姜油的化学成分分析与姜辣素的分离纯化研究
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摘要
生姜(Zingiber officinale Roscoe)根茎中含有挥发性的精油和非挥发性的姜辣素物质,其中精油呈现出生姜的芳香气味,而姜辣素则呈现出生姜的辛辣风味,同时,也是生姜中主要药理活性成分。为加快对生姜姜油的开发利用,本文在对生姜根茎精油和姜辣素组织化学定位基础上,研究了姜油化学成分的GC/MS测定方法,建立了用HSCCC技术分离纯化姜辣素标准样品的新方法,并探讨了生姜不同品种、不同器官、不同生长期、不同栽培因素等对姜油含量及化学成分的影响。主要研究结果如下:
1.通过对多种染色剂进行试验比较,确定NADI试剂可作为生姜精油和姜辣素组织化学定位的特异性染色剂。该试剂可使精油呈棕红色,姜辣素呈天蓝色。通过光镜观察及透射电镜观察,确定姜精油和姜辣素混合存在于同一种类型的油细胞中,油细胞在生姜根茎中不同程度地分布于韧皮部和木质部的薄壁细胞中。
2.姜油无需衍生化处理,即可用GC/MS联用技术测定其中的挥发性精油和非挥发性姜辣素成分。用GC/MS联用技术在莱芜大姜的姜油中共分析出77种化学成分,其中精油成分50种,姜辣素成分27种。精油相对含量为59.31%,主要为萜类及其氧化物,且以倍半萜为主(50.15%),其中主要成分为α-姜烯(22.29%)、β-倍半水芹烯(8.58%)、α-法尼烯(3.93%)、β-没药烯(3.87%)、α-姜黄烯(2.63%);姜辣素的相对含量为40.69%,其中主要成分为6-姜酚(9.38%)、6-姜烯酚(7.59%)及姜辣素类的分解产物姜油酮(9.24%)。在莱芜大姜中发现3种为新的姜辣素化合物,分别为6-异姜酚、Z-10-异姜烯酚和E-10-异姜烯酚。
3.不同提取方法姜油得率及化学成分差异较大,新收获的莱芜大姜根茎采用水蒸气蒸馏法、乙醇浸提法和超临界CO2萃取法的姜油提取率分别为0.95%、3.75%和4.67%;水蒸气蒸馏所得精油主要是呈现芳香性气味的倍半萜类化合物(63.46%)和单萜类化合物(34.91%);乙醇浸提所得浸膏主要是呈现辛辣味的姜辣素类化合物(86.41%),其中主要为6-姜酚(16.86%)、6-姜烯酚(16.58%)和姜油酮(17.68%);超临界CO2萃取所得油树脂中挥发性的芳香味化合物和非挥发性的姜辣素类化合物的相对含量分别为59.31%和40.69%,具有浓郁的芳香气味和强烈的辛辣味。
4.老姜的姜油含量比鲜姜高,虽然主要化学成分相同,但其相对含量相差较大。老姜中α-姜黄烯和姜辣素的相对含量分别比鲜姜高3.60%和3.89%。老姜的芳香性气味比鲜姜淡,但其辛辣味较强,具有更高的营养保健价值。
5.生姜植株的根、根茎韧皮部、根茎木质部和周皮等部位中均含有丰富的姜油成分,含量分别达2.1±0.1%、4.64±0.13%、4.62±0.17%和0.94±0.04%,因而,在生产中无需脱皮即可提取生姜姜油;生姜地上茎和叶片的超临界CO2提取物中含姜油成分极低,其中姜辣素含量仅占9.52%、2.28%,提取姜油的利用价值不大。
6.不同品种生姜姜油的化学成分差异较小,仅各组分的相对含量差异显著。其中姜油含量和姜辣素相对含量较高的生姜品种有:莱芜大姜、日本大姜、山农1号、山农2号、安丘大姜。姜油含量和姜辣素相对含量较低的生姜品种有:房州姜、金时姜和安丘小姜。
7.不同生长期生姜姜油成分没有显著差异,但各组分相对含量变化较大。生姜姜油含量及姜辣素相对含量均从发芽期到收获期呈逐渐上升趋势,分别由初始的1.86±0.09%和32.7%上升至收获时的4.56±0.15%和40.11%,说明随着生姜的生长,次生代谢物——姜油被不断地合成,并贮存于根茎的油细胞中。
8.生姜幼苗期采用不同有色膜遮光对生姜姜油含量有一定影响。其中绿膜、红膜和白膜对生姜的姜油含量和成分影响不大,适用于生姜遮光栽培,但蓝膜使姜油含量和姜辣素相对含量明显减少,分别降至3.85±0.11%和33.68%,不适于生产中应用。
9.用HSCCC技术可以快速地从生姜乙醇浸提物中大量分离纯化高纯度的6-姜酚、8-姜酚和10-姜酚。从200 mg生姜粗提物中在170 min内即可分离纯化6-姜酚30.2 mg、8-姜酚40.5 mg和10-姜酚50.5 mg,其纯度分别达到99.9%、99.9%和92.4%。分离制备的纯品可以用于生理活性实验及分析检测用标样。
Ginger (Zingiber officinale Roscoe) rhizome contains the volatile essential oil responsible for the distinct aroma and the nonvolatile pungent compounds responsible for the pungent aroma and mainly pharmacologically active components in ginger. In order to promote the development and utilization of ginger oil, this paper studied the histochemical localization method of ginger essential oil and pungent compounds; the GC/MS analytical method for the determination of the chemical compositions of ginger oil; a novel HSCCC method for the separation and purification of major gingerols reference substances from ginger and effects of the growing development of ginger, cultivars, cultivated factors, different organs on the content and chemical compositions of ginger oil. The main results were as follows:
1. NADI reagent can be used for histochemical localization staining of essential oils and gingerols by comparing the number of stains. And the essential oil was stained red brown, but gingerols was stained azure by NADI reagent. The essential oil and gingerols existed in the same type of oil cells and the number of points in the rhizomeby light microscope and transmission electron microscopy. They both were stored and accumulated in parenchyma cells of phloem and xylem.
2. GC / MS technology can be applied to determinate the chemical compositions of the volatile essential oil and non-volatile gingerols in ginger oil without derivatization. The analysis resulted in 77 compounds in ginger oil from Zingiber officinale Rosc. var. Laiwudajiang, in which contained non-volatile ginger pungent compounds (40.69%) and abundant volatile compounds (59.31%). The volatile compounds were mainlyα- zingiberene (22.29%),β-sesquiphellandrene (8.58%),α-farnesene(3.93%),β-bisobolene (3.87%),α-curcumene (2.63%), which was mostly consisted of sesquiterpene hydrocarbons (50.15%). The pungent compounds of ginger were mainly 6-gingerol (9.38%), 6-shogaols (7.59%), zingerone (9.24%) produced by thermal degradation of the gingerols or shogaols. This analysis resulted in the detection of 3 hitherto unknown natural compounds from ginger var. Laiwudajiang, which were 6-isogingerol, Z-10-isoshogaol and E-10-isoshogaol, respectively.
3. There were significant differences in ginger oil extraction rate and chemical components among different extraction methods. The ginger oil extraction rate by steam distillation, ethanol leaching and supercritical carbon dioxide was 0.95%,3.75% and 4.67%,respectively. The ginger essential oil obtained by steam distillation was mainly the sesquiterpenoids (63.46%) and the monoterpenoids (34.91%) responsible for the distinct aroma; The ginger concrete obtained by ethanol leaching was mainly the pungent compounds (86.41%) responsible for the pungent aroma, 6-gingerol (16.86%), 6-shogaol (16.58%) and zingerone (17.68%) among them; The ginger oleoresin obtained from supercritical carbon dioxide contained abundant non-volatile ginger pungent compounds (40.69%) and abundant volatile aromatic compounds (59.31%), and presented intensely the aroma and pungency of ginger.
4. Ginger oil content of seed-ginger were more higher than that of fresh ginger. And the chemical components in both were the same, however, the relative content of chemical components was a significant difference. The relative content ofα-curcumene and pungent principles in seed-ginger was 3.60%, 3.89% higher than that in fresh ginger, respectively. The seed-ginger had a lighter fragrance than fresh ginger, but had a strong pungent taste and higher value of nutition and health care.
5. Root, ligament, xylem and periderm contained abundant ginger oil, and the content of ginger oil was 2.1±0.1%, 4.64±0.13%, 4.6 2±0.17%, 0.94±0.04%, respectively. Ginger oil can be extracted without peeling ginger in processing. Extracts with SEF-CO2 from stem and leaf have little chemical compounds of ginger oil and can make use of little value from extrating ginger oil.
6. There were non-significant differences between different ginger cultivars. However, the relative content of chemical composition was significant differences. The following ginger cultivars were contained more higher the content of ginger oil and the relative content of pungent principles: laiwedajiang, ribendajiang, shannongyihao, shannongrehao, anqiudajiang. The following ginger cultivars were contained more lower the content of ginger oil and the relative content of pungent principles: fangzhoujiang, jingshijiang, anqiuxiaojiang.
7. There were non-significant differences between chemical compounds of ginger oil during different growth times. But the relative content of chemical composition was significant differences. The content of ginger oil and the relative content of pungent priciples were a gradual upward trend from 1.86±0.09% and 32.7% to 4.56±0.15% and 40.11% from germinating stage to harvesting stage, espectively. The results indicated that the second metabolites (ginger oil) were continuously synthesized and stored in the rhizomes of ginger.
8. Green film, red film and white film in ginger cultivation had non-significant effect on the content of ginger oil and chemical components of ginger oil, and can be applied to ginger cultivation. However, blue film was unsuitable for ginger cultivation due to making ginger oil content (3.85±0.11%) and the relative content of pungent priciples (33.68%) a significant decrease.
9. High-speed counter-current chromatography can be applied to the separation and purification of 6-gingerol,8-gingerol and 10-gingerol from a crude extract of ginger. The experiment yielded 30.2 mg of 6-gingerol, 40.5 mg of 8-gingerol, 50.5 mg of 10-gingerol from 200mg of crude extract in one-step separation. And the purity of these compounds was 99.9%, 99.9% and 99.2%, respectively, as determined by high-performance liquid chromatography (HPLC). Gingerols may be used for in vitro and in vivo studies and as reference substances for analytical purposes
1.通过对多种染色剂进行试验比较,确定NADI试剂可作为生姜精油和姜辣素组织化学定位的特异性染色剂。该试剂可使精油呈棕红色,姜辣素呈天蓝色。通过光镜观察及透射电镜观察,确定姜精油和姜辣素混合存在于同一种类型的油细胞中,油细胞在生姜根茎中不同程度地分布于韧皮部和木质部的薄壁细胞中。
2.姜油无需衍生化处理,即可用GC/MS联用技术测定其中的挥发性精油和非挥发性姜辣素成分。用GC/MS联用技术在莱芜大姜的姜油中共分析出77种化学成分,其中精油成分50种,姜辣素成分27种。精油相对含量为59.31%,主要为萜类及其氧化物,且以倍半萜为主(50.15%),其中主要成分为α-姜烯(22.29%)、β-倍半水芹烯(8.58%)、α-法尼烯(3.93%)、β-没药烯(3.87%)、α-姜黄烯(2.63%);姜辣素的相对含量为40.69%,其中主要成分为6-姜酚(9.38%)、6-姜烯酚(7.59%)及姜辣素类的分解产物姜油酮(9.24%)。在莱芜大姜中发现3种为新的姜辣素化合物,分别为6-异姜酚、Z-10-异姜烯酚和E-10-异姜烯酚。
3.不同提取方法姜油得率及化学成分差异较大,新收获的莱芜大姜根茎采用水蒸气蒸馏法、乙醇浸提法和超临界CO2萃取法的姜油提取率分别为0.95%、3.75%和4.67%;水蒸气蒸馏所得精油主要是呈现芳香性气味的倍半萜类化合物(63.46%)和单萜类化合物(34.91%);乙醇浸提所得浸膏主要是呈现辛辣味的姜辣素类化合物(86.41%),其中主要为6-姜酚(16.86%)、6-姜烯酚(16.58%)和姜油酮(17.68%);超临界CO2萃取所得油树脂中挥发性的芳香味化合物和非挥发性的姜辣素类化合物的相对含量分别为59.31%和40.69%,具有浓郁的芳香气味和强烈的辛辣味。
4.老姜的姜油含量比鲜姜高,虽然主要化学成分相同,但其相对含量相差较大。老姜中α-姜黄烯和姜辣素的相对含量分别比鲜姜高3.60%和3.89%。老姜的芳香性气味比鲜姜淡,但其辛辣味较强,具有更高的营养保健价值。
5.生姜植株的根、根茎韧皮部、根茎木质部和周皮等部位中均含有丰富的姜油成分,含量分别达2.1±0.1%、4.64±0.13%、4.62±0.17%和0.94±0.04%,因而,在生产中无需脱皮即可提取生姜姜油;生姜地上茎和叶片的超临界CO2提取物中含姜油成分极低,其中姜辣素含量仅占9.52%、2.28%,提取姜油的利用价值不大。
6.不同品种生姜姜油的化学成分差异较小,仅各组分的相对含量差异显著。其中姜油含量和姜辣素相对含量较高的生姜品种有:莱芜大姜、日本大姜、山农1号、山农2号、安丘大姜。姜油含量和姜辣素相对含量较低的生姜品种有:房州姜、金时姜和安丘小姜。
7.不同生长期生姜姜油成分没有显著差异,但各组分相对含量变化较大。生姜姜油含量及姜辣素相对含量均从发芽期到收获期呈逐渐上升趋势,分别由初始的1.86±0.09%和32.7%上升至收获时的4.56±0.15%和40.11%,说明随着生姜的生长,次生代谢物——姜油被不断地合成,并贮存于根茎的油细胞中。
8.生姜幼苗期采用不同有色膜遮光对生姜姜油含量有一定影响。其中绿膜、红膜和白膜对生姜的姜油含量和成分影响不大,适用于生姜遮光栽培,但蓝膜使姜油含量和姜辣素相对含量明显减少,分别降至3.85±0.11%和33.68%,不适于生产中应用。
9.用HSCCC技术可以快速地从生姜乙醇浸提物中大量分离纯化高纯度的6-姜酚、8-姜酚和10-姜酚。从200 mg生姜粗提物中在170 min内即可分离纯化6-姜酚30.2 mg、8-姜酚40.5 mg和10-姜酚50.5 mg,其纯度分别达到99.9%、99.9%和92.4%。分离制备的纯品可以用于生理活性实验及分析检测用标样。
Ginger (Zingiber officinale Roscoe) rhizome contains the volatile essential oil responsible for the distinct aroma and the nonvolatile pungent compounds responsible for the pungent aroma and mainly pharmacologically active components in ginger. In order to promote the development and utilization of ginger oil, this paper studied the histochemical localization method of ginger essential oil and pungent compounds; the GC/MS analytical method for the determination of the chemical compositions of ginger oil; a novel HSCCC method for the separation and purification of major gingerols reference substances from ginger and effects of the growing development of ginger, cultivars, cultivated factors, different organs on the content and chemical compositions of ginger oil. The main results were as follows:
1. NADI reagent can be used for histochemical localization staining of essential oils and gingerols by comparing the number of stains. And the essential oil was stained red brown, but gingerols was stained azure by NADI reagent. The essential oil and gingerols existed in the same type of oil cells and the number of points in the rhizomeby light microscope and transmission electron microscopy. They both were stored and accumulated in parenchyma cells of phloem and xylem.
2. GC / MS technology can be applied to determinate the chemical compositions of the volatile essential oil and non-volatile gingerols in ginger oil without derivatization. The analysis resulted in 77 compounds in ginger oil from Zingiber officinale Rosc. var. Laiwudajiang, in which contained non-volatile ginger pungent compounds (40.69%) and abundant volatile compounds (59.31%). The volatile compounds were mainlyα- zingiberene (22.29%),β-sesquiphellandrene (8.58%),α-farnesene(3.93%),β-bisobolene (3.87%),α-curcumene (2.63%), which was mostly consisted of sesquiterpene hydrocarbons (50.15%). The pungent compounds of ginger were mainly 6-gingerol (9.38%), 6-shogaols (7.59%), zingerone (9.24%) produced by thermal degradation of the gingerols or shogaols. This analysis resulted in the detection of 3 hitherto unknown natural compounds from ginger var. Laiwudajiang, which were 6-isogingerol, Z-10-isoshogaol and E-10-isoshogaol, respectively.
3. There were significant differences in ginger oil extraction rate and chemical components among different extraction methods. The ginger oil extraction rate by steam distillation, ethanol leaching and supercritical carbon dioxide was 0.95%,3.75% and 4.67%,respectively. The ginger essential oil obtained by steam distillation was mainly the sesquiterpenoids (63.46%) and the monoterpenoids (34.91%) responsible for the distinct aroma; The ginger concrete obtained by ethanol leaching was mainly the pungent compounds (86.41%) responsible for the pungent aroma, 6-gingerol (16.86%), 6-shogaol (16.58%) and zingerone (17.68%) among them; The ginger oleoresin obtained from supercritical carbon dioxide contained abundant non-volatile ginger pungent compounds (40.69%) and abundant volatile aromatic compounds (59.31%), and presented intensely the aroma and pungency of ginger.
4. Ginger oil content of seed-ginger were more higher than that of fresh ginger. And the chemical components in both were the same, however, the relative content of chemical components was a significant difference. The relative content ofα-curcumene and pungent principles in seed-ginger was 3.60%, 3.89% higher than that in fresh ginger, respectively. The seed-ginger had a lighter fragrance than fresh ginger, but had a strong pungent taste and higher value of nutition and health care.
5. Root, ligament, xylem and periderm contained abundant ginger oil, and the content of ginger oil was 2.1±0.1%, 4.64±0.13%, 4.6 2±0.17%, 0.94±0.04%, respectively. Ginger oil can be extracted without peeling ginger in processing. Extracts with SEF-CO2 from stem and leaf have little chemical compounds of ginger oil and can make use of little value from extrating ginger oil.
6. There were non-significant differences between different ginger cultivars. However, the relative content of chemical composition was significant differences. The following ginger cultivars were contained more higher the content of ginger oil and the relative content of pungent principles: laiwedajiang, ribendajiang, shannongyihao, shannongrehao, anqiudajiang. The following ginger cultivars were contained more lower the content of ginger oil and the relative content of pungent principles: fangzhoujiang, jingshijiang, anqiuxiaojiang.
7. There were non-significant differences between chemical compounds of ginger oil during different growth times. But the relative content of chemical composition was significant differences. The content of ginger oil and the relative content of pungent priciples were a gradual upward trend from 1.86±0.09% and 32.7% to 4.56±0.15% and 40.11% from germinating stage to harvesting stage, espectively. The results indicated that the second metabolites (ginger oil) were continuously synthesized and stored in the rhizomes of ginger.
8. Green film, red film and white film in ginger cultivation had non-significant effect on the content of ginger oil and chemical components of ginger oil, and can be applied to ginger cultivation. However, blue film was unsuitable for ginger cultivation due to making ginger oil content (3.85±0.11%) and the relative content of pungent priciples (33.68%) a significant decrease.
9. High-speed counter-current chromatography can be applied to the separation and purification of 6-gingerol,8-gingerol and 10-gingerol from a crude extract of ginger. The experiment yielded 30.2 mg of 6-gingerol, 40.5 mg of 8-gingerol, 50.5 mg of 10-gingerol from 200mg of crude extract in one-step separation. And the purity of these compounds was 99.9%, 99.9% and 99.2%, respectively, as determined by high-performance liquid chromatography (HPLC). Gingerols may be used for in vitro and in vivo studies and as reference substances for analytical purposes
引文
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