黔产青钱柳化学成分及α-葡萄糖苷酶抑制活性研究
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摘要
为了阐明青钱柳中的降血糖功效成分,实验对黔产青钱柳进行了系统化学成分研究和α-葡萄糖苷酶抑制活性评价。利用各种色谱学手段和波谱学方法,从青钱柳叶80%乙醇提取物中分离鉴定出13个化合物,分别为阿福豆苷(1)、山柰酚3-O-(4″-O-乙酰基)-α-L-吡喃鼠李糖苷(2)、juglanoside J(3)、1α,2α,4β-3羟基-1,2,3,4-四氢萘酮(4)、青钱柳苷III(5)、青钱柳苷J(6)、黄体酮(7)、去酰基萝藦苷元(8)、20-乙酰氧基-4-烯-3-酮(9)、齐墩果酸(10)、5-O-P香豆酰奎宁酸甲酯(11)、亚麻酸甲酯(12)、软脂酸(13)。其中,化合物9为新天然产物,化合物2～4、7、8、11、13均为首次从该植物中分离得到。用PNPG法对化合物1～10进行了α-葡萄糖苷酶抑制活性筛选,结果显示,化合物1、2有较强的α-葡萄糖苷酶抑制活性,表明黄酮类成分是青钱柳降血糖功效的物质基础之一。
In order to elucidate the hypoglycemic components of C.paliurus,the chemical constituents and the inhibitory activity of α-glucosidase were systematic studied.13 compounds were isolated and identified from 80% ethanol extract of C.paliurus leaves by means of various chromatographic methods and spectroscopic methods.These compounds were characterized as afzelin(1),Kaempferol 3-O-(4″-O-acetyl)-α-L-rhamnopyranoside(2),juglanoside J(3),1α,2α,4β-triol-1,2,3,4-tetrahydronaphthalene(4),Cyclocarioside III(5),Cyclocarioside J(6),Progesterone(7),12-O-deacetylmetaplexigenin(8),20α-acetoxypregn-4-en-3-one(9),Oleanolic acid(10),5-O-P-coumaroylquinic acid methyl ester(11),Methyl linolenate(12),Palmitic acid(13).Among them,compound 9 was a new natural product;compounds 2-4,7,8,11,and 13 were isolated from this plant for the first time.The inhibitory activity of α-glucosidase was screened by PNPG method;the results showed that compounds 1 and 2 have strong α-glucosidase inhibitory activity.These results indicated that flavonoid is one kind of hypoglycemic active components of C.paliurus plant.
In order to elucidate the hypoglycemic components of C.paliurus,the chemical constituents and the inhibitory activity of α-glucosidase were systematic studied.13 compounds were isolated and identified from 80% ethanol extract of C.paliurus leaves by means of various chromatographic methods and spectroscopic methods.These compounds were characterized as afzelin(1),Kaempferol 3-O-(4″-O-acetyl)-α-L-rhamnopyranoside(2),juglanoside J(3),1α,2α,4β-triol-1,2,3,4-tetrahydronaphthalene(4),Cyclocarioside III(5),Cyclocarioside J(6),Progesterone(7),12-O-deacetylmetaplexigenin(8),20α-acetoxypregn-4-en-3-one(9),Oleanolic acid(10),5-O-P-coumaroylquinic acid methyl ester(11),Methyl linolenate(12),Palmitic acid(13).Among them,compound 9 was a new natural product;compounds 2-4,7,8,11,and 13 were isolated from this plant for the first time.The inhibitory activity of α-glucosidase was screened by PNPG method;the results showed that compounds 1 and 2 have strong α-glucosidase inhibitory activity.These results indicated that flavonoid is one kind of hypoglycemic active components of C.paliurus plant.
引文
1 Chen W,Zhang LX,Chen XX.Study on effects of Guizhou Cyclocarya paliurus on blood glucose and blood lipid type Ⅱ diabetic rats[J].Word J Tradit Chin Med(世界中医药),2018,10:590-594.
2 Hu W,Yang ZW,Chen H,et al.Optimization of ultrasonic and enzyme-assisted extraction of polysaccharides from Cyclocarya paliurus by Plackett-Burman and Box-Behnken experiment and analysis of its structure[J].Nat Pro Res Dev(天然产物研究与开发),2017,29:671-679.
3 Xie YM,Li L.Review in studies on chemical constituents and bioactivities of Cyclocarya paliurus[J].China Tradit Herb Drugs(中草药),2001,32:365-367.
4 Wang KQ,Cao Y.Research progress in the chemical constituents and pharmacologic activities of Cyclocarya paliurus(Batal.)Il jinshaja[J].Heilongjiang Med J(黑龙江医学),2007,31:577-579.
5 Fan BD,Wei Y,Li CH,et al.Research progress in chemical constituents and hpyerglycemic activity of Cyclocarya paliurus[J].Chin J Exp Tradit Med Form(中国实验方剂学杂志),2014,20:239-242.
6 Chen Z,Hao J,Wang L,et al.New α-glucosidase inhibitors from marine algae-derived streptomyces sp.OUCMDZ-3434[J].Sci Rep,2016,6:1-8.
7 Li QJ,Ni ZH,Yang Y,et al.Chemical constituents from an ethnic drug Dicranopteris pedata[J].Chin Pharm J.(中国药学杂志),2016,51:1274-1277.
8 Xu YM,Smith JA,Deborah A et al.Three acetylated flavonol glycosides from Forsteronia refracta that specifically inhibit p90 RSK[J].Bio Med Chem,2006,14:3974-3977.
9 Sebastian S,Birgit K,Jorg H.Phytochemical study of Juglans regia L.leaves[J] Phytochemistry,2017,144:58-70.
10 Xiu MC,Qian MH,Feng F.Two new tetrahydronaphthalenes from the stem of Impatiens balsamina L[J].CCL,2010,21:440-442.
11 Ren GS,Chang RX,Li LN,et al.CyclocariosidesII and III:Two secodammarane triterpenoid saponins from C paliurus[J].Planta Med,1995,61:551-553.
12 Liu Y,Zhang MQ,Li XL,et al.Study on chemical constituents of Cyclocarya paliurus[J].J Asian Nat Prod Res,2014,16:206-209.
13 Joseph KR,Kipngeno JR.Relationships between molecular properties and antimycobacterial activities of steroids[J].Nat.Prod.Lett,2001,16:107-113.
14 Li X,Sun H,Ye Y,et al.Four new immunomodulating steroidal glycosides from the stems of Stephanotis mucronata[J].Steroids,2006,71:683-690.
15 Holland H,Lakshmaiah G,Ruddock P.Microbial hydroxylation of acetylaminosteroids[J].Steroids,1998,63:484-495.
16 Ines K,Khaled H,Mohamed D.A new triterpene from Olea europeastem with antidiabetic activity[J] Chem Nat Compd,2012,48:799-802.
17 Taichi O,Kyoko Y.Constituents of pollen.XV :constituents of Biota orientalis(L.) ENDL(1)[J].Chem Pham Bull,1988,36:807-809.
18 Chang MH,Wang GJ,Kuo,YH,et al.The low polar constituents from Bidens Pilosa L.var.Minor(Blume) Sherff[J].J Chin Chem Soc,2000,47:1131-1136.
19 Huang X,Yang,RZ.A new hydroquinone diglucoside from Lysimachia fordiana[J].Chem Nat Compd,2004,40:457-459.
2 Hu W,Yang ZW,Chen H,et al.Optimization of ultrasonic and enzyme-assisted extraction of polysaccharides from Cyclocarya paliurus by Plackett-Burman and Box-Behnken experiment and analysis of its structure[J].Nat Pro Res Dev(天然产物研究与开发),2017,29:671-679.
3 Xie YM,Li L.Review in studies on chemical constituents and bioactivities of Cyclocarya paliurus[J].China Tradit Herb Drugs(中草药),2001,32:365-367.
4 Wang KQ,Cao Y.Research progress in the chemical constituents and pharmacologic activities of Cyclocarya paliurus(Batal.)Il jinshaja[J].Heilongjiang Med J(黑龙江医学),2007,31:577-579.
5 Fan BD,Wei Y,Li CH,et al.Research progress in chemical constituents and hpyerglycemic activity of Cyclocarya paliurus[J].Chin J Exp Tradit Med Form(中国实验方剂学杂志),2014,20:239-242.
6 Chen Z,Hao J,Wang L,et al.New α-glucosidase inhibitors from marine algae-derived streptomyces sp.OUCMDZ-3434[J].Sci Rep,2016,6:1-8.
7 Li QJ,Ni ZH,Yang Y,et al.Chemical constituents from an ethnic drug Dicranopteris pedata[J].Chin Pharm J.(中国药学杂志),2016,51:1274-1277.
8 Xu YM,Smith JA,Deborah A et al.Three acetylated flavonol glycosides from Forsteronia refracta that specifically inhibit p90 RSK[J].Bio Med Chem,2006,14:3974-3977.
9 Sebastian S,Birgit K,Jorg H.Phytochemical study of Juglans regia L.leaves[J] Phytochemistry,2017,144:58-70.
10 Xiu MC,Qian MH,Feng F.Two new tetrahydronaphthalenes from the stem of Impatiens balsamina L[J].CCL,2010,21:440-442.
11 Ren GS,Chang RX,Li LN,et al.CyclocariosidesII and III:Two secodammarane triterpenoid saponins from C paliurus[J].Planta Med,1995,61:551-553.
12 Liu Y,Zhang MQ,Li XL,et al.Study on chemical constituents of Cyclocarya paliurus[J].J Asian Nat Prod Res,2014,16:206-209.
13 Joseph KR,Kipngeno JR.Relationships between molecular properties and antimycobacterial activities of steroids[J].Nat.Prod.Lett,2001,16:107-113.
14 Li X,Sun H,Ye Y,et al.Four new immunomodulating steroidal glycosides from the stems of Stephanotis mucronata[J].Steroids,2006,71:683-690.
15 Holland H,Lakshmaiah G,Ruddock P.Microbial hydroxylation of acetylaminosteroids[J].Steroids,1998,63:484-495.
16 Ines K,Khaled H,Mohamed D.A new triterpene from Olea europeastem with antidiabetic activity[J] Chem Nat Compd,2012,48:799-802.
17 Taichi O,Kyoko Y.Constituents of pollen.XV :constituents of Biota orientalis(L.) ENDL(1)[J].Chem Pham Bull,1988,36:807-809.
18 Chang MH,Wang GJ,Kuo,YH,et al.The low polar constituents from Bidens Pilosa L.var.Minor(Blume) Sherff[J].J Chin Chem Soc,2000,47:1131-1136.
19 Huang X,Yang,RZ.A new hydroquinone diglucoside from Lysimachia fordiana[J].Chem Nat Compd,2004,40:457-459.