derivative with antioxidant and cytotoxic activities from the fungus Phellinus igniarius.  Org Lett. 2005;  7 1675-1678
    CrossrefPubMedGoogle Scholar
  • 3 Wang Y, Wang S J, Mo S Y, Li S, Yang Y C, Shi J G. Phelligridimer A, a highly oxygenated and unsaturated 26-membered macrocyclic metabolite with antioxidant activity from the fungus Phellinus igniarius.  Org Lett. 2005;  7 4733-4736
    CrossrefPubMedGoogle Scholar
  • 4 Mo S Y, Wang S J, Zhou G X, Yang Y C, Li Y, Chen X G, Shi J G. Phelligridins C – F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius.  J Nat Prod. 2004;  67 823-828
    CrossrefPubMedGoogle Scholar
  • 5 Wang Y, Shang X Y, Wang S J, Mo S Y, Li S, Yang Y C, Ye F, Shi J G, He L. Structures, biogenesis, and biological activities of pyrano[4,3-c]isochromen-4-one derivatives from the fungus Phellinus igniarius.  J Nat Prod. 2007;  70 296-299
    CrossrefPubMedGoogle Scholar
  • 6 Yang Y, Zhang J S, Liu Y F, Tang Q J, Zhao Z G, Xia W S. Structural elucidation of a 3-O-methyl-D-galactose-containing neutral polysaccharide from the fruiting bodies of Phellinus igniarius.  Carbohydr Res. 2007;  342 1063-1070
    CrossrefPubMedGoogle Scholar
  • 7 MacMicking J, Xie Q W, Nathan C. Nitric oxide and macrophage function.  Annu Rev Immunol. 1997;  15 323-350
    CrossrefPubMedGoogle Scholar
  • 8 Bogdan C. Nitric oxide and the immune response.  Nat Immunol. 2001;  2 907-916
    CrossrefPubMedGoogle Scholar
  • 9 Cho K H, Kim Y S, Bae H S, Moon S K, Jung W S, Park E K, Kim D H. Inhibitory effect of Chunghyuldan in prostaglandin E2 and nitric oxide biosynthesis of lipopolysaccharide-induced RAW 264.7 cells.  Biol Pharm Bull. 2004;  27 1810-1813
    CrossrefPubMedGoogle Scholar
  • 10 Kim S J, Ha M S, Choi E Y, Choi J I, Choi I S. Prevotella intermedia lipopolysaccharide stimulates release of nitric oxide by inducing expression of inducible nitric oxide synthase.  J Periodontal Res. 2004;  39 424-431
    CrossrefPubMedGoogle Scholar
  • 11 Wang G J, Chen S M, Chen W C, Chang Y M, Lee T H. Selective inducible nitric oxide synthase suppression by new bracteanolides from Murdannia bracteata.  J Ethnopharmacol. 2007;  112 221-227
    CrossrefPubMedGoogle Scholar
  • 12 Green L C, Wagner D A, Glogowski J, Wishnik I S, Tannenbaum S R. Analysis of nitrate, nitrite and [15N]nitrate in biologic fluids.  Anal Biochem. 1982;  126 131-138
    CrossrefPubMedGoogle Scholar
  • 13 Kwack K, Lynch R G. A new non-radioactive method for IL‐2 bioassay.  Moll Cell. 2000;  10 575-578
    PubMedGoogle Scholar
  • 14 Liu H K, Tsai T H, Chang T T, Chou C J, Lin L C. Lanostane-triterpenoids from fungus Phellinus gilvus. .  Phytochemistry. 2009;  70 558-563
    CrossrefPubMedGoogle Scholar
  • 15 Kobori M, Yoshida M, Ohnishi-Kameyama M, Takei T, Shinmoto H. 5α,8α-Epidioxy-22E-ergosta-6,9(11),22-trien-3β‐ol from an edible mushroom suppresses growth of HL60 leukemia and HT29 colon adenocarcinoma cells.  Biol Pharm Bull. 2006;  29 755-759
    CrossrefPubMedGoogle Scholar
  • 16 Akihisa T, Kokke W CMC, Yokota T, Tamura T, Matsumoto T. 4α,14α-Dimethyl-5α-ergosta-7,9(11),24(28)-trien-3β‐ol from Phaseolus vulgaris and Gynostemma pentaphyllum.  Phytochemistry. 1990;  29 1647-1651
    CrossrefPubMedGoogle Scholar
  • 17 Claydon N, Grove J F, Pople M. New metabolic products of Verticillium lecanii. Part 1. 3 beta-hydroxy-4,4,14 alpha-trimethyl-5alpha-pregna-7,9(11)-diene-20S-carboxylic acid and the isolation and characterization of some minor metabolites.  J Chem Soc [Perkin I]. 1984;  497-502
    PubMedGoogle Scholar
  • 18 Lobo A M, Abreu P MD, Prabhakar S, Godinho L S, Jones R. Triterpenoids of the fungus Pisolithus tinctorius.  Phytochemistry. 1988;  27 3569-3574
    CrossrefPubMedGoogle Scholar
  • 19 Tanaka R, Kasubuchi K, Kita S, Matsunaga S. Obtusifoliol and related steroids from the whole herb of Euphorbia chamaesyce.  Phytochemistry. 1999;  51 457-463
    CrossrefPubMedGoogle Scholar
  • 20 Lee T H, Huang N K, Lai T C, Yang A TY, Wang G J. Anemonin, from Clematis crassifolia, potent and selective inducible nitric oxide synthase inhibitor.  J Ethnopharmacol. 2008;  116 518-527
    CrossrefPubMedGoogle Scholar

Prof. Dr. Lie-Chwen Lin

National Research Institute of Chinese Medicine

Li-Nong

Taipei 112

Taiwan

Republic of China

Phone: + 88 62 28 20 19 99 ext. 71 01

Fax: + 88 62 28 26 42 76

Email: lclin@nricm.edu.tw

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