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
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
收藏
页数:9
相关论文
共 50 条
  • [41] Asperones A-E, five dimeric polyketides with new carbon skeletons from the fungus Aspergillus sp AWG 1-15
    Yin, Guo-Ping
    Wu, Ya-Rong
    Han, Chao
    Wang, Xiao-Bing
    Gao, Hong-Liang
    Yin, Yong
    Kong, Ling-Yi
    Yang, Ming-Hua
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (16): : 2432 - 2436
  • [42] Sorbicillamines A-E, Nitrogen-Containing Sorbicillinoids from the Deep-Sea-Derived Fungus Penicillium sp F23-2
    Guo, Wenqiang
    Peng, Jixing
    Zhu, Tianjiao
    Gu, Qianqun
    Keyzers, Robert A.
    Li, Dehai
    JOURNAL OF NATURAL PRODUCTS, 2013, 76 (11): : 2106 - 2112
  • [43] Targeted isolation of prenylated indole alkaloids from the marine-derived fungus Penicillium janthinellum HK1-6 using molecular networking
    Hao, Bao-Cong
    Zheng, Yao-Yao
    Li, Zhong-Hui
    Zheng, Cai-Juan
    Wang, Chang-Yun
    Chen, Min
    NATURAL PRODUCT RESEARCH, 2024, 38 (13) : 2252 - 2257
  • [44] Speradines B-D, oxygenated cyclopiazonic acid alkaloids from the sponge-derived fungus Aspergillus flavus MXH-X104
    Ma, Xinhua
    Peng, Jixing
    Wu, Guangwei
    Zhu, Tianjiao
    Li, Guoqiang
    Gu, Qianqun
    Li, Dehai
    TETRAHEDRON, 2015, 71 (21) : 3522 - 3527
  • [45] Neuropyrones A-E, five undescribed α-pyrone derivatives with tyrosinase inhibitory activity from the endophytic fungus Neurospora dictyophora WZ-497
    Li, Xin
    Gong, Yuan-Xiang
    Feng, Li
    Wang, Xin-Jia
    Wang, Jing-Wen
    Zhang, An-Xin
    Tan, Ning-Hua
    Wang, Zhe
    PHYTOCHEMISTRY, 2023, 207
  • [46] Maeruines A-E, elusive indole alkaloids from stems of Maerua siamensis and their inhibitory effects on cyclooxygenases and HT-29 colorectal cancer cell proliferation
    Nukulkit, Sasiwimon
    Nalinratana, Nonthaneth
    Aree, Thammarat
    Suriya, Utid
    Suttisri, Rutt
    Nuengchamnong, Nitra
    Chang, Hsun-Shuo
    Chansriniyom, Chaisak
    PHYTOCHEMISTRY, 2025, 229
  • [47] ISOLATION OF FESTUCLAVINE AND 3 NEW INDOLE ALKALOIDS, ROQUEFORTINE A, B AND C FROM CULTURES OF PENICILLIUM-ROQUEFORTI .12. PRODUCTION OF ALKALOIDS AND RELATED SUBSTANCES BY FUNGI
    OHMOMO, S
    SATO, T
    UTAGAWA, T
    ABE, M
    JOURNAL OF THE AGRICULTURAL CHEMICAL SOCIETY OF JAPAN, 1975, 49 (11): : 615 - 623
  • [48] Asperorydines N-P, three new cyclopiazonic acid alkaloids from the marine-derived fungus Aspergillus flavus SCSIO F025
    Xiang, Yao
    Zeng, Qi
    Mai, Zhi-Mao
    Chen, Yu-Chan
    Shi, Xue-Feng
    Chen, Xia-Yu
    Zhong, Wei-Mao
    Wei, Xiao-Yi
    Zhang, Wei-Min
    Zhang, Si
    Wang, Fa-Zuo
    FITOTERAPIA, 2021, 150
  • [49] Structure, absolute configuration, and conformational study of resorcylic acid derivatives and related congeners from the fungus Penicillium brocae
    Zhang, Peng
    Meng, Ling-Hong
    Mandi, Attila
    Li, Xiao-Ming
    Kurtan, Tibor
    Wang, Bin-Gui
    RSC ADVANCES, 2015, 5 (50) : 39870 - 39877
  • [50] Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae
    Zhang, Peng
    Meng, Ling-Hong
    Mandi, Attila
    Kurtan, Tibor
    Li, Xiao-Ming
    Liu, Yang
    Li, Xin
    Li, Chun-Shun
    Wang, Bin-Gui
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (19) : 4029 - 4036