蜂胶中抗意大利青霉活性成分的追踪及抑菌作用研究
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摘要
蜂胶是蜜蜂从植物芽苞或树干分泌物中采集的树脂类物质,用于防护、抵御病原微生物、修补巢房和内环境消毒杀菌等。研究表明蜂胶提取物具有广谱的抑菌活性,素有“天然抗生素”之称。同时蜂胶中含有黄酮类、酚酸类、萜烯类、脂肪酸及氨基酸等多种活性物质,近年来已从不同产地的蜂胶中分离鉴定出300多种化合物。因此蜂胶是筛选天然抗菌剂的理想材料。本论文以引起柑橘采后腐烂变质的重要病原菌意大利青霉(Penicilum.italicum)为指示菌,采用生物活性追踪的方法,对蜂胶中抑制意大利青霉的活性成分进行了分离、纯化,并研究了活性成分的抑菌机理;同时对蜂胶提取物在柑橘上的防病效果及保鲜机理进行了初步研究。主要研究结果如下:
1.蜂胶提取物的抑菌活性与黄酮、酚类物质含量密切相关。在水、乙醇、乙酸乙酯、氯仿、石油醚等五种不同极性的溶剂中,乙酸乙酯和乙醇所提取的蜂胶液中含有高含量的黄酮和酚类物质,抑菌活性最强,抑制率达100%;其次为氯仿;石油醚和水所提取的蜂胶提取液中的黄酮类和酚类物质含量最低,抑菌活性最差。来自河北永年、河北保定和湖北当阳等三个产地的蜂胶的主要成分相似,各个成分的相对含量存在差异;与河北蜂胶相比,湖北蜂胶中酚酸类物质的相对含量较高,而黄酮类物质的相对含量较低。来自河北保定的蜂胶的总黄酮和酚类物质含量最高,品质最好,抑菌活性最强;其次为河北永年蜂胶;湖北当阳蜂胶的品质和抑菌活性最差。
2.采用溶剂萃取、薄层层析及柱层析等分离方法对蜂胶乙醇提取物和乙酸乙酯提取物中的抑菌活性成分进行生物活性追踪及分离,发现两种提取物的活性部位中的化学组成相同。对活性组分进行黄酮体的颜色反应和和紫外光谱分析,结果显示活性组分遇硼氢化钠变浅蓝色;在甲醇溶液中的特征吸收峰为291 nm,在可见区无明显吸收;在甲醇钠和醋酸钠溶液中主要吸收波长向长波移动38 nm;以上结果具备5,7-二羟基-双氢黄酮的典型特征。进一步对活性组分进行液质分析和紫外光谱分析,推断活性组分中化合物分别是短叶松素、松属素、白杨素和高良姜素,其中松属素的相对含量最高。
3.对活性组分进一步通过Sephadex LH-20凝胶色谱柱分离、纯化得到松属素、白杨素、高良姜素。液相检测的纯度分别为87.13%,97.00%,94.55%。对浓度为200mg/L的松属素、白杨素和高良姜素的抑菌活性进行比较,发现松属素对意大利青霉的抑制效果最强,抑制率达70.28%;其次为白杨素,抑制率为34.12%;高良姜素的抑菌效果最差,抑制率仅为12.5%。
4.采用生长速率法对松属素抑制意大利青霉菌丝体生长的效果进行评价,松属素对菌丝体表现出显著地抑制作用。通过毒力回归分析,松属素对意大利青霉的抑制作用呈浓度-效应依赖关系。松属素处理浓度与抑制率之间的线性回归方程为y=1.77lnx+1.54,r=0.98283,P=0.01717,达显著水平。EC_(50)和EC_(90)分别为89.06 mg/L和469.78 mg/L。同时,松属素对温度的变化和酸碱性环境具有良好的适应性,在35～100℃的温度范围内及pH 4.0～7.0的酸碱环境中仍能保持稳定的抑菌活性。
5.松属素处理使意大利青霉的细胞结构受损。显微结构的观察结果表明经过松属素处理的意大利青霉在孢子萌发和菌丝体的培养过程中均出现了原生质分布不均匀,发生凝聚,菌丝体膨大变形,液泡增大等细胞走向衰亡的症状。超微结构的观察结果显示经过松属素处理的菌丝体发生严重的质壁分离,大量胞内容物外渗。同时松属素处理的意大利青霉菌丝体的几丁质酶活性和β-1,3-葡聚糖酶活性显著高于对照,反映菌体细胞壁的降解代谢增强。此外,松属素处理的菌丝体相对渗透率上升迅速,在整个培养过程中始终高于对照,表明松属素处理破坏了意大利青霉菌丝体细胞壁和细胞膜结构的完整性,是松属素抑制意大利青霉活性的原因之一。
6.通过对意大利青霉菌丝体培养过程中的呼吸代谢及物质代谢相关指标等进行测定,结果显示松属素处理的菌丝体呼吸强度在整个培养过程中均保持在较低的水平;ATP、ADP、AMP含量也同样明显低于对照。同时实验结果发现经过松属素处理的意大利青霉菌丝体中的蛋白质含量很低,在培养8 h和24 h时,蛋白质含量仅为对照的62.29%和42.72%;而在培养24 h时经过松属素处理的意大利青霉菌丝体内出现了还原糖的累积,还原糖的含量约为同期对照还原糖含量的2.5倍。结果暗示松属素通过抑制呼吸作用,使菌丝体的能量代谢受阻,呼吸底物累积,使菌体的物质代谢发生紊乱,加之细胞壁降解酶活性的加强促进几丁质和葡聚糖等降解,还原糖累积,蛋白质合成受阻;以上结果暗示松属素导致了意大利青霉菌丝体的能量代谢和合成代谢发生紊乱,是菌丝体逐渐走向衰亡的另一重要原因。
7.经过蜂胶提取物处理的柑橘果实贮藏期间青、绿霉病的发病率明显低于对照;同时能够延缓果实色度、可溶性固形物、V_C、有机酸等品质指标的下降;因此PEAE处理可以有效地控制柑橘贮藏期间青、绿霉病的发生。
8.通过对蜂胶提取物诱导柑橘青霉病的表达时间以及蜂胶提取物处理对柑橘果实抗病性相关的物质及酶活性的影响研究,发现蜂胶提取物对柑橘果实诱导抗病性的最佳表达时间是处理后8h。蜂胶提取物处理增加了柑橘果皮中酚类物质的含量,提高了柑橘果皮中苯丙氨酸解氨酶(PAL)、过氧化物酶(POD)、多酚氧化酶(PPO)、几丁质酶(CHT)等与诱导抗病性密切相关的酶的活性。因此,蜂胶提取物增强了柑橘果实的防御系统,对柑橘表现出良好的保鲜效果,具有进一步研究及开发的潜在价值。
Propolis is a resinous material collected by bees from plant buds and exudates, which is employed for resisting pathogenic microorganism, construction and repair of the honeycomb and sterilization of surroundings. There was a substantial evidence indicating that propolis had broad antimicrobial activity and was named as "natural antibiotics". At the same time, propolis is a complex mixture of chemical constituents including flavonoids, phenolic acids and esters, terpenes, fatty acids and amino acid etc. More than 300 kinds of compounds were identified from propolis of different origin. It indicated propolis was a desirable material for screening out natural antimicrobial. In current study, Penicillum italicum (P.italicum) , an important pathogenic fungi which lead to blue mold during the citrus storage as the indicator., bioassay was used to separate the active compound ; the action mechanism of active compounds against P.italicum was studied; Inhibitory effect of propolis ethyl acetate extract(PEAE) against citrus blue mold was evaluated. The main results as follow:
1. The extracted solvent and origin of propolis affected the chemical constituent and antifungal activity against P. italicum. Propolis ethyl acetate extract(PEAE) and propolis ethanol extract (PEE) demonstrated the most powerful activities, followed by propolis chloroform extract, while propolis petroleum ether extract and propolis water extract showed weak acivities, and the inhibitory activities were consistant with the contents of flavonoids or phenols in the corresponding extracts. Propolis from Hebei Baoding was of the highest contents of flavonoids or phenols and strongest inhibitory effect on the P. italicum; followed by Hebei Yongnian propolis; Propolis from Hubei Dangyang was last one.
2. The antifungal fractions from PEE and PEAE were separated by organic solvent extract, thin-layer chromatography (TLC) or column chromatography combined with bioassay and they had the similar chemical constitutes assayed by HPLC. The color reaction and UV behaviour for flavonoids were determined to identify the substance in the active fraction .The results showed its color became blue when meeting with NaHBO_3; Its characteristic wavelength was 292 nm in methol and would be shifed 38nm to the longer wave in MeONa or NaAc. This main flavonoids in active fraction were of the typical characteristic of 5,7-dihydroxyflavanone. Using the HPLC-PDA-ESI-MS method, it was deduced that the main compounds in the active fraction were pinobanksin, pinocembrine, chrysin and galangin; and pinocembrine had the highest relative content in the four compounds.
3. Purified pinocembrine, chrysin and galangin were attained by further separating active fraction through sephadex LH-20 chromatography, which purity for HPLC were 87.13%, 97.00%, 94.55% respectively. Among the three compounds, pinocembrine had the strongest inhibitory effect against P.italicum, followed by chrysin, and galangin was the last one; Their inhibition percents against P.italicum were 70.28%, 34.12%,12.5% separately at the concentration of 200 mg/L.
4. Effect of pinocembrine on the P.italicum were evaluated by growth rate method . Pinocembine appeared obviously inhibitory effect on the P.italicum and had the line relaxtion between the concentration and inhibition rate. The regression equation of toxicity was y = 1.77 lnx+1.54, ( r =0.98283, P =0.01717). EC_(50)=89.06 mg/L and EC_(90) =469.78 mg/L. At the same time, pinocembrime were still of the stable antifungal activity at at the temeperature range of 35～100℃and pH4～7.
5. Pinocembrine treatment damaged the cell structure of P.italicum during spore germination and mycelium culture. Microscopic structure of P.italicum hyphas treated with pinocembrine became swollen and abnormal, the protoplasm concentrated and the cell wall degraded, which indicated that hyphas deem to death. The results of ultrastructure indicated evident plasmolysis, intracellular components were extravasation. At the same time, activity of chitinase andβ-1, 3-glucanase were higher than contolled after treated with pinocembrine. Pinocembrine also destroyed the integrality of cell membrane and the relative leakage rate was increasing greatly after treated with pinocembrine.
6. Indexes on respiration metabolism and material metabolism were measured , the results indicated mycelium treated with pinocembine had the lower respiratory rate , ATP, ADP , AMP and protein contents . After culturing 8h and 24h, protein in the treated mycelium were only up to 62.29% and 42.72% compared with controlled. While the reduced sugar content in treated mycelium was higher than controlled mycelium at 24 h. It suggested that pinocembrine treatment blocked energy metabolism of mycelium through inhibited respiration; At the same time , Cell wall degrading enzyme in the mycelium accelerated the degradation of chitin and dextran. therefore , it led to the accumulation of reduced sugar and decreasing of protein, mycelium became deathward.
7. Compared with control, PEAE treatment decreased the disease incidence of blue mold and green mold , and delayed the decline of color , total soluble solids(TSS) ,titratable acidity(TA) ,vitamin C level and eatable quality of citrus fruits during storage at 26°C. Therefore, PEAE could effectively controlled postharvest diseases of citrus fruit during storage.
8.Expressive time of propolis extract on the induced resistance against citrus blue mold and influence of propolis extract on the activities of defensive related enzymes were investigated. The results showed that at 48 h after treatment with propolis extract, citrus fruit exhibited the strongest resistance against blue mold. Propolis extract treatment maintained higher level of the total phenolic contents, enhanced activities of phenylalanine ammonia-lyase, polyphenol oxidase and peroxidase, and stimulated chitinase in citrus fruit peel. Therefore, propolis treatment strengthened the defense system of citrus fruits and reduced disease incidence of citrus blue mold, and appeared great potential on postharvest disease control of citrus fruit.
1.蜂胶提取物的抑菌活性与黄酮、酚类物质含量密切相关。在水、乙醇、乙酸乙酯、氯仿、石油醚等五种不同极性的溶剂中,乙酸乙酯和乙醇所提取的蜂胶液中含有高含量的黄酮和酚类物质,抑菌活性最强,抑制率达100%;其次为氯仿;石油醚和水所提取的蜂胶提取液中的黄酮类和酚类物质含量最低,抑菌活性最差。来自河北永年、河北保定和湖北当阳等三个产地的蜂胶的主要成分相似,各个成分的相对含量存在差异;与河北蜂胶相比,湖北蜂胶中酚酸类物质的相对含量较高,而黄酮类物质的相对含量较低。来自河北保定的蜂胶的总黄酮和酚类物质含量最高,品质最好,抑菌活性最强;其次为河北永年蜂胶;湖北当阳蜂胶的品质和抑菌活性最差。
2.采用溶剂萃取、薄层层析及柱层析等分离方法对蜂胶乙醇提取物和乙酸乙酯提取物中的抑菌活性成分进行生物活性追踪及分离,发现两种提取物的活性部位中的化学组成相同。对活性组分进行黄酮体的颜色反应和和紫外光谱分析,结果显示活性组分遇硼氢化钠变浅蓝色;在甲醇溶液中的特征吸收峰为291 nm,在可见区无明显吸收;在甲醇钠和醋酸钠溶液中主要吸收波长向长波移动38 nm;以上结果具备5,7-二羟基-双氢黄酮的典型特征。进一步对活性组分进行液质分析和紫外光谱分析,推断活性组分中化合物分别是短叶松素、松属素、白杨素和高良姜素,其中松属素的相对含量最高。
3.对活性组分进一步通过Sephadex LH-20凝胶色谱柱分离、纯化得到松属素、白杨素、高良姜素。液相检测的纯度分别为87.13%,97.00%,94.55%。对浓度为200mg/L的松属素、白杨素和高良姜素的抑菌活性进行比较,发现松属素对意大利青霉的抑制效果最强,抑制率达70.28%;其次为白杨素,抑制率为34.12%;高良姜素的抑菌效果最差,抑制率仅为12.5%。
4.采用生长速率法对松属素抑制意大利青霉菌丝体生长的效果进行评价,松属素对菌丝体表现出显著地抑制作用。通过毒力回归分析,松属素对意大利青霉的抑制作用呈浓度-效应依赖关系。松属素处理浓度与抑制率之间的线性回归方程为y=1.77lnx+1.54,r=0.98283,P=0.01717,达显著水平。EC_(50)和EC_(90)分别为89.06 mg/L和469.78 mg/L。同时,松属素对温度的变化和酸碱性环境具有良好的适应性,在35～100℃的温度范围内及pH 4.0～7.0的酸碱环境中仍能保持稳定的抑菌活性。
5.松属素处理使意大利青霉的细胞结构受损。显微结构的观察结果表明经过松属素处理的意大利青霉在孢子萌发和菌丝体的培养过程中均出现了原生质分布不均匀,发生凝聚,菌丝体膨大变形,液泡增大等细胞走向衰亡的症状。超微结构的观察结果显示经过松属素处理的菌丝体发生严重的质壁分离,大量胞内容物外渗。同时松属素处理的意大利青霉菌丝体的几丁质酶活性和β-1,3-葡聚糖酶活性显著高于对照,反映菌体细胞壁的降解代谢增强。此外,松属素处理的菌丝体相对渗透率上升迅速,在整个培养过程中始终高于对照,表明松属素处理破坏了意大利青霉菌丝体细胞壁和细胞膜结构的完整性,是松属素抑制意大利青霉活性的原因之一。
6.通过对意大利青霉菌丝体培养过程中的呼吸代谢及物质代谢相关指标等进行测定,结果显示松属素处理的菌丝体呼吸强度在整个培养过程中均保持在较低的水平;ATP、ADP、AMP含量也同样明显低于对照。同时实验结果发现经过松属素处理的意大利青霉菌丝体中的蛋白质含量很低,在培养8 h和24 h时,蛋白质含量仅为对照的62.29%和42.72%;而在培养24 h时经过松属素处理的意大利青霉菌丝体内出现了还原糖的累积,还原糖的含量约为同期对照还原糖含量的2.5倍。结果暗示松属素通过抑制呼吸作用,使菌丝体的能量代谢受阻,呼吸底物累积,使菌体的物质代谢发生紊乱,加之细胞壁降解酶活性的加强促进几丁质和葡聚糖等降解,还原糖累积,蛋白质合成受阻;以上结果暗示松属素导致了意大利青霉菌丝体的能量代谢和合成代谢发生紊乱,是菌丝体逐渐走向衰亡的另一重要原因。
7.经过蜂胶提取物处理的柑橘果实贮藏期间青、绿霉病的发病率明显低于对照;同时能够延缓果实色度、可溶性固形物、V_C、有机酸等品质指标的下降;因此PEAE处理可以有效地控制柑橘贮藏期间青、绿霉病的发生。
8.通过对蜂胶提取物诱导柑橘青霉病的表达时间以及蜂胶提取物处理对柑橘果实抗病性相关的物质及酶活性的影响研究,发现蜂胶提取物对柑橘果实诱导抗病性的最佳表达时间是处理后8h。蜂胶提取物处理增加了柑橘果皮中酚类物质的含量,提高了柑橘果皮中苯丙氨酸解氨酶(PAL)、过氧化物酶(POD)、多酚氧化酶(PPO)、几丁质酶(CHT)等与诱导抗病性密切相关的酶的活性。因此,蜂胶提取物增强了柑橘果实的防御系统,对柑橘表现出良好的保鲜效果,具有进一步研究及开发的潜在价值。
Propolis is a resinous material collected by bees from plant buds and exudates, which is employed for resisting pathogenic microorganism, construction and repair of the honeycomb and sterilization of surroundings. There was a substantial evidence indicating that propolis had broad antimicrobial activity and was named as "natural antibiotics". At the same time, propolis is a complex mixture of chemical constituents including flavonoids, phenolic acids and esters, terpenes, fatty acids and amino acid etc. More than 300 kinds of compounds were identified from propolis of different origin. It indicated propolis was a desirable material for screening out natural antimicrobial. In current study, Penicillum italicum (P.italicum) , an important pathogenic fungi which lead to blue mold during the citrus storage as the indicator., bioassay was used to separate the active compound ; the action mechanism of active compounds against P.italicum was studied; Inhibitory effect of propolis ethyl acetate extract(PEAE) against citrus blue mold was evaluated. The main results as follow:
1. The extracted solvent and origin of propolis affected the chemical constituent and antifungal activity against P. italicum. Propolis ethyl acetate extract(PEAE) and propolis ethanol extract (PEE) demonstrated the most powerful activities, followed by propolis chloroform extract, while propolis petroleum ether extract and propolis water extract showed weak acivities, and the inhibitory activities were consistant with the contents of flavonoids or phenols in the corresponding extracts. Propolis from Hebei Baoding was of the highest contents of flavonoids or phenols and strongest inhibitory effect on the P. italicum; followed by Hebei Yongnian propolis; Propolis from Hubei Dangyang was last one.
2. The antifungal fractions from PEE and PEAE were separated by organic solvent extract, thin-layer chromatography (TLC) or column chromatography combined with bioassay and they had the similar chemical constitutes assayed by HPLC. The color reaction and UV behaviour for flavonoids were determined to identify the substance in the active fraction .The results showed its color became blue when meeting with NaHBO_3; Its characteristic wavelength was 292 nm in methol and would be shifed 38nm to the longer wave in MeONa or NaAc. This main flavonoids in active fraction were of the typical characteristic of 5,7-dihydroxyflavanone. Using the HPLC-PDA-ESI-MS method, it was deduced that the main compounds in the active fraction were pinobanksin, pinocembrine, chrysin and galangin; and pinocembrine had the highest relative content in the four compounds.
3. Purified pinocembrine, chrysin and galangin were attained by further separating active fraction through sephadex LH-20 chromatography, which purity for HPLC were 87.13%, 97.00%, 94.55% respectively. Among the three compounds, pinocembrine had the strongest inhibitory effect against P.italicum, followed by chrysin, and galangin was the last one; Their inhibition percents against P.italicum were 70.28%, 34.12%,12.5% separately at the concentration of 200 mg/L.
4. Effect of pinocembrine on the P.italicum were evaluated by growth rate method . Pinocembine appeared obviously inhibitory effect on the P.italicum and had the line relaxtion between the concentration and inhibition rate. The regression equation of toxicity was y = 1.77 lnx+1.54, ( r =0.98283, P =0.01717). EC_(50)=89.06 mg/L and EC_(90) =469.78 mg/L. At the same time, pinocembrime were still of the stable antifungal activity at at the temeperature range of 35～100℃and pH4～7.
5. Pinocembrine treatment damaged the cell structure of P.italicum during spore germination and mycelium culture. Microscopic structure of P.italicum hyphas treated with pinocembrine became swollen and abnormal, the protoplasm concentrated and the cell wall degraded, which indicated that hyphas deem to death. The results of ultrastructure indicated evident plasmolysis, intracellular components were extravasation. At the same time, activity of chitinase andβ-1, 3-glucanase were higher than contolled after treated with pinocembrine. Pinocembrine also destroyed the integrality of cell membrane and the relative leakage rate was increasing greatly after treated with pinocembrine.
6. Indexes on respiration metabolism and material metabolism were measured , the results indicated mycelium treated with pinocembine had the lower respiratory rate , ATP, ADP , AMP and protein contents . After culturing 8h and 24h, protein in the treated mycelium were only up to 62.29% and 42.72% compared with controlled. While the reduced sugar content in treated mycelium was higher than controlled mycelium at 24 h. It suggested that pinocembrine treatment blocked energy metabolism of mycelium through inhibited respiration; At the same time , Cell wall degrading enzyme in the mycelium accelerated the degradation of chitin and dextran. therefore , it led to the accumulation of reduced sugar and decreasing of protein, mycelium became deathward.
7. Compared with control, PEAE treatment decreased the disease incidence of blue mold and green mold , and delayed the decline of color , total soluble solids(TSS) ,titratable acidity(TA) ,vitamin C level and eatable quality of citrus fruits during storage at 26°C. Therefore, PEAE could effectively controlled postharvest diseases of citrus fruit during storage.
8.Expressive time of propolis extract on the induced resistance against citrus blue mold and influence of propolis extract on the activities of defensive related enzymes were investigated. The results showed that at 48 h after treatment with propolis extract, citrus fruit exhibited the strongest resistance against blue mold. Propolis extract treatment maintained higher level of the total phenolic contents, enhanced activities of phenylalanine ammonia-lyase, polyphenol oxidase and peroxidase, and stimulated chitinase in citrus fruit peel. Therefore, propolis treatment strengthened the defense system of citrus fruits and reduced disease incidence of citrus blue mold, and appeared great potential on postharvest disease control of citrus fruit.
引文
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