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Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog,asperpyrroindotide A,using LC–MS/MS-based molecular networking

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marine Life Science & Technology 2023年第1期5卷 85-93页

作者： Yi-Qian Han Qun Zhang Wei-Feng Xu Yang Hai Rong Chao Cui-Fang Wang Xue-Mei Hou Mei-Yan Wei Yu-Cheng Gu Chang-Yun Wang Chang-Lun Shao Key Laboratory of marine Drugs the Ministry of Education of ChinaSchool of Medicine and PharmacyOcean University of ChinaQingdao 266003China State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources School of Chemistry and Pharmaceutical SciencesGuangxi Normal UniversityGuilin 541004China College of Food Science and Engineering Ocean University of ChinaQingdao 266003China Syngenta Jealott’s Hill International Research Centre BracknellBerkshire RG426EYUK Laboratory for marine Drugs and Bioproducts Qingdao National Laboratory for Marine Science and TechnologyQingdao 266237China

Further insights on the secondary metabolites of a soft coral-derived fungus Aspergillus versicolor under the guidance of MS/MS-based molecular networking led to the isolation of seven known cycloheptapeptides,namely,asperversiamides A–C(1–3)and asperheptatides A–D(4–7)and an unusual pyrroloindoline-containing new cycloheptapeptide,asperpyrroindotide A(8).The structure of 8 was elucidated by comprehensive spectroscopic data analysis,and its absolute configuration was determined by advanced Marfey’s method.The semisynthetic transformation of 1 into 8 was successfully achieved and the reaction conditions were optimized.Additionally,a series of new derivatives(10−19)of asperversiamide A(1)was semi-synthesized and their anti-tubercular activities were evaluated against Mycobacterium tuberculosis H37Ra.The preliminary structure−activity relationships revealed that the serine hydroxy groups and the tryptophan residue are important to the activity.

关键词： marine natural product MS/MS-based molecular networking Cycloheptapeptides Semi-synthesis Anti-tubercular activity

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Structure modification,antialgal,antiplasmodial,and toxic evaluations of a series of new marine-derived 14-membered resorcylic acid lactone derivatives

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marine Life Science & Technology 2022年第1期4卷 88-97页

作者： Wei-Feng Xu Na-Na Wu Yan-Wei Wu Yue-Xuan Qi Mei-Yan Wei Laura M.Pineda Michelle G.Ng Carmenza Spadafora Ji-Yong Zheng Ling Lu Chang-Yun Wang Yu-Cheng Gu Chang-Lun Shao Key Laboratory of marine Drugs the Ministry of Education of ChinaSchool of Medicine and PharmacyOcean University of ChinaQingdao266003China Laboratory for marine Drugs and Bioproducts Qingdao National Laboratory for Marine Science and TechnologyQingdao266237China State Key Laboratory for marine Corrosion and Protection Luoyang Ship Material Research Institute(LSMRI)Qingdao266237China Center of Cellular and Molecular Biology of Diseases Instituto de Investigaciones Científcas y Servicios de Alta TecnologíaCity of KnowledgeClaytonApartado0816-02852Panama Syngenta Jealott’s Hill International Research Centre BracknellBerkshireRG426EYUK

marine natural products play critical roles in the chemical defense of many marine organisms and are essential,reputable sources of successful drug leads.Sixty-seven 14-membered resorcylic acid lactone derivatives 3–27 and 30–71 of the natural product zeaenol(1)isolated from the marine-derived fungus Cochliobolus lunatus were semisynthesized by chlorination,acylation,esterification,and acetalization in one to three steps.The structures of these new derivatives were established by HRESIMS and NMR techniques.All the compounds(1–71)were evaluated for their antialgal and antiplasmodial activities.Among them,14 compounds displayed antifouling activities against adhesion of the fouling diatoms.In particular,9 and 34 exhibited strong and selective inhibitory effects against the diatoms Navicula laevissima and Navicula exigua(EC50=6.67 and 8.55μmol/L),respectively,which were similar in efficacy to those of the positive control SeaNine 211(EC50=2.90 and 9.74μmol/L).More importantly,38,39,and 69–71 showed potent antiplasmodial activities against Plasmodium falciparum with IC50 values ranging from 3.54 to 9.72μmol/L.Very interestingly,the five antiplasmodial derivatives displayed non-toxicity in the cytotoxicity assays and the zebrafish embryos model,thus,representing potential promising antiplasmodial drug agents.The preliminary structure–activity relationships indicated that biphenyl substituent at C-2,acetonide at positions C-5′and C-6′,and tri-or tetra-substituted of acyl groups increased the antiplasmodial activity.Therefore,combining evaluation of chemical ecology with pharmacological models will be implemented as a systematic strategy,not only for environmentally friendly antifoulants but also for structurally novel drugs.

关键词： marine natural product 14-Membered resorcylic acid lactone Zeaenol Semisynthesis Antialgal activity Antiplasmodial activity

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Arenicolsterol A, a Novel Cytotoxic Enolic Sulfated Sterol from a marine Annelid Arenicola cristata

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Chinese Journal of Chemistry 2005年第5期23卷 599-602页

作者：陈彬沈先荣孔继烈 DepartmentofChemistry FudanUniversityShanghai200433China NavalMedicineInstitute Shanghai200433China

marine organisms are the important source of the bioactive metabolites. A novel enolic sulfated sterol, arenicolsterol A, has been isolated from a marine annelid Arenicola cristata collected in the coast of Mainland of China. The structure was elucidated using all sorts of spectroscopic data including ESIMS, 1D and 2D NMR etc . The cytotoxic bioactivity of this sterol was evaluated by MTT assay. It could inhibit the growth of human cervix cancer cell line (Hela) and human non‐small cell lung cancer cell line (NCI‐h6) with IC 50 of (3.1±0.6) µg/mL and (7.6±0.8) µg/mL.

关键词： marine natural product carcinoma Arenicola cristata sterol

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