α-葡萄糖苷酶抑制剂活性指导下的HPLC-Q-TOF-MS/MS鉴定臭牡丹中化学成分（英文）
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摘要
目的本研究旨在通过HPLC-Q-TOF-MS/MS方法确定臭牡丹中抑制α-葡萄糖苷酶的活性成分。方法臭牡丹乙醇提取物分别用石油醚、乙酸乙酯、正丁醇萃取得到3个提取部位;利用体外α-葡萄糖苷酶活性测定3个提取物的α-葡萄糖苷酶抑制活性,然后通过HPLC-ESI-QTOF-MS/MS方法鉴定乙酸乙酯部位的α-葡萄糖苷酶抑制活性成分。结果我们共鉴定出29个化合物,其中有12种苯乙醇苷(化合物5-6,12-17,20-22,24),7种黄酮类化物(化合物10,19,23,25-28)和5种酚酸(化合物2-4,7,9)以及5种其他化合物。通过查阅相关文献,初步确定化合物2-4,7,9-10,12-13,15,19和26具有潜在α-葡糖苷酶活抑制活性。结论本研究所应用的方法可行,可靠并且能快速地鉴定已知化合物,以及鉴定臭牡丹中新的天然α-葡萄糖苷酶抑制候选物。
Objective To identify the compounds with α-glucosidase inhibitory activity from Clerodendrum bungei Steud(Chou Mu Dan,臭牡丹) using HPLC-ESI-QTOF-MS/MS.Methods The ethanol extracts of Clerodendrum bungei Steud(Chou Mu Dan,臭牡丹) were partitioned with petroleum ether,ethyl acetate,n-butanol,and water.The assay for α-glucosidase inhibitory activity revealed strong α-glucosidase inhibitory activity in the ethyl acetate fraction,and the bioactive compounds present in this fraction were identified by the HPLCESI-QTOF-MS/MS method.Results A total of 29 compounds were determined,among the identified bioactive components;these included 12 phenylethanoid glycosides(compounds 5,6,12-17,20-22,24),7 flavonoids(compounds 10,19,23,25-28),5 phenolic acids(compounds 2-4,7,9),and 5 other compounds.Compounds 2-4,7,9-10,12-13,15,19,and 26,with a potential α-glucosidase inhibitory activity,have been reported previously.Conclusions Our results show that the methodology used in this study is feasible,credible,and rapid in identifying known compounds and also for characterizing new natural α-glucosidase inhibitory candidates from Clerodendrum bungei Steud(Chou Mu Dan,臭牡丹).
Objective To identify the compounds with α-glucosidase inhibitory activity from Clerodendrum bungei Steud(Chou Mu Dan,臭牡丹) using HPLC-ESI-QTOF-MS/MS.Methods The ethanol extracts of Clerodendrum bungei Steud(Chou Mu Dan,臭牡丹) were partitioned with petroleum ether,ethyl acetate,n-butanol,and water.The assay for α-glucosidase inhibitory activity revealed strong α-glucosidase inhibitory activity in the ethyl acetate fraction,and the bioactive compounds present in this fraction were identified by the HPLCESI-QTOF-MS/MS method.Results A total of 29 compounds were determined,among the identified bioactive components;these included 12 phenylethanoid glycosides(compounds 5,6,12-17,20-22,24),7 flavonoids(compounds 10,19,23,25-28),5 phenolic acids(compounds 2-4,7,9),and 5 other compounds.Compounds 2-4,7,9-10,12-13,15,19,and 26,with a potential α-glucosidase inhibitory activity,have been reported previously.Conclusions Our results show that the methodology used in this study is feasible,credible,and rapid in identifying known compounds and also for characterizing new natural α-glucosidase inhibitory candidates from Clerodendrum bungei Steud(Chou Mu Dan,臭牡丹).
引文
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[2]SHOBANA S,SREERAMA YN,MALLESHI NG.Composition and enzyme inhibitory properties of finger millet(Eleusine coracana L.)seed coat phenolics:Mode of inhibition ofα-glucosidase and pancreatic amylase.Food Chemistry,2009,115(4):1268-1273.
[3]GAO X,ZHANG W,ZOU W,et al.Screening for alphaglucosidase inhibitors from extracts of traditional Chinese medicine.Natural Product Research and Development,2003,15(6):536-538.
[4]ZHU YP,LI XT,LI LT.The Source of the Naturalα-glucosidase Inhibitor and its Application Research Situation.Journal of Chinese Institute of Food Science and Technology,2011,11(04):154-160.
[5]BOY HIA,RUTILLA AJH,SANTOS KA,et al.Recommended medicinal plants as source of natural products:a review.Digital Chinese Medicine,2018,1(2):131-142.
[6]ZHAO Y,ZHANG LY,HU XY,et al.Purification and activity of a new naturalα-glucosidase inhibitor.Chinese Journal of Biochemical Pharmaceutics,2007,28(1):20.
[7]XU LF,SHEN ZM,YIN JW.Study on the characteristics of alpha-glucosidase inhibitor from Schizandra Chinensis.Chinese Journal of Biochemical Pharmaceutics,2001,22(3):127-129.
[8]LIU Q,HU HJ,LI PF,et al.Diterpenoids and phenylethanoid glycosides from the roots of Clerodendrum bungei and their inhibitory effects against angiotensin converting enzyme andα-glucosidase.Phytochemistry,2014,103:196-202.
[9]Medica,CM.Editorial Committee of Chinese Materia Medica.Shanghai Science and Technology:Shanghai.1999,13,149-151.
[10]KIM JS,HYUN TK,KIM MJ,et al.The inhibitory effects of ethanol extracts from sorghum,foxtail millet and proso millet onα-glucosidase andα-amylase activities.Food Chemistry,2011,124(4):1647-1651.
[11]SPIEGLER V,SENDKER J,PETEREIT F,et al.Bioassayguided fractionation of a leaf extract from Combretum mucronatum with anthelmintic activity:oligomeric procyanidins as the active principle.Molecules,2015,20(8):14810-14832.
[12]LING Y,FU Z,ZHANG Q,et al.Identification and structural elucidation of steroidal saponins from the root of Paris polyphylla by HPLC-ESI-QTOF-MS/MS.Natural Product Research,2015,29(19):1798-1803.
[13]LING Y,ZHENG Y,LIU K,et al.Structure characterization and identification of triterpenoid saponins from the root of Platycodon grandiflorum by HPLC/ESI-QTOF-MS/MS.Asian Journal of Chemistry,2014,26(20):132-134.
[14]WANG YM,ZHANG SJ,LUO GA,et al.Analysis of phenylethanoid glycosides in the extract of herba Cistanchis by LC/ESI-MS/MS.Acta Pharmaceutica Sinica,2000,35(11):839.
[15]ZHANG J,LI C,CHE Y,et al.LTQ-Orbitrap-based strategy for traditional Chinese medicine targeted class discovery,identification and herbomics research:a case study on phenylethanoid glycosides in three different species of Herba Cistanches.RSC Advances,2015,5(98):80816-80828.
[16]KURODA M,IWABUCHI K,MIMAKI Y.Chemical constituents of the aerial parts of Scutellaria lateriflora and their alpha-glucosidase inhibitory activities.Natural Product Communications,2012,7(4):471-474.
[17]YIN LL,DONG J,XU Y,et al.Study on the cleavage of flavonoids by negative ESI-IT-TOF/MS~n method.Chinese Pharmaceutical Association:Academic Conference of the Chinese Pharmaceutical Association,2007,10.
[18]WANG XL.Screening of Pinellia analgesic activity and chemical composition analysis of rattan tea based on UPLC-MS/MS technology.Guangzhou:Guangdong Pharmaceutical College.2015.
[19]WANG Y,LI XB,LI JJ,et al.Fragmentation pathway comparison of 5,6,7,4′-Tetrahydroxy-Flavone and 5,6,7,4′-Tetramethoxy-Flavone by high resolution electrospray ionization tandem mass spectroscopy.Journal of Chinese Mass Spectrometry Society,2016,37(5):385-392.
[20]YANG WJ,HE J,LIU C,et al.Medicinal development of Xinjiang new characteristic flower.The 10th Chinese Medicine and Natural Science Proceedings of the Symposium on Drug Resources,2012,2.
[21]GENG S,CHEN Y,ABBASI AM,et al.Tannin fraction from Ampelopsis grossedentata leaves tea(Tengcha)as an antioxidant andα-glucosidase inhibitory nutraceutical.International Journal of Food Science&Technology,2016,51(12):2692-2700.
[22]LIN H,YI L,MEI L,et al.The inhibition activity and mechanisms of myricetin onα-glucosidase.Science&Technology of Food Industry,2017,38(22):51-55+60.
[23]JIE T,CHEN J,LIU G.Study on the molecular inhibition mechanisms of apigenin onα-glucosidase.Biotechnology,2015,25(4):369-374.
[24]TU J,CHEN J,LIU G.Study on the molecular inhibition mechanisms of apigenin onα-glucosidase.Biotechnology,2015,43(12):26-27.
[25]ZHANG HF,DONG YL,ZHANG Y.The research of gallic acid’s a-glycosidase inhibition and the hypoglycemic mechanism.China Pharmaceuticals,2011,20(21):8-10.
[26]MBAZE LM,POUMALE HM,WANSI JD,et al.α-glucosidase inhibitory pentacyclic triterpenes from the stem bark of Fagara tessmannii(Rutaceae).Phytochemistry,2007,68(5):591-595.
[27]MIAO J,LI X,ZHAO C,et al.Active compounds,antioxidant activity andα-glucosidase inhibitory activity of different varieties of Chaenomeles fruits.Food Chemistry,2018,248:330-339.
[28]JABEEN B,RIAZ N,SALEEM M,et al.Isolation of natural compounds from Phlomis stewartii showingα-glucosidase inhibitory activity.Phytochemistry,2013,96:443-448.
[29]LEE J,JANG SI,KANG BH,et al.Changes in Antioxidant andα-Glucosidase inhibitory activities of Coffee bean extracts by heat processing.The FASEB Journal,2016,30(1-supplement):903.3-903.3.
[30]YU ZX.Study on chemical constituents and quality control of Radix Gentiana.Beijing:Beijing University of Chinese Medicine.2006.
[31]MU SZ.Study on the chemical constituents isolated from Chryanthemum parthenium.Journal of Anhui Agricultural Sciences,2013,41(15):6663-6664.