高山猴头菌的化学成分及抑制α-葡萄糖苷酶活性研究  

Chemical constituents from Hericium alpestre and itsα-glucosidase inhibitory activities

作　　者：周洁[1,2] 王雨曦 魏玉莲 武昕[1] 袁海生[1,2] ZHOU Jie;WANG Yuxi;WEI Yulian;WU Xin;YUAN Haisheng(School of Life Sciences and Biopharmaceuticals,Shenyang Pharmaceutical University,Shenyang 110016,China;CAS Key Laboratory of Forest Ecology and Management,Institute of Applied Ecology,Chinese Academy of Sciences,Shenyang 110164,China)

机构地区：[1]沈阳药科大学生命科学与生物制药学院,辽宁沈阳110016 [2]中国科学院森林生态与管理重点实验室,中国科学院沈阳应用生态研究所,辽宁沈阳110164

出　　处：《中草药》2024年第16期5407-5417,共11页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金青年项目(32100013);沈阳市科技计划项目(22-322-3-07);辽宁省应用基础研究计划项目(2022JH2/101300182)。

摘　　要：目的研究高山猴头菌Hericium alpestre大米固体发酵物中的化学成分及其α-葡萄糖苷酶抑制活性。方法采用硅胶柱色谱、ODS柱色谱、HP20柱色谱和高效液相色谱(high performance liquid chromatography,HPLC)等色谱方法进行分离纯化,利用质谱(mass spectrometer,MS)、核磁共振(nuclear magnetic resonance,NMR)等方法对单体化合物进行结构鉴定。同时通过pNPG法对化合物进行抑制α-葡萄糖苷酶活性的测试。结果从高山猴头菌固体发酵物中分离得到21个化合物,分别鉴定为枸橼蒽类固醇B(1)、7-氧代-β-谷甾醇(2)、22E-7α-甲氧基-5α,6α-环氧麦角甾-8(14),22-二烯-3β-醇(3)、5α,8α-过氧麦角甾醇(4)、4-羟基-17R-甲基甾醇(5)、dankasteronesA(6)、14α-羟基麦角甾-4,7,9,22-四烯-3,6-二酮(7)、5′-epichaxineB(8)、dankasteroneB(9)、灵芝果苷D(10)、5α,6α-环氧-3β-羟基-(22E,24R)-麦角甾-8,22-二烯-7-酮(11)、(3β,5α,6β,22E)-6-甲氧基麦角甾-7,22-二烯-3,5-二醇(12)、6β-甲氧基麦角甾-7,9(11),22E-三烯-3β,5α-二醇(13)、(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇(14)、3β,5α,9α-三羟基-(22E,24R)-麦角甾-7,22-二烯-6-酮(15)、4-对羟基苯甲醛(16)、(S)-2-羟基-2-(4-甲氧基苯基)乙酸(17)、对羟基苯乙醇(18)、1-O-(9Z,12Z-十八碳二烯酰基)甘油(19)、亚油酸甲酯(20)和9,10-二羟基十八烷酸酯(21)。化合物1、3、6、8、10、14、15、17和19具有较好的α-葡萄糖苷酶抑制活性,其半数抑制浓度(median inhibition concentration,IC50)分别为1.38、2.61、2.61、6.22、2.28、1.86、1.59、3.15、2.96μmol/L。结论化合物17为新天然产物,化合物1~3、9~11、13、16~21首次从猴头菌属真菌中分离得到,化合物1、3、6、8、10、14、15、17和19具有潜在的降血糖作用。Objective To investigate the chemical constituents from the rice solid culture of Hericium alpestre and theirα-glucosidase inhibitory activities.Methods All compounds were separated and purified by chromatography methods such as silica gel column chromatography,ODS column chromatography,HP20 column chromatography and high-performance liquid chromatography.The structures were identified through mass spectrometry(MS)and nuclear magnetic resonance(NMR).The inhibitory activities of the compounds toα-glucosidase were tested by pNPG method.Results Twenty-one compounds were isolated from H.alpestre,and identified as citreoanthrasteroid B(1),7-oxo-β-sitosterol(2),22E-7α-methoxy-5α,6α-epoxyergosta-8(14),22-dien-3β-ol(3),5α,8α-peroxyergosterol(4),4-hydroxy-17R-methylincisterol(5),dankasterones A(6),calvasterol A(7),5′-epichaxine B(8),dankasterone B(9),ganodermaside D(10),5α,6α-epoxy-3β-hydroxy-(22E,24R)-ergosta-8,22-dien-7-one(11),(3β,5α,6β,22E)-6-methoxyergosta-7,22-diene-3,5-diol(12),6β-methoxyergosta 7,9(11),22E-triene-3β,5α-diol(13),(22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol(14),3β,5α,9α-trihydroxy-(22E,24R)-ergosta-7,22-dien-6-one(15),4-hydroxybenzaldehyde(16),(S)-2-hydroxy-2-(4-methoxyphenyl)acetic acid(17),p-hydroxyphenylethanol(18),1-O-(9Z,12Z-octadecadienoyl)glycerol(19),methyl linoleate(20)and 9,10-dihydroxyoctadecanoate(21).Compounds 1,3,6,8,10,14,15,17 and 19 had significantα-glucosidase inhibitory activity,with IC50 values of 1.38,2.61,2.61,6.22,2.28,1.86,1.59,3.15,2.96μmol/L,respectively.Conclusion Compound 17 is a new natural product.Compounds 1-3,9-11,13,16-21 were isolated for the first time from fungi of genus Hericium.Compounds 1,3,6,8,10,14,15,17 and 19 have potential hypoglycemic effects.

关 键 词：高山猴头菌 甾体类化合物 α-葡萄糖苷酶抑制活性 枸橼蒽类固醇B 22E-7α-甲氧基-5α 6α-环氧麦角甾-8(14) 22-二烯-3β-醇 灵芝果苷D (S)-2-羟基-2-(4-甲氧基苯基)乙酸 

分 类 号：R284.1[医药卫生—中药学]