摘要
目的研究腺梗豨莶Siegesbeckia pubescens的化学成分及其蛋白酪氨酸磷酸酶1B(protein tyrosine phosphatase 1B,PTP1B)抑制活性。方法综合运用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、MCI柱色谱、半制备高效液相色谱(HPLC)等多种现代色谱技术对其化学成分进行分离纯化,利用质谱、核磁共振等波谱技术鉴定了单体化合物结构,并通过体外酶促反应对化合物进行PTP1B抑制剂活性评价。结果从腺梗豨莶75%乙醇提取物中分离鉴定了32个化合物,分别为对映-16βH,17-羟基贝壳杉烷-19-羧酸(1)、对映-16α,17-二羟基贝壳杉烷-19-羧酸(2)、豨莶酸(3)、对映-16βH,17-异丁酰氧基-18-羟基贝壳杉烷-19-羧酸(4)、对映-18-乙酰氧基-17羟基-16βH-贝壳杉烷-19-羧酸(5)、奇壬醇(6)、对映-16-乙酰氧基-2α,15,19-三羟基海松烷-8(14)-烯(7)、darutoside(8)、对映-1β,3β,15,16-四羟基海松烷-8(14)-烯(9)、对映-(15R),16,19-三羟基海松烷-8(14)-烯-19-O-β-D-吡喃葡萄糖苷(10)、对映-15-乙酰氧基-2α,16,19-三羟基海松烷-8(14)-烯(11)、对映-2α,15R,16,19-四羟基海松烷-8(14)-烯(12)、16-O-acetyldarutoside(13)、15-O-acetyldarutoside(14)、对映-15,16,19-三羟基海松烷-8(14)-烯(15)、(4β,10E)-6α,14,15-trihydroxy-8β(tigloyloxy)-germacra-1(10),11(13)-diene-12-oicacid12,6-lactone(16)、2-propenoicacid,2-methyl-2,3,3α,4,5,8,9,10,11,11α-decahydro-6,10-bis(hydroxyl-methyl)-3-methylene-2-oxocyclodeca[b]furan-4-ylester(17)、(4β,10E)-6α,14,15-trihydroxy-8β-(isobutyryloxy)germacra-10,11(13)-diene-12-oic acid 12,6-lactone(18)、siegesbeckialide K(19)、(4β,10E)-6a,14,15-trihydroxy-8β-(senecioyloxy)-germacra-1(10),11(13)-diene-12-oicacid12,6-lactone(20)、1(10)E,4Z-9α-ethoxy-6α,15-dihydroxy-8β-(tigloyloxy)-14-oxogermacra-1(10),4,11(13)-triene-12-oicacid 12,6-lactone(21)、17(13→4)-abeo-ent-3S^(*),13S^(*),16-trihydroxystrob-8(15)-ene(22)、strobol A(23)、2β,19-dihydroxy-15-devinyl-ent-pimar-8,11,13-triene(24)、阿亚黄素(25)、山柰酚-3-O-芸香糖苷(26)、3,5,3′-三羟基-7,4′-二甲氧基黄酮(27)、黑麦草内酯(28)、(6R,9S)-roseoside(29)、咖啡酸(30)、(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5-tetrameth-oxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′-sesquineolignan-7″,9″-diol(31)、(-)-(7R,7′R,7″S,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5-tetrameth-oxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′-sesquineolignan-7″,9″-diol(32)。结论化合物25~27、31、32为首次从豨莶草中分离得到。化合物1、2、4对PTP1B有一定的抑制作用。
Objective The study focuses on the chemical constituents of Siegesbeckia pubescens and their inhibitory activity against protein tyrosine phosphatase 1B(PTP1B).Methods A combination of silica gel column chromatography,Sephadex LH-20 gel column,MCI column,and semi-preparative HPLC was employed for the separation and purification of its chemical components.The structures of individual compounds were identified using mass spectrometry and nuclear magnetic resonance spectroscopy.Additionally,the inhibitory activity of the compounds against PTP1B was assessed through in vitro enzymatic assays.Results A total of 32 compounds were isolated and identified from the 75%ethanol extract of S.pubescens,which are as follows:ent-16βH,17-hydroxy-kauran-19-oic acid(1),ent-16α,17-dihydroxykauran-19-oic acid(2),siegesbeckic acid(3),ent-16βH,17-isobutyryloxy-18-hydroxy-kauran-19-oic acid(4),18-acetoxy-ent-17-hydroxy-16βH-kauran-19-oicacid(5),kirenol(6),ent-16-acetoxy-2α,15,19-trihydroxypimar-8(14)-ene(7),darutoside(8),ent-1β,3β,15,16-tetrahydroxypimar-8(14)-ene(9),ent-(15R),16,19-trihydroxypimar-8(14)-ene-19-O-β-D-glucopyranoside(10),ent-15-acetoxy-2α,16,19-trihydroxypimar-8(14)-ene(11),ent-2α,15R,16,19-tetrahydroxypimar-8(14)-ene(12),16-O-acetyldarutoside(13),15-O-acetyldarutoside(14),ent-15,16,19-tetrahydroxypimar-8(14)-ene(15),(4β,10E)-6α,14,15-trihydroxy-8β(tigloyloxy)-germacra-1(10),11(13)-diene-12-oic acid 12,6-lactone(16),2-propenoicacid,2-methyl-2,3,3α,4,5,8,9,10,11,11α-decahydro-6,10-bis(hydroxyl-methyl)-3-methylene-2-oxocyclodeca[b]furan-4-yl ester(17),(4β,10E)-6α,14,15-trihydroxy-8β-(isobutyryloxy)germacra-10,11(13)-diene-12-oic acid 12,6-lactone(18),siegesbeckialide K(19),(4β,10E)-6a,14,15-trihydroxy-8β-(senecioyloxy)-germacra-1(10),11(13)-diene-12-oic acid 12,6-lactone(20),1(10)E,4Z-9α-ethoxy-6α,15-dihydroxy-8β-(tigloyloxy)-14-oxogermacra-1(10),4,11(13)-triene-12-oic acid 12,6-lactone(21),17(13→4)-abeo-ent-3S^(*),13S^(*),16-trihydroxystrob-8(15)-ene(22),strobol A(23),2β,19-dihydroxy-15-devinyl-ent-pimar-8,11,13-triene(24),ayanin(25),kaempferol 3-O-rutinoside(26),3,5,3′-trihydroxy-7,4′-dimethoxyflavone(27),loliolide(28),(6R,9S)-roseoside(29),caffeic acid(30),(-)-(7R,7′R,7″R,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5-tetrameth-oxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′-sesquineolignan-7″,9″-diol(31),(-)-(7R,7′R,7″S,8S,8′S,8″S)-4′,4″-dihydroxy-3,3′,3″,5-tetrameth-oxy-7,9′:7′,9-diepoxy-4,8″-oxy-8,8′-sesquineolignan-7″,9″-diol(32).Conclusion Compounds 25-27,31,and 32 were isolated from S.pubescens for the first time.Compounds 1,2,and 4 exhibited certain inhibitory effects on PTP1B.
作者
张雪琪
闵建国
卢志标
石媛慧
邹洵
周艳林
ZHANG Xueqi;MIN Jianguo;LU Zhibiao;SHI Yuanhui;ZOU Xun;ZHOU Yanlin(School of Pharmacy,Guangxi University of Chinese Medicine,Nanning 530200,China;Guilin Sanjin Pharmaceutical Co.,Ltd.,Gulin 541004,China;Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201,China)
出处
《中草药》
北大核心
2025年第11期3806-3818,共13页
Chinese Traditional and Herbal Drugs
基金
广西科技基地和人才专项(桂科AD25069106)。
