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
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 21 条
  • [1] Antibacterial cannabinoids from Cannabis sativa:: A structure-activity study
    Appendino, Giovanni
    Gibbons, Simon
    Giana, Anna
    Pagani, Alberto
    Grassi, Gianpaolo
    Stavri, Michael
    Smith, Eileen
    Rahman, Mukhlesur
    [J]. JOURNAL OF NATURAL PRODUCTS, 2008, 71 (08): : 1427 - 1430
  • [2] Determination of relative configuration in organic compounds by NMR spectroscopy and computational methods
    Bifulco, Giuseppe
    Dambruoso, Paolo
    Gomez-Paloma, Luigi
    Riccio, Raffaele
    [J]. CHEMICAL REVIEWS, 2007, 107 (09) : 3744 - 3779
  • [3] Marine natural products
    Blunt, John W.
    Copp, Brent R.
    Keyzers, Robert A.
    Munro, Murray H. G.
    Prinsep, Michele R.
    [J]. NATURAL PRODUCT REPORTS, 2015, 32 (02) : 116 - 211
  • [4] Marine-derived fungi: a chemically and biologically diverse group of microorganisms
    Bugni, TS
    Ireland, CM
    [J]. NATURAL PRODUCT REPORTS, 2004, 21 (01) : 143 - 163
  • [5] Polyhydroxylated Sterols from the South China Sea Gorgonian Verrucella umbraculum
    Cao, Fei
    Shao, Chang-Lun
    Wang, Yu
    Xu, Kai-Xia
    Qi, Xin
    Wang, Chang-Yun
    [J]. HELVETICA CHIMICA ACTA, 2014, 97 (06) : 900 - 908
  • [6] Antiviral C-25 Epimers of 26-Acetoxy Steroids from the South China Sea Gorgonian Echinogorgia rebekka
    Cao, Fei
    Shao, Chang-Lun
    Chen, Min
    Zhang, Meng-Qi
    Xu, Kai-Xia
    Meng, Hong
    Wang, Chang-Yun
    [J]. JOURNAL OF NATURAL PRODUCTS, 2014, 77 (06): : 1488 - 1493
  • [7] Frisch M. J., 2009, Gaussian 09 Rev. D.01
  • [8] NEW PLANT-GROWTH REGULATORS, CLADOSPOLIDE-A AND CLADOSPOLIDE-B, MACROLIDES PRODUCED BY CLADOSPORIUM-CLADOSPORIOIDES
    HIROTA, A
    SAKAI, H
    ISOGAI, A
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1985, 49 (03): : 731 - 735
  • [9] New macrolides and furan carboxylic acid derivative from the sponge-derived fungus Cladosporium herbarum
    Jadulco, R
    Proksch, P
    Wray, V
    Sudarsono
    Berg, A
    Gräfe, U
    [J]. JOURNAL OF NATURAL PRODUCTS, 2001, 64 (04): : 527 - 530
  • [10] Bioactive natural products from a sclerotium-colonizing isolate of Humicola fuscoatra
    Joshi, BK
    Gloer, JB
    Wicklow, DT
    [J]. JOURNAL OF NATURAL PRODUCTS, 2002, 65 (11): : 1734 - 1737