柯拉斯那沉香中2-(2-苯乙基)色酮类化学成分研究
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摘要
为研究柯拉斯那(Aquilaria crassna Pierre ex Lecomte)沉香的化学成分。实验采用多种柱色谱方法从该沉香中分离得到9个2-(2-苯乙基)色酮类化合物,通过现代波谱学技术分别鉴定为6-甲氧基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮(1)、5-羟基-6-甲氧基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮(2)、tetrahydrochromone F(3)、6-甲氧基-2-[2-(3′-甲氧基-4′-羟基苯基)乙基]色酮(4)、6-甲氧基-7-羟基-2-[2-(4′-甲氧基苯基)乙基]色酮(5)、6,7-二甲氧基-2-[2-(3′-羟基-4′-甲氧基苯基)乙基]色酮(6)、6,7-二甲氧基-2-[2-(4′-甲氧基苯基)乙基]色酮(7)、6-羟基-2-[2-(4′-羟基苯基)乙基]色酮(8)、5-羟基-2-[2-(2′-羟基苯基)乙基]色酮(9)。化合物2、3和5～9均为首次从柯拉斯那所得沉香中分离得到。采用MTT法对单体化合物的细胞毒活性进行测试,测试结果表明,化合物1,2和4具有微弱的细胞毒活性。
In order to study the chemical constituents of Aquilaria crassna,nine 2-(2-phenylethyl)chromones were isolated by various column chromatographic techniques from the agarwood of Aquilaria crassna,and their structures were identified on the basis of spectroscopic data analysis as 6-methoxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone(1),5-hydroxy-6-methoxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone(2),tetrahydrochromone F(3),6-methoxy-2-[2-(3′-methoxy-4′-hydroxyphenyl)ethyl]chromone(4),6-methoxy-7-hydroxy-2-[2-(4′-methoxyphenyl)ethyl]chromone(5),6,7-dimethoxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone(6),6,7-dimethoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone(7),6-hydroxy-2-[2-(4′-hydroxyphenyl)ethyl]chromone(8),5-hydroxy-2-[2-(2′-hydroxyphenyl)ethyl]chromone(9).Compounds 2,3 and 5-9 were isolated from the agarwood of Aquilaria crassna for the first time.These compounds were tested for cytotoxicity by MTT method.Among them,compounds 1,2 and 4 showed weak cytotoxic activity.
In order to study the chemical constituents of Aquilaria crassna,nine 2-(2-phenylethyl)chromones were isolated by various column chromatographic techniques from the agarwood of Aquilaria crassna,and their structures were identified on the basis of spectroscopic data analysis as 6-methoxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone(1),5-hydroxy-6-methoxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone(2),tetrahydrochromone F(3),6-methoxy-2-[2-(3′-methoxy-4′-hydroxyphenyl)ethyl]chromone(4),6-methoxy-7-hydroxy-2-[2-(4′-methoxyphenyl)ethyl]chromone(5),6,7-dimethoxy-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]chromone(6),6,7-dimethoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone(7),6-hydroxy-2-[2-(4′-hydroxyphenyl)ethyl]chromone(8),5-hydroxy-2-[2-(2′-hydroxyphenyl)ethyl]chromone(9).Compounds 2,3 and 5-9 were isolated from the agarwood of Aquilaria crassna for the first time.These compounds were tested for cytotoxicity by MTT method.Among them,compounds 1,2 and 4 showed weak cytotoxic activity.
引文
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2 Dai HF,Mei WL.Culture and artificial agarwood technology of Aquilaria(沉香实用栽培和人工结香技术)[M].Beijing:China Agriculture Press,2015:16-19.
3 Chinese Pharmacopoeia Commission.Pharmacopoeia of the People’s Republic of China:Vol Ⅰ(中华人民共和国药典:第一部)[M].Beijing:China Medical Science Press,2010.
4 Wang HN,Dong WH,Li W,et al.Identification of chemical constituents of agarwood of Aquilaria crassna[J].J Trop Bio(热带生物学报),2016,7:111-116.
5 Yang Y,Mei WL,Dong WH,et al.Study on the bioactive components of Aquilaria crassna[J].J Trop & Subtrop Bot(热带亚热带植物学报),2016,24:577-583.
6 Kang KX,Dai HF,Wang P,et al.study on chemical constituents of sesquiterpenoids of agarwood from Aquilaria crassna[J].Chin Tradit Herb Drugs(中草药),2017,48:4601-4607.
7 Wang HN,Dong WH,Huang SZ,et al.Three new sesquiterpenoids from agarwood of Aquilaria crassna[J].Fitoterapia,2016,114:7-11.
8 Wang HN,Mei WL,Dong WH,et al.Two new 2-(2-hydroxy-2-phenylethyl)chromens from agarwood originating from Aquilaria crassna[J].J Asian Nat Prod Res,2017,20(2):1.
9 Yang Y,Mei WL,Kong FD,et al.Four new bi-2-(2-phenylethyl)chromone derivatives of agarwood from Aquilaria crassna[J].Fitoterapia,2017,119:20.
10 Yang Y,Chen HQ,Kong FD,et al.Dimeric sesquiterpenoid-4H-chromone derivatives from agarwood of Aquilaria crassna and their cytotoxicity[J].Phytochemistry,2018,145:207-213.
11 Wang P,Kang KX,Kong FD,et al.A new sesquiterpenoid of agarwood from Aquilaria crassna[J].Chin Tradit Herb Drugs(中草药),2018,49:4480-4483.
12 Li W,Cai CH,Dong WH,et al.2-(2-Phenylethyl)chromone derivatives from Chinese agarwood induced by artificial holing[J].Fitoterapia,2014,98:117-123.
13 Liao G,Mei WL,Kong FD,et al.5,6,7,8-Tetrahydro-2-(2-phenylethyl)chromones from artificial agarwood of Aquilaria sinensis and their inhibitory activity against acetylcholinesterase[J].Phytochemistry,2017,139:98-108.
14 Konishi T,Konoshima T,Shimada Y,et al.Six new 2-(2-phenylethyl)chromones from Agarwood[J].Chem Pharm Bull,2002,50:419.
15 Wu B,Kwon SW,Hwang GS,et al.Eight New 2-(2-phenylethyl)chromone 2-(2-phenylethyl)-4H-1-benzopyran-4-one) derivatives from Aquilaria malaccensis Agarwood[J].Helv Chim Acta,2012,95:1657-1665.
16 Yang L,Qiao L,Xie D,et al.2-(2-phenylethyl)chromones from Chinese eaglewood[J].Phytochemistry,2012,76(12):92-97.
17 Iwagoe K,Konishi T,Kiyosawa S,et al.Studies on the agalwood(jinko).VII.structures of phenylethyl chromone derivatives AH7,AH8 and AH9[J].Chem Pharm Bull,1988,36:2417-2422.
18 Konishi T,Konoshima T,Shimada Y,et al.Six new 2-(2-Phenylethyl)chromones from Agarwood[J].Chem Pharm Bull,2002,50:419.
19 Wang T,Li LF,Zhang K,et al.New 2-(2-Phenylethyl)chromones from Bothriochloa Ischaemum[J].J Asian Nat Prod Res,2001,3:145-149.
20 Wang HS,Dai HF,Wang P,et al.Chemical constituents from litters of Casuarina equisetifolia and their biological activity[J].Nat Prod Res Dev(天然产物研究与开发),2018,30:390-395.
21 Shao H,Mei WL,Dong WH,et al.2-(2-Phenylethyl)chromone derivatives of agarwood originating from Gyrinops salicifolia[J].Molecules,2016,21:1313.
22 DAI HF.Research progress of Agarwood(沉香的现代研究)[M].Beijing:China Science Press,2017.