瑞香狼毒和柚皮抗癫痫活性成分的研究
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摘要
在民间用药的基础上，通过药效学实验证实作为中药狼毒入药的狼毒大戟(Euphorbia fischeriana Steud)和瑞香狼毒(Stellera chamaejasme L.)均具有不同程度的抗癫痫活性，其中瑞香狼毒的抗癫痫活性强于狼毒大戟。通过对瑞香狼毒抗癫痫活性部位的研究发现其中化学成分主要为黄酮和香豆素类化合物。根据活性部位化学成分的结构类型并结合文献，推测柚(Citrus grandis Osbeck)的果皮也具有抗癫痫活性。经药效学实验证实柚皮确有较强的活性。
采用溶剂萃取法结合药效学实验，确定了这两种植物的活性部位。并主要对这两种植物活性部位的化学成分进行了研究。从瑞香狼毒的提取物中分离得到了24个化合物，从柚皮提取物中分离得到了16个化合物。通过理化性质和波谱数据确定了它们的化学结构。从瑞香狼毒中分离得到的化合物分别为新瑞香素(1)，isomohsenone(2)，stelleranol(3)，7-甲氧基新狼毒素A(4)，异新狼毒素A(5)，(+)狼毒素(6)，1，5-二苯基-1-戊酮(7)，1，5-二苯基-2-烯-1-戊酮(8)，对羟基桂皮酸正二十二酯(9)，咖啡酸正二十酯(10)，荛花醇A(11)，荛花醇B(12)，(+)枇杷素(13)，bursehernin(14)，狼毒色原酮(15)，mohsenone(16)，新狼毒素A(17)，新狼毒素B(18)，7-甲氧基狼毒素(19)，狼毒素B(20)，西瑞香素(21)，伞形花内酯(22)，东莨菪素(23)，S-(+)-1，5-二苯基-3-羟基-1-戊酮(24)；从柚皮中分离得到的化合物分别是葡萄内酯(25)，异前胡素(26)，marmin acetonide (27)，pranferin(28)，isomerancin(29)，花椒毒酚(30)，伞形花内酯(22)，meranzin hydrate(31)，8-(3-β-葡萄糖氧基-2-羟基-3-甲基丁基)-7-甲氧基香豆素(32)，东莨菪素(23)，roseoside(33)，木栓酮(34)，5-羟甲基糠醛(35)，柠檬苦素(36)，闹米林(37)及柚皮苷(38)。其中化合物1，2，3，4，5，6为新化合物；化合物7，8，9，10是新天然产物；化合物11，12，13，14为首次从狼毒属植物中分离得到的化合物。化合物25，26，27，28，30，33，34，35为首次从柚中分离得到的化合物。上述化合物中22和23是两种植物中所共有的成分。
Isomohsenone (2)和mohsenone(16)在瑞香狼毒中的发现进一步证实了Niwa等人关于狼毒色原酮是由狼毒素转化而来的推断。
对中药狼毒的化学成分和药理研究进行了综述。
一
通过对瑞香狼毒中双黄酮类化合物的研究，结合文献，总结了瑞香科中双黄
酮类化合物的结构特点、波谱规律和立体化学研究方法；同时对双黄酮类化合物
在瑞香科植物中的分布规律进行了总结，发现双黄酮类化合物在瑞香科的植物化
学分类学方面具有重要作用。通过总结发现，在瑞香属的植物中仅存在含有黄烷
单元的双黄酮类化合物；狼毒属植物中存在双二氢黄酮类，狼毒色原酮类以及少
数含有黄烷单元的双黄酮，而且目前发现狼毒色原酮类仅存在于该属植物中；尧
花属植物中存在含有黄烷单元的双黄酮类和双二氢黄酮类／正了文献中认为双
二氢黄酮类化合物是狼毒属的特征性化学成分的观点。从双黄酮类化学成分的分
布角度来看，支持将瑞香族（狭义瑞香科）分为瑞香亚族、芜花亚族和狼毒亚族
的观点。
经药效学研究表明瑞香狼毒中含量较高的双黄酮类化合物没有狮厥作用，
而两种植物中共有的伞形花内酯能够明显的延长小鼠惊厥潜伏期，推测香豆素类
化合物是这2种植物中的抗癫痫活性成分。
Upon the basis of experience on folk medicine, two kinds of plants, Euphorbia fischeriana Steud and Stellera chamaejasme L., used as "langdu" were confirmed to have the anti-epilepsy activity through pharmacodynamical study. S. chamaejasme L. showed better effect than E. fischeriana Steud. Major chemical constituents of the active site of S. chamaejasme L. were flavonoids and coumarins. According to the structural type and literatures, we think that the peels of Citrus grandis Osbeck may have similar effect. Pharmacodynamical results confirmed our hypothesis.
24 compounds and 16 compounds were isolated from the active sites of the roots extract of Stellera chamaejasme L. and the peels extract of Citrus grandis Osbeck, respectively. Compounds from Stellera chamaejasme L. are neostellerin (1), isomohsenone (2) , stelleranol (3), 7-methoxyneochamaejasmin A (4) , mesoneochamaejasmin A (5), (+)chamaejasmine (6), 1, 5-diphenyl-1-pentanone (7), 1, 5-diphenyl-2-penten-l-one (8), p-coumaric acid w-eicosanyl ester (9), caffeic acid n-dueicosanyl ester (10), wikstrol A (11), wikstrol B (12), (+) -afzelechin (13), bursehernin (14), chamaechromone (15), mohsenone (16), neochamaejasmin A (17), neochamaejasmin B (18), 7-methoxychamaejasmine (19), chamaejasmenin B (20), daphnoretin (21), umbelliferone (22), scopoletin (23), S- ( + ) -1, 5-diphenyl -3-hydroxy-1-pentanone (24). Compounds from the peels of Citrus grandis were aurepten (25), isoimperatorin (26), marmin acetonide (27), pranferin (28), isomerancin (29), xanthotoxol (30), umbellif
erone (22), meranzin hydrate (31), 8-(3-β-D-glucosyl-2-hydroxy-3-methyl- butyl) -7- methoxycoumarin (32), scopoletin (23), roseoside (33), friedelin (34), 5-hydroxmethylfuraldehyde (35), linonin (36), nomilin (37) and narigin (38). Among them, compounds 1, 2, 3, 4, 5, 6 were determined to be new compounds. Compounds 7, 8, 9 and 10 were new natural products. Compounds 11, 12, 13, 14 were first isolated from Stellera genus. Compounds 25, 26, 27, 28, 30, 33, 34, 35 were first isolated from Citrus grandis Osbeck. Among the above compounds, 22, 23 are the common constituents of the two plants.
The existence of isomohsenone (2) and mohsenone (16) in Stellera chamaejasme L. proved Niwa's hypothesis that chamaechromonoids were transformed from chamaejasminoids.
The research on chemical constituents and pharmacology were concluded.
On the basis of our research on Stellera chamaejasme L. and the literatures, the spectral and structural characteristics, the stereochemical researching methods, the distribution in the 3 subtribes of Thymeleaceae and chemotaxonomy of biflavonoids were concluded. We found that biflavonoids played a very important role in the chemotaxonomy of Thymelaeaceous plants. We got a conclusion that only biflavonoids bearing flavan moiety existed in Daphne gemus, that biflavanones and chamaechromonoids existed in Stellera genus, and that biflavanones and biflavonoids bearing flavan moiety existed Wikstroemia species. The opinion that biflavanones only existed in Stellera genus was corrected and they were also found hi Wikstroemia genus. According to the distribution of biflavonoids, we support the viewpoint of classifying the Thymelaeaceae family into three subtribes: Wikstroemiinae, Daphninae and Passerininae.
The anti-convulsive experiments suggested that the biflavonoids didn't show any anticonvulsive activity, but that umbelliferone, which is the common constituent of these two plants, could delay the convulsive stroke.
采用溶剂萃取法结合药效学实验，确定了这两种植物的活性部位。并主要对这两种植物活性部位的化学成分进行了研究。从瑞香狼毒的提取物中分离得到了24个化合物，从柚皮提取物中分离得到了16个化合物。通过理化性质和波谱数据确定了它们的化学结构。从瑞香狼毒中分离得到的化合物分别为新瑞香素(1)，isomohsenone(2)，stelleranol(3)，7-甲氧基新狼毒素A(4)，异新狼毒素A(5)，(+)狼毒素(6)，1，5-二苯基-1-戊酮(7)，1，5-二苯基-2-烯-1-戊酮(8)，对羟基桂皮酸正二十二酯(9)，咖啡酸正二十酯(10)，荛花醇A(11)，荛花醇B(12)，(+)枇杷素(13)，bursehernin(14)，狼毒色原酮(15)，mohsenone(16)，新狼毒素A(17)，新狼毒素B(18)，7-甲氧基狼毒素(19)，狼毒素B(20)，西瑞香素(21)，伞形花内酯(22)，东莨菪素(23)，S-(+)-1，5-二苯基-3-羟基-1-戊酮(24)；从柚皮中分离得到的化合物分别是葡萄内酯(25)，异前胡素(26)，marmin acetonide (27)，pranferin(28)，isomerancin(29)，花椒毒酚(30)，伞形花内酯(22)，meranzin hydrate(31)，8-(3-β-葡萄糖氧基-2-羟基-3-甲基丁基)-7-甲氧基香豆素(32)，东莨菪素(23)，roseoside(33)，木栓酮(34)，5-羟甲基糠醛(35)，柠檬苦素(36)，闹米林(37)及柚皮苷(38)。其中化合物1，2，3，4，5，6为新化合物；化合物7，8，9，10是新天然产物；化合物11，12，13，14为首次从狼毒属植物中分离得到的化合物。化合物25，26，27，28，30，33，34，35为首次从柚中分离得到的化合物。上述化合物中22和23是两种植物中所共有的成分。
Isomohsenone (2)和mohsenone(16)在瑞香狼毒中的发现进一步证实了Niwa等人关于狼毒色原酮是由狼毒素转化而来的推断。
对中药狼毒的化学成分和药理研究进行了综述。
一
通过对瑞香狼毒中双黄酮类化合物的研究，结合文献，总结了瑞香科中双黄
酮类化合物的结构特点、波谱规律和立体化学研究方法；同时对双黄酮类化合物
在瑞香科植物中的分布规律进行了总结，发现双黄酮类化合物在瑞香科的植物化
学分类学方面具有重要作用。通过总结发现，在瑞香属的植物中仅存在含有黄烷
单元的双黄酮类化合物；狼毒属植物中存在双二氢黄酮类，狼毒色原酮类以及少
数含有黄烷单元的双黄酮，而且目前发现狼毒色原酮类仅存在于该属植物中；尧
花属植物中存在含有黄烷单元的双黄酮类和双二氢黄酮类／正了文献中认为双
二氢黄酮类化合物是狼毒属的特征性化学成分的观点。从双黄酮类化学成分的分
布角度来看，支持将瑞香族（狭义瑞香科）分为瑞香亚族、芜花亚族和狼毒亚族
的观点。
经药效学研究表明瑞香狼毒中含量较高的双黄酮类化合物没有狮厥作用，
而两种植物中共有的伞形花内酯能够明显的延长小鼠惊厥潜伏期，推测香豆素类
化合物是这2种植物中的抗癫痫活性成分。
Upon the basis of experience on folk medicine, two kinds of plants, Euphorbia fischeriana Steud and Stellera chamaejasme L., used as "langdu" were confirmed to have the anti-epilepsy activity through pharmacodynamical study. S. chamaejasme L. showed better effect than E. fischeriana Steud. Major chemical constituents of the active site of S. chamaejasme L. were flavonoids and coumarins. According to the structural type and literatures, we think that the peels of Citrus grandis Osbeck may have similar effect. Pharmacodynamical results confirmed our hypothesis.
24 compounds and 16 compounds were isolated from the active sites of the roots extract of Stellera chamaejasme L. and the peels extract of Citrus grandis Osbeck, respectively. Compounds from Stellera chamaejasme L. are neostellerin (1), isomohsenone (2) , stelleranol (3), 7-methoxyneochamaejasmin A (4) , mesoneochamaejasmin A (5), (+)chamaejasmine (6), 1, 5-diphenyl-1-pentanone (7), 1, 5-diphenyl-2-penten-l-one (8), p-coumaric acid w-eicosanyl ester (9), caffeic acid n-dueicosanyl ester (10), wikstrol A (11), wikstrol B (12), (+) -afzelechin (13), bursehernin (14), chamaechromone (15), mohsenone (16), neochamaejasmin A (17), neochamaejasmin B (18), 7-methoxychamaejasmine (19), chamaejasmenin B (20), daphnoretin (21), umbelliferone (22), scopoletin (23), S- ( + ) -1, 5-diphenyl -3-hydroxy-1-pentanone (24). Compounds from the peels of Citrus grandis were aurepten (25), isoimperatorin (26), marmin acetonide (27), pranferin (28), isomerancin (29), xanthotoxol (30), umbellif
erone (22), meranzin hydrate (31), 8-(3-β-D-glucosyl-2-hydroxy-3-methyl- butyl) -7- methoxycoumarin (32), scopoletin (23), roseoside (33), friedelin (34), 5-hydroxmethylfuraldehyde (35), linonin (36), nomilin (37) and narigin (38). Among them, compounds 1, 2, 3, 4, 5, 6 were determined to be new compounds. Compounds 7, 8, 9 and 10 were new natural products. Compounds 11, 12, 13, 14 were first isolated from Stellera genus. Compounds 25, 26, 27, 28, 30, 33, 34, 35 were first isolated from Citrus grandis Osbeck. Among the above compounds, 22, 23 are the common constituents of the two plants.
The existence of isomohsenone (2) and mohsenone (16) in Stellera chamaejasme L. proved Niwa's hypothesis that chamaechromonoids were transformed from chamaejasminoids.
The research on chemical constituents and pharmacology were concluded.
On the basis of our research on Stellera chamaejasme L. and the literatures, the spectral and structural characteristics, the stereochemical researching methods, the distribution in the 3 subtribes of Thymeleaceae and chemotaxonomy of biflavonoids were concluded. We found that biflavonoids played a very important role in the chemotaxonomy of Thymelaeaceous plants. We got a conclusion that only biflavonoids bearing flavan moiety existed in Daphne gemus, that biflavanones and chamaechromonoids existed in Stellera genus, and that biflavanones and biflavonoids bearing flavan moiety existed Wikstroemia species. The opinion that biflavanones only existed in Stellera genus was corrected and they were also found hi Wikstroemia genus. According to the distribution of biflavonoids, we support the viewpoint of classifying the Thymelaeaceae family into three subtribes: Wikstroemiinae, Daphninae and Passerininae.
The anti-convulsive experiments suggested that the biflavonoids didn't show any anticonvulsive activity, but that umbelliferone, which is the common constituent of these two plants, could delay the convulsive stroke.
引文
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