血耳子实体中化学成分研究
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摘要
综合运用硅胶柱色谱、ODS柱色谱、Sephadex LH-20凝胶柱色谱以及制备型高效液相色谱等现代色谱分离技术对银耳科银耳属真菌血耳Tremella sanguinea子实体中的化学成分进行系统研究。根据化合物的理化性质和波谱数据,并通过与文献对照,鉴定了从血耳子实体的90%乙醇提取物中分离得到的16个化合物,分别鉴定为:(22E)-5α,8α-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol (1),(22E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (2),酒酵母甾醇(3),ergosta-7-ene-3β,5α,6β-triol (4),(22E)-6β-methoxyergosta-7,22-diene-3β,5α-diol(5),ergosta-7-en-3β-ol(6),4-hydroxy-methylincisterol(7),2-吡咯酮(8),烟酰胺(9),1-(3-indolyl)-2,3-dihydroxypropan-1-one(10),yangambin(11),亚油酸(12)、(9Z,12Z,15Z)-2,3-二羟丙基十八碳三烯酸酯(13),(9Z,12Z)-2,3-二羟丙基十八碳二烯酸酯(14),crypticin B(15)和3-苯基乳酸(16)。其中化合物1～7为甾体类化合物,化合物8～10为生物碱类化合物,化合物11为木脂素类化合物,化合物12～14为脂肪酸类化合物,化合物15和16为酚酸类化合物,所有化合物均为首次从血耳中分离得到,除化合物6,9和12以外,其他化合物均为首次从银耳属真菌中分离得到。
The chemical constituents from the fruiting bodies of Tremella sanguinea were separated and purified by column chromatography on silica gel,ODS,Sephadex LH-20,and RP-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic data analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the fruiting bodies of T. sanguinea,which were identified as( 22 E)-5α,8α-epidioxy-24-methyl-cholesta-6,9( 11),22-trien-3β-ol( 1),( 22 E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol( 2),cerevisterol( 3),ergosta-7-ene-3β,5α,6β-triol( 4),( 22 E)-6β-methoxyergosta-7,22-diene-3β,5α-diol( 5),ergosta-7-en-3β-ol( 6),4-hydroxy-methylincisterol( 7),2-pyrrolidone( 8),nicotinamide( 9),1-( 3-indolyl)-3-dihydroxypropan-1-one( 10),yangambin( 11),linoleic acid( 12),( 9 Z,12 Z,15 Z)-2,3-dihydroxypropyl octadeca-trienoate( 13),( 9 Z,12 Z)-2,3-dihydroxypropyl-octadeca-dienoate( 14),crypticin B( 15)and 3-phenyllactic acid( 16). All compounds were isolated from T. sanguinea for the first time. Except for compounds 6,9 and 12,the remained compounds were isolated from the genus Tremella for the first time.
The chemical constituents from the fruiting bodies of Tremella sanguinea were separated and purified by column chromatography on silica gel,ODS,Sephadex LH-20,and RP-HPLC. The structures of the isolated compounds were identified on the basis of physicochemical properties and spectroscopic data analysis,as well as comparisons with the data reported in the literature. Sixteen compounds were isolated from the 90% ethanol extract of the fruiting bodies of T. sanguinea,which were identified as( 22 E)-5α,8α-epidioxy-24-methyl-cholesta-6,9( 11),22-trien-3β-ol( 1),( 22 E)-5α,8α-epidioxyergosta-6,22-dien-3β-ol( 2),cerevisterol( 3),ergosta-7-ene-3β,5α,6β-triol( 4),( 22 E)-6β-methoxyergosta-7,22-diene-3β,5α-diol( 5),ergosta-7-en-3β-ol( 6),4-hydroxy-methylincisterol( 7),2-pyrrolidone( 8),nicotinamide( 9),1-( 3-indolyl)-3-dihydroxypropan-1-one( 10),yangambin( 11),linoleic acid( 12),( 9 Z,12 Z,15 Z)-2,3-dihydroxypropyl octadeca-trienoate( 13),( 9 Z,12 Z)-2,3-dihydroxypropyl-octadeca-dienoate( 14),crypticin B( 15)and 3-phenyllactic acid( 16). All compounds were isolated from T. sanguinea for the first time. Except for compounds 6,9 and 12,the remained compounds were isolated from the genus Tremella for the first time.
引文
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[4]李艳军,李小霞,陈国栋,等.内生真菌Sporormiella irregularis(No.71-11-4-1)中一个新的二裂甾体[J].沈阳药科大学学报,2012,29(1):678.
[5]Qi S H,Zhang S,Yang L H,et al. Antifouling and antibacterial compounds from the gorgonians Subergorgia suberosa and Scripearia gracillis[J]. Nat Prod Res,2008,22(2):154.
[6]Madaio A,Piccialli V,Sica D,et al. New polyhydrozysterols from the dictyoceratid sponges Hippospongia communis,Spongia officinalis,Ircinia variabilis,and Spongionella gracilis[J]. J Nat Prod,1989,52(5):952.
[7]Gao H,Hong K,Zhang X,et al. New steryl esters of fatty acids from the mangrove fungus Aspergillus awamori[J]. Helv Chim Acta,2007,90(6):1165.
[8]Kim K H,Choi S U,Park K M,et al. Cytotoxic constituents of Amanita subjunquillea[J]. Arch Pharm Res,2008,31(5):579.
[9]周静,陈敏,李筠,等.一株枝网刺柳珊瑚共附生真菌Peniophora sp.次级代谢产物研究[J].中国海洋药物,2012,31(4):8.
[10]何立华,华会明,张娜,等.多茎委陵菜化学成分的分离与鉴定[J].沈阳药科大学学报,2009,26(2):108.
[11]Reshma M V,Jacob J,Syamnath V L,et al. First report on isolation of 2,3,4-trihydroxy-5-methylacetophenone from palmyra palm(Borassus flabellifer Linn.)syrup,its antioxidant and antimicrobial properties[J]. Food Chem,2017,228(1):491.
[12]Hu Z X,Xue Y B,Bi X B,et al. Five new secondary metabolites produced by a marine-associated fungus, Daldinia eschscholzii[J]. Mar Drugs,2014,12(11):5563.
[13]Zhang W J,Wang Y,Geng Z F,et al. Antifeedant activities of lignans from stem bark of Zanthoxylum armatum DC. against Tribolium castaneum[J]. Molecules,2018,23(3):617.
[14]Marwah R G,Fatope M O,Deadman M L,et al. Musanahol:a new aureonitol-related metabolite from a Chaetomium sp[J]. Tetrahedron,2007,63(34):8174.
[15]刘真,姜薇,邓志威,等.红树植物海漆中一个二萜化合物绝对构型的确定[J].中国药学:英文版,2010,19(5):387.
[16]Chung W,Goo Y M,Na D S,et al. A phospholipase A 2,inhibitor from Arisaema amurense Max. var. serratum Nakai[J]. Arch Pharm Res,1995,18(4):293.
[17]Cimmino A,Nocera P,Linaldeddu B T,et al. Phytotoxic metabolites produced by Diaporthella cryptica,the causal agent of hazelnut branch canker[J]. J Agric Food Chem,2018,66(13):3435.
[18]张晓瑢,彭树林,肖顺昌,等.单条草化学成分的研究[J].应用与环境生物学报,1998,4(2):145.