Triterpenoids and an alkamide from Ganoderma tsugae

被引：18

作者：

Lin, Kai-Wei ^{[1
]}

Maitraie, Dravidum ^{[1
]}

Huang, A-Mei ^{[2
]}

Wang, Jih-Pyang ^{[3
]}

Lin, Chun-Nan ^{[4
,5
]}

机构：

[1] Kaohsiung Med Univ, Sch Pharm, Kaohsiung 80708, Taiwan

[2] Kaohsiung Med Univ, Grad Inst Clin Med, Coll Med, Kaohsiung 80708, Taiwan

[3] Taichung Vet Gen Hosp, Dept Educ & Res, Taichung 40705, Taiwan

[4] Kaohsiung Med Univ, Fac Fragrance & Cosmet, Coll Pharm, Kaohsiung 80708, Taiwan

[5] Kaohsiung Med Univ, Dept Med Res, Chung Ho Mem Hosp, Kaohsiung 80708, Taiwan

来源：

FITOTERAPIA | 2016年 / 108卷

关键词：

Lanostanoid; Seco-lanostanoid; Ganoderma tsugae; Antioxidant; Anti-inflammatory; Cytotoxicity; OXIDASE; EPOXIDATION; STEROIDS;

D O I：

10.1016/j.fitote.2015.11.003

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Ganoderma tsugae is a medicinal mushroom. In a continual study on the bioactive constituents of this fungus, a new lanostanoid, 3 beta-acetoxy-16 alpha-hydroxy-24 xi-methyl-5 alpha-lanosta-8,25-dien-21-oic acid, named tsugaric acid F (1) and a novel palmitamide, N-(3'alpha,4'beta-dihydroxy-2'beta-(hydroxymethyl)-1'beta-(cyclobutyl)palmitamide (2) were isolated and characterized from the fruit bodies of G. tsugae, and three novel seco-lanostanoids, 3,4-seco-8 alpha,9 alpha-epoxy-5 alpha-lanosta-21-oic acid 3,4 lactone (5), 3,4-seco-5 beta-lanosta-7,9(11),4(29)-trien-3,21-dioic acid-3-methyl ester (6), 3,4-seco-5 beta-lanosta-7,9(11),4(29)-trien-3,21-dioic acid (7), and a known compound, 3-oxo-5 alpha-lanosta-8-en-21-oic acid (4) were prepared from 3. The structures of new compounds, 1, 2, 5-7 were determined by spectroscopic methods. Compounds 1 and 4 showed inhibitory effects on xanthine oxidase (XO) with an IC50 values of 3133 +/- 80.0 and 43.9 +/- 29.9 mu M, respectively when 7 exhibited potent inhibitory effect on superoxide anion generation in rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB) with an IC50 values of 1.3 +/- 0.2 mu M. Compounds 4-7 showed weak cytotoxic activities against PC3 cells. These results indicated that 4 and 7 may be used as cancer chemopreventive agents. (C) 2015 Elsevier B.V. All rights reserved.

引用

页码：73 / 80

页数：8

共 21 条

[1] Secondary metabolites from Ganoderma [J].

Baby, Sabulal ;

Johnson, Anil John ;

Govindan, Balaji .

PHYTOCHEMISTRY, 2015, 114 :66-101

[2]

Canonica L., 1959, GAZZ CHIM ITAL, V89, P818

[3] Regio- and stereoselectivity of β-himachalene epoxidation by m-CPBA.: A theoretical study [J].

Chekroun, A ;

Jarid, A ;

Benharref, A ;

Boutalib, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4431-4434

[4] Triterpenoid saponins and sapogenin lactones from Albizia gummifera [J].

Debella, A ;

Haslinger, E ;

Schmid, MG ;

Bucar, F ;

Michl, G ;

Abebe, D ;

Kunert, O .

PHYTOCHEMISTRY, 2000, 53 (08) :885-892

[5]

Hour TC, 2000, ANTICANCER RES, V20, P3221

[6] An apigenin-derived xanthine oxidase inhibitor from Palhinhaea cernua [J].

Jiao, Rui H. ;

Ge, Hui M. ;

Shi, Da H. ;

Tan, Ren X. .

JOURNAL OF NATURAL PRODUCTS, 2006, 69 (07) :1089-1091

[7] Structure-activity relationship studies on chalcone derivatives: The potent inhibition of chemical mediators release [J].

Ko, HH ;

Tsao, LT ;

Yu, KL ;

Liu, CT ;

Wang, JP ;

Lin, CN .

BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (01) :105-111

[8] Antiinflammatory triterpenoids and steroids from Ganoderma lucidum and G. tsugae [J].

Ko, Horng-Huey ;

Hung, Chi-Feng ;

Wang, Jih-Pyang ;

Lin, Chun-Nan .

PHYTOCHEMISTRY, 2008, 69 (01) :234-239

[9] Inhibition of xanthine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis [J].

Kong, LD ;

Zhang, Y ;

Pan, X ;

Tan, RX ;

Cheng, CHK .

CELLULAR AND MOLECULAR LIFE SCIENCES, 2000, 57 (03) :500-505

[10] Ganodone, a Bioactive Benzofuran from the Fruiting Bodies of Ganoderma tsugae [J].

La Clair, James J. ;

Rheingold, Arnold L. ;

Burkart, Michael D. .

JOURNAL OF NATURAL PRODUCTS, 2011, 74 (10) :2045-2051

← 1 2 3 →