Pegriseofamines A-E: Five cyclopiazonic acid related indole alkaloids from the fungus Penicillium griseofulvum

被引：7

作者：

Liang, Yu ^{[1
]}

Liao, Hong ^{[1
]}

Chen, Xuanni ^{[1
]}

Wang, Qiwei ^{[1
]}

Li, Qin ^{[1
]}

Shen, Yong ^{[1
]}

Zheng, Yuyi ^{[1
]}

Li, Xiao-Nian ^{[2
]}

Zhu, Hucheng ^{[1
]}

Li, Dongyan ^{[3
]}

Sun, Weiguang ^{[1
]}

Chen, Chunmei ^{[1
]}

Zhang, Yonghui ^{[1
]}

机构：

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

[2] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Chi, Kunming 650204, Peoples R China

[3] Huazhong Univ Sci & Technol, Tongji Hosp, Tongji Med Coll, Dept Pharm, Wuhan 430030, Peoples R China

来源：

BIOORGANIC CHEMISTRY | 2023年 / 136卷

关键词：

Penicillium griseofulvum; Alkaloid; Cyclopiazonic acid; Immunosuppression activity;

D O I：

10.1016/j.bioorg.2023.106553

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：

Five new cyclopiazonic acid related indole alkaloids, pegriseofamines A-E (1-5), were isolated from the fungus Penicillium griseofulvum. Their structures and absolute configurations were determined by NMR, HRESIMS, quantum-chemical calculation, and X-ray diffraction experiments. Among them, pegriseofamine A (1) possesses an undescribed 6/5/6/7 tetracyclic ring system generated by the fusion of an azepine and an indole unit via a cyclohexane, and the postulated biosynthetic origin of 1 was discussed. Compound 4 could relieve liver injury and prevent hepatocyte apoptosis in ConA-induced autoimmune liver disease.

引用

页数：9

共 50 条

[1] Penigrines A-E: Five undescribed azepine-indole alkaloids from Penicillium griseofulvum
Liang, Yu
Zhao, Huimin
Wang, Qiwei
Chen, Xuanni
Li, Qin
Chen, Chunmei
Zhu, Hucheng
Zhang, Yonghui
PHYTOCHEMISTRY, 2024, 220
[2] Griseofulvin Derivative and Indole Alkaloids from Penicillium griseofulvum CPCC 400528
Zhang, Dewu
Zhao, Lili
Wang, Lining
Fang, Xiaomei
Zhao, Jianyuan
Wang, Xinwei
Li, Li
Liu, Hongyu
Wei, Yuzhen
You, Xuefu
Cen, Shan
Yu, Liyan
JOURNAL OF NATURAL PRODUCTS, 2017, 80 (02): : 371 - 376
[3] Three New Indole-Containing Diketopiperazine Alkaloids from a Deep-Ocean Sediment Derived Fungus Penicillium griseofulvum
Zhou, Li-Na
Zhu, Tian-Jiao
Cai, Sheng-Xin
Gu, Qian-Qun
Li, De-Hai
HELVETICA CHIMICA ACTA, 2010, 93 (09) : 1758 - 1763
[4] Alstilobanines A-E, new indole alkaloids from Alstonia angustiloba
Koyama, Koichiro
Hirasawa, Yusuke
Zaima, Kazumasa
Hoe, Teh Chin
Chan, Kit-Lam
Morita, Hiroshi
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (13) : 6483 - 6488
[5] Voacalgines A-E, new indole alkaloids from Voacanga grandifolia
Hirasawa, Yusuke
Arai, Hiroko
Rahman, Abdul
Kusumawati, Idha
Zaini, Noor Cholies
Shirota, Osamu
Morita, Hiroshi
TETRAHEDRON, 2013, 69 (51) : 10869 - 10875
[6] Rauvotetraphyllines A-E, new indole alkaloids from Rauvolfia tetraphylla
Gao Y.
Zhou D.-S.
Kong L.-M.
Hai P.
Li Y.
Wang F.
Liu J.-K.
Natural Products and Bioprospecting, 2012, 2 (2) : 65 - 69
[7] Indole alkaloids fusarindoles A-E from marine-derived fungus Fusarium equiseti LJ-1
Dai, Xiao-Ming
Pan, Hui-Lin
Lan, Wen-Jian
Chen, Liu -Ping
Feng, Gong-Kan
Deng, Rong
Zhu, Xiao-Feng
Li, Hou-Jin
PHYTOCHEMISTRY, 2022, 204
[8] Naucleamides A-E, new monoterpene indole alkaloids from Nauclea latifolia
Shigemori, H
Kagata, T
Ishiyama, H
Morah, F
Ohsaki, A
Kobayashi, J
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (01) : 58 - 61
[9] Melotenuines A-E, cytotoxic monoterpenoid indole alkaloids from Melodinus tenuicaudatus
Liu, Jian-Wen
Huo, Zong-Qing
Zhao, Qian
Hao, Xiao-Jiang
He, Hong-Ping
Zhang, Yu
FITOTERAPIA, 2019, 138
[10] Penicibrocazines A-E, Five New Sulfide Diketopiperazines from the Marine-Derived Endophytic Fungus Penicillium brocae
Meng, Ling-Hong
Zhang, Peng
Li, Xiao-Ming
Wang, Bin-Gui
MARINE DRUGS, 2015, 13 (01): : 276 - 287

← 1 2 3 4 5 →