[关键词]
[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)、dankasterones A(6)、14α-羟基麦角甾-4,7,9,22-四烯-3,6-二酮(7)、5'-epichaxine B(8)、dankasterone B(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、2.96 μmol/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。
[Key word]
[Abstract]
Objective To investigate the chemical constituents from the rice solid culture of Hericium alpestre and their α-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 to α-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 significant α-glucosidase inhibitory activity, with IC50 values of 1.38, 2.61, 2.61, 6.22, 2.28, 1.86, 1.59, 3.15, 2.96 μmol/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.
[中图分类号]
R284.1
[基金项目]
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)