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Four undescribed ergostane-type steroids from Lasiodiplodia pseudotheobromae and their neuroprotective activity

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单位: [1]Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China [2]Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochemistry & Plant Resources Wes, Kunming 650204, Peoples R China [3]Huazhong Univ Sci & Technol, Tongji Hosp, Tongji Med Coll, Wuhan 430030, Peoples R China
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关键词: Lasiodiplodia pseudotheobromae Botryosphaeriaceae Ergostane-type steroids Single-crystal X-ray diffraction Neuroprotective activity

摘要:
Four undescribed ergostane-type steroids, (22E,24R)-4 alpha,5 alpha-epoxyergosta-9 alpha,14 beta-dihydroxy-7,22-diene-3,6dione, (22E,24R)-4 alpha,5 alpha-epoxyergosta-9 alpha,14 alpha-dihydroxy-7,22-diene-3,6-dione, 12 alpha-hydroxyergosta-7,22,24(28)triene-3-one, and 3 beta,12 alpha-dihydroxyergosta-7,24(28)-diene, along with a known congener (22E,24R)-9 alpha,14 beta dihydroxyergosta-4,7,22-triene-3,6-dione, were isolated from the fungus Lasiodiplodia pseudotheobromae. Their structures were elucidated using NMR, HRESIMS, ECD calculation, and X-ray diffraction analyses. (22E,24R)4 alpha,5 alpha-epoxyergosta-9 alpha,14 beta-dihydroxy-7,22-diene-3,6-dione and (22E,24R)-4 alpha,5 alpha-epoxyergosta-9 alpha,14 alpha-dihydroxy-7,22-diene-3,6-dione are a pair of C-14 epimers possessing an unusual epoxy group between C-4 and C-5, which was demonstrated using single-crystal X-ray diffraction analyses. The absolute configurations of 12 alpha hydroxyergosta-7,22,24(28)-triene-3-one and 3 beta,12 alpha-dihydroxyergosta-7,24(28)-diene were determined by ECD calculations. Moreover, 3 beta,12 alpha-dihydroxyergosta-7,24(28)-diene exhibited neuroprotective activity in vitro in glutamate-treated SH-SY5Y cell lines.

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出版当年[2021]版:
大类 | 2 区 生物学
小类 | 2 区 生化与分子生物学 2 区 植物科学
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大类 | 2 区 生物学
小类 | 2 区 生化与分子生物学 2 区 植物科学
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出版当年[2020]版:
Q1 PLANT SCIENCES Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY
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Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Q2 PLANT SCIENCES

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第一作者单位: [1]Huazhong Univ Sci & Technol, Tongji Med Coll, Sch Pharm, Hubei Key Lab Nat Med Chem & Resource Evaluat, Wuhan 430030, Peoples R China
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