神香草倍半萜类化学成分研究
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摘要
目的研究神香草Hyssopus cuspidatus干燥地上部分的倍半萜类化学成分。方法采用D101大孔吸附树脂、硅胶柱色谱、ODS、Toyopearl HW-40C、Sephadex LH-20以及半制备HPLC等方法进行分离纯化,根据理化性质以及波谱数据对化合物进行结构鉴定。结果从神香草95%乙醇提取物中分离得到15个化合物,分别鉴定为3-eudesmene-1β-11-diol(1)、4-eudesmene-1β,11-diol(2)、1β,11-dihydroxy-5-eudesmene(3)、ent-4(15)-eudesmen-1α,11-diol(4)、7α,11-dihydroxy-cadin-10(14)-ene(5)、eudesmane-1β,5α,11-triol(6)、5-epi-eudesma-4(15)-ene-1β,6β-diol(7)、4(15)-eudesmene-1β,6α-diol(8)、(7R*)-opposit-4(15)-ene-1β,11-diol(9)、cryptomeridiol(10)、octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)-1H-indene-1-methanol(11)、caryolane-1,9β-diol(12)、(3S,5R,6S,7E)-3,5,6-trihydroxy-7-megastigmen-9-one(13)、spathulenol(14)、4β,10α-aromadendranediol(15)。结论化合物1～15均为首次从该属植物中分离得到。
Objective To study the sesquiterpenes from the aerial parts of Hyssopus cuspidatus. Methods The compounds were isolated and purified by a combination of various chromatographic techniques including D101 macroporous adsorption resin, silica gel,ODS, Toyopearl HW-40 C, Sephadex LH-20, and semi-preparative HPLC. Their structures were elucidated on the basis of physicochemical properties and spectroscopic data. Results Fifteen sesquiterpenes were isolated from the 95% EtOH extracts of H.cuspidatus and their structures were elucidated as 3-eudesmene-1β-11-diol(1), 4-eudesmene-1β,11-diol(2), 1β,11-dihydroxy-5-eudesmene(3), ent-4(15)-eudesmen-1α,11-diol(4), 7α,11-dihydroxy-cadin-10(14)-ene(5), eudesmane-1β,5α,11-triol(6), 5-epieudesma-4(15)-ene-1β,6β-diol(7), 4(15)-eudesmene-1β,6α-diol(8),(7 R*)-opposit-4(15)-ene-1β,11-diol(9), cryptomeridiol(10),octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)-1 H-indene-1-methanol(11), caryolane-1,9β-diol(12),(3 S,5 R,6 S,7 E)-3,5,6-trihydroxy-7-megastigmen-9-one(13), spathulenol(14), and 4β,10α-aromadendranediol(15), respectively. Conclusion Compounds 1—15 are isolated from the plants of Hyssopus genus for the first time.
Objective To study the sesquiterpenes from the aerial parts of Hyssopus cuspidatus. Methods The compounds were isolated and purified by a combination of various chromatographic techniques including D101 macroporous adsorption resin, silica gel,ODS, Toyopearl HW-40 C, Sephadex LH-20, and semi-preparative HPLC. Their structures were elucidated on the basis of physicochemical properties and spectroscopic data. Results Fifteen sesquiterpenes were isolated from the 95% EtOH extracts of H.cuspidatus and their structures were elucidated as 3-eudesmene-1β-11-diol(1), 4-eudesmene-1β,11-diol(2), 1β,11-dihydroxy-5-eudesmene(3), ent-4(15)-eudesmen-1α,11-diol(4), 7α,11-dihydroxy-cadin-10(14)-ene(5), eudesmane-1β,5α,11-triol(6), 5-epieudesma-4(15)-ene-1β,6β-diol(7), 4(15)-eudesmene-1β,6α-diol(8),(7 R*)-opposit-4(15)-ene-1β,11-diol(9), cryptomeridiol(10),octahydro-4-hydroxy-3α-methyl-7-methylene-α-(1-methylethyl)-1 H-indene-1-methanol(11), caryolane-1,9β-diol(12),(3 S,5 R,6 S,7 E)-3,5,6-trihydroxy-7-megastigmen-9-one(13), spathulenol(14), and 4β,10α-aromadendranediol(15), respectively. Conclusion Compounds 1—15 are isolated from the plants of Hyssopus genus for the first time.
引文
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[5]Furukawa M,Makino M,Ohkoshi E,et al.Terpenoids and phenethyl glucosides from Hyssopus cuspidatus(Labiatae)[J].Phytochemistry,2011,72(17):2244-2252.
[6]Skrzypek Z,Wysokińska H.Sterols and triterpenes in cell culture of Hyssopus cuspidatus L[J].Z Naturforsch C,2003,58(5/6):308-312.
[7]Wang N,Yang X W.Two new flavonoid glycosides from the whole herbs of Hyssopus cuspidatus[J].J Asian Nat Prod Res,2010,12(12):1044-1050.
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[11]Bl?s B,Zapp J,Becker H.ent-Clerodane diterpenes and other constituents from the liverwort Adelanthus lindenbergianus(Lehm.)Mitt.[J].Phytochemistry,2004,65(1):127-137.
[12]Isaka M,Palasarn S,Lapanun S,et al.Gamma-lactones and ent-eudesmane sesquiterpenes from the endophytic fungus Eutypella sp.BCC 13199[J].J Nat Prod,2009,72(9):1720-1722.
[13]Elaskary H I,Meselhy M R,Galal A M.Sesquiterpenes from Cymbopogon proximus[J].Molecules,2003,8(9):670-677.
[14]Shen T,Wan W,Yuan H,et al.Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells[J].Phytochemistry,2007,68(9):1331-1337.
[15]Sun Z,Chen B,Zhang S,et al.Four new eudesmanes from Caragana intermedia and their biological activities[J].J Nat Prod,2004,67(12):1975-1979.
[16]Leo M D,Vera Saltos M B,Naranjo Puente B F,et al.Sesquiterpenes and diterpenes from Ambrosia arborescens[J].Phytochemistry,2010,71(7):804-809.
[17]Hoye T R,Hanson P R,Vyvyan J R.A practical guide to first-order multiplet analysis in 1H NMR spectroscopy[J].J Org Chem,1994,59(15):4096-4103.
[18]Ragasa C Y,Co A L,Rideout J A.Antifungal metabolites from Blumea balsamifera[J].Nat Prod Res,2005,19(3):231-237.
[19]Zhang H J,Tan G T,Santarsiero B D,et al.New sesquiterpenes from Litsea verticillata[J].J Nat Prod,2003,66(5):609-615.
[20]张培培,高莎莎,张甜甜,等.香血藤中倍半萜类化学成分研究[J].中国中药杂志,2012,37(22):3426-3429.
[21]Park J H,Lee D G,Yeon S W,et al.Isolation of megastigmane sesquiterpenes from the silkworm(Bombyx mori L.)droppings and their promotion activity on HO-1 and SIRT1[J].Arch Pharm Res,2011,34(4):533-542.
[22]Ragasa C Y,Ganzon J,Hofilena J,et al.A new furanoid diterpene from Caesalpinia pulcherrima[J].Chem Pharm Bull,2003,51(10):1208-1210.
[23]胡引明.幌伞枫及海南三角瓣花的化学成分研究[D].深圳:深圳大学,2016.
[2]国家中医药管理局《中华本草》编委会.中华本草,维吾尔药卷[M].上海:科学技术出版社,2005.
[3]朱琪,关祥祖.维吾尔族医药学[M].云南:民族出版社,1995.
[4]Venditti A,Bianco A,Frezza C,et al.Essential oil composition,polar compounds,glandular trichomes and biological activity of Hyssopus cuspidatus subsp.aristatus(Godr.)Nyman from central Italy[J].Ind Crops Prod,2015,77:353-363.
[5]Furukawa M,Makino M,Ohkoshi E,et al.Terpenoids and phenethyl glucosides from Hyssopus cuspidatus(Labiatae)[J].Phytochemistry,2011,72(17):2244-2252.
[6]Skrzypek Z,Wysokińska H.Sterols and triterpenes in cell culture of Hyssopus cuspidatus L[J].Z Naturforsch C,2003,58(5/6):308-312.
[7]Wang N,Yang X W.Two new flavonoid glycosides from the whole herbs of Hyssopus cuspidatus[J].J Asian Nat Prod Res,2010,12(12):1044-1050.
[8]Matsuura H,Miyazaki H,Asakawa C,et al.Isolation ofα-glusosidase inhibitors from hyssop(Hyssopus cuspidatus)[J].Phytochemistry,2004,65(1):91-97.
[9]帕丽达·阿不力孜,丛媛媛,朱焱,等.神香草化学成分研究[J].中国现代应用药学,2011,28(8):735-737.
[10]Su W C,Fang J M,Cheng Y S.Sesquiterpenes from leaves of Cryptomeria japonica[J].Phytochemistry,1995,39(3):603-607.
[11]Bl?s B,Zapp J,Becker H.ent-Clerodane diterpenes and other constituents from the liverwort Adelanthus lindenbergianus(Lehm.)Mitt.[J].Phytochemistry,2004,65(1):127-137.
[12]Isaka M,Palasarn S,Lapanun S,et al.Gamma-lactones and ent-eudesmane sesquiterpenes from the endophytic fungus Eutypella sp.BCC 13199[J].J Nat Prod,2009,72(9):1720-1722.
[13]Elaskary H I,Meselhy M R,Galal A M.Sesquiterpenes from Cymbopogon proximus[J].Molecules,2003,8(9):670-677.
[14]Shen T,Wan W,Yuan H,et al.Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells[J].Phytochemistry,2007,68(9):1331-1337.
[15]Sun Z,Chen B,Zhang S,et al.Four new eudesmanes from Caragana intermedia and their biological activities[J].J Nat Prod,2004,67(12):1975-1979.
[16]Leo M D,Vera Saltos M B,Naranjo Puente B F,et al.Sesquiterpenes and diterpenes from Ambrosia arborescens[J].Phytochemistry,2010,71(7):804-809.
[17]Hoye T R,Hanson P R,Vyvyan J R.A practical guide to first-order multiplet analysis in 1H NMR spectroscopy[J].J Org Chem,1994,59(15):4096-4103.
[18]Ragasa C Y,Co A L,Rideout J A.Antifungal metabolites from Blumea balsamifera[J].Nat Prod Res,2005,19(3):231-237.
[19]Zhang H J,Tan G T,Santarsiero B D,et al.New sesquiterpenes from Litsea verticillata[J].J Nat Prod,2003,66(5):609-615.
[20]张培培,高莎莎,张甜甜,等.香血藤中倍半萜类化学成分研究[J].中国中药杂志,2012,37(22):3426-3429.
[21]Park J H,Lee D G,Yeon S W,et al.Isolation of megastigmane sesquiterpenes from the silkworm(Bombyx mori L.)droppings and their promotion activity on HO-1 and SIRT1[J].Arch Pharm Res,2011,34(4):533-542.
[22]Ragasa C Y,Ganzon J,Hofilena J,et al.A new furanoid diterpene from Caesalpinia pulcherrima[J].Chem Pharm Bull,2003,51(10):1208-1210.
[23]胡引明.幌伞枫及海南三角瓣花的化学成分研究[D].深圳:深圳大学,2016.
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