海洋来源真菌Eutypel...9次级代谢产物研究（英文）_易继凌.pdf

有机化学有机化学 Chinese Journal of Organic Chemistry ARTICLE *Corresponding authors.E-mail:; Received June 26,2022;revised August 16,2022;published online September 15,2022.Project supported by the Key Science and Technology Program of Hainan Province(No.ZDKJ202008),the Hainan Provincial Natural Science Foundation of China(No.221QN229)and Innovation and Entrepreneurship Training Program for College Students(No.202111658007).海南省重大科技计划(No.ZDKJ202008)、海南省自然科学基金(No.221QN229)和大学生创新创业训练计划(No.202111658007)资助项目.Chin.J.Org.Chem.2023,43,295298 2023 Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences http:/sioc- DOI:10.6023/cjoc202206046 研究论文研究论文 海洋来源真菌 Eutypella sp.F0219 次级代谢产物研究 易继凌a,b 施康琦a,b 吴冰林a,b 黎婉珊*,a,b 陈光英*,a,b(a海南师范大学化学与化工学院 热带药用资源化学教育部重点实验室 海口 571158)(b海南师范大学化学与化工学院 热带药用植物化学海南省重点实验室 海口 571158)摘要摘要 弯孢聚壳属真菌能产生结构丰富多样的活性化合物.对一株来自海洋沉积物的真菌 Eutypella sp.F0219 代谢产物研究中,分离得到一个新的异戊烯基取代二氢异香豆素和一个新的色烯酰胺衍生物,分别命名为 eutypellarins A 和 B(1 和 2),以及两个已知的异戊二烯取代苯甲醛衍生物(3 和 4).通过高分辨质谱、核磁共振波谱以及量子化学计算对新化合物的结构进行确定.首次从弯孢聚壳属真菌中发现异戊二烯取代二氢异香豆素和色烯酰胺衍生物.采用 2,2-联氮-双-3-乙基苯并噻唑啉-6-磺酸(ABTS)自由基清除法和铁离子还原(FRAP)法对所有化合物进行总抗氧化能力的测定.结果显示化合物 1 和 4 具有中等的抗氧化效果,其 Trolox 等效抗氧化能力分别为(0.510.016)和(0.760.007).关键词关键词 海洋真菌;弯孢聚壳属;异戊二烯取代二氢异香豆素;色烯酰胺衍生物;总抗氧化能力测试 Study on Secondary Metabolites of Marine-Derived Fungus Eutypella sp.F0219 Yi,Jilinga,b Shi,Kangqia,b Wu,Binglina,b Li,Wanshan*,a,b Chen,Guangying*,a,b(a Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education,College of Chemistry and Chemical Engineering,Hainan Normal University,Haikou 571158)(b Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province,College of Chemistry and Chemical Engineering,Hainan Normal University,Haikou 571158)Abstract The fungus Eutypella sp.is well known for producing bioactive compounds with diverse structures.Chemical investigation of the fungi Eutypella sp.F0219 isolated from marine sediment,yielded a new prenylated dihydroisocoumarin and a new chromene amide derivative,named eutypellarins A and B(1 and 2),together with two known prenylated benzaldehyde derivatives(3 and 4).The structures of these compounds were elucidated based on HR-ESIMS,extensive nucler magneti resonance(NMR)experiments,and quantum-chemical electronic circular dichroism(ECD)calculations.Prenylated dihydroisocoumarin and chromene amide derivatives are reported from the genus Eutypella for the first time.The total antioxidant capacities of all compounds were measured through 2,2-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid(ABTS)and ferric-reducing antioxidant power(FRAP)assay.The results showed that compounds 1 and 4 exhibited moderate antioxidant properities with Trolox equivalent antioxidant capacity(TEAC)values(0.510.016)and(0.760.007),respectively.Keywords marine-derived fungi;Eutypella sp.;prenylated dihydroisocoumarins;chromene amide derivatives;total antioxidant capacity assays 1 Introduction Marine-derived fungi continue to attract considerable attention as an important spring of novel secondary metab-olites displaying promising biological and pharmacological properties.1 The Eutypella species are mainly reported to be distributed in the South China Sea,the soil of Antarctica and Arctic,and tropical forests of Australia and Thai-land.2 So far,a variety of secondary metabolites have been isolated from the genus of Eutypella,such as-lactones,sesquiterpenoids,3-5 cytochalasin derivatives,6 pimarane diterpenoids,7-14 thiodiketopiperazines,15-16 and cytosporin-related compounds,17 many of which indicated antitumor,anti-inflammatory,anti-human immunodefi-有机化学 研究论文 296 http:/sioc- Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences Chin.J.Org.Chem.2023,43,295298 ciency virus(HIV),immunosuppressive,and antimicrobial activities.3-18 However,the prenylated dihydroisocouma-rin and chromene amide derivatives have not been reported from this species.In the course of our systematic investigation of fungus Eutypella sp.F0219 isolated from the sediment and col-lected in the northern part of the South China Sea,we firstly found a new prenylated dihydroisocoumarin and a new chromene amide derivative,named eutypellarins A(1)and B(2),together with two known prenylated benzalde-hyde derivatives(3 and 4)(Figure 1).Compounds 1 and 4 displayed moderate antioxidant properties,whose Trolox equivalent antioxidant capacity(TEAC)values were found to be(0.510.016)and(0.760.007),respectively.Herein,we report the isolation,structural elucidation,and antioxidant activities of these compounds.OH21341357135245ONHOOHO311712111597510OHOO4a8a1OHOHCHOOHOHCHO Figure 1 Structures of eutypellarins A and B(1 and 2)and two known benzaldehyde derivatives 2 Results and discussion Compound 1 was obtained as pale yellow powder.Its negative HR-ESIMS measurements suggested a molecular formula of C19H26O4(m/z 317.1739,calcd for MH 317.1747),indicating that 1 had seven degrees of unsatura-tion.Based on the 1D-NMR spectroscopic data for 1(Ta-ble 1),five degrees of unsaturation were due to e