柬埔寨柯拉斯那沉香的化学成分研究
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摘要
该文采用ODS、硅胶、Sephadex LH-20等柱色谱技术,对柬埔寨野生柯拉斯那沉香(Aquilaria crassna)进行了研究。结果表明:从柬埔寨柯拉斯那所产沉香的乙醇提取物中进行分离共得到了10个化合物,包括一对对映异构体(9a/9b)。经波谱解析分别鉴定为6-甲氧基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(1)、6-甲氧基-2-[2-(3-甲氧基-4-羟基苯)乙基]色酮(2)、6,7-二甲氧基-2-(2-苯乙基)色酮(3)、6-羟基-2-(2-苯乙基)色酮(4)、6-羟基-2-[2-(4-甲氧基苯)乙基]色酮(5)、8-氯-6-羟基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(6)、8-氯-6-羟基-2-[2-(4-甲氧基苯)乙基]色酮(7)、oxidoagarochromone B(8)、4'-demethoxyaqusisnenone D(9)。其中,化合物6、7和9均为首次从柯拉斯那沉香中分离得到。活性测试结果显示,化合物1和2对乙酰胆碱脂酶具有一定的抑制活性,化合物2对人慢性髓原白血病细胞K562具有较弱的抑制作用。
Ten compounds,including one pair of enantiomers (9 a/9 b),were isolated from the ethanol extract of agarwood originating from Aquilaria crassna in Cambodia by comprehensive chromatographic techniques including ODS,silica gel and Sephadex LH-20. On the basis of spectroscopic data,they were identified as 6-methoxy-2-[2- (3-hydroxy-4-methoxyphenyl) ethyl]chromone (1),6-methoxy-2-[2- (3-methoxy-4-hydroxyphenyl) ethyl] chromone (2),6,7-dimethoxy-2- (2-phenylethyl) chromone (3),6-hydroxy-2- (2-phenylethyl) chromone (4),6-hydroxy-2-[2- (4-methoxyphenyl) ethyl ]chromone (5),8-chloro-6-hydroxy-2-[2- (3-hydroxy-4-methoxyphenyl) ethyl]chromone (6),8-chloro-6-hydroxy-2-[2- (4-methoxyphenyl) ethyl] chromone (7),oxidoagarochromone B (8),4'-demethoxyaqusisnenone D (9). Compounds 6,7 and 9 were isolated from agarwood of A. crassna for the first time. Among those,compounds 1 and 2 showed inhibitory activities against acetylcholinesterase. Compound 2 had weak inhibitory effect on K562 cell lines.
Ten compounds,including one pair of enantiomers (9 a/9 b),were isolated from the ethanol extract of agarwood originating from Aquilaria crassna in Cambodia by comprehensive chromatographic techniques including ODS,silica gel and Sephadex LH-20. On the basis of spectroscopic data,they were identified as 6-methoxy-2-[2- (3-hydroxy-4-methoxyphenyl) ethyl]chromone (1),6-methoxy-2-[2- (3-methoxy-4-hydroxyphenyl) ethyl] chromone (2),6,7-dimethoxy-2- (2-phenylethyl) chromone (3),6-hydroxy-2- (2-phenylethyl) chromone (4),6-hydroxy-2-[2- (4-methoxyphenyl) ethyl ]chromone (5),8-chloro-6-hydroxy-2-[2- (3-hydroxy-4-methoxyphenyl) ethyl]chromone (6),8-chloro-6-hydroxy-2-[2- (4-methoxyphenyl) ethyl] chromone (7),oxidoagarochromone B (8),4'-demethoxyaqusisnenone D (9). Compounds 6,7 and 9 were isolated from agarwood of A. crassna for the first time. Among those,compounds 1 and 2 showed inhibitory activities against acetylcholinesterase. Compound 2 had weak inhibitory effect on K562 cell lines.
引文
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HUO HX,ZHU ZX,SONG YL,et al.,2018.Antiinflammatory dimeric 2-(2-phenylethyl)chromones from the resinous wood of Aquilaria sinensis[J].J Nat Prod,81(3):543-553.
KANG KX,DAI HF,WANG P,et al.,2017.Sesquiterpenoids of agarwood from Aquilaria crassna[J].Chin Trad Herb Drugs,48(22):4601-4607.[康科星,戴好富,王佩,等,2017.柯拉斯那沉香的倍半萜类化学成分研究[J].中草药,48(22):4601-4607.]
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LI W,2014.Study on the chemical constituents and their bioactivities from Aquilaria sinensis and agarwood induced by artificial holing[D].Haikou:Hainan University:39-54.[李薇,2014.白木香与人工打洞沉香的化学成分与生物活性研究[D].海口:海南大学:39-54.]
LIAO G,MEI WL,DONG WH,et al.,2016.2-(2-Phenylethyl)chromone derivatives in artificial agarwood from Aquilaria sinensis[J].Fitoterapia,110:38-43.
MEI WL,LIU J,LI XN,et al.,2010.Study on the chemical constituents from Chinese eaglewood in Hainan[J].J Trop Subtrop Bot,18(5):573-576.[梅文莉,刘俊,李小娜,等,2010.海南国产沉香的化学成分研究[J].热带亚热带植物学报,18(5):573-576.]
MOSMANN T,1983.Rapid colorimetric assay for cellular growth and survival:Application to proliferation and cytotoxicity assays[J].J Immuno Methods,65(1-2):55-63.
NEAF R,2015.The volatile and semi-volatile constituents of agarwood,the infected heartwood of Aquilaria species:A review[J].Flavour Fragrance J,26(2):73-87.
SHAO H,MEI WL,KONG FD,et al.,2016.Fragrant sesquiterpenes of agarwood from Gyrinops salicifolia[J].Fitoterapia,113:182-187.
SHAO H,MEI WL,LI W,et al.,2015.Chemical constituents of agarwood originating from Gyrinops salicifolia[J].Nat Prod Res Dev,27(12):2046-2049.[邵杭,梅文莉,李薇,等,2015.柳叶拟沉香所产沉香的化学成分研究[J].天然产物研究与开发,27(12):2046-2049.]
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WANG HN,DONG WH,MEI WL,et al.,2016.Analysis on chemical constituents of Aquilaria crassna[J].J Trop Biol,7(1):111-116.[王红妮,董文化,梅文莉,等,2016.柯拉斯那沉香化学成分分析[J].热带生物学报,7(1):111-116.]
WU B,KWON SW,HWANG GS,et al.,2012.Eight new 2-(2-phenylethyl)chromone(=2-(2-phenylethyl)-4H-1-benzopyran-4-one)derivatives from Aquilaria malaccensis agarwood[J].Helv Chim Acta,95(9):1657-1665.
XIANG P,MEI WL,CHEN HQ,et al.,2017.Four new biphenylethylchromones from artificial agarwood[J].Fitoterapia,120:61-66.
XIANG P,ZENG YB,MEI WL,et al.,2017.Chemical constituents and bioactivities of Aquilariae Lignum Resinatum by artificial holing method[J].J Chin Med Mat,40(10):2339-2343.[向盼,曾艳波,梅文莉,等,2017.人工打洞沉香的化学成分及生物活性研究[J].中药材,40(10):2339-2343.]
YANG DL,WANG H,GUO ZK,et al.,2014.Fragrant agarofuran and eremophilane sesquiterpenes in agarwood‘Qi-Nan’from Aquilaria sinensis[J].Phytochem Lett,8:121-125.
YANG JS,WANG YL,SU YL,et al.,1989.Studies on the chemical constituents of Aquilaria sinensis(Lour.)Gilg IV.Isolation and characterization of 2-(2-phenylethyl)chromone derivatives[J].Acta Pharm Sin,24(9):678-683.[杨峻山,王玉兰,苏亚伦,等,1989.国产沉香化学成分研究Ⅳ.2-(2-苯乙基)色酮类化合物的分离与鉴定[J].药学学报,24(9):678-683.]
YAGURA T,ITO M,KIUCHI F,et al.,2003.Four new 2-(2-phenylethyl)chromone derivatives from withered wood of Aquilaria sinensis[J].Chem Pharm Bull,51(5):560-564.
YANG Y,MEI WL,DONG WH,et al.,2016.Bioactive components from agarwood originating from Aquilaria crassna[J].J Trop Subtrop Bot,24(5):577-583.[杨洋,梅文莉,董文化,等,2016.柯拉斯那沉香的生物活性成分研究[J].热带亚热带植物学报,24(5):577-583.]
YANG Y,MEI WL,KONG FD,et al.,2017.Four new bi-2-(2-phenylethyl)chromone derivatives of agarwood from Aquilaria crassna[J].Fitoterapia,119:20-25.
ALKHATHLAN HZ,AL-HAZIMI HM,2005.Three 2-(2-phenylethyl)chromones and two terpenes from agarwood[J].Nat Prod Res,19(4):367-372.
CHEN HQ,WEI JH,YANG JS,et al.,2012.Chem Inform abstract:Chemical constituents of agarwood originating from the endemic genus Aquilaria plants[J].Chem Biodivers,9(2):236-250.
DAI HF,2017.Research progress of agarwood[M].Beijing:Science Press:3-10.[戴好富,2017.沉香的现代研究[M].北京:科学出版社:3-10.]
DAI HF,MEI WL,2015.Culture and artificial agarwood technology of aquilaria[M].Beijing:China Agriculture Press:16-19.[戴好富,梅文莉,2015.沉香实用栽培和人工结香技术[M].北京:中国农业出版社:16-19.]
ELLMAN GL,COURTNEY KD,JR AV,et al.,1961.A new and rapid colorimetric determination of acetylcholinesterase activity[J].Biochem Pharmacol,7(2):88-95.
GAO YH,LIU JM,LU HX,et al.,2012.Two new 2-(2-phenylethyl)chromone-4-ones from Aquilaria sinensis(Lour.)Gilg[J].Helvet Chim Acta,95(6):951-954.
HUO HX,ZHU ZX,SONG YL,et al.,2018.Antiinflammatory dimeric 2-(2-phenylethyl)chromones from the resinous wood of Aquilaria sinensis[J].J Nat Prod,81(3):543-553.
KANG KX,DAI HF,WANG P,et al.,2017.Sesquiterpenoids of agarwood from Aquilaria crassna[J].Chin Trad Herb Drugs,48(22):4601-4607.[康科星,戴好富,王佩,等,2017.柯拉斯那沉香的倍半萜类化学成分研究[J].中草药,48(22):4601-4607.]
KONISHI T,KONOSHIMA T,SHIMADA Y,et al.,2002.Six new 2-(2-phenylethyl)chromones from agarwood[J].Chem Pharm Bull,50(3):419-422.
LI W,2014.Study on the chemical constituents and their bioactivities from Aquilaria sinensis and agarwood induced by artificial holing[D].Haikou:Hainan University:39-54.[李薇,2014.白木香与人工打洞沉香的化学成分与生物活性研究[D].海口:海南大学:39-54.]
LIAO G,MEI WL,DONG WH,et al.,2016.2-(2-Phenylethyl)chromone derivatives in artificial agarwood from Aquilaria sinensis[J].Fitoterapia,110:38-43.
MEI WL,LIU J,LI XN,et al.,2010.Study on the chemical constituents from Chinese eaglewood in Hainan[J].J Trop Subtrop Bot,18(5):573-576.[梅文莉,刘俊,李小娜,等,2010.海南国产沉香的化学成分研究[J].热带亚热带植物学报,18(5):573-576.]
MOSMANN T,1983.Rapid colorimetric assay for cellular growth and survival:Application to proliferation and cytotoxicity assays[J].J Immuno Methods,65(1-2):55-63.
NEAF R,2015.The volatile and semi-volatile constituents of agarwood,the infected heartwood of Aquilaria species:A review[J].Flavour Fragrance J,26(2):73-87.
SHAO H,MEI WL,KONG FD,et al.,2016.Fragrant sesquiterpenes of agarwood from Gyrinops salicifolia[J].Fitoterapia,113:182-187.
SHAO H,MEI WL,LI W,et al.,2015.Chemical constituents of agarwood originating from Gyrinops salicifolia[J].Nat Prod Res Dev,27(12):2046-2049.[邵杭,梅文莉,李薇,等,2015.柳叶拟沉香所产沉香的化学成分研究[J].天然产物研究与开发,27(12):2046-2049.]
The State Pharmacopoeia Committee,2015.Chinese Pharmacopoeia,Part 1[S].Beijing:Chemical Industry Press:185-186.[中国药典委员会,2015.中华人民共和国药典2015版.一部[S].北京:化学工业出版社:185-186.]
WANG HN,DONG WH,MEI WL,et al.,2016.Analysis on chemical constituents of Aquilaria crassna[J].J Trop Biol,7(1):111-116.[王红妮,董文化,梅文莉,等,2016.柯拉斯那沉香化学成分分析[J].热带生物学报,7(1):111-116.]
WU B,KWON SW,HWANG GS,et al.,2012.Eight new 2-(2-phenylethyl)chromone(=2-(2-phenylethyl)-4H-1-benzopyran-4-one)derivatives from Aquilaria malaccensis agarwood[J].Helv Chim Acta,95(9):1657-1665.
XIANG P,MEI WL,CHEN HQ,et al.,2017.Four new biphenylethylchromones from artificial agarwood[J].Fitoterapia,120:61-66.
XIANG P,ZENG YB,MEI WL,et al.,2017.Chemical constituents and bioactivities of Aquilariae Lignum Resinatum by artificial holing method[J].J Chin Med Mat,40(10):2339-2343.[向盼,曾艳波,梅文莉,等,2017.人工打洞沉香的化学成分及生物活性研究[J].中药材,40(10):2339-2343.]
YANG DL,WANG H,GUO ZK,et al.,2014.Fragrant agarofuran and eremophilane sesquiterpenes in agarwood‘Qi-Nan’from Aquilaria sinensis[J].Phytochem Lett,8:121-125.
YANG JS,WANG YL,SU YL,et al.,1989.Studies on the chemical constituents of Aquilaria sinensis(Lour.)Gilg IV.Isolation and characterization of 2-(2-phenylethyl)chromone derivatives[J].Acta Pharm Sin,24(9):678-683.[杨峻山,王玉兰,苏亚伦,等,1989.国产沉香化学成分研究Ⅳ.2-(2-苯乙基)色酮类化合物的分离与鉴定[J].药学学报,24(9):678-683.]
YAGURA T,ITO M,KIUCHI F,et al.,2003.Four new 2-(2-phenylethyl)chromone derivatives from withered wood of Aquilaria sinensis[J].Chem Pharm Bull,51(5):560-564.
YANG Y,MEI WL,DONG WH,et al.,2016.Bioactive components from agarwood originating from Aquilaria crassna[J].J Trop Subtrop Bot,24(5):577-583.[杨洋,梅文莉,董文化,等,2016.柯拉斯那沉香的生物活性成分研究[J].热带亚热带植物学报,24(5):577-583.]
YANG Y,MEI WL,KONG FD,et al.,2017.Four new bi-2-(2-phenylethyl)chromone derivatives of agarwood from Aquilaria crassna[J].Fitoterapia,119:20-25.