木荷的化学成分研究
摘要
木荷(Schima superba Gardn.et Champ.),为山茶科(Theaceae)木荷属(Schima)植物,又名何树、木艾树、荷木等,广泛分布于我国福建、江苏、浙江、安徽等省,该植物有毒,具清热解毒之功效,主治疔疮,无名肿毒等。目前,国内外对本属植物化学成分的研究报道并不多,为了更深入地了解其化学成分并从中寻找活性化合物,本论文对木荷茎的化学成分进行了较为系统的研究。
基于木荷茎95%乙醇提取物及其所萃取的氯仿和乙酸乙酯部位对肿瘤细胞株具有明显的细胞毒活性,我们采用各种色谱分离技术,对该部位进行了系统的化学成分研究,从中分离得到25个化合物,并通过现代谱学和化学方法,鉴定了其中22个化合物的结构,它们分别是:2,6-二甲氧基苯醌(2,6-dimethoxy-benzoquinone,1),2,4,6-三甲氧基苯酚(2,4,6-trimethoxyphenol,2),丁香酸(syringicacid,3),松柏醛(coniferyl aldehyde,4),丁香醛(syringaldehyde,5),Al-barrigenol(6),camelliagenin A(7),barringtogenol C(8),丁香脂素(syringaresinol,9),松脂素(pinoresinol,10),落叶松脂醇(lariciresinol,11),balanophonin(12),3-acetoxymethyl-5-[(E)-2-formylethen-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-benzofuran(13),二聚松柏醇(dihydrodehydrodieonifery alcohol,14),4,9-dihydroxy-3,3′-dimethoxy-4′,7-epoxy-8,5′-neolignane-9′-yl acetate(15),异落叶松脂素(isolariciresinol,16),(7R,8S)-1-(3,4-dimethoxyphenyl)-2-O-(2-methoxy-4-omega-hydroxypropylphenyl)propane-1,3-diol(17),acernikol(18),山柰酚(kaempferol,19),槲皮素-3-O-β-D-吡喃葡萄糖苷(quercetin-3-O-β-D-glucopyranoside,20),槲皮素-3-O-β-D-吡喃半乳糖苷(quercetin-3-O-β-D-galactopyranosde,21)和木荷脂素(schimanin,22)。其中,化合物22为新化合物,所有化合物均为首次从该种植物中分离得到;除化合物6以外,其它化合物均为首次从该属植物分离得到。
Mu He(Schima superba Gardn.et Champ.),alternately named as He Shu,Mu Ai Shu and He Mu in chinese,is widely destributed in Fujian,Jiangshu,Zhejian,Anhui and other provinces in south china.Although it is known that the plant has been used as a source of timber,and that its root bark has been used as a traditional chinese herb to treat furuncle and some kind of sore,little chemical work has been reported. Based on the cytotoxicity of its 95%alcoholic extract of the stem and the CHCl_3 and EtOAc fractions from the extract against a few cancer cell lines,we had systematically investigated the chemical constituents on both the fractions from Schima superba.25 compounds had been isolated from the fractions.By means of spectroscopic techniques as well as physical and chemical properties,the structures of 22 compounds were elucidated as 2,6-dimethoxybenzoquinone(1),2,4,6-trimethoxy -phenol(2),syringic acid(3),coniferyl aldehyde(4),syringaldehyde(5),Albarrigenol (6),camelliagenin A(7),barringtogenol C(8),syringaresinol(9), pinoresinol(10),lariciresinol(11),balanophonin(12),3-acetoxymethyl-5-[(E)-2-for -mylethen-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro benzo furan (13),dihydrodehydrodiconifery alcohol(14),4,9-dihydroxy-3,3'-dimethoxy-4',7-epoxy-8,5'-neolignane-9'-yl acetate(15),isolariciresinol(16),(7R,8S)-l-(3,4-dimethoxyphenyl)-2-O-(2-methoxy-4-omegahydroxypropylphenyl)propane-1,3-diol (17),acernikol(18),kaempferol(19),quercetin-3-O-β-D-glucopyranoside(20), quercetin-3-O-β-D-galactopyranosde(21) and schimanin(22).Among these compounds,compound 22 is a new lignin,and all the others are for the first time isolated from this plant and from Schima.except compound 6.
基于木荷茎95%乙醇提取物及其所萃取的氯仿和乙酸乙酯部位对肿瘤细胞株具有明显的细胞毒活性,我们采用各种色谱分离技术,对该部位进行了系统的化学成分研究,从中分离得到25个化合物,并通过现代谱学和化学方法,鉴定了其中22个化合物的结构,它们分别是:2,6-二甲氧基苯醌(2,6-dimethoxy-benzoquinone,1),2,4,6-三甲氧基苯酚(2,4,6-trimethoxyphenol,2),丁香酸(syringicacid,3),松柏醛(coniferyl aldehyde,4),丁香醛(syringaldehyde,5),Al-barrigenol(6),camelliagenin A(7),barringtogenol C(8),丁香脂素(syringaresinol,9),松脂素(pinoresinol,10),落叶松脂醇(lariciresinol,11),balanophonin(12),3-acetoxymethyl-5-[(E)-2-formylethen-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro-benzofuran(13),二聚松柏醇(dihydrodehydrodieonifery alcohol,14),4,9-dihydroxy-3,3′-dimethoxy-4′,7-epoxy-8,5′-neolignane-9′-yl acetate(15),异落叶松脂素(isolariciresinol,16),(7R,8S)-1-(3,4-dimethoxyphenyl)-2-O-(2-methoxy-4-omega-hydroxypropylphenyl)propane-1,3-diol(17),acernikol(18),山柰酚(kaempferol,19),槲皮素-3-O-β-D-吡喃葡萄糖苷(quercetin-3-O-β-D-glucopyranoside,20),槲皮素-3-O-β-D-吡喃半乳糖苷(quercetin-3-O-β-D-galactopyranosde,21)和木荷脂素(schimanin,22)。其中,化合物22为新化合物,所有化合物均为首次从该种植物中分离得到;除化合物6以外,其它化合物均为首次从该属植物分离得到。
Mu He(Schima superba Gardn.et Champ.),alternately named as He Shu,Mu Ai Shu and He Mu in chinese,is widely destributed in Fujian,Jiangshu,Zhejian,Anhui and other provinces in south china.Although it is known that the plant has been used as a source of timber,and that its root bark has been used as a traditional chinese herb to treat furuncle and some kind of sore,little chemical work has been reported. Based on the cytotoxicity of its 95%alcoholic extract of the stem and the CHCl_3 and EtOAc fractions from the extract against a few cancer cell lines,we had systematically investigated the chemical constituents on both the fractions from Schima superba.25 compounds had been isolated from the fractions.By means of spectroscopic techniques as well as physical and chemical properties,the structures of 22 compounds were elucidated as 2,6-dimethoxybenzoquinone(1),2,4,6-trimethoxy -phenol(2),syringic acid(3),coniferyl aldehyde(4),syringaldehyde(5),Albarrigenol (6),camelliagenin A(7),barringtogenol C(8),syringaresinol(9), pinoresinol(10),lariciresinol(11),balanophonin(12),3-acetoxymethyl-5-[(E)-2-for -mylethen-1-yl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydro benzo furan (13),dihydrodehydrodiconifery alcohol(14),4,9-dihydroxy-3,3'-dimethoxy-4',7-epoxy-8,5'-neolignane-9'-yl acetate(15),isolariciresinol(16),(7R,8S)-l-(3,4-dimethoxyphenyl)-2-O-(2-methoxy-4-omegahydroxypropylphenyl)propane-1,3-diol (17),acernikol(18),kaempferol(19),quercetin-3-O-β-D-glucopyranoside(20), quercetin-3-O-β-D-galactopyranosde(21) and schimanin(22).Among these compounds,compound 22 is a new lignin,and all the others are for the first time isolated from this plant and from Schima.except compound 6.
引文
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[4]Hatano Tsutomu,Han Li,Taniguchi shoko.Anti-HIV tannins from Camellia japonica and related plant species[J].Tennen YukiK Agobutsu ToronkaiKoen Yoshishu,1992,34:510-517.
[5]Chen W H,Wu D G.Study on sapogenin of Schima argentea Pritz[J].Hua H such H such Pao,1978,36(3):229-232.
[6]Perry L M.Medicinal Plants of East and Southeast Asia[M].MIT Press:MA,1980:403.
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[9]陈维新,吴大刚.银木荷皂昔元研究[J].化学学报,1977,36(3):229-232.
[10]陈昌祥,叶海亚,申永乐,等.红木荷树皮的化学成分[J].云南植物研究,1997,19(2):201-206.
[11]Yoshida T,Chou T,Nitta A,et,al.Tannins and related polyphenols of Theaeeous plants.Ⅳ.monomeric and dimeric hydrolyzable tannins having a dilaetionized valoneoyl group from Schima wallichii.Korth.[j].Chem.Pharm.Bull.,1991,39:2247-2251.
[12]谢惜媚,陆慧宁.木荷花挥发性成分的GC-MS分析[J].热带亚热带植物学报,2008,16(4):373-376.
[13]Ohtsuki T,Sato M,Koyano T,et,al.Steroidal saponins from Calamus insignis, and their cell growth and cell cycle inhibitory activities[J].Bioorg.Med.Chem.,2006,14:659-665.
[14]Dhar M L,Dhar M M,Dhawan B N,et,al.Screening of Indian plants for biological activity.Ⅳ[J].Indian J.Exp.Biol.,1973,11:43-47.
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