鹿角蕨化学成分及生物活性的研究
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摘要
鹿角蕨（Platycerium wallichii Hook.）是鹿角蕨科鹿角蕨属植物，为国
家二级保护植物。该植物主要分布在云南西南部盈江县那邦坝，在当地用作跌
打药。有关鹿角蕨属的系统关系存在一些假设，关于鹿角蕨属植物化学成分及
生物活性的研究未见报道。从鹿角蕨（Platycerium wallichii Hook.）叶95％
乙醇提取物中，我们分离得到了七个已知化合物。根据理化常数及波谱数据
（IR、UV、MS及NMR），其结构分别鉴定为：（Ⅰ）β-谷甾醇、（Ⅱ）胡萝卜甙、
（Ⅲ）2-propenoic acid，3-[（2R，3S）-2，3-dihydro-2-（4-hydroxy-3-
methoxyphenyl）-3-（hydroxymethyl）-7-methoxy-5-benzofuranyl]-、（Ⅳ）松
脂素-4'-O-β-D-葡萄糖甙、（Ⅴ）松脂素、（Ⅵ）2，5-二羟基苯甲酸甲酯、（Ⅶ）
槲皮素3-O-β-半乳糖甙。七个成分均为首次从该种植物中获得。
我们对鹿角蕨（Platycerium wallichii Hook.）能育叶部分以及基生叶部
分的乙醇提取物进行了镇痛试验和抗炎试验，试验表明鹿角蕨（Platycerium
wallichii Hook.）的叶有弱镇痛作用。
Platycerium wallichii Hook is one species of the genus Platycerium Desv., Platyceriaceae, its conservation rating is second degree in China. It mainly distributes in Nabangba of Yingjiang County, southwestern of Yunnan province, and it is used locally in curing injuries from falls. There are several assumptions about systematic position of Platycerium Desv. and there is no report about chemical constituents and biological activities of the plants from this genus. From the 95% ethanol extract of the leaves of Platycerium wallichii Hook., seven known compounds were isolated. Based on analysis of their UV, MS, NMR and IR spectra, their structures were identified, respectively as
B-sitosteroK(Ⅰ)、daucosterol (Ⅱ)、 2-propenoic acid, 3-[2, 3-dihydro-2-(4-hydroxy-3-me thoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranyl]-
(Ⅲ)、pinoresinol-4'-0-β-D-monoglucoside(Ⅳ)、
pinoresinol (Ⅴ)、 benzoic acid,2,5-dihydroxy-, methyl ester
(Ⅵ)、 quercetin 3-0-β-galactoside (Ⅶ).They were all isolated from the plant for the first time.
Antalgesic effect experiment was carried out respectively for the ethanol extracts of basal fronds and fertile leaves of Platycerium wallichii Hook.. The result demonstrated that extract of leaves of Platycerium wallichii showed faint antalgesic effect.
家二级保护植物。该植物主要分布在云南西南部盈江县那邦坝，在当地用作跌
打药。有关鹿角蕨属的系统关系存在一些假设，关于鹿角蕨属植物化学成分及
生物活性的研究未见报道。从鹿角蕨（Platycerium wallichii Hook.）叶95％
乙醇提取物中，我们分离得到了七个已知化合物。根据理化常数及波谱数据
（IR、UV、MS及NMR），其结构分别鉴定为：（Ⅰ）β-谷甾醇、（Ⅱ）胡萝卜甙、
（Ⅲ）2-propenoic acid，3-[（2R，3S）-2，3-dihydro-2-（4-hydroxy-3-
methoxyphenyl）-3-（hydroxymethyl）-7-methoxy-5-benzofuranyl]-、（Ⅳ）松
脂素-4'-O-β-D-葡萄糖甙、（Ⅴ）松脂素、（Ⅵ）2，5-二羟基苯甲酸甲酯、（Ⅶ）
槲皮素3-O-β-半乳糖甙。七个成分均为首次从该种植物中获得。
我们对鹿角蕨（Platycerium wallichii Hook.）能育叶部分以及基生叶部
分的乙醇提取物进行了镇痛试验和抗炎试验，试验表明鹿角蕨（Platycerium
wallichii Hook.）的叶有弱镇痛作用。
Platycerium wallichii Hook is one species of the genus Platycerium Desv., Platyceriaceae, its conservation rating is second degree in China. It mainly distributes in Nabangba of Yingjiang County, southwestern of Yunnan province, and it is used locally in curing injuries from falls. There are several assumptions about systematic position of Platycerium Desv. and there is no report about chemical constituents and biological activities of the plants from this genus. From the 95% ethanol extract of the leaves of Platycerium wallichii Hook., seven known compounds were isolated. Based on analysis of their UV, MS, NMR and IR spectra, their structures were identified, respectively as
B-sitosteroK(Ⅰ)、daucosterol (Ⅱ)、 2-propenoic acid, 3-[2, 3-dihydro-2-(4-hydroxy-3-me thoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranyl]-
(Ⅲ)、pinoresinol-4'-0-β-D-monoglucoside(Ⅳ)、
pinoresinol (Ⅴ)、 benzoic acid,2,5-dihydroxy-, methyl ester
(Ⅵ)、 quercetin 3-0-β-galactoside (Ⅶ).They were all isolated from the plant for the first time.
Antalgesic effect experiment was carried out respectively for the ethanol extracts of basal fronds and fertile leaves of Platycerium wallichii Hook.. The result demonstrated that extract of leaves of Platycerium wallichii showed faint antalgesic effect.
引文
1．吴兆洪，秦仁昌．中国蕨类植物科属志，科学出版社，1991：47-70
2．林尤兴等．中国植物志，科学出版社，2000：293-296
3．林尤兴等．中国植物志，科学出版社，2000：294
4，吴兆洪，秦仁昌．中国蕨类植物科属志，科学出版社，1991：549
5. Nobutoshi Tanaka, et al. Chemical and Chemotaxonomical Studies of Filices. LXXI. Chemical Studies on the Constituents of Cheiropleuria bicuspis (BL,) PR. (chem. Pharm. Bull. 1987, 35 (10): 4016-4021
6. Rumiko Kamaya, Yoshiko Tanaka, et al. Fern Constituents: Triterpenoids Isolated from leaves of Cheiropleuria bicuspis. Chem. Pharm. Bull. 1990, 38 (8): 2130-2132
7. Nobutoshi Tanaka, et al. Chemical and Chemotaxonomical Studies of Filices. LXXI. Chemical Studies on the Constituents of Dipteri conjugata REINW. Chem. Pharm. Bull. 1985, 33 (1): 152-157
8．钟国跃．四川省石韦属植物的种类分布及药用状况．中草药，1991，22 (7)：321-323
9．李洁，童玉懿．石韦有效成分的高效液相色谱测定，药学学报，1992，27 (2)：153-156
10．水野瑞夫。闵知大等．石韦的化学成分，植物学报，1986，28 (3)：339-340
11．郑兴等．西南石韦化学成分的研究，中国中药杂志，1998，23 (2)：98-99
12．包文芳等，中国石韦化学成分与分类学的研究，沈阳药学院学报，1982，15：62-69
13. Kenneth R. Markham, et al. Kaempferol 3-o-sophoroside-7-o-α-L-arabinofuranoside, Neohesperidosi des and Other Flavonoids from the Fern pyrrosia serpens , Phytochemistry, 1990, 29 (12): 3919-3920
14. Hikino H., et al. Isolation of diploptene from pyrrosia lingua Farwell. chem. Pharm. Bull. 1963, 11: 409-410
15. Kazuo M., et al. Fern Constituents: Triterpenoids Isolated from Rhizomes of Pyrrosia linguaL, chem. Pharm. Bull. 1997, 45 (4) :590
16. Hiroshi Y., et al. Fern Constituents: Cyclohopenol and Cyclohopanediol, Novel Skeletal Triterpenoids from Rhizomes of Pyrrosia lingua, chem. Pharm. Bull. 1998, 46 (4): 730-732
17，丛浦珠．质谱学在天然有机化学中的应用，科学出版社，1987：752
18，官智等，红豆杉(Taxus chinensis(Piger)Rehd．)中的非紫杉烷类化合物，热带亚热带植物学报，2000，8 (2)：182-183
19．于德泉，杨峻山．分析化学手册第七分册，核磁共振波谱分析，化学工业出版社，873-874
20. Mitsumasa Haruna, et al. Balanophonin, a new neo-lignan from Balanophora japonica Makino. Chem. Pharm. Bull 1982, 30 (4): 1525-1527
21. Osama Salama, et al. a Lignan glucoside from Euphrasia rostkoviana Phytochemistry, 1981, 20 (11): 2603-2604
22. Masahiko Ohta, et al. Microbial Degradation of Dehydrodiconiferyl Alcohol, a Lignin Substructure Model. Arch. Microbiol. 1979, 121: 23-28
23．刘东雷，徐绥绪．连翘属中木脂素成分生物合成研究进展．中国药物化学杂志，1996，21 (3)：221
24．赵瑶兴，孙祥玉．光谱解析与有机结构鉴定，中国科学技术大学出版社，278-279．
25．孔令义，闵知大．大戟根化学成分的研究．药学学报 1996，31 (7)：524-529
26．于德泉，杨峻山．分析化学手册第七分册，核磁共振波谱分析，化学工业出版社，862
27. Barbara Vermes, Otto Seligmann. Synthesis of Biologically active tetrahydro-furofuranlignan-(syringin, pinoresinol)- and Bisglucosides. phytochemistry, 1991, 30 (9): 3087-3089
28. Pankaja K. Kadaba. New Compounds: Convenient Selective Esterification of Aromatic Carboxylic Acids Bearing Other Reactive Groups Using a Boron Trifluoride Etherate-Alcohol Reagent. Journal oF Pharmaceutical Sciences, 1974, 63 (8): 1333-1335
29. S. R. Heller and G. W. A. Milne , EPA/NIH Mass Spectral Data Base , volume 1, 723-724
30．周志宏等．怒茶素—怒江山茶的一个新黄酮甙．云南植物研究，2000，22 (1)：94
31．黄斌，王忠华．跌打止痛液药理作用再研究． 陕西中医，1995，16 (2)：89-90
32．张西相，郭立中等．跌打活血散治疗软组织损伤500例的临床研究．陕西中医，1996，17 (11)：499
33．W. Donald MacRae，G，H. Neil Towers. Biological Activities of Lignans．Phytochemistry, 1984，23 (6)：1207-1220
34．国家医药管理局中草药情报中心站编．植物药有效成分手册，人民卫生出版社，1986，597-598
2．林尤兴等．中国植物志，科学出版社，2000：293-296
3．林尤兴等．中国植物志，科学出版社，2000：294
4，吴兆洪，秦仁昌．中国蕨类植物科属志，科学出版社，1991：549
5. Nobutoshi Tanaka, et al. Chemical and Chemotaxonomical Studies of Filices. LXXI. Chemical Studies on the Constituents of Cheiropleuria bicuspis (BL,) PR. (chem. Pharm. Bull. 1987, 35 (10): 4016-4021
6. Rumiko Kamaya, Yoshiko Tanaka, et al. Fern Constituents: Triterpenoids Isolated from leaves of Cheiropleuria bicuspis. Chem. Pharm. Bull. 1990, 38 (8): 2130-2132
7. Nobutoshi Tanaka, et al. Chemical and Chemotaxonomical Studies of Filices. LXXI. Chemical Studies on the Constituents of Dipteri conjugata REINW. Chem. Pharm. Bull. 1985, 33 (1): 152-157
8．钟国跃．四川省石韦属植物的种类分布及药用状况．中草药，1991，22 (7)：321-323
9．李洁，童玉懿．石韦有效成分的高效液相色谱测定，药学学报，1992，27 (2)：153-156
10．水野瑞夫。闵知大等．石韦的化学成分，植物学报，1986，28 (3)：339-340
11．郑兴等．西南石韦化学成分的研究，中国中药杂志，1998，23 (2)：98-99
12．包文芳等，中国石韦化学成分与分类学的研究，沈阳药学院学报，1982，15：62-69
13. Kenneth R. Markham, et al. Kaempferol 3-o-sophoroside-7-o-α-L-arabinofuranoside, Neohesperidosi des and Other Flavonoids from the Fern pyrrosia serpens , Phytochemistry, 1990, 29 (12): 3919-3920
14. Hikino H., et al. Isolation of diploptene from pyrrosia lingua Farwell. chem. Pharm. Bull. 1963, 11: 409-410
15. Kazuo M., et al. Fern Constituents: Triterpenoids Isolated from Rhizomes of Pyrrosia linguaL, chem. Pharm. Bull. 1997, 45 (4) :590
16. Hiroshi Y., et al. Fern Constituents: Cyclohopenol and Cyclohopanediol, Novel Skeletal Triterpenoids from Rhizomes of Pyrrosia lingua, chem. Pharm. Bull. 1998, 46 (4): 730-732
17，丛浦珠．质谱学在天然有机化学中的应用，科学出版社，1987：752
18，官智等，红豆杉(Taxus chinensis(Piger)Rehd．)中的非紫杉烷类化合物，热带亚热带植物学报，2000，8 (2)：182-183
19．于德泉，杨峻山．分析化学手册第七分册，核磁共振波谱分析，化学工业出版社，873-874
20. Mitsumasa Haruna, et al. Balanophonin, a new neo-lignan from Balanophora japonica Makino. Chem. Pharm. Bull 1982, 30 (4): 1525-1527
21. Osama Salama, et al. a Lignan glucoside from Euphrasia rostkoviana Phytochemistry, 1981, 20 (11): 2603-2604
22. Masahiko Ohta, et al. Microbial Degradation of Dehydrodiconiferyl Alcohol, a Lignin Substructure Model. Arch. Microbiol. 1979, 121: 23-28
23．刘东雷，徐绥绪．连翘属中木脂素成分生物合成研究进展．中国药物化学杂志，1996，21 (3)：221
24．赵瑶兴，孙祥玉．光谱解析与有机结构鉴定，中国科学技术大学出版社，278-279．
25．孔令义，闵知大．大戟根化学成分的研究．药学学报 1996，31 (7)：524-529
26．于德泉，杨峻山．分析化学手册第七分册，核磁共振波谱分析，化学工业出版社，862
27. Barbara Vermes, Otto Seligmann. Synthesis of Biologically active tetrahydro-furofuranlignan-(syringin, pinoresinol)- and Bisglucosides. phytochemistry, 1991, 30 (9): 3087-3089
28. Pankaja K. Kadaba. New Compounds: Convenient Selective Esterification of Aromatic Carboxylic Acids Bearing Other Reactive Groups Using a Boron Trifluoride Etherate-Alcohol Reagent. Journal oF Pharmaceutical Sciences, 1974, 63 (8): 1333-1335
29. S. R. Heller and G. W. A. Milne , EPA/NIH Mass Spectral Data Base , volume 1, 723-724
30．周志宏等．怒茶素—怒江山茶的一个新黄酮甙．云南植物研究，2000，22 (1)：94
31．黄斌，王忠华．跌打止痛液药理作用再研究． 陕西中医，1995，16 (2)：89-90
32．张西相，郭立中等．跌打活血散治疗软组织损伤500例的临床研究．陕西中医，1996，17 (11)：499
33．W. Donald MacRae，G，H. Neil Towers. Biological Activities of Lignans．Phytochemistry, 1984，23 (6)：1207-1220
34．国家医药管理局中草药情报中心站编．植物药有效成分手册，人民卫生出版社，1986，597-598