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Endogenous biosynthesis of docosahexaenoic acid(DHA)regulates fish oocyte maturation by promoting pregnenolone production

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Zoological Research 2024年第1期45卷 176-188页

作者： Yi Li Xuehui Li Ding Ye Ru Zhang Chengjie Liu Mudan He Houpeng Wang Wei Hu Yonghua Sun State Key Laboratory of Freshwater Ecology and Biotechnology Institute of HydrobiologyInnovation Academy for Seed DesignChinese Academy of SciencesWuhanHubei 430072China College of Advanced Agricultural Sciences University of Chinese Academy of SciencesBeijing 100049China Hubei Hongshan Laboratory WuhanHubei 430070China

Omega-3 polyunsaturated fatty acids(n-3 PUFAs),particularly docosahexaenoic acid(22:6n-3,DHA),play crucial roles in the reproductive health of vertebrates,including humans.Nevertheless,the underlying mechanism related to this phenomenon remains largely unknown.In this study,we employed two zebrafish genetic models,i.e.,elovl2^(-/-)mutant as an endogenous DHAdeficient model and fat1(omega-3 desaturase encoding gene)transgenic zebrafish as an endogenous DHA-rich model,to investigate the effects of DHA on oocyte maturation and quality.Results show that the elovl2^(-/-)mutants had much lower fecundity and poorer oocyte quality than the wild-type controls,while the fat1 zebrafish had higher fecundity and better oocyte quality than wildtype controls.DHA deficiency in elovl2^(-/-)embryos led to defects in egg activation,poor microtubule stability,and reduced pregnenolone levels.Further study revealed that DHA promoted pregnenolone synthesis by enhancing transcription of cyp11a1,which encodes the cholesterol side-chain cleavage enzyme,thereby stabilizing microtubule assembly during oogenesis.In turn,the hypothalamic-pituitary-gonadal axis was enhanced by DHA.In conclusion,using two unique genetic models,our findings demonstrate that endogenously synthesized DHA promotes oocyte maturation and quality by promoting pregnenolone production via transcriptional regulation of cyp11a1.

关键词： Docosahexaenoic acid Oocyte maturation Oocyte quality pregnenolone Microtubule

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Rapid Microwave Assisted Synthesis and Antiproliferative Evaluation of Novel Steroidal Thiazole Derivatives

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Chemical Research in Chinese Universities 2017年第2期33卷 206-212页

作者： HUANG Yanmin ZHAO Dandan LIU Chang GAN Chunfang ZHAN Junyan LIN Qifu SHI Haixin CUI Jianguo College of Chemistry and Material Science Guangxi Teachers Education University Nanning 530001 P. R. China Guangxi Colleges and University Key Laboratory of Beibu Gulf Oil and Natural Gas Resource Effectfve Utffizat~'on Qizhou University Qizhou 535011 P. R. China

Three series of novel steroidal thiazole derivatives were synthesized by microwave assisted one-potreaction from pregnenolone, testosterone and estrone, respectively. Their structures were characterized by IR, NMRand HRMS, and the antiproliferative activities of all the synthesized compounds against human cervical carcinoma（HeLa）, human liver carcinoma（HepG2）, human lung carcinoma（A549）, nasopharyngeal carcinoma（CNE2） andnormal kidney epithelial cells（HEK293T） were screened. Among the compounds, 1-estron-17＇-ylidene-2-[4＇-（p-bromophenyl）-2＇-thiazol]hydrazone（12） displayed distinct antiproliferative activity against all the tested cancercell lines and was almost inactive to normal kidney epithelial cells.

关键词： Microwave assisted synthesis pregnenolone Testosterone Estrone Steroidal thiazole derivative

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Rapid microwave assisted synthesis and antiproliferative evaluation of novel steriadal thiazole derivatives

Rapid microwave assisted synthesis and antiproliferative eva...

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中国化学会全国第十二届有机合成化学学术研讨会

作者： Huang,Yanmin Zhao,Dandan Gan,Chunfang Liu,Zhipin Lin,Qifu Yang,Chunhui Shi,Haixin Cui,Jianguo College of Chemistry and Material Science Guangxi Teachers Education University Guangxi Colleges and University Key Laboratory of Beibu Gulf Oil and Natural Gas Resoure Effective Utilization Qizhou University

Heterocycles can enhance binding affinity and improve in vitro potency via hydrogen bond interactions.The compounds containing heterocycles had been widely applied to the field of medicine or pesticide because of its good biological activity 1].Thiazole is an important five-membered aromatic heterocycle possessing N and S atom.Compounds containing thiazole cycle display various biological functions due to its special chemical structure,such as antimicrobial,antiinflammatory,anticancer,anti-HIV-1 etc,and have obtained an extensive application in drugs,pesticides,and materials science etc2].Recently,some steroidal thiazole derivatives possessing a D-ring fused a thiazole were reported as anti-inflammatory and anti-tumor agents[3].In present studies,three series of novel steroidal thiazole derivatives were respectively synthesized through microwave assisted one-pot reaction of pregnenolone,testosterone and estrone with thiosemicarbazide and 4-substituted-ω-bromoacetophenones.Their structures were characterized by IR,NMR and HRMS,and the anticancer activity of all synthesized compounds against human cervical carcinoma(He La),human lung carcinoma(A549),human liver carcinoma cells(HEPG2) and normal kidney epithelial cells(HEK293T) was screened.Some compounds displayed distinct antiproliferative activity against all tested cancer cell lines,and was almost inactive to normal kidney epithelial cells.

关键词： microwave assisted synthesis pregnenolone testosterone estrone steroidal thiazole derivatives

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