Cytotoxic 1,3-Thiazole and 1,2,4-Thiadiazole Alkaloids from Penicillium oxalicum: Structural Elucidation and Total Synthesis

被引:22
|
作者
Yang, Zheng [1 ]
Huang, Nianyu [1 ]
Xu, Bang [1 ,2 ,3 ]
Huang, Wenfeng [4 ]
Xie, Tianpeng [1 ]
Cheng, Fan [1 ]
Zou, Kun [1 ]
机构
[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
[2] China Three Gorges Univ Peoples Hosp, Yichang 443000, Peoples R China
[3] Yichang First Peoples Hosp, Yichang 443000, Peoples R China
[4] China Three Gorges Univ, Coll Med, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
基金
中国国家自然科学基金;
关键词
Penicillium oxalicum; alkaloids; total synthesis; structure elucidation; cytotoxicity; IMMUNOSUPPRESSIVE POLYKETIDES; DALDINIA-ESCHSCHOLZII; MYXOCOCCUS-FULVUS; FUNGUS; 1,3,4-THIADIAZOLE; INHIBITORS; GLUCOSIDE; CANCER; ANALOG;
D O I
10.3390/molecules21030232
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Two new thiazole and thiadiazole alkaloids, penicilliumthiamine A and B (2 and 3), were isolated from the culture broth of Penicillium oxalicum, a fungus found in Acrida cinerea. Their structures were elucidated mainly by spectroscopic analysis, total synthesis and X-ray crystallographic analysis. Biological evaluations indicated that compound 1, 3a and 3 exhibit potent cytotoxicity against different cancer cell lines through inhibiting the phosphorylation of AKT/PKB (Ser 473), one of important cancer drugs target.
引用
收藏
页数:12
相关论文
共 50 条
  • [21] Synthesis of some 1,3-thiazole, 1,3,4-thiadiazole, pyrazolo[5,1-c]-1,2,4-triazine, and 1,2,4-triazolo[5,1-c]-1,2,4-triazine derivatives based on the thiazolo[3,2-a]benzimidazole moiety
    Hamdy, Nehal A.
    Abdel-Aziz, Hatem A.
    Farag, Ahmad M.
    Fakhr, Issa M. I.
    MONATSHEFTE FUR CHEMIE, 2007, 138 (10): : 1001 - 1010
  • [22] The effect of docosahexaenoic acid moiety on the cytotoxic activity of 1,2,4-thiadiazole derivatives
    Akimov M.G.
    Gretskaya N.M.
    Karnoukhova V.A.
    Serkov I.V.
    Proshin A.N.
    Shtratnikova V.Yu.
    Bezuglov V.V.
    Biochemistry (Moscow) Supplement Series B: Biomedical Chemistry, 2014, 8 (1) : 43 - 46
  • [23] Synthesis of new 1,3-thiazole derivatives from 2(5)-hydroxyalkyl-1,3-thiazole-5(2)-carbaldehydes
    Sinenko, V. O.
    Slivchuk, S. R.
    Pil'o, S. G.
    Raenko, G. F.
    Brovarets, V. S.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2016, 86 (07) : 1597 - 1603
  • [24] Synthesis of new 1,3-thiazole derivatives from 2(5)-hydroxyalkyl-1,3-thiazole-5(2)-carbaldehydes
    V. O. Sinenko
    S. R. Slivchuk
    S. G. Pil’o
    G. F. Raenko
    V. S. Brovarets
    Russian Journal of General Chemistry, 2016, 86 : 1597 - 1603
  • [25] Synthesis, structure elucidation and cytotoxic activities of 2,5-disubstituted-1,3,4-thiadiazole and 1,2,4-triazole-3-thione derivatives
    Kandemir, Levent
    Karakus, Sevgi
    Ozbas, Suna
    Rollas, Sevim
    Akbuga, Julide
    JOURNAL OF RESEARCH IN PHARMACY, 2022, 26 (04): : 941 - 953
  • [26] Synthesis and Biological Evaluation of 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives as Potential Cytotoxic Agents
    Shi, Yao-Jie
    Song, Xue-Jiao
    Li, Xiao
    Ye, Ting-Hong
    Xiong, Ying
    Yu, Luo-Ting
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (11) : 1099 - 1104
  • [27] Novel binary compounds derived from 1,2,4-thiadiazole
    A. N. Proshin
    I. V. Serkov
    S. O. Bachurin
    Doklady Chemistry, 2012, 446 : 171 - 173
  • [28] Novel binary compounds derived from 1,2,4-thiadiazole
    Proshin, A. N.
    Serkov, I. V.
    Bachurin, S. O.
    DOKLADY CHEMISTRY, 2012, 446 : 171 - 173
  • [29] Design, Synthesis and Anticancer Activity of 1,2,4-Thiadiazole Derivatives Bearing 1,2,4-Oxadiazole
    D. G. S. Sudhakar
    A. Srinivasa Rao
    Ch. Venkata Ramana Reddy
    Russian Journal of General Chemistry, 2019, 89 : 1696 - 1701
  • [30] Heterocyclization of Isoniazid: Synthesis and Antimicrobial Activity of Some New Pyrimidine, 1, 3-Thiazole, 1, 2, 4-Thiadiazole, and 1, 2, 4-Triazole Derivatives Derived from Isoniazid
    Farhan, Mona E.
    Assy, Mohammed G.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2019, 62 (02): : 171 - 180