Bresmycins A and B, potent anti-breast cancer indolocarbazole alkaloids from the sponge-associated Streptomyces sp. NBU3142

被引:4
|
作者
Ding, Lijian [1 ]
Li, Wenhao [1 ]
Zhong, Xiaodan [2 ]
Feng, Fangjian [1 ]
Xin, Yi [1 ]
Yan, Xiaojun [1 ]
Lazaro, J. Enrico H. [4 ]
Zhang, Bin [1 ]
Shi, Yutong [1 ]
Yang, Guan-Jun [2 ]
He, Shan [1 ,3 ]
机构
[1] Ningbo Univ, Coll Food & Pharmaceut Sci, Li Dak Sum Yip Yio Chin Kenneth Li Marine Biopharm, Dept Marine Pharm, Ningbo 315832, Peoples R China
[2] Ningbo Univ, Sch Marine Sci, Ningbo 315832, Peoples R China
[3] Peking Univ, Ningbo Inst Marine Med, Ningbo 315800, Peoples R China
[4] Univ Philippines Diliman, Natl Inst Mol Biol & Biotechnol, Quezon City 1101, Philippines
基金
中国国家自然科学基金;
关键词
Streptomyces; Secondary metabolites; Anticancer; Breast cancer; RHODIUM(III) COMPLEX; INHIBITION; DISCOVERY; PRODUCTS; BIOLOGY;
D O I
10.1016/j.molstruc.2023.135809
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Two previously undescribed indolocarbazole alkaloids, bresmycins A (1) and B (2) were isolated from the culture extract of the marine mesophotic zone sponge-associated Streptomyces sp. NBU3142. Their structures were assigned by using the detailed NMR and MS spectroscopic analyses. Their relative and absolute configurations were established by coupling constants, NOESY correlations and comparison of experimental ECD spectra. Biological evaluation revealed that compounds 1 and 2 exhibited significant cytotoxicity against breast cancer cell line MCF-7 with IC50 values in the range of 2.01-7.08 & mu;M. In addition, compound 2 was found to display a strong inhibitory effect (IC50 = 4.47 & mu;M) against adriamycin-resistant MCF-7 (MCF-7/ADR) cells. The structure-activity differences of bresmycins A and B suggested that an additional N-methyl group in O-acetylhy-droxylamine moiety should be the key factors to their anticancer activities.
引用
收藏
页数:6
相关论文
共 24 条
  • [1] Alkaloids from the Sponge-Associated Fungus Aspergillus sp.
    Zhou, Yaming
    Debbab, Abdessamad
    Mandi, Attila
    Wray, Victor
    Schulz, Barbara
    Mueller, Werner E. G.
    Kassack, Matthias
    Lin, WenHan
    Kurtan, Tibor
    Proksch, Peter
    Aly, Amal H.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (05) : 894 - 906
  • [2] An “olivomycin A” derivative from a sponge-associated Streptomyces sp. strain SP 85
    Mohsen Gozari
    Nima Bahador
    Mohammad Seddiq Mortazavi
    Ebrahim Eftekhar
    Amir Reza Jassbi
    3 Biotech, 2019, 9
  • [3] Novel Antimycin Analogues with Agricultural Antifungal Activities from the Sponge-Associated Actinomycete Streptomyces sp. NBU3104
    Li, Wenhao
    Ding, Lijian
    Li, Juan
    Wen, Huimin
    Liu, Yang
    Tan, Shuangling
    Yan, Xiaojun
    Shi, Yutong
    Lin, Wenhan
    Lin, Hou-Wen
    He, Shan
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2022, 70 (27) : 8309 - 8316
  • [4] An "olivomycin A" derivative from a sponge-associated Streptomyces sp. strain SP 85
    Gozari, Mohsen
    Bahador, Nima
    Mortazavi, Mohammad Seddiq
    Eftekhar, Ebrahim
    Jassbi, Amir Reza
    3 BIOTECH, 2019, 9 (12)
  • [5] A new xanthostatin analogue from the marine sponge-associated actinomycete Streptomyces sp. SCSIO 40064
    Chen, Siqiang
    Zhang, Qingbo
    Zhang, Xinya
    Jiang, Xiaodong
    Zhang, Haibo
    Zhu, Yiguang
    Zhang, Changsheng
    Zhang, Liping
    NATURAL PRODUCT RESEARCH, 2022, 36 (14) : 3529 - 3537
  • [6] A New Benzofuran Glycoside and Indole Alkaloids from a Sponge-Associated Rare Actinomycete, Amycolatopsis sp.
    Kwon, Yun
    Kim, Seong-Hwan
    Shin, Yoonho
    Bae, Munhyung
    Kim, Byung-Yong
    Lee, Sang Kook
    Oh, Ki-Bong
    Shin, Jongheon
    Oh, Dong-Chan
    MARINE DRUGS, 2014, 12 (04): : 2326 - 2340
  • [7] Molecular networking-guided isolation of undescribed antifungal odoriferous sesquiterpenoids from a marine mesophotic zone sponge-associated Streptomyces sp. NBU3428
    Wen, Huimin
    Zhang, Dashuai
    Zhao, Hang
    Zhang, Yawen
    Yan, Xiaojun
    Lin, Wenhan
    He, Shan
    Ding, Lijian
    PHYTOCHEMISTRY, 2023, 213
  • [8] VIRIDOBRUNNINES A AND B, ANTIMICROBIAL PHENOXAZINONE ALKALOIDS FROM A SOIL ASSOCIATED STREPTOMYCES SP.
    Zhang, Xiu Mei
    Liu, Xu
    Wang, Zhe
    Tian, Zhen Hua
    Xie, Wei Dong
    HETEROCYCLES, 2015, 91 (09) : 1809 - 1814
  • [9] Optimization and production of pyrrolidone antimicrobial agent from marine sponge-associated Streptomyces sp. MAPS15
    G. Sathiyanarayanan
    R. Gandhimathi
    B. Sabarathnam
    G. Seghal Kiran
    Joseph Selvin
    Bioprocess and Biosystems Engineering, 2014, 37 : 561 - 573
  • [10] SPONGE-ASSOCIATED FUNGI ISOLATES FROM ANCORINA SP. SHOWED ANTI-CANCER ACTIVITY AGAINST HELA CELL LINES
    Pramana, Abrory Agus Cahya
    Ramadhani, Eka
    Priyambada, Fajar
    Pertiwi, Gian Aditya
    Setiawibawa, R. Aditya Aryandi
    Wijayanti, Nastiti
    JOURNAL OF MICROBIOLOGY BIOTECHNOLOGY AND FOOD SCIENCES, 2022, 12 (01):