凤眼草和蓬子菜化学成分及生物活性研究
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摘要
1．凤眼草为苦木科臭椿属臭椿(Ailanthus altissima(Mill)Swingle)的果实，我国南北均有分布。中医认为凤眼草味苦、涩，性凉。用于清热燥湿，止痢，止血。主治痢疾，白浊，带下，便血，尿血，崩漏。
本论文对凤眼草的95％乙醇提取物和水提取物进行了研究，利用系统溶剂萃取法、重结晶法、硅胶柱色谱、聚酰胺柱色谱、Sephadex LH-20柱色谱、制备性TLC和HPLC等手段分离得到41个化合物。通过理化性质和波谱数据分析鉴定了它们的结构。分别属于甾体类：豆甾烷-3，6-二酮(stigmastane-3，6-dione，1)，豆甾烷-3β，6β-二醇(stigmastane-3β，6β-diol，2)，豆甾-4-烯-3，6-二酮(stigmast-4-ene-3，6-dione，3)，6β-羟基-豆甾-4-烯-3-酮(6β-hydroxystigmast-4-en-3-one，4)，6α-羟基-豆甾-4-烯-3-酮(6α-hydroxystigmast-4-en-3-one，5)，豆甾-4-烯-3β，6β-二醇(stigmast-4-ene-3β，6β-diol，6)，豆甾-4-烯-3β，6α-二醇(stigmast-4-ene-3β，6α-diol，7)，豆甾-4-烯-3-酮(stigmast-4-en-3-one，8)，β-谷甾醇(β-sitosterol，9)，胡萝卜苷(daucosterol，10)，3β-羟基-豆甾-5-烯-7-酮(3β-hydroxystigmast-5-en-7-one，11)，豆甾-5-烯-3β，7α-二醇(stigmast-5-ene-3β，7α-diol，12)，豆甾-5-烯-3β，7α，20ξ-三醇(stigmast-5-ene-3β，7α，20ξ-triol，13)，麦角甾-4，6，8(14)，22-四烯-3-酮(ergesta-4，6，8(14)，22-tetraen-3-one，14)，5α，8α-表二氧化麦角甾-6，22-二烯-3β-醇(5α，8α-epidioxyergesta-6，22-dien-3β-ol，15)，5α，8α-表二氧化麦角甾-6，9(11)，22-三烯-3β-醇(5α，8α-epidioxyergesta-6，9(11)，22-trien-3β-ol，16)。三萜类：9，19-环阿尔廷-23(Z)-烯-3β，25-二醇(9，19-cyclolanost-23(Z)-ene-3β，25-diol，17)，环阿尔廷-25-烯-3β，24ξ-二醇(cycloart-25-ene-3β，24ξ-diol，18/19)，2β，20(S)-二羟基-达玛烷-24-烯-3-酮(2β，20(S)-dihydroxydammar-24-en-3-one，20)，β-香树脂醇(β-amyin，21)，齐敦果烷-9(11)，12-二烯-3β-醇(olean-9(11)，12-dien-3β-ol，22)，异齐敦果烷-14-烯-3-酮(D-friedoolean-14-en-3-one，23)，熊果酸(ursolic acid，24)，22-羟基-何伯烷-3-酮(22-hydroxyhopan-3-one，25)，臭椿苦酮A(11β，20-epoxy-1β，2α，12α-pentahydroxypicrasa-3，13(21)-dien-16-one，26)。神经鞘苷类：1-O-β-D-吡喃葡萄糖基-(2S，3R，4E，9E)-2-(2′R-羟基十六烷酰胺基)-4，9-二烯十八烷-1，3-二醇(1-O-β-D-glucopyranosyl-(2S，3R，4E，9E)-2-(2′R-hydroxyhexadecenoylamino)-4，9-octadecadiene-1，3-diol，27)。黄酮类：山柰酚(kaempferol，32)，槲皮素(quercetin，33)，槲皮素3-O-β-D-吡喃葡萄糖苷(quercetin 3-O-β-D-glucopyranoside，34)，山柰酚3，7-O-二α-L-吡喃鼠李糖苷(kaempferol 3，7-O-bis-α-L-rhamnopyranoside，35)，3-O-α-L-呋喃阿拉伯糖基-山柰酚7-O-α-L-吡喃鼠李糖苷(3-O-α-L-arabinofuranosyl kaempferol 7-O-α-L-rhamnopyranoside，36)。木脂素类：(+)-异落叶松树脂醇[(+)-isolariciresinol，40]，(+)-异落叶松树脂醇9-O-β-D-吡喃葡萄糖苷[(+)-isolariciresinol 9-O-β-D-glucopyranoside，41]。酚酸类：香草醛(vanillin，37)，没食子酸(gallic acid，38)，七叶内酯(6，7-dihydroxycoumarin，39)。其他类：正三十四烷(n-tetratriacontane，28)，卫矛醇(L-evonymitol，29)，甘露醇(D-mannitol，30)，山梨醇(D-sorbitol，31)。其中，化合物27为未见文献报道的新化合物；化合物2为新天然产物；化合物1-8，11-25，28-31，34-41均是首次从该属分离得到。化合物10，26，32，33均是首次从凤眼草中分离得到。
本文利用文献，从结构类型、植物分布、生物活性、生合成途径及人工合成方法、结构研究方法等方面对苦味苦素类化合物的研究进展进行了综述。2．蓬子菜为茜草科拉拉藤属(Galium)植物药用全草，我国南北均有分布。中医认为蓬子菜味微辛、苦，性微寒。用于清热解毒、活血通经、祛风止痒。主治肝炎、腹水、咽喉肿痛、疮疔肿毒、妇女闭经、带下、荨麻疹。
本论文对蓬子菜的95％乙醇回流提取物进行研究，利用系统溶剂萃取法、硅胶柱色谱、聚酰胺柱色谱、Sephadex LH-20柱色谱、制备性TLC和HPLC等手段分离得到34个化合物。通过理化性质和波谱数据分析鉴定了他们的结构。分别属于黄酮类：异鼠李素(isorhamnetin，1)，异鼠李素3-O-α-L-吡喃鼠李糖基-(1-6)-β-D-吡喃葡萄苷(isorhamnetin 3-O-α-L-rhamnopyranosyl-(1-6)-β-D-glucopyranoside，2)，香叶木素(diosmetin，3)，香叶木素7-O-β-D-吡喃葡萄糖苷(diosmetin 7-O-β-D-glucopyranoside，4)，香叶木素7-O-β-D-吡喃木糖基-(1-6)-β-D-吡喃葡萄糖苷(diosmetin 7-O-β-D-xylopyranosyl-(1-6)-β-D-glucopyranoside，5)，香叶木素7-O-α-L-吡喃鼠李糖基-(1-2)[β-D-吡喃木糖基-(1-6)]-β-D-吡喃葡萄糖苷(diosmetin 7-O-α-L-rhamnopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-6)]-β-D-glucopyranoside，6)，山柰酚(kaempferol，7)，槲皮素(quercetin，8)，3，5，7，3′，4′，3″，5″，7″，3′″，4′″-十羟基-[8-亚甲基-8″]-双黄酮(3，5，7，3′，4′，3″，5″，7″，3′″，4′″-decahydroxyl-[8-CH_2-8″]-biflavone，9)。蒽醌类：2，5-二羟基-1，3-二甲氧基-蒽醌(2，5-dihydroxy-1，3-dimethoxy-anthra-quinone，10)，2-羟基-1，3-二甲氧基-蒽醌(2-hydroxy-1，3-dimethoxy-anthraquinone，11)，大黄素甲醚(physcione，12)，1，3-二羟基-2-甲基-蒽醌(1，3-dihydroxy-2-methyl-anth-raquinone，13)，2，8-二羟基-1-甲氧基-蒽醌(2，8-dihydroxy-1-methoxy-anthraquinone，14)，1-羟基-2-羟甲基-3-甲氧基-蒽醌(1-hydroxy-2-hydroxymethy-3-methoxy-anthraquinine，15)。木脂素类：(+)-松脂素4，4′-O-二β-D-吡喃葡萄苷[(+)-pinoresinol 4，4′-O-bis-β-D-glucopyranoside，16]，(+)-表松脂素[(+)-epipinoresinol，17]，松脂素【(+)-medioresinol，18]。环烯醚萜类：morindolide(19)，水晶兰苷(monotropein，20)，去乙酰车叶草甙酸(deacetyl-asperulosidic acid，21)，6α-羟基-京尼平苷(6α-hydroxygeniposide，22)，车叶草甙(deacetyl-asperuloside，23)。三萜类：熊果酸(ursolic acid，29)，rubifolic acid(30)，熊果醛(ursolic aldehyde，31)。酚酸类：东莨菪素(scopoletin，24)，阿魏酸(ferulic acid，25)，phthalic acid bis-(2-ethyl-hexyl)ester(26)，对羟基-苯丙酸(p-hydroxy-phenylpropionic acid，27)，香豆酸三十二酯(trans-dotriacontyl-coumarate，28)。其它类：正三十二烷醇(n-dotriacontanol，32)，β-谷甾醇(β-sitosterol，33)，胡萝卜苷(daucosterol，34)。其中，化合物6，9，10为未见文献报道的新化合物；化合物1，2，11，14-19，23，25-32为首次从该属分离得到。化合物12，24为首次从蓬子菜中分离得到。
本论文以E．coli，S．aureus，P．aeruginosa和S．typhiuriun为受试菌，采用琼脂扩散纸片法对凤眼草和蓬子菜抗菌活性成分进行追踪，测定凤眼草水提大孔树脂洗脱物、95％乙醇提取物乙酸乙酯萃取部分和正丁醇萃取部分均有不同程度的抗菌活性，有效成分的分离鉴定表明，黄酮类化合物和木脂素类物质是主要的抗菌活性物质。蓬子菜的95％乙醇回流提取液的正丁醇层具有抗菌作用，所得单体化合物中，黄酮类化合物活性最强，部分蒽醌、环烯醚萜和木脂素类化合物具有较好的抗菌活性。利用二倍稀释法测定抗菌活性化合物的最小抑菌浓度(MIC)。
借助超氧化歧化酶(SOD)测试盒，对29个单体化合物(7个来自凤眼草，22个来自蓬子菜)进行体外清除超氧阴离子(O_2~(-.))测试研究。同时，采用MTT法，对凤眼草和蓬子菜粗提物体外肿瘤抑制活性进行了初步研究，其中蓬子菜提取物的正丁醇层对人体肿瘤细胞(MCF-7和SF188)均有潜在的生长抑制抑制活性，对MCF-7的IC_(50)为424μg/ml。而石油醚乳化层对SF188显示出明显的抑制活性，IC_(50)为342μg/ml。
1．Ailanthus altissima Swingle (Simaroubaceae) is widespread in China. The fruits ofthis plant have traditionally been used for the treatment of antimalarial, antibacterial andgynecopathia.
Forty-one compounds were separated from the fruits of A. altissima Swingle byusing chromatographic and recrystallized methods.
On the basis of physico-chemical properties and spectroscopic analysis, theirstructures were identified as follows. Steroids: stigmastane-3,6-dione (1) , stigmastane-3β,6β-diol (2) , stigmast-4-ene-3,6-dione (3) , 6β-hydroxystigmast-4-en-3-one (4) ,6α-hydroxystigmast-4-en-3-one (5) , stigmast-4-ene-3β,6β-diol (6) , stigmast-4-ene-3β,6α-diol (7) , stigmast-4-en-3-one (8) ,β-sitosterol (9) , daucosterol (10) , 3β-hydroxy-stigmast-5-en-7-one (11) , stigmast-5-ene-3β,7α-diol (12) , stigmast-5-ene-3β,7α,20ξ-triol (13) , ergesta-4,6,8(14) ,22-tetraen-3-one (14) , 5α,8α-epidioxyergesta-6,22-dien-3β-ol (15) , 5α,8α-epidioxyergesta-6,9(11) ,22-trien-3β-ol (16) . Triterpenoids: 9,19-cyclolanost-23(Z)-ene-3β,25-diol (17) , cycloart-25-ene-3β, 24ξ-diol (18/19) , 2β,20(S)-dihydroxydammar-24-en-3-one (20) ,β-amyirn (21) , olean-9(11) ,12-dien-3β-ol (22) ,D-friedoolean-14-en-3-one (23) , ursolic acid (24) , 22-hydroxyhopan-3-one (25) ,11β,20-epoxy-1β,2α,12α-pentahydroxypicrasa-3,13(21) -dien-16-one (26) . Cerebrosides: 1-O-β-D-glucopyranosyl-(2S,3R,4E,9E)-2-(2'R-hydroxyhexadecenoylamino)-4,9-octa-decadiene-1,3-diol (27) . Flavonoids: kaempferol (32) , quercetin (33) , quercetin 3-O-β-D-glucopyranoside (34) , kaempferol 3,7-O-bis-α-L-rhamnopyranoside (35) , 3-O-α-L-arabinofuranosyl kaempferol 7-O-α-L-rhamnopyranoside (36) . Lignanoids: (+)-isolariciresinol (40) , (+)-isolariciresinol 9-O-β-D-glucopyranoside (41) . Phenolicacids: vanillin (37) , gallic acid (38) , 6,7-dihydroxycoumarin (39) . Others: n-tetra-triacontane (28) , L-evonymitol (29) , D-mannitol (30) , D-sorbitol (31) .
Among them, compound 27 was a new compound; compound 2 was a new naturalproduct; compounds 1-8, 11-25, 28-31, 34-41 were firstly isolated from this genus;compounds 10, 26, 32, 33 were isolated from the fruits of Ailanthus altissima Swinglefor the first time.
A review on the biosynthesis, pharmacological actions and spectral characters of 锘縬uassinoid type triterpenoids was given on the base of references and our study work.2．Galium verum L. (Rubiaceae) is an herbal medicine widely distributed in the China,which has good therapy effect on phlebophlogosis and hepatitis as a famous folkmedicine.鈽匱hirty-four compounds were separated from G. verum L. by using chromatographicand recrystallized methods.鈽匫n the basis of physico-chemical properties and spectroscopic analysis, theirstructures were identified as follows. Flavonoids: isorhamnetin (1) , isorhamnetin3-O-伪-L-rhamnopyranosyl (1-6) -尾-D-glucopyranoside (2) , diosmetin (3) , diosmetin7-O-尾-D-glucopyranoside (4) , diosmetin 7-O-尾-D-xylopyranosyl-(1-6) -尾-D-gluco-pyranoside(5) , diosmetin 7-O-伪-L-rhamnopyranosyl-( 1-2) -[尾-D-xylopyranosyl-( 1-6) ]-尾-D-glucopyranoside (6) , kaempferol (7) , quercetin (8) , 3,5,7,3',4',3",5",7",3"',4"'-decahydroxyl-[8-CH_2-8"]-biflavone (9) . Anthraquinones.路2, 5-dihydroxy-1, 3-di-methoxy-anthraquinone (10) , 2-hydroxy-1, 3-dimethoxy-anthraquinone (11) , physcione(12) , 1,3-dihydroxy-2-methyl-anthraquinone (13) , 2,8-dihydroxy-1-methoxy-anthra-quinone (14) ,1-hydroxy-2-hydroxymethyl-3-methoxy-anthraquinone (15) . Lignanoids:(+)-pinoresinol 4,4'-O-bis-尾-D-glucopyranoside (16) , (+)-epipinoresinol (17) , (+)-medioresinol (18) . Iridoids: morindolide (19) , monotropein (20) , deacetyl-asperulo-sidic acid (21) , 6伪-hydroxygeniposide (22) , deacetyl-asperuloside (23) . Triterpenoids:ursolic acid (29) , rubifolic acid (30) , ursolic aldehyde (31) . Phenolic acids:scopoletin (24) , ferulic acid (25) , phthalic acid bis-(2-ethyl-hexyl) ester (26) , p-hydroxy-phenylpropionic acid (27) , trans-dotriacontyl-coumarate (28) . Others: n-dotriacontanol (32) ,尾-sitosterol (33) , daucosterol (34) .鈽匒mong them, compounds 6, 9 and 10 were new compounds; compounds 1, 2,11,14-19, 23, 25-32 were firstly isolated from this genus; compounds 12, 24 were isolatedfrom the Galium verum L. for the first time.鈽匬harmacological tests showed that the extract of fruits of Ailanthus altissimaSwingle had the effect on E. coli, S. aureus, P. aeruginosa and S. typhiuriun in vitro.The EtOAc extract exhibited the best result, which gave the effective activity againsttested bacterium. By the chromatographic isolation, the major compounds obtained from this part were flavonoids and lignanoids. The n-butanol extract from G. verum L.showed the potential activity against tested bacterium. By the chromatographic isolation,the major compounds obtained from this part were flavonoids. Minimal inhibitoryconcentrations (MIC) of effective components were measured using two-fold dilutionmethod.
The anti-oxidative activity of twenty-nine compounds isolated from fruits of A.altissima Swingle (seven compounds) and G. verum L. (twenty-two compounds) wastested, and some of them showed effective antioxidations.
By MTT methods, the in vitro cytotoxicity activities against cancer cell lines of theextract were assayed. The emulsive part between petroleum and water of G. verum L.showed moderate activity against human cancer cell line (SF188) with an IC_(50) value of342μg/ml; the n-butanol part displayed potential activity with an IC_(50) value of 424μg/ml against MCF-7 cell line.
本论文对凤眼草的95％乙醇提取物和水提取物进行了研究，利用系统溶剂萃取法、重结晶法、硅胶柱色谱、聚酰胺柱色谱、Sephadex LH-20柱色谱、制备性TLC和HPLC等手段分离得到41个化合物。通过理化性质和波谱数据分析鉴定了它们的结构。分别属于甾体类：豆甾烷-3，6-二酮(stigmastane-3，6-dione，1)，豆甾烷-3β，6β-二醇(stigmastane-3β，6β-diol，2)，豆甾-4-烯-3，6-二酮(stigmast-4-ene-3，6-dione，3)，6β-羟基-豆甾-4-烯-3-酮(6β-hydroxystigmast-4-en-3-one，4)，6α-羟基-豆甾-4-烯-3-酮(6α-hydroxystigmast-4-en-3-one，5)，豆甾-4-烯-3β，6β-二醇(stigmast-4-ene-3β，6β-diol，6)，豆甾-4-烯-3β，6α-二醇(stigmast-4-ene-3β，6α-diol，7)，豆甾-4-烯-3-酮(stigmast-4-en-3-one，8)，β-谷甾醇(β-sitosterol，9)，胡萝卜苷(daucosterol，10)，3β-羟基-豆甾-5-烯-7-酮(3β-hydroxystigmast-5-en-7-one，11)，豆甾-5-烯-3β，7α-二醇(stigmast-5-ene-3β，7α-diol，12)，豆甾-5-烯-3β，7α，20ξ-三醇(stigmast-5-ene-3β，7α，20ξ-triol，13)，麦角甾-4，6，8(14)，22-四烯-3-酮(ergesta-4，6，8(14)，22-tetraen-3-one，14)，5α，8α-表二氧化麦角甾-6，22-二烯-3β-醇(5α，8α-epidioxyergesta-6，22-dien-3β-ol，15)，5α，8α-表二氧化麦角甾-6，9(11)，22-三烯-3β-醇(5α，8α-epidioxyergesta-6，9(11)，22-trien-3β-ol，16)。三萜类：9，19-环阿尔廷-23(Z)-烯-3β，25-二醇(9，19-cyclolanost-23(Z)-ene-3β，25-diol，17)，环阿尔廷-25-烯-3β，24ξ-二醇(cycloart-25-ene-3β，24ξ-diol，18/19)，2β，20(S)-二羟基-达玛烷-24-烯-3-酮(2β，20(S)-dihydroxydammar-24-en-3-one，20)，β-香树脂醇(β-amyin，21)，齐敦果烷-9(11)，12-二烯-3β-醇(olean-9(11)，12-dien-3β-ol，22)，异齐敦果烷-14-烯-3-酮(D-friedoolean-14-en-3-one，23)，熊果酸(ursolic acid，24)，22-羟基-何伯烷-3-酮(22-hydroxyhopan-3-one，25)，臭椿苦酮A(11β，20-epoxy-1β，2α，12α-pentahydroxypicrasa-3，13(21)-dien-16-one，26)。神经鞘苷类：1-O-β-D-吡喃葡萄糖基-(2S，3R，4E，9E)-2-(2′R-羟基十六烷酰胺基)-4，9-二烯十八烷-1，3-二醇(1-O-β-D-glucopyranosyl-(2S，3R，4E，9E)-2-(2′R-hydroxyhexadecenoylamino)-4，9-octadecadiene-1，3-diol，27)。黄酮类：山柰酚(kaempferol，32)，槲皮素(quercetin，33)，槲皮素3-O-β-D-吡喃葡萄糖苷(quercetin 3-O-β-D-glucopyranoside，34)，山柰酚3，7-O-二α-L-吡喃鼠李糖苷(kaempferol 3，7-O-bis-α-L-rhamnopyranoside，35)，3-O-α-L-呋喃阿拉伯糖基-山柰酚7-O-α-L-吡喃鼠李糖苷(3-O-α-L-arabinofuranosyl kaempferol 7-O-α-L-rhamnopyranoside，36)。木脂素类：(+)-异落叶松树脂醇[(+)-isolariciresinol，40]，(+)-异落叶松树脂醇9-O-β-D-吡喃葡萄糖苷[(+)-isolariciresinol 9-O-β-D-glucopyranoside，41]。酚酸类：香草醛(vanillin，37)，没食子酸(gallic acid，38)，七叶内酯(6，7-dihydroxycoumarin，39)。其他类：正三十四烷(n-tetratriacontane，28)，卫矛醇(L-evonymitol，29)，甘露醇(D-mannitol，30)，山梨醇(D-sorbitol，31)。其中，化合物27为未见文献报道的新化合物；化合物2为新天然产物；化合物1-8，11-25，28-31，34-41均是首次从该属分离得到。化合物10，26，32，33均是首次从凤眼草中分离得到。
本文利用文献，从结构类型、植物分布、生物活性、生合成途径及人工合成方法、结构研究方法等方面对苦味苦素类化合物的研究进展进行了综述。2．蓬子菜为茜草科拉拉藤属(Galium)植物药用全草，我国南北均有分布。中医认为蓬子菜味微辛、苦，性微寒。用于清热解毒、活血通经、祛风止痒。主治肝炎、腹水、咽喉肿痛、疮疔肿毒、妇女闭经、带下、荨麻疹。
本论文对蓬子菜的95％乙醇回流提取物进行研究，利用系统溶剂萃取法、硅胶柱色谱、聚酰胺柱色谱、Sephadex LH-20柱色谱、制备性TLC和HPLC等手段分离得到34个化合物。通过理化性质和波谱数据分析鉴定了他们的结构。分别属于黄酮类：异鼠李素(isorhamnetin，1)，异鼠李素3-O-α-L-吡喃鼠李糖基-(1-6)-β-D-吡喃葡萄苷(isorhamnetin 3-O-α-L-rhamnopyranosyl-(1-6)-β-D-glucopyranoside，2)，香叶木素(diosmetin，3)，香叶木素7-O-β-D-吡喃葡萄糖苷(diosmetin 7-O-β-D-glucopyranoside，4)，香叶木素7-O-β-D-吡喃木糖基-(1-6)-β-D-吡喃葡萄糖苷(diosmetin 7-O-β-D-xylopyranosyl-(1-6)-β-D-glucopyranoside，5)，香叶木素7-O-α-L-吡喃鼠李糖基-(1-2)[β-D-吡喃木糖基-(1-6)]-β-D-吡喃葡萄糖苷(diosmetin 7-O-α-L-rhamnopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-6)]-β-D-glucopyranoside，6)，山柰酚(kaempferol，7)，槲皮素(quercetin，8)，3，5，7，3′，4′，3″，5″，7″，3′″，4′″-十羟基-[8-亚甲基-8″]-双黄酮(3，5，7，3′，4′，3″，5″，7″，3′″，4′″-decahydroxyl-[8-CH_2-8″]-biflavone，9)。蒽醌类：2，5-二羟基-1，3-二甲氧基-蒽醌(2，5-dihydroxy-1，3-dimethoxy-anthra-quinone，10)，2-羟基-1，3-二甲氧基-蒽醌(2-hydroxy-1，3-dimethoxy-anthraquinone，11)，大黄素甲醚(physcione，12)，1，3-二羟基-2-甲基-蒽醌(1，3-dihydroxy-2-methyl-anth-raquinone，13)，2，8-二羟基-1-甲氧基-蒽醌(2，8-dihydroxy-1-methoxy-anthraquinone，14)，1-羟基-2-羟甲基-3-甲氧基-蒽醌(1-hydroxy-2-hydroxymethy-3-methoxy-anthraquinine，15)。木脂素类：(+)-松脂素4，4′-O-二β-D-吡喃葡萄苷[(+)-pinoresinol 4，4′-O-bis-β-D-glucopyranoside，16]，(+)-表松脂素[(+)-epipinoresinol，17]，松脂素【(+)-medioresinol，18]。环烯醚萜类：morindolide(19)，水晶兰苷(monotropein，20)，去乙酰车叶草甙酸(deacetyl-asperulosidic acid，21)，6α-羟基-京尼平苷(6α-hydroxygeniposide，22)，车叶草甙(deacetyl-asperuloside，23)。三萜类：熊果酸(ursolic acid，29)，rubifolic acid(30)，熊果醛(ursolic aldehyde，31)。酚酸类：东莨菪素(scopoletin，24)，阿魏酸(ferulic acid，25)，phthalic acid bis-(2-ethyl-hexyl)ester(26)，对羟基-苯丙酸(p-hydroxy-phenylpropionic acid，27)，香豆酸三十二酯(trans-dotriacontyl-coumarate，28)。其它类：正三十二烷醇(n-dotriacontanol，32)，β-谷甾醇(β-sitosterol，33)，胡萝卜苷(daucosterol，34)。其中，化合物6，9，10为未见文献报道的新化合物；化合物1，2，11，14-19，23，25-32为首次从该属分离得到。化合物12，24为首次从蓬子菜中分离得到。
本论文以E．coli，S．aureus，P．aeruginosa和S．typhiuriun为受试菌，采用琼脂扩散纸片法对凤眼草和蓬子菜抗菌活性成分进行追踪，测定凤眼草水提大孔树脂洗脱物、95％乙醇提取物乙酸乙酯萃取部分和正丁醇萃取部分均有不同程度的抗菌活性，有效成分的分离鉴定表明，黄酮类化合物和木脂素类物质是主要的抗菌活性物质。蓬子菜的95％乙醇回流提取液的正丁醇层具有抗菌作用，所得单体化合物中，黄酮类化合物活性最强，部分蒽醌、环烯醚萜和木脂素类化合物具有较好的抗菌活性。利用二倍稀释法测定抗菌活性化合物的最小抑菌浓度(MIC)。
借助超氧化歧化酶(SOD)测试盒，对29个单体化合物(7个来自凤眼草，22个来自蓬子菜)进行体外清除超氧阴离子(O_2~(-.))测试研究。同时，采用MTT法，对凤眼草和蓬子菜粗提物体外肿瘤抑制活性进行了初步研究，其中蓬子菜提取物的正丁醇层对人体肿瘤细胞(MCF-7和SF188)均有潜在的生长抑制抑制活性，对MCF-7的IC_(50)为424μg/ml。而石油醚乳化层对SF188显示出明显的抑制活性，IC_(50)为342μg/ml。
1．Ailanthus altissima Swingle (Simaroubaceae) is widespread in China. The fruits ofthis plant have traditionally been used for the treatment of antimalarial, antibacterial andgynecopathia.
Forty-one compounds were separated from the fruits of A. altissima Swingle byusing chromatographic and recrystallized methods.
On the basis of physico-chemical properties and spectroscopic analysis, theirstructures were identified as follows. Steroids: stigmastane-3,6-dione (1) , stigmastane-3β,6β-diol (2) , stigmast-4-ene-3,6-dione (3) , 6β-hydroxystigmast-4-en-3-one (4) ,6α-hydroxystigmast-4-en-3-one (5) , stigmast-4-ene-3β,6β-diol (6) , stigmast-4-ene-3β,6α-diol (7) , stigmast-4-en-3-one (8) ,β-sitosterol (9) , daucosterol (10) , 3β-hydroxy-stigmast-5-en-7-one (11) , stigmast-5-ene-3β,7α-diol (12) , stigmast-5-ene-3β,7α,20ξ-triol (13) , ergesta-4,6,8(14) ,22-tetraen-3-one (14) , 5α,8α-epidioxyergesta-6,22-dien-3β-ol (15) , 5α,8α-epidioxyergesta-6,9(11) ,22-trien-3β-ol (16) . Triterpenoids: 9,19-cyclolanost-23(Z)-ene-3β,25-diol (17) , cycloart-25-ene-3β, 24ξ-diol (18/19) , 2β,20(S)-dihydroxydammar-24-en-3-one (20) ,β-amyirn (21) , olean-9(11) ,12-dien-3β-ol (22) ,D-friedoolean-14-en-3-one (23) , ursolic acid (24) , 22-hydroxyhopan-3-one (25) ,11β,20-epoxy-1β,2α,12α-pentahydroxypicrasa-3,13(21) -dien-16-one (26) . Cerebrosides: 1-O-β-D-glucopyranosyl-(2S,3R,4E,9E)-2-(2'R-hydroxyhexadecenoylamino)-4,9-octa-decadiene-1,3-diol (27) . Flavonoids: kaempferol (32) , quercetin (33) , quercetin 3-O-β-D-glucopyranoside (34) , kaempferol 3,7-O-bis-α-L-rhamnopyranoside (35) , 3-O-α-L-arabinofuranosyl kaempferol 7-O-α-L-rhamnopyranoside (36) . Lignanoids: (+)-isolariciresinol (40) , (+)-isolariciresinol 9-O-β-D-glucopyranoside (41) . Phenolicacids: vanillin (37) , gallic acid (38) , 6,7-dihydroxycoumarin (39) . Others: n-tetra-triacontane (28) , L-evonymitol (29) , D-mannitol (30) , D-sorbitol (31) .
Among them, compound 27 was a new compound; compound 2 was a new naturalproduct; compounds 1-8, 11-25, 28-31, 34-41 were firstly isolated from this genus;compounds 10, 26, 32, 33 were isolated from the fruits of Ailanthus altissima Swinglefor the first time.
A review on the biosynthesis, pharmacological actions and spectral characters of 锘縬uassinoid type triterpenoids was given on the base of references and our study work.2．Galium verum L. (Rubiaceae) is an herbal medicine widely distributed in the China,which has good therapy effect on phlebophlogosis and hepatitis as a famous folkmedicine.鈽匱hirty-four compounds were separated from G. verum L. by using chromatographicand recrystallized methods.鈽匫n the basis of physico-chemical properties and spectroscopic analysis, theirstructures were identified as follows. Flavonoids: isorhamnetin (1) , isorhamnetin3-O-伪-L-rhamnopyranosyl (1-6) -尾-D-glucopyranoside (2) , diosmetin (3) , diosmetin7-O-尾-D-glucopyranoside (4) , diosmetin 7-O-尾-D-xylopyranosyl-(1-6) -尾-D-gluco-pyranoside(5) , diosmetin 7-O-伪-L-rhamnopyranosyl-( 1-2) -[尾-D-xylopyranosyl-( 1-6) ]-尾-D-glucopyranoside (6) , kaempferol (7) , quercetin (8) , 3,5,7,3',4',3",5",7",3"',4"'-decahydroxyl-[8-CH_2-8"]-biflavone (9) . Anthraquinones.路2, 5-dihydroxy-1, 3-di-methoxy-anthraquinone (10) , 2-hydroxy-1, 3-dimethoxy-anthraquinone (11) , physcione(12) , 1,3-dihydroxy-2-methyl-anthraquinone (13) , 2,8-dihydroxy-1-methoxy-anthra-quinone (14) ,1-hydroxy-2-hydroxymethyl-3-methoxy-anthraquinone (15) . Lignanoids:(+)-pinoresinol 4,4'-O-bis-尾-D-glucopyranoside (16) , (+)-epipinoresinol (17) , (+)-medioresinol (18) . Iridoids: morindolide (19) , monotropein (20) , deacetyl-asperulo-sidic acid (21) , 6伪-hydroxygeniposide (22) , deacetyl-asperuloside (23) . Triterpenoids:ursolic acid (29) , rubifolic acid (30) , ursolic aldehyde (31) . Phenolic acids:scopoletin (24) , ferulic acid (25) , phthalic acid bis-(2-ethyl-hexyl) ester (26) , p-hydroxy-phenylpropionic acid (27) , trans-dotriacontyl-coumarate (28) . Others: n-dotriacontanol (32) ,尾-sitosterol (33) , daucosterol (34) .鈽匒mong them, compounds 6, 9 and 10 were new compounds; compounds 1, 2,11,14-19, 23, 25-32 were firstly isolated from this genus; compounds 12, 24 were isolatedfrom the Galium verum L. for the first time.鈽匬harmacological tests showed that the extract of fruits of Ailanthus altissimaSwingle had the effect on E. coli, S. aureus, P. aeruginosa and S. typhiuriun in vitro.The EtOAc extract exhibited the best result, which gave the effective activity againsttested bacterium. By the chromatographic isolation, the major compounds obtained from this part were flavonoids and lignanoids. The n-butanol extract from G. verum L.showed the potential activity against tested bacterium. By the chromatographic isolation,the major compounds obtained from this part were flavonoids. Minimal inhibitoryconcentrations (MIC) of effective components were measured using two-fold dilutionmethod.
The anti-oxidative activity of twenty-nine compounds isolated from fruits of A.altissima Swingle (seven compounds) and G. verum L. (twenty-two compounds) wastested, and some of them showed effective antioxidations.
By MTT methods, the in vitro cytotoxicity activities against cancer cell lines of theextract were assayed. The emulsive part between petroleum and water of G. verum L.showed moderate activity against human cancer cell line (SF188) with an IC_(50) value of342μg/ml; the n-butanol part displayed potential activity with an IC_(50) value of 424μg/ml against MCF-7 cell line.
引文
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