Pleosmaranes A-R, Isopimarane and 20-nor Isopimarane Diterpenoids with Anti-inflammatory Activities from the Mangrove Endophytic Fungus Pleosporales sp. HNQQJ-1

被引:4
作者
Wang, Guisheng [1 ,2 ,3 ]
Yuan, Yilin [2 ]
Li, Zhaokun [1 ]
Liu, Xuguang [2 ]
Chu, Yanhai [2 ]
She, Zhigang [3 ]
Kang, Wenyi [2 ]
Chen, Yan [1 ,2 ]
机构
[1] Anhui Med Univ, Sch Pharm, Hefei 230032, Peoples R China
[2] Henan Univ, Natl R&D Ctr Edible Fungus Proc Technol, Kaifeng 475004, Peoples R China
[3] Sun Yat Sen Univ, Sch Chem, Guangzhou 510275, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2024年 / 87卷 / 02期
基金
中国国家自然科学基金;
关键词
DERIVATIVES;
D O I
10.1021/acs.jnatprod.3c00893
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Pleosmaranes A-R (1-18), 18 new isopimarane-type diterpenoids, together with four known analogs (19-22), were isolated from the mangrove endophytic fungus Pleosporales sp. HNQQJ-1. Their structures and absolute configurations were established by analysis of their spectroscopic data and electronic circular dichroism (ECD) calculations. Compounds 1-9 possess an unusual aromatic B ring and a 20-nor-isopimarane skeleton. Compounds 15-17 contain a unique 2-oxabicyclo[2.2.2]octane moiety. Compound 18 features an unexpected 2-oxabicyclo[3.2.1]octane moiety. Compounds 8 and 12 exhibited a moderate inhibitory effect against LPS-induced NO production, with IC50 values of 19 and 25 mu M, respectively.
引用
收藏
页码:304 / 314
页数:11
相关论文
共 19 条
  • [1] [Anonymous], 2016, Gaussian16
  • [2] Immunosuppressive Nor-isopimarane Diterpenes from Cultures of the Fungicolous Fungus Xylaria longipes HFG1018
    Chen, He-Ping
    Zhao, Zhen-Zhu
    Cheng, Gui-Guang
    Zhao, Kuan
    Han, Kai-Yue
    Zhou, Lin
    Feng, Tao
    Li, Zheng-Hui
    Liu, Ji-Kai
    [J]. JOURNAL OF NATURAL PRODUCTS, 2020, 83 (02): : 401 - 412
  • [3] Secondary metabolites from mangrove-associated fungi: source, chemistry and bioactivities
    Chen, Senhua
    Cai, Runlin
    Liu, Zhaoming
    Cui, Hui
    She, Zhigang
    [J]. NATURAL PRODUCT REPORTS, 2022, 39 (03) : 560 - 595
  • [4] Anti-inflammatory activities of alkaloids from the mangrove endophytic fungus Phomopsis sp. SYSUQYP-23
    Chen, Yan
    Zhang, Lishan
    Zou, Ge
    Li, Changqun
    Yang, Wencong
    Liu, Hongju
    She, Zhigang
    [J]. BIOORGANIC CHEMISTRY, 2020, 97
  • [5] Ascomylactams A-C, Cytotoxic 12-or 13-Membered-Ring Macrocyclic Alkaloids Isolated from the Mangrove Endophytic Fungus Didymella sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C
    Chen, Yan
    Liu, Zhaoming
    Huang, Yun
    Liu, Lan
    He, Jianguo
    Wang, Lan
    Yuan, Jie
    She, Zhigang
    [J]. JOURNAL OF NATURAL PRODUCTS, 2019, 82 (07): : 1752 - 1758
  • [6] Tedanol: A potent anti-inflammatory ent-pimarane diterpene from the Caribbean Sponge Tedania ignis
    Costantino, Valeria
    Fattorusso, Ernesto
    Mangoni, Alfonso
    Perinu, Cristina
    Cirino, Giuseppe
    De Gruttola, Luana
    Roviezzo, Fiorentina
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (21) : 7542 - 7547
  • [7] Diaporisoindoles A-C: Three Isoprenylisoindole Alkaloid Derivatives from the Mangrove Endophytic Fungus Diaporthe sp SYSU-HQ3
    Cui, Hui
    Lin, Yun
    Luo, Mingchu
    Lu, Yongjun
    Huang, Xishan
    She, Zhigang
    [J]. ORGANIC LETTERS, 2017, 19 (20) : 5621 - 5624
  • [8] Sphaeropsidins B and C, phytotoxic pimarane diterpenes from Sphaeropsis sapinea f. sp. Cupressi and Diplodia mutila
    Evidente, A
    Sparapano, L
    Fierro, O
    Bruno, G
    Giordano, F
    Motta, A
    [J]. PHYTOCHEMISTRY, 1997, 45 (04) : 705 - 713
  • [9] Asperterpenoid A, a New Sesterterpenoid as an Inhibitor of Mycobacterium tuberculosis Protein Tyrosine Phosphatase B from the Culture of Aspergillus sp 16-5c
    Huang, Xishan
    Huang, Hongbo
    Li, Hanxiang
    Sun, Xuefeng
    Huang, Huarong
    Lu, Yongjun
    Lin, Yongcheng
    Long, Yuhua
    She, Zhigang
    [J]. ORGANIC LETTERS, 2013, 15 (04) : 721 - 723
  • [10] Aspewentins D-H, 20-Nor-isopimarane Derivatives from the Deep Sea Sediment-Derived Fungus Aspergillus wentii SD-310
    Li, Xiao-Dong
    Li, Xiao-Ming
    Li, Xin
    Xu, Gang-Ming
    Liu, Yang
    Wang, Bin-Gui
    [J]. JOURNAL OF NATURAL PRODUCTS, 2016, 79 (05): : 1347 - 1353