铁皮石斛多糖成分研究
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摘要
石斛为我国传统中药材,其药用价值为人们所共识。经研究发现,多糖是石
斛属植物的主要活性成分。本文以石斛之上品-铁皮石斛-为主要研究对象,首
次探讨其不同部位主要化学成分及分布规律,研究其多糖成分的提取、分离、纯
化,以及主要组分的结构鉴定,比较了不同种石斛及不同生长方式铁皮石斛的多
糖成分的差异,证实了石斛多糖的药理活性,为石斛的生产与使用提供了依据,
并且为石斛多糖的构效关系的深入研究奠定了基础。获得的主要结果如下:
1.铁皮石斛不同部位主要成分及分布规律探讨
铁皮石斛茎的上、中、下三部分总多糖和水溶性多糖含量较高,3个部位之
间差异不大,根部含量很低,尤其是水溶性多糖,含量不足2%,只有茎部的13
%左右,说明传统用药上铁皮石斛以茎为入药部分在主要化学成分分析上是合理
的。铁皮石斛各部分总生物碱含量相差较大,茎部按上、中、下部依次降低,根
部又有所升高,仅次于茎上部;但总体含量较低,仅相当于金钗石斛含量的10
%,表明铁皮石斛的药用价值高于其它石斛属植物很可能体现在多糖部分。
2.三种石斛多糖成分的比较研究
发现铁皮石斛、细茎石斛和细叶石斛均含有较高的总多糖,但就水溶性多糖
含量而言,前两种石斛较高,而细叶石斛很低(仅为另两种的1/3);认为总多糖
和水溶性多糖在各部位的分布情况,粗多糖中蛋白质、糖醛酸、中性糖等成分的
含量,以及粗多糖的离子柱色谱以及FT-IR图谱,不同种间存有较大差异。
3.铁皮石斛原药材与组培原球茎多糖成分的比较研究
和铁皮石斛原药材相比,发现组培原球茎中的水溶性多糖DOPP含量明显偏
低,约为原药材的1/3,尤其粗多糖中的中性糖DOPP-1比例更低,仅占27.6%,
但糖醛酸成分含量较高。DOPP-1-A1的单糖组成以D-Glc为主,与以D-Man为
Herba Dendrobii, prepared from the dried stems of Dendrobium species, is a Chinese materia medica as a tonic. Many researches focus on its basic constituents as well as pharmacological activity. As well known, polysaccharides, widespread in Dendrobium species, is the main active constituent; and Dendrobium officinale Kimura et Migo is one of the most precious Dendrobium species. Its pharmacological activity on immune enhancement and hypoglycemic effects has been verified by many animal-model tests. In this dissertation, we have reported the main components as well as their distribution in different parts of the plant, and isolation, purification, properties and structure elucidation of the main ingredient from the crude polysaccharide; we have investigated the diversities of polysaccharides between from three medicinal dendrobium plants, and from Natural Dendrobium officinale and its tissue-cultured protocorm; and we have proved pharmacological activity of the polysaccharide, too. All the above-mentioned aim to conduct the production and application of dendrobiums, and to promote the research of configuration-activity relationship of dendrobium polysaccharide.1. The main components as well as its distribution in the stem of Dendrobium officinaleThe total polysaccharides (TPs) and water-soluble polysaccharides (WPs) are high in stems with a little variation of polysaccharides content between three parts from them. Polysaccharides content in the roots is quite lower, especially the water-soluble polysaccharides accounting for less than 2%, which indicates reasonable to take stems as the medicinal part. The content of alkaloid between different parts is various, upper-stem highest, root, middle-stem and the lower-stem lower in turn. The total content of alkaloid is 10% lower than that of D. nobile.2. comparative study on polysaccharides from three dendrobuim spiciesThe content of TPs from three medicinal plants, D. officinale, D. moniliforme and D. hancockii, are all quite higher. As far as WPs concerned, the latter one is 1/3 lower than the former two. Considering distribution of TPs and WPs in the plants, contents of proteins, uronic acid and
neutral polysaccharide in crude polysaccharide, and anion exchange chromatographies and FT-IR, diversities exists markedly between the three dendrobuim spicies.3. Comparative study on polysaccharides from natural Dendrobium officinale and its tissue-cultured protocormCompared with natural Dendrobium officinale, content of WPs from tissue-cultured protocorm is very lower, especially the neutral polysaccharide in crude polysaccharide. While content of uronic acid is higher. DOPP-1-A1, a neutral polysaccharide composed mostly of ￡>-Glc, was quite distinct from DOPP-1-A1 which is consisted mostly of D-Man. Furthermore, DOPP-1-Alhave two ingredients: DOPP-1-Alland DOPP-1-A12, the molecular weight of which is different from that of DOP-1-A1.4. Extraction, fractionation, purification and structural determination of DOPA crude polysaccharide, obtained from aqueous extract of Dendrobium officinale Kimura et Migo, was fractionation and purified by DEAE-cellulose anion-exchange chromatography and Sephadex G-10, Sephadex S-200/ S-400 gel-permeation chromatography, giving a neutral polysaccharide DOP-1-A1 and five acidic polysaccharides DOP-2-A1, 3-A1, 4-A1, 5-A1, 6-A1. The latter five ingredients were presumed to be proteoglycans with /3-D-Manp.DOP-1-A1, its weight-average molar mass estimated to be 128 kDa by HP-GPC, has been investigated by chromatographies (TLC, GC and GC-MS), spectroscopies (UV, IR and 'H/13C NMR) and chemical techniques (periodate oxidation-Smith degradation, methylation, partial acid hydrolysis, and deacetylation). The results demonstrate that it is a 2-0-acetyl-glucomannan, composed of mannose, glucose and arabinose in the molar ratios of 40.2: 8.4: 1. It has a backbone of (1—+4)-linked (3-D-mannopyranosyl residues and P-D-glucopyranosyl residues, with branches substituted at O-6 consisting of terminal and (1—>3)-linked Man/?, (1—>3)-linked Glcp, and a small proportion of arabinofuranosyl residues at the terminal position. The acetyl groups are found to be substituted at O-2 of (1—>4)-linked Man/? and Glcp. So the main repeating units are as the following structure:
p-D-Manp-(l —?3)-￡-D-l Vlanp-(1 —>3)-p-D-Man/> D-Ara/-(1 ->3)-|3-D-Glc/>OAc i OAc 11 I 1 i2 6 2 64)-p-D-Manp-(l-?4)-p-D-Man/j-(l->4)-)5-D-Maiip-(l->4)-p-D-Mary>(l-*]5. Pharmacological activity on anti-oxidation and anti-inflammationDendrobium polysaccharides were verified to have a scavenging effect on O2"?-. OH, and H2O2 by anti-oxidation experiments in vitro. And the polysaccharides also showed anti-inflammatory activity by inhibition of production of plasma hemolysin, croton oil-induced dermatitis, 2ymosan-induced oedemas, and hemolytic activity of complement. Compared with other anti-inflammatory medicines, they were characteristic of moderate potenty and slowly taking effect, which indicated that the anti-inflammatory activity of polysaccharides not owing to inhibit production and distribution directly of inflammatory mediators such as PG-E2, histamine, 5-HT and bradykinin and so on, but to modulate physiological variation of inflammatory focus and inhibit production of inflammatory cytokines. As a whole, as for the anti-oxidative and anti-inflammatory activiy, natural Dendrobium officinale is better than greenhouse-cultivated plants and tissue-cultured protocorm, and each has its strong point in the pharmacological activity between the latter two; Dendrobium moniliforme is similar with Dendrobium officinale, and Dendrobium hancockii inferior. It was supposed that Dendrobium officinale can be substituted appropriately by Dendrobium moniliforme on some pharmacological activity.
斛属植物的主要活性成分。本文以石斛之上品-铁皮石斛-为主要研究对象,首
次探讨其不同部位主要化学成分及分布规律,研究其多糖成分的提取、分离、纯
化,以及主要组分的结构鉴定,比较了不同种石斛及不同生长方式铁皮石斛的多
糖成分的差异,证实了石斛多糖的药理活性,为石斛的生产与使用提供了依据,
并且为石斛多糖的构效关系的深入研究奠定了基础。获得的主要结果如下:
1.铁皮石斛不同部位主要成分及分布规律探讨
铁皮石斛茎的上、中、下三部分总多糖和水溶性多糖含量较高,3个部位之
间差异不大,根部含量很低,尤其是水溶性多糖,含量不足2%,只有茎部的13
%左右,说明传统用药上铁皮石斛以茎为入药部分在主要化学成分分析上是合理
的。铁皮石斛各部分总生物碱含量相差较大,茎部按上、中、下部依次降低,根
部又有所升高,仅次于茎上部;但总体含量较低,仅相当于金钗石斛含量的10
%,表明铁皮石斛的药用价值高于其它石斛属植物很可能体现在多糖部分。
2.三种石斛多糖成分的比较研究
发现铁皮石斛、细茎石斛和细叶石斛均含有较高的总多糖,但就水溶性多糖
含量而言,前两种石斛较高,而细叶石斛很低(仅为另两种的1/3);认为总多糖
和水溶性多糖在各部位的分布情况,粗多糖中蛋白质、糖醛酸、中性糖等成分的
含量,以及粗多糖的离子柱色谱以及FT-IR图谱,不同种间存有较大差异。
3.铁皮石斛原药材与组培原球茎多糖成分的比较研究
和铁皮石斛原药材相比,发现组培原球茎中的水溶性多糖DOPP含量明显偏
低,约为原药材的1/3,尤其粗多糖中的中性糖DOPP-1比例更低,仅占27.6%,
但糖醛酸成分含量较高。DOPP-1-A1的单糖组成以D-Glc为主,与以D-Man为
Herba Dendrobii, prepared from the dried stems of Dendrobium species, is a Chinese materia medica as a tonic. Many researches focus on its basic constituents as well as pharmacological activity. As well known, polysaccharides, widespread in Dendrobium species, is the main active constituent; and Dendrobium officinale Kimura et Migo is one of the most precious Dendrobium species. Its pharmacological activity on immune enhancement and hypoglycemic effects has been verified by many animal-model tests. In this dissertation, we have reported the main components as well as their distribution in different parts of the plant, and isolation, purification, properties and structure elucidation of the main ingredient from the crude polysaccharide; we have investigated the diversities of polysaccharides between from three medicinal dendrobium plants, and from Natural Dendrobium officinale and its tissue-cultured protocorm; and we have proved pharmacological activity of the polysaccharide, too. All the above-mentioned aim to conduct the production and application of dendrobiums, and to promote the research of configuration-activity relationship of dendrobium polysaccharide.1. The main components as well as its distribution in the stem of Dendrobium officinaleThe total polysaccharides (TPs) and water-soluble polysaccharides (WPs) are high in stems with a little variation of polysaccharides content between three parts from them. Polysaccharides content in the roots is quite lower, especially the water-soluble polysaccharides accounting for less than 2%, which indicates reasonable to take stems as the medicinal part. The content of alkaloid between different parts is various, upper-stem highest, root, middle-stem and the lower-stem lower in turn. The total content of alkaloid is 10% lower than that of D. nobile.2. comparative study on polysaccharides from three dendrobuim spiciesThe content of TPs from three medicinal plants, D. officinale, D. moniliforme and D. hancockii, are all quite higher. As far as WPs concerned, the latter one is 1/3 lower than the former two. Considering distribution of TPs and WPs in the plants, contents of proteins, uronic acid and
neutral polysaccharide in crude polysaccharide, and anion exchange chromatographies and FT-IR, diversities exists markedly between the three dendrobuim spicies.3. Comparative study on polysaccharides from natural Dendrobium officinale and its tissue-cultured protocormCompared with natural Dendrobium officinale, content of WPs from tissue-cultured protocorm is very lower, especially the neutral polysaccharide in crude polysaccharide. While content of uronic acid is higher. DOPP-1-A1, a neutral polysaccharide composed mostly of ￡>-Glc, was quite distinct from DOPP-1-A1 which is consisted mostly of D-Man. Furthermore, DOPP-1-Alhave two ingredients: DOPP-1-Alland DOPP-1-A12, the molecular weight of which is different from that of DOP-1-A1.4. Extraction, fractionation, purification and structural determination of DOPA crude polysaccharide, obtained from aqueous extract of Dendrobium officinale Kimura et Migo, was fractionation and purified by DEAE-cellulose anion-exchange chromatography and Sephadex G-10, Sephadex S-200/ S-400 gel-permeation chromatography, giving a neutral polysaccharide DOP-1-A1 and five acidic polysaccharides DOP-2-A1, 3-A1, 4-A1, 5-A1, 6-A1. The latter five ingredients were presumed to be proteoglycans with /3-D-Manp.DOP-1-A1, its weight-average molar mass estimated to be 128 kDa by HP-GPC, has been investigated by chromatographies (TLC, GC and GC-MS), spectroscopies (UV, IR and 'H/13C NMR) and chemical techniques (periodate oxidation-Smith degradation, methylation, partial acid hydrolysis, and deacetylation). The results demonstrate that it is a 2-0-acetyl-glucomannan, composed of mannose, glucose and arabinose in the molar ratios of 40.2: 8.4: 1. It has a backbone of (1—+4)-linked (3-D-mannopyranosyl residues and P-D-glucopyranosyl residues, with branches substituted at O-6 consisting of terminal and (1—>3)-linked Man/?, (1—>3)-linked Glcp, and a small proportion of arabinofuranosyl residues at the terminal position. The acetyl groups are found to be substituted at O-2 of (1—>4)-linked Man/? and Glcp. So the main repeating units are as the following structure:
p-D-Manp-(l —?3)-￡-D-l Vlanp-(1 —>3)-p-D-Man/> D-Ara/-(1 ->3)-|3-D-Glc/>OAc i OAc 11 I 1 i2 6 2 64)-p-D-Manp-(l-?4)-p-D-Man/j-(l->4)-)5-D-Maiip-(l->4)-p-D-Mary>(l-*]5. Pharmacological activity on anti-oxidation and anti-inflammationDendrobium polysaccharides were verified to have a scavenging effect on O2"?-. OH, and H2O2 by anti-oxidation experiments in vitro. And the polysaccharides also showed anti-inflammatory activity by inhibition of production of plasma hemolysin, croton oil-induced dermatitis, 2ymosan-induced oedemas, and hemolytic activity of complement. Compared with other anti-inflammatory medicines, they were characteristic of moderate potenty and slowly taking effect, which indicated that the anti-inflammatory activity of polysaccharides not owing to inhibit production and distribution directly of inflammatory mediators such as PG-E2, histamine, 5-HT and bradykinin and so on, but to modulate physiological variation of inflammatory focus and inhibit production of inflammatory cytokines. As a whole, as for the anti-oxidative and anti-inflammatory activiy, natural Dendrobium officinale is better than greenhouse-cultivated plants and tissue-cultured protocorm, and each has its strong point in the pharmacological activity between the latter two; Dendrobium moniliforme is similar with Dendrobium officinale, and Dendrobium hancockii inferior. It was supposed that Dendrobium officinale can be substituted appropriately by Dendrobium moniliforme on some pharmacological activity.
引文
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