C28 steroids from the fruiting bodies of Ganoderma resinaceum with potential anti-inflammatory activity

被引:27
作者
Shi, Qiangqiang [1 ,2 ,3 ]
Huang, Yanjie [1 ,2 ,3 ]
Su, Haiguo [1 ,2 ,3 ]
Gao, Ya [1 ,2 ,3 ]
Peng, Xingrong [1 ,3 ]
Zhou, Lin [1 ,3 ]
Li, Xiaonian [1 ,3 ]
Qiu, Minghua [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[3] Chinese Acad Sci, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China
基金
中国国家自然科学基金;
关键词
Ganoderma resinaceum boud; Ganodermataceae; Ergostane-type; Steroids; Anti-inflammatory activity; POLYCYCLIC MEROTERPENOIDS; PLEUROTUS-ERYNGII; CONSTITUENTS; TRITERPENOIDS; ERGOSTEROLS; INHIBITORS; LUCIDUM; RING;
D O I
10.1016/j.phytochem.2019.112109
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Eight undescribed ergostane-type steroids, (22E,24R)-ergosta-7,22-dien-3 beta,5 alpha-diol- 6,5-olide, (22E,24R)-er-gosta-7,9(11),22-trien-3 beta,5 beta,6 beta-triol, (22E,24R)-6 beta-methoxy ergosta-7,9(11),22-trien-3 beta,5 alpha,14 beta-triol, (22E,24R)-9 alpha,15 alpha-dihydroxyergosta-4,6,8 (14),22-tetraen-3-one, (22E,24R)-ergosta-5,8,22-trien-3 beta,11 alpha-dihydroxyl-7-one, (22E,24R)-ergosta-4,7,22-trien-3 beta,9 alpha,14 beta-trihydroxy1-6-one, (22E,24R)-ergosta-7,22- dien-3 beta,9 alpha,14 beta-trihydroxy1-6-one, and (22E,24R)-6 beta-methoxyergosta-7,22-dien-3 beta, 5 alpha,9 alpha,14 beta-tetraol, and twentyone known analogues were isolated from the fruiting bodies of Ganoderma resinaceum Boud. Their chemical structures were determined on the basis of comprehensive spectroscopic analysis and X-ray crystal diffraction, as well as empirical pyridine-induced deshielding effects. Furthermore, selected compounds were evaluated for their inhibitory effects on macrophage activation using an inhibition of nitric oxide production assay. Finally, (22E,24R)-ergosta-5,8,22- trien-3/3,11 alpha-dihydroxy1-7-one, (22E,24R)-ergosta-4,7,22-trien-3 beta,9 alpha,14 beta-tri hydroxyl-6-one, (22E,24R)-6 beta-methoxyergosta-7,22-dien-3 beta,5 alpha,9 alpha,14 beta-tetrao1, (22E,24R)-ergosta-6,9,22-trien-3 beta,5 alpha,8 alpha-triol,ergost-6,22-dien-3 beta,5 alpha,8 alpha-triol, 5 alpha,6 alpha-epoxy-(22E,24R)-ergosta-8,22-diene-3 beta,7 alpha-diol, 5 alpha,6 alpha-epoxy-(22E,24R)- ergosta-8(14),22-diene-3 beta,7 alpha-diol, 5 alpha,6 alpha-epoxy-(22E,24R)-ergosta-8(14),22-diene-3 beta, 7 beta-diol, and 22E-7 alpha-methoxy-5 alpha,6 alpha-epoxyergosta-8(14),22-dien-3 beta-ol showed inhibitory effects on NO production with IC50 values ranging from 3.24 +/- 0.02 to 35.19 0.41 mu M compared with L-NMMA (IC50 49.86 +/- 2.13 mu M), indicating that they have potential anti-inflammatory activity.
引用
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页数:8
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