Xylarins A-D, Two Pairs of Diastereoisomeric Isoindoline Alkaloids from the Endolichenic Fungus Xylaria sp.

被引：12
|
作者：
Xu, Ke [1 ,2 ]
Li, Ruijuan [3 ]
Zhu, Rongxiu [4 ]
Li, Xiaobin [5 ]
Xu, Yuliang [1 ]
He, Qiaobian [1 ]
Xie, Fei [1 ]
Qiao, Yanan [1 ]
Luan, Xiaoyi [1 ]
Lou, Hongxiang [1 ]
机构：
[1] Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol,Minist Educ, Jinan 250012, Peoples R China
[2] Shandong Univ, Hosp 2, Cheeloo Coll Med, Dept Clin Pharm, Jinan 250033, Peoples R China
[3] Shandong Univ, Helmholtz Inst Biotechnol, State Key Lab Microbial Technol, Qingdao 266237, Shandong, Peoples R China
[4] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
[5] Qilu Univ Technol, Biol Inst, Shandong Acad Sci, Jinan 250103, Peoples R China
来源：
ORGANIC LETTERS | 2021年 / 23卷 / 20期
基金：
中国国家自然科学基金; 国家重点研发计划;
关键词：
GENE-CLUSTER; SESQUITERPENES; IDENTIFICATION; REVEAL;
D O I：
10.1021/acs.orglett.1c02730
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two pairs of diastereoisomeric isoindoline alkaloids, xylarins A-D (1-4), were isolated from the endolichenic fungus Xylaria sp. Xylarins A and B (1 and 2) possess a previously undescribed 5/6/5-5/6 polycyclic scaffold, featuring a combination of a novel dihydrobenzofurone unit and an isoindoline unit, while xylarins C and D (3 and 4) contain an additional N,N-dimethylaniline at the C-3' position. Their structures were elucidated by comprehensive spectroscopic analyses combined with single-crystal X-ray diffraction and electronic circular dichroism calculations. The plausible biosynthetic pathways and gene clusters for 1-4 were proposed. Compound 1 exhibited significant antithrombotic activity.
引用
收藏
页码：7751 / 7754
页数：4
相关论文
共 50 条
  • [31] Two new cytochalasins from the endophytic fungus Xylaria sp. GDGJ-77B
    Xu, Zhao-Long
    Li, Ben-Chao
    Huang, Li-Li
    Lv, Liu-Xia
    Luo, Yan
    Xu, Wei-Feng
    Yang, Rui-Yun
    NATURAL PRODUCT RESEARCH, 2024, 38 (09) : 1503 - 1509
  • [32] Guaiane sesquiterpenes and isopimarane diterpenes from an endophytic fungus Xylaria sp.
    Wu, Shao-Hua
    He, Jian
    Li, Xiao-Nian
    Huang, Rong
    Song, Fei
    Chen, You-Wei
    Miao, Cui-Ping
    PHYTOCHEMISTRY, 2014, 105 : 197 - 204
  • [33] A New Compound from the Endophytic Fungus Xylaria sp. from Sophora tonkinensis
    Na Zheng
    Quan Liu
    Dong-Lan He
    Yan Liang
    Jun Li
    Rui-Yun Yang
    Chemistry of Natural Compounds, 2018, 54 : 447 - 449
  • [34] Secondary metabolites of Xylaria sp., an endophytic fungus from Taxus mairei
    Lin, Xiao
    Yu, Miao
    Lin, Ting
    Zhang, Lianru
    NATURAL PRODUCT RESEARCH, 2016, 30 (21) : 2442 - 2447
  • [35] CYTOCHALASINS PRODUCED BY Xylaria sp., AN ENDOPHYTIC FUNGUS FROM Piper aduncum
    Silva, Geraldo H.
    de Oliveira, Camila M.
    Teles, Helder L.
    Bolzani, Vanderlan da S.
    Araujo, Angela R.
    Pfenning, Ludwig H.
    Young, Maria Claudia M.
    Costa-Neto, Claudio M.
    Haddad, Renato
    Eberlin, Marcos N.
    QUIMICA NOVA, 2010, 33 (10): : 2038 - 2041
  • [36] Pseudoceramines A-D, new antibacterial bromotyrosine alkaloids from the marine sponge Pseudoceratina sp.
    Yin, Sheng
    Davis, Rohan A.
    Shelper, Todd
    Sykes, Melissa L.
    Avery, Vicky M.
    Elofsson, Mikael
    Sundin, Charlotta
    Quinn, Ronald J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) : 6755 - 6760
  • [37] Xyloketal H from the mangrove endophytic fungus Xylaria sp. 2508
    X. Liu
    F. Xu
    Y. Zhang
    L. Liu
    H. Huang
    X. Cai
    Y. Lin
    W. Chan
    Russian Chemical Bulletin, 2006, 55 : 1091 - 1092
  • [38] Polyketides with antimicrobial activity from the solid culture of an endolichenic fungus Ulocladium sp.
    Wang, Quan-Xin
    Bao, Li
    Yang, Xiao-Li
    Guo, Hui
    Yang, Rui-Nan
    Ren, Biao
    Zhang, Li-Xin
    Dai, Huan-Qin
    Guo, Liang-Dong
    Liu, Hong-Wei
    FITOTERAPIA, 2012, 83 (01) : 209 - 214
  • [39] Neopestolides A-D, Diphenyl Ether Derivatives from the Plant Endophytic Fungus Neopestalotiopsis sp.
    Li, Chuan
    Xu, Yang
    Fu, Peinan
    Guo, Liangdong
    Che, Yongsheng
    JOURNAL OF NATURAL PRODUCTS, 2022, 85 (03): : 607 - 613
  • [40] Austdiol, fulvic acid and citromycetin derivatives from an endolichenic fungus, Myxotrichum sp.
    Yuan, Chao
    Wang, Hai-Ying
    Wu, Chang-Sheng
    Jiao, Yang
    Li, Ming
    Wang, Yan-Yan
    Wang, Shu-Qi
    Zhao, Zun-Tian
    Lou, Hong-Xiang
    PHYTOCHEMISTRY LETTERS, 2013, 6 (04) : 662 - 666
12345