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

Qiangqiang Shi¹, Yanjie Huang², Haiguo Su³, Ya Gao⁴, Xingrong Peng⁵, Lin Zhou⁶, Xiaonian Li⁷, Minghua Qiu⁸

Affiliations

¹ 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. Electronic address: shiqiangqiang13@mails.ucas.ac.cn.
² 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. Electronic address: huangyanjie@mail.kib.ac.cn.
³ 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. Electronic address: suhaiguo@mail.kib.ac.cn.
⁴ 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. Electronic address: gaoya@mail.kib.ac.cn.
⁵ 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. Electronic address: pengxingrong@mail.kib.ac.cn.
⁶ 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. Electronic address: zhoulin@mail.kib.ac.cn.
⁷ 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. Electronic address: lixiaonian@mail.kib.ac.cn.
⁸ 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. Electronic address: mhchiu@mail.kib.ac.cn.

PMID: 31494344
DOI: 10.1016/j.phytochem.2019.112109

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

Qiangqiang Shi et al. Phytochemistry. 2019 Dec.

. 2019 Dec:168:112109.

doi: 10.1016/j.phytochem.2019.112109. Epub 2019 Sep 5.

Authors

Qiangqiang Shi¹, Yanjie Huang², Haiguo Su³, Ya Gao⁴, Xingrong Peng⁵, Lin Zhou⁶, Xiaonian Li⁷, Minghua Qiu⁸

Affiliations

¹ 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. Electronic address: shiqiangqiang13@mails.ucas.ac.cn.
² 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. Electronic address: huangyanjie@mail.kib.ac.cn.
³ 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. Electronic address: suhaiguo@mail.kib.ac.cn.
⁴ 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. Electronic address: gaoya@mail.kib.ac.cn.
⁵ 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. Electronic address: pengxingrong@mail.kib.ac.cn.
⁶ 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. Electronic address: zhoulin@mail.kib.ac.cn.
⁷ 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. Electronic address: lixiaonian@mail.kib.ac.cn.
⁸ 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. Electronic address: mhchiu@mail.kib.ac.cn.

PMID: 31494344
DOI: 10.1016/j.phytochem.2019.112109

Abstract

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 IC₅₀ values ranging from 3.24 ± 0.02 to 35.19 ± 0.41 μM compared with L-NMMA (IC₅₀ 49.86 ± 2.13 μM), indicating that they have potential anti-inflammatory activity.

Keywords: Anti-inflammatory activity; Ergostane-type; Ganoderma resinaceum boud; Ganodermataceae; Steroids.

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

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

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