Cordycepamides A-E and cordyglycoside A, new alkaloidal and glycoside metabolites from the entomopathogenic fungus Cordyceps sp.

被引：7
作者：
Fan, Wenwen [1 ,2 ,3 ]
Li, Erwei [3 ]
Ren, Jinwei [3 ]
Wang, Wenzhao [3 ]
Liu, Xingzhong [3 ,4 ]
Zhang, Yongjie [1 ]
机构：
[1] Shanxi Univ, Sch Life Sci, Taiyuan 030006, Peoples R China
[2] Shanxi Univ, Inst Biotechnol, Taiyuan 030006, Peoples R China
[3] Chinese Acad Sci, Inst Microbiol, State Key Lab Mycol, Beijing 100101, Peoples R China
[4] Nankai Univ, Coll Life Sci, Dept Microbiol, Tianjin 300071, Peoples R China
来源：
FITOTERAPIA | 2020年 / 142卷
基金：
中国国家自然科学基金;
关键词：
Cordyceps sp; Entomopathogenic fungus; Alkaloidal metabolite; Enantiomer; BEAUVERICIN; BASSIATIN;
D O I：
10.1016/j.fitote.2020.104525
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Five new alkaloidal metabolites cordycepamides A-E (1-5), and one glycoside metabolite cordyglycoside A (6), together with six known compounds (7-12) were isolated from the entomopathogenic fungus Cordyceps sp. (LB1.18060004) from unidentified insect collected in Baoshan City, Yunnan Province, People's Republic of China. The structures were characterized by NMR and HRESIMS spectroscopic analyses. Cordycepamides A and B (1 and 2) were mixtures of two isomers in 5:4 ratio by integration of H-1 NMR spectra. In additional, the structure of cordycepamide A (1) was further confirmed by X-ray crystallography as a pair of enantiomers. Absolute configurations of sugar moiety of cordyglycoside A (6) was confirmed by the acid hydrolysis and subsequent HPLC analysis. The isolated metabolites were evaluated for antimicrobial, cytotoxicity, and the DPPH scavenging assay, only 4 showed modest antioxidant effects in the DPPH scavenging assay (IC50 = 51.42 +/- 3.08 mu M).
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页数：7
相关论文
共 23 条
  • [1] [Anonymous], 2011, CRYSALISPRO VERS 1 1
  • [2] Resorcinosides A and B, Glycosylated Alkylresorcinols from a Marine-Derived Strain of the Fungus Penicillium janthinellum
    Choi, Byeoung-Kyu
    Thi Hoai Trinh Phan
    Hwang, Sunghoon
    Oh, Dong-Chan
    Kang, Jong Soon
    Lee, Hwa-Sun
    Thi Duy Ngoc Ngo
    Thi Thanh Van Tran
    Shin, Hee Jae
    [J]. JOURNAL OF NATURAL PRODUCTS, 2019, 82 (11): : 3186 - 3190
  • [3] Coniochaetones E-I, new 4H-chromen-4-one derivatives from the Cordyceps-colonizing fungus Fimetariella sp.
    Deng, Lianwu
    Niu, Shubing
    Liu, Xingzhong
    Che, Yongsheng
    Li, Erwei
    [J]. FITOTERAPIA, 2013, 89 : 8 - 14
  • [4] New beauvericins, potentiators of antifungal miconazole activity, produced by Beauveria sp FKI-1366 -: I.: Taxonomy, fermentation, isolation and biological properties
    Fukuda, T
    Arai, M
    Yamaguchi, Y
    Masuma, R
    Tomoda, H
    Omura, S
    [J]. JOURNAL OF ANTIBIOTICS, 2004, 57 (02) : 110 - 116
  • [5] ISOLATION OF BEAUVERICIN AS AN INSECT TOXIN FROM FUSARIUM-SEMITECTUM AND FUSARIUM-MONILIFORME VAR SUBGLUTINANS
    GUPTA, S
    KRASNOFF, SB
    UNDERWOOD, NL
    RENWICK, JAA
    ROBERTS, DW
    [J]. MYCOPATHOLOGIA, 1991, 115 (03) : 185 - 189
  • [6] ISOLATION OF NOVEL BEAUVERICIN ANALOGS FROM THE FUNGUS BEAUVERIA-BASSIANA
    GUPTA, S
    MONTLLOR, C
    HWANG, YS
    [J]. JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (05): : 733 - 738
  • [7] New alkaloidal metabolites from cultures of entomopathogenic fungus Cordyceps takaomontana NBRC 101754
    Hama, Maichi
    Elshamy, Abdelsamed, I
    Yoneyama, Tatsuro
    Kasai, Yusuke
    Yamamoto, Hirohumi
    Tanigawa, Kana
    Oshiro, Ayari
    Noji, Masaaki
    Ban, Sayaka
    Imagawa, Hiroshi
    Umeyama, Akemi
    [J]. FITOTERAPIA, 2019, 139
  • [8] Total synthesis of bassiatin and its stereoisomers: Novel divergent Behavior of substrates in Mitsunobu cyclizations
    Hughes, AB
    Sleebs, MM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) : 3079 - 3088
  • [9] Unique diketopiperazine dimers from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449
    Isaka, M
    Palasarn, S
    Rachtawee, P
    Vimuttipong, S
    Kongsaeree, P
    [J]. ORGANIC LETTERS, 2005, 7 (11) : 2257 - 2260
  • [10] Structures of cordypyridones A-D, antimalarial N-hydroxy- and N-methoxy-2-pyridones from the insect pathogenic fungus Cordyceps nipponica
    Isaka, M
    Tanticharoen, M
    Kongsaeree, P
    Thebtaranonth, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) : 4803 - 4808
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