大苞鞘石斛酚类化学成分研究  

Phenolic chemical components from Dendrobium wardianum

作　　者：李汉芬 秦诗慧 周泽琴 杨柳[1] 胡江苗[1,2] LI Hanfen;QIN Shihui;ZHOU Zeqin;YANG Liu;HU Jiangmiao(State Key Laboratory of Phytochemistry and Plant Resources in West China,Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201,China;University of Chinese Academy of Science,Beijing 100049,China;Anhui University of Chinese Medicine,Hefei 230012,China)

机构地区：[1]中国科学院昆明植物研究所植物化学与西部资源持续利用国家重点实验室,云南昆明650201 [2]中国科学院大学,北京100049 [3]安徽中医药大学,安徽合肥230012

出　　处：《中草药》2024年第3期711-719,共9页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金面上项目(32170407)。

摘　　要：目的研究大苞鞘石斛Dendrobium wardianum茎中的酚类化学成分。方法运用硅胶柱色谱、Sephadex LH-20柱色谱、半制备液相色谱和制备薄层色谱等分离技术进行分离纯化。通过1H-NMR、13C-NMR、X射线单晶衍射、质谱等波谱数据和理化性质对化合物结构进行鉴定。结果从大苞鞘石斛茎中共分离得到31个酚类化合物,分别鉴定为4-羟基-3,3′,5′-三甲氧基联苄(1)、denbinobine(2)、柚皮素(3)、3,3′-二羟基-5,5′-二甲氧基联苄(4)、3,4ʹ-二羟基-5-甲氧基联苄(5)、5,7-二羟基色原酮(6)、dihydrotricin(7)、4,5-二羟基-3,7-二甲氧基-9,10-二氢菲(8)、1,4,7-三羟基-5-甲氧基芴酮(9)、二氢松柏醇二氢对羟基桂皮酸酯(10)、4,4′-二羟基-3,5-二甲氧基联苄(11)、(+)-丁香脂(12)、(+)-杜仲树脂酚(13)、N-反式桂皮酸酰对羟基苯乙胺(14)、丁香酸(15)、二氢松柏醇(16)、苜蓿素(17)、3,5,4′-三羟基-3′-甲氧基联苄(18)、threo-7-O-ethyl-9-O-(4-hydroxyphenyl)propionyl-guaiacylglycerol(19)、balanophonin(20)、ω-hydroxypropioguaiacone(21)、对羟基苯甲醛(22)、3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one(23)、(−)-铁皮石斛素B(24)、(+)-铁皮石斛素B(25)、dendrowillol A(26)、香草醛(27)、dihydro-p-cinnamic acid(28)、p-hydroxyphenethyl trans-ferulate(29)、对羟基苯甲酸(30)、对羟基肉桂酸(31)。结论首次获得了铁皮石斛素B的单晶并通过X射线单晶衍射,发现该化合物为一对外消旋体,其绝对构型分别为2S,3S和2R,3R,并对铁皮石斛素B进行了手性拆分。化合物20、25首次从石斛属植物中分离得到,化合物5、6、14、19、24、26、29、31均为首次从大苞鞘石斛中分离得到。Objective To study the phenolic chemical constituents of the Dendrobium wardianum stem.Methods The compounds were isolated and purified by silica gel column chromatography,Sephadex LH-20 column chromatography,semi-preparative liquid chromatography and preparative thin layer chromatography.Their structures were identified by the analysis of their spectra data of 1H-NMR,13C-NMR,X-single crystal diffraction,mass spectrum and the physiochemical properties.Results A total of 31 phenolic compounds were isolated from the stem of D.wardianum.They were identified as aloifol(1),denbinobine(2),naringenin(3),3,3′-dihydroxy-5,5′-dimethoxybibenzyl(4),gigantol(5),5,7′-dihydrochromone(6),dihydrotricin(7),4,5-dihydroxy-3,7-dimethoxy-9,10-dihydrophenanthrene(8),dendroflorin(9),dihydroconiferyl dihydro-p-coumarate(10),4,4′-dihydroxy-3,5-dimethoxybibenzyl(11),(+)-episyringaresinol(12),(+)-hydroxymedioresinol(13),N-trans-cinnamoyltyramine(14),syringic acid(15),dihydroconiferyl alcohol(16),tricin(17),3,5,4′-trihydroxy-3′-methoxybibenzyl(18),threo-7-O-ethyl-9-O-(4-hydroxyphenyl)propionyl-guaiacylglycerol(19),balanophonin(20),ω-hydroxypropioguaiacone(21),p-hydroxybenzaldehyde(22),3-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one(23),(−)-dendrocandin B(24),(+)-dendrocandin B(25),dendrowillol A(26),vanillin(27),dihydro-p-cinnamic acid(28),p-hydroxyphenethyl trans-ferulate(29),p-hydroxy-benzonic acid(30),(E)-p-hydroxy-cinnamic acid(31).Conclusion The single crystal of dendrocandin B was obtained for the first time and the compound was found to be a racemate by X-ray single crystal diffraction,their absolute configuration is 2S,3S and 2R,3R,and the chiral resolution of dendrocandin B was carried out.Compounds 20 and 25 were isolated from Dendrobium for the first time,and compounds 5,6,14,19,24,26,29,31 were isolated from Dendrobium wardianum for the first time.

关 键 词：大苞鞘石斛 外消旋体 3 4’-二羟基-5-甲氧基联苄 5 7-二羟基色原酮 铁皮石斛素B balanophonin 

分 类 号：R284.1[医药卫生—中药学]