State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China; University of the Chinese Academy of Sciences, Beijing, 100049, People's Republic of China; Yunnan Key Laboratory of Natural Medicinal Chemistry Chinese Academy of Sciences, Kunming, 650201, People's Republic of China.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China; Yunnan Key Laboratory of Natural Medicinal Chemistry Chinese Academy of Sciences, Kunming, 650201, People's Republic of China.
Phytochemistry. 2019 Dec;168:112109. doi: 10.1016/j.phytochem.2019.112109. Epub 2019 Sep 5.
Eight undescribed ergostane-type steroids, (22E,24R)-ergosta-7,22-dien-3β,5α-diol- 6,5-olide, (22E,24R)-ergosta-7,9(11),22-trien-3β,5β,6β-triol, (22E,24R)-6β-methoxy ergosta-7,9(11),22-trien-3β,5α,14β-triol, (22E,24R)-9α,15α-dihydroxyergosta-4,6,8 (14),22-tetraen-3-one, (22E,24R)-ergosta-5,8,22-trien-3β,11α-dihydroxyl-7-one, (22E,24R)-ergosta-4,7,22-trien-3β,9α,14β-trihydroxyl-6-one, (22E,24R)-ergosta-7,22- dien-3β,9α,14β-trihydroxyl-6-one, and (22E,24R)-6β-methoxyergosta-7,22-dien-3β, 5α,9α,14β-tetraol, and twenty-one 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-3β,11α-dihydroxyl-7-one, (22E,24R)-ergosta-4,7,22-trien-3β,9α,14β-tri hydroxyl-6-one, (22E,24R)-6β-methoxyergosta-7,22-dien-3β,5α,9α,14β-tetraol, (22E,24R)-ergosta-6,9,22-trien-3β,5α,8α-triol,ergost-6,22-dien-3β,5α,8α-triol, 5α,6α-epoxy-(22E,24R)-ergosta-8,22-diene-3β,7α-diol, 5α,6α-epoxy-(22E,24R)- ergosta-8(14),22-diene-3β,7α-diol, 5α,6α-epoxy-(22E,24R)-ergosta-8(14),22-diene-3β, 7β-diol, and 22E-7α-methoxy-5α,6α-epoxyergosta-8(14),22-dien-3β-ol showed inhibitory effects on NO production with IC values ranging from 3.24 ± 0.02 to 35.19 ± 0.41 μM compared with L-NMMA (IC 49.86 ± 2.13 μM), indicating that they have potential anti-inflammatory activity.
从灵芝子实体中分离得到了 8 种未描述的麦角甾烷型甾体化合物，分别为（22E，24R）-麦角甾-7，22-二烯-3β，5α-二醇-6，5-内酯、（22E，24R）-麦角甾-7，9（11），22-三烯-3β，5β，6β-三醇、（22E，24R）-6β-甲氧基麦角甾-7，9（11），22-三烯-3β，5α，14β-三醇、（22E，24R）-9α，15α-二羟基麦角甾-4，6，8（14），22-四烯-3-酮、（22E，24R）-麦角甾-5，8，22-三烯-3β，11α-二羟基-7-酮、（22E，24R）-麦角甾-4，7，22-三烯-3β，9α，14β-三羟基-6-酮、（22E，24R）-麦角甾-7，22-二烯-3β，9α，14β-三羟基-6-酮和（22E，24R）-6β-甲氧基麦角甾-7，22-二烯-3β，5α，9α，14β-四醇，以及 21 种已知类似物。通过综合光谱分析和 X 射线晶体衍射以及经验吡啶诱导去屏蔽效应，确定了它们的化学结构。此外，还通过抑制一氧化氮产生的测定法评估了选定化合物对巨噬细胞激活的抑制作用。最后，（22E，24R）-麦角甾-5，8，22-三烯-3β，11α-二羟基-7-酮、（22E，24R）-麦角甾-4，7，22-三烯-3β，9α，14β-三羟基-6-酮、（22E，24R）-6β-甲氧基麦角甾-7，22-二烯-3β，5α，9α，14β-四醇、（22E，24R）-麦角甾-6，9，22-三烯-3β，5α，8α-三醇、麦角甾-6，22-二烯-3β，5α，8α-三醇、5α，6α-环氧-（22E，24R）-麦角甾-8，22-二烯-3β，7α-二醇、5α，6α-环氧-（22E，24R）-麦角甾-8（14），22-二烯-3β，7α-二醇、5α，6α-环氧-（22E，24R）-麦角甾-8（14），22-二烯-3β，7β-二醇和 22E-7α-甲氧基-5α，6α-环氧麦角甾-8（14），22-二烯-3β-醇对 NO 产生具有抑制作用，IC 值范围为 3.24±0.02 至 35.19±0.41 μM，与 L-NMMA（IC 49.86±2.13 μM）相比，表明它们具有潜在的抗炎活性。
