Subscribe to RSS
DOI: 10.1055/s-0029-1185813
© Georg Thieme Verlag KG Stuttgart · New York
Lanostanes from Phellinus igniarius and Their iNOS Inhibitory Activities
Publication History
received February 28, 2009
revised May 16, 2009
accepted May 20, 2009
Publication Date:
25 June 2009 (online)

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
- 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
- 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
- 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
- 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
- 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
- 7 MacMicking J, Xie Q W, Nathan C. Nitric oxide and macrophage function. Annu Rev Immunol. 1997; 15 323-350
- 8 Bogdan C. Nitric oxide and the immune response. Nat Immunol. 2001; 2 907-916
- 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
- 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
- 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
- 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
- 13 Kwack K, Lynch R G. A new non-radioactive method for IL‐2 bioassay. Moll Cell. 2000; 10 575-578
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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