中山大学学报（自然科学版）2021，Vol.60Issue(3)：19-29,11.DOI:10.13471/j.cnki.acta.snus.2020.03.21.2020C007
深绿卷柏中木脂素成分及10个木脂素结构的修订
Lignans from Selaginella doederleinii and revision of structures of ten lignans
摘要
Abstract
Five known lignans including three 8,4′?oxyneolignans[(?)?erythro?(7′E)?4,9?dihy-droxy?3,3′,5′?trimethoxy?8,4′?oxyneolign?7′?en?9′?al(1),(?)?erythro?guaiacylglycerol?β?O?4′?sinapyl ether(2),and(7′E)?3,5,3′,5′?tetramethoxy?8,4′?oxyneolign?7′?ene?4,9,9′?triol (3)],a benzofuran[(+)?(7R,8S)?5?methoxydihydrodehydrodiconiferyl alcohol(4)],and one furofu-ran[syringaresinol(5)]were isolated from the traditional Chinese medicine Selaginella doederleinii. Their structures were elucidated by HRMS and 1D and 2D NMR data. The inhibitory activities of 1?5 against thioredoxin reductase(TrxR)were evaluated,and three compounds showed moderate activities with IC50 values ranging from 10. 1 to 20. 2μmol/L. Compounds 1?4 were isolated from S. doederleinii for the first time. In addition,it was found that the structures of ten known lignans[2,6,2′,6′?tetrame-thoxy?4,4′?bis(2,3?epoxy?1?hydroxypropyl)biphenyl(Ⅰ),griffilignan A(Ⅱ),2?hydroxy?3,2′, 6′?trimethoxy?4′?(2,3?epoxy?1?hydroxypropyl)?5?(3?hydroxy?l?propenyl)biphenyl(Ⅲ),2?hy-droxy?3,2′?dimethoxy?4′?(2,3?epoxy?1?hydroxypropyl)?5?(3?hydroxy?1?propenyl)biphenyl (Ⅳ),2,2′?dimethoxy?4?(3?hydroxy?l?propenyl)?4′?(1,2,3?trihydroxypropyl)diphenyl ethers(ⅤandⅥ),(7?R,8?R)?2,2′?dimethoxy?4?(3?hydroxyl?propenyl)?4′?(1,2,3?trihydroxypropyl)biphe-nyl ether(Ⅶ),utiline B(Ⅷ),and rhemaneolignans A and B(ⅨandⅩ)]were erroneously identified as the types of biphenylneolignans and 4,4′?oxyneolignans due to incorrect elucidation. By comparison of their NMR data with those of model compounds such as some reported synthetic products and the iso-lates(1?5),the structures ofⅠ?Ⅹwere revised as(+)?syringaresinol(5),(+)?pinoresinol(6),(?)?simulanol(7),(?)?dehydrodiconiferyl alcohol(8),(?)?threo?guaiacylglycerol?β?O?4′?coniferyl ether(9),(+)?erythro?guaiacylglycerol?β?O?4′?coniferyl ether(10a),(?)?erythro?guaiacylglycerol?β?O?4′?coniferyl ether(10b),(+)?threo?guaiacylglycerol?β?O?4′?sinapyl ether(11),(?)?threo?methyl 4?O?[2?hydroxy?2?(4?hydroxy?3?methoxyphenyl)?1?(hydroxymethyl)ethyl]ferulate(12), and(+)?erythro?methyl 4?O?[2?hydroxy?2?(4?hydroxy?3?methoxyphenyl)?1?(hydroxymethyl)eth-yl]ferulate(13),respectively. So,it noteworthy that there is no evidence for the existence of the ten lig-nans in nature,and their revised structures are actually represented as the types of furofurans,benzofu-rans,and 8,4′?oxyneolignans,respectively.关键词
卷柏科(Selaginellaceae)/深绿卷柏(Selaginella doederleinii)/木脂素/联苯新木脂素/结构修订Key words
Selaginellaceae/Selaginella doederleinii/lignan/biphenylneolignan/structural revision分类
化学化工引用本文复制引用
汤卓雅,潘月华,邹明锋,胡荣,唐贵华..深绿卷柏中木脂素成分及10个木脂素结构的修订[J].中山大学学报（自然科学版）,2021,60(3):19-29,11.基金项目
广东省中医药局项目(20191058) （20191058）
国家自然科学基金(81973203) （81973203）
广东省基础与应用基础研究基金(2020A1515010841) （2020A1515010841）
