Antibacterial Gilvocarcin-Type Aryl-C-Glycosides from a Soil-Derived Streptomyces Species

被引:9
|
作者
Ma, Rui [1 ]
Cheng, Shan [1 ]
Sun, Jiwen [1 ]
Zhu, Weiming [1 ,2 ]
Fu, Peng [1 ,2 ]
机构
[1] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ China, Qingdao 266003, Peoples R China
[2] Pilot Natl Lab Marine Sci & Technol Qingdao, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China
来源
JOURNAL OF NATURAL PRODUCTS | 2022年 / 85卷 / 10期
基金
中国国家自然科学基金;
关键词
ANTI-TUMOR ANTIBIOTICS; BETA-CARBOLINE ALKALOIDS; RESISTANCE;
D O I
10.1021/acs.jnatprod.2c00438
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Seven new gilvocarcin-type aryl -C-glycosides (1-7) and six known analogues (8-13) were isolated from the soil-derived Streptomyces sp. OUCMDZ-945. Their structures including absolute configurations were determined based on detailed spectroscopic analysis, chemical methods, ECD curves, and quantum chemical calculations. Compound 1, which we named digilvocarcin A, is the first reported bis-gilvocarcin derivative possessing a novel cyclobutane moiety. This dimeric skeleton was confirmed to be formed from gilvocarcin V (8) through a light-induced [2 + 2] cycloaddition. Compounds 1, 2, 5-8, and 11 showed antibacterial activity against Staphylococcus aureus ATCC 6538 and methicillin-resistant Staphylococcus aureus subsp. aureus ATCC 43300 (MIC values: 0.25-64 mu g/mL).
引用
收藏
页码:2282 / 2289
页数:8
相关论文
共 50 条
  • [41] New bioactive secondary metabolites from the soil-derived Streptomyces sp. S045 and their anti-bacterial and anti-type III secretion system activities
    Zhang, Xiaochun
    Song, Yuliang
    Zhang, Zhiqiang
    Lu, Chunhua
    Shen, Yuemao
    NATURAL PRODUCT RESEARCH, 2024,
  • [42] Penicillanthone and penicillidic acids A-C from the soil-derived fungus Penicillium aculeatum PSU-RSPG105
    Daengrot, Charuwan
    Rukachaisirikul, Vatcharin
    Tadpetch, Kwanruthai
    Phongpaichit, Souwalak
    Bowornwiriyapan, Kawitsara
    Sakayaroj, Jariya
    Shen, Xu
    RSC ADVANCES, 2016, 6 (46): : 39700 - 39709
  • [43] Jugiones A-D: Antibacterial Xanthone-Anthraquinone Heterodimers from Australian Soil-Derived Penicillium shearii CMB-STF067
    Sritharan, Thulasi
    Salim, Angela A.
    Khalil, Zeinab G.
    Capon, Robert J.
    ANTIBIOTICS-BASEL, 2024, 13 (01):
  • [44] Isolation of Secondary Metabolites from the Soil-Derived Fungus Clonostachys rosea YRS-06, a Biological Control Agent, and Evaluation of Antibacterial Activity
    Zhai, Ming-Ming
    Qi, Feng-Ming
    Li, Jie
    Jiang, Chun-Xiao
    Hou, Yue
    Shi, Yan-Ping
    Di, Duo-Long
    Zhang, Ji-Wen
    Weu, Quan-Xiang
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2016, 64 (11) : 2298 - 2306
  • [45] Geninthiocins E and F, two new cyclic thiopeptides with antiviral activities from soil-derived Streptomyces sp. CPCC 200267 using OSMAC strategy
    Fang, Yuan
    Wang, Jing
    Tang, Yan
    Guo, Zhe
    Bai, Jinglin
    Wu, Linzhuan
    Su, Jing
    Cen, Shan
    Yu, Liyan
    Zhang, Dewu
    JOURNAL OF ANTIBIOTICS, 2023, 76 (02): : 101 - 104
  • [46] Geninthiocins E and F, two new cyclic thiopeptides with antiviral activities from soil-derived Streptomyces sp. CPCC 200267 using OSMAC strategy
    Yuan Fang
    Jing Wang
    Yan Tang
    Zhe Guo
    Jinglin Bai
    Linzhuan Wu
    Jing Su
    Shan Cen
    Liyan Yu
    Dewu Zhang
    The Journal of Antibiotics, 2023, 76 : 101 - 104
  • [47] Marmycins a and b, cytotoxic pentacyclic c-glycosides from a marine sediment-derived actinomycete related to the genus Streptomyces
    Martin, Glenroy D. A.
    Tan, Lik T.
    Jensen, Paul R.
    Dimayuga, Rosalba Encarnacion
    Fairchild, Craig R.
    Raventos-Suarez, Carmen
    Fenical, William
    JOURNAL OF NATURAL PRODUCTS, 2007, 70 (09): : 1406 - 1409
  • [48] Asperidines A-C, pyrrolidine and piperidine derivatives from the soil-derived fungus Aspergillus sclerotiorum PSU-RSPG178
    Phainuphong, Patima
    Rukachaisirikul, Vatcharin
    Saithong, Saowanit
    Phongpaichit, Souwalak
    Sakayaroj, Jariya
    Srimaroeng, Chutima
    Ontawong, Atcharaporn
    Duangjai, Acharaporn
    Muangnil, Paradorn
    Muanprasat, Chatchai
    BIOORGANIC & MEDICINAL CHEMISTRY, 2018, 26 (15) : 4502 - 4508
  • [49] Discovery of Antifungal Norsesquiterpenoids from a Soil-Derived Streptomyces microflavus: Targeting Biofilm Formation and Synergistic Combination with Amphotericin B against Yeast-like Fungi
    Cao, Lu
    Tan, Junfeng
    Zhang, Zengguang
    Lin, Bin
    Mu, Yu
    Jiang, Mingguo
    Jiang, Yi
    Huang, Xueshi
    Han, Li
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (15) : 8521 - 8535
  • [50] Ilyomycins A- K, radicicol-type resorcylic acid lactones as potential immunosuppressants from a soil-derived Ilyonectria sp.
    Gao, Ying
    Zhou, Jia
    Meng, Xianggao
    Ouyang, Qianxi
    Gan, Yutian
    Ruan, Hanli
    BIOORGANIC CHEMISTRY, 2022, 123