Polyoxygenated ergosteroids from the macrofungus Omphalia lapidescens and the structure-cytotoxicity relationship in a human gastric cancer cell line. (June 2018)

• Record Type: Journal Article
• Authors: Wang, Yue; Dai, Ou; Peng, Cheng; Su, Hai-Guo; Miao, Lu-Lin; Liu, Lu-Si; Xiong, Liang
• Is Part Of: Phytochemistry letters. Volume 25(2018)
• Page Start: 99
• Page End: 104
• Publication Date: 2018-06
• Subjects: Omphalia lapidescens -- Polyoxygenated ergosteroids -- Cytotoxic activity -- HGC-27 -- Apoptosis; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2018.04.005
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: Seventeen polyoxygenated Δ 22 -ergosteroids were isolated from Omphalia lapidescens . Two previously undescribed ergosteroids were isolated. The structure-cytotoxicity relationship in HGC-27 cancer cell line of the isolates was studied. Hoechst fluorescence 33342 staining was performed to investigate the apoptosis-inducing effect. Abstract: Seventeen polyoxygenated Δ 22 -ergosteroids (1 –17 ), including two new compounds (1 and15 ), were isolated from the ethyl acetate soluble fraction of a 95% ethanol extract of Omphalia lapidescens Schroet. According to the oxidation degree and the oxidation positions of A and B rings, the isolates could be divided into three subtypes: 3, 5, 6-trioxygenated Δ 7 -ergosteroids (1 –9 ), 3, 5, 6, 7-tetraoxygenated ergosteroids (10 –14 ), and conjugated Δ 4, 6, 8 -3-one ergosteroids (15–17 ). The cytotoxic effects were studied using a human gastric cancer cell line, HGC-27, in vitro and the relationships between structure and cytotoxicity of the three subtypes were investigated. Among these subtypes, (3 β, 5α, 6 β, 22 E )-6-methoxyergosta-7, 22-diene-3, 5-diol (5 ) exhibited the highest cytotoxicity, with an IC50 value of 4.17 ± 0.48 μM. Furthermore, Hoechst fluorescence 33342 staining demonstrated that compound5 could induce HGC-27 cell apoptosis significantly.