Bioactive 7-Oxabicyclic[6.3.0]lactam and 12-Membered Macrolides from a Gorgonian-Derived Cladosporium sp Fungus

被引：31
|
作者：
Cao, Fei [1 ]
Yang, Qin [2 ,3 ]
Shao, Chang-Lun [1 ]
Kong, Chui-Jian [1 ]
Zheng, Juan-Juan [1 ]
Liu, Yun-Feng [1 ]
Wang, Chang-Yun [1 ]
机构：
[1] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ China, Qingdao 266003, Peoples R China
[2] Hebei Univ, Chinese Ctr Chiral, Key Lab Med Chem & Mol Diag, Minist Educ, Baoding 071002, Peoples R China
[3] Hebei Univ, Coll Pharm Sci, Baoding 071002, Peoples R China
来源：
MARINE DRUGS | 2015年 / 13卷 / 07期
基金：
中国国家自然科学基金;
关键词：
gorgonian-derived fungus; Cladosporium sp; bicyclic lactam; 12-membered macrolides; cytotoxic activity; ABSOLUTE-CONFIGURATION; GROWTH; ASSAY;
D O I：
10.3390/md13074171
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
One new bicyclic lactam, cladosporilactam A (1), and six known 12-membered macrolides (2-7) were isolated from a gorgonian-derived Cladosporium sp. fungus collected from the South China Sea. Their complete structural assignments were elucidated by comprehensive spectroscopic investigation. Quantum chemistry calculations were used in support of the structural determination of 1. The absolute configuration of 1 was determined by calculation of its optical rotation. Cladosporilactam A (1) was the first example of 7-oxabicyclic[6.3.0]lactam obtained from a natural source. Compound 1 exhibited promising cytotoxic activity against cervical cancer HeLa cell line with an IC50 value of 0.76 M.
引用
收藏
页码：4171 / 4178
页数：8
相关论文
共 35 条
  • [21] Thiocladospolides F-J, antibacterial sulfur containing 12-membered macrolides from the mangrove endophytic fungus Cladosporium oxysporum HDN13-314
    Wang, Wenxue
    Feng, Huimin
    Sun, Chunxiao
    Che, Qian
    Zhang, Guojian
    Zhu, Tianjiao
    Li, Dehai
    PHYTOCHEMISTRY, 2020, 178
  • [22] Aspergilones A and B, two benzylazaphilones with an unprecedented carbon skeleton from the gorgonian-derived fungus Aspergillus sp.
    Shao, Chang-Lun
    Wang, Chang-Yun
    Wei, Mei-Yan
    Gu, Yu-Cheng
    She, Zhi-Gang
    Qian, Pei-Yuan
    Lin, Yong-Cheng
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (02) : 690 - 693
  • [23] Structure, Absolute Configuration, and Conformational Study of 12-Membered Macrolides from the Fungus Dendrodochium sp Associated with the Sea Cucumber Holothuria nobilis Selenka
    Sun, Peng
    Xu, Dong-Xiao
    Mandi, Attila
    Kurtan, Tibor
    Li, Tie-Jun
    Schulz, Barbara
    Zhang, Wen
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14): : 7030 - 7047
  • [24] Bisabolane-Type Sesquiterpenoids from a Gorgonian-Derived Aspergillus sp Fungus Induced by DNA Methyltransferase Inhibitor
    Wang, Chao-Yi
    Liu, Yun-Feng
    Cao, Fei
    Wang, Chang-Yun
    CHEMISTRY OF NATURAL COMPOUNDS, 2016, 52 (06) : 1129 - 1132
  • [25] Bisabolane-Type Sesquiterpenoids from a Gorgonian-Derived Aspergillus sp. Fungus Induced by DNA Methyltransferase Inhibitor
    Chao-Yi Wang
    Yun-Feng Liu
    Fei Cao
    Chang-Yun Wang
    Chemistry of Natural Compounds, 2016, 52 : 1129 - 1132
  • [26] Lumazine Peptides Penilumamides B-D and the Cyclic Pentapeptide Asperpeptide A from a Gorgonian-Derived Aspergillus sp Fungus
    Chen, Min
    Shao, Chang-Lun
    Fu, Xiu-Mei
    Kong, Chui-Jian
    She, Zhi-Gang
    Wang, Chang-Yun
    JOURNAL OF NATURAL PRODUCTS, 2014, 77 (07): : 1601 - 1606
  • [27] Merosesquiterpenoids and Ten-Membered Macrolides from a Soft Coral-Derived Lophiostoma sp Fungus
    Zheng, Cai-Juan
    Shao, Chang-Lun
    Chen, Min
    Niu, Zhi-Gang
    Zhao, Dong-Lin
    Wang, Chang-Yun
    CHEMISTRY & BIODIVERSITY, 2015, 12 (09) : 1407 - 1414
  • [28] Aspergillolide, a new 12-membered macrolide from sea cucumber-derived fungus Aspergillus sp. S-3-75
    Tan, Jun-Jie
    Liu, Xiao-Yu
    Yang, Yang
    Li, Feng-Hua
    Tan, Chang-Heng
    Li, Yi-Ming
    NATURAL PRODUCT RESEARCH, 2020, 34 (08) : 1131 - 1137
  • [29] Bioactive chemical constituents from the marine-derived fungus Cladosporium sp. DLT-5
    Dai, Luting
    Xie, Qingyi
    Guo, Jiaocen
    Ma, Qingyun
    Yang, Li
    Yuan, Jingzhe
    Dai, Haofu
    Yu, Zhifang
    Zhao, Youxing
    JOURNAL OF OCEANOLOGY AND LIMNOLOGY, 2024, 42 (03) : 905 - 914
  • [30] Bioactive cyclohexene derivatives from a mangrove-derived fungus Cladosporium sp. JJM22
    Zhang, Bin
    Wu, Jia-Ting
    Zheng, Cai-Juan
    Zhou, Xue-Ming
    Yu, Zhang-Xin
    Li, Wan-Shan
    Chen, Guang-Ying
    Zhu, Guo-Yuan
    FITOTERAPIA, 2021, 149
1234