姜科药用植物益智Alpinia oxyphylla资源化学研究
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摘要
本论文研究工作为“十二五”国家科技支撑计划区域基地项目子课题《益智规范化种植基地及其SOP建立》和海南省中药现代化专项资金项目《海南益智规范化种植基地药材及其饮片质量标准的建立》的部分研究内容。
本论文的研究工作以益智的文献为起点,综合了益智的资源化学研究、资源化学评价研究和传统功效的诠释研究,基本阐述了益智的资源内涵及其功效基础。以此为基础进行了益智的质量标准研究和产业化开发研究,为益智资源的合理高效利用奠定科学基础。
一、文献研究
文献是科学研究的起点,为了全面准确的提挈益智的资源现状,本文系统综述了姜科植物药用概况、姜科山姜属植物研究进展、益智历史应用沿革及其现代化学药理研究基础,并藉此凝练出本论文的研究思路和整体实验方案。
二、益智的资源化学研究
(一)益智各部位的资源性成分研究
1益智果实资源性成分研究
为了全面阐述益智果实的资源化学分布,阐明其基于传统功效的药效物质基础,促进益智资源的合理使用,本文采用硅胶柱层析、制备薄层层析、凝胶柱色谱及反相柱色谱等色谱技术对益智果实所含资源性成分进行分离、纯化和结构鉴定。从益智果实中共分离得到了11个化合物,分别鉴定为9-羟基表圆柚醇(1)、乔松素(2)、圆柚酮(3)、杨芽黄素(4)、β-谷甾醇(5)、益智酮甲(6)、伊砂黄素(7)、p-胡萝卜苷(8)、p-谷甾醇棕榈酸酯(9)、(S)-2-戊醇-2-O-β-D-吡喃葡萄糖苷(10)、原儿茶酸(11)。其中化合物1和化合物10为新天然产物,化合物2为首次从益智中分离得到。以上研究为益智的进一步深入研究奠定了基础。
2益智根茎资源性成分研究
为了探索益智根茎废弃资源的可利用价值,本文采用硅胶柱层析及聚酰胺柱层析等色谱技术对益智根茎所含资源性成分进行分离、纯化,根据所分离化学成分的理化性质及波谱数据鉴定其结构。结果从益智根茎乙醇提取物中共分离鉴定13个化合物,分别鉴定为三十二烷醇(1)、伊砂黄素(2)、杨芽黄素(3)、山奈酚-7,4'-O-二甲醚(4)、p-谷甾醇(5)、对羟基桂皮酸(6)、双氢山奈素(7)、益智酮甲(8)、白杨素(9)、乔松素(10)、山奈酚-4'-o-甲醚(11)、肉豆蔻酸(12)、球松素(13),所有化合物均为首次从益智根茎中分离得到。以上研究为今后益智根茎的资源利用奠定科学基础。
3益智茎叶资源性成分研究
基于发现与挖掘益智茎叶可利用的物质基础,本文采用硅胶柱层析及聚酰胺柱层析等色谱技术对益智茎叶所含资源性成分进行分离、纯化,根据其理化性质及波谱数据鉴定其结构。结果从益智茎叶乙醇提取物中共分离鉴定了11个化合物,分别鉴定为伊砂黄素(1)、杨芽黄素(2)、芹菜素-4',7-O-二甲醚(3)、山奈素-4'-o-甲醚(4)、反式对羟基桂皮酸(5)、白杨素(6)、乔松素(7)、刺槐素(8)、棕榈酸(9)、球松素(10)、5,7,4'-三甲氧基黄酮(11),所有化合物均为首次从益智根茎中分离得到。以上研究为今后益智茎叶的资源利用奠定科学基础。
(二)益智资源化学评价
1益智果实挥发性成分分析
通过对来自我国云南省、广西省、广东省及海南省(包括来自白沙县、琼中县、万宁市及屯昌县)等共21份益智果实挥发油中资源性成分进行比较研究。研究证实：各产地益智挥发油所含成分种类及含量差异较大,其中β-panasinsene和humulene两种成分含量较高。采用系统聚类分析方法对该21批益智果实进行聚类分析,结果表明：海南省白沙县、琼中县和屯昌县三个县的益智挥发油中所含成分相似,说明这些地区的区域环境相似；广东阳江、广西和云南三个省份的益智挥发油中所含成分接近,但是与上述三个县的益智药材有所差别。
2不同生长期益智果实、根茎及茎叶中资源性成分动态累积研究
本研究对不同生长期益智不同部位中圆柚酮、益智酮甲、益智酮乙、益智醇、杨芽黄素、伊砂黄素、白杨素、山奈素和芹菜素二甲醚9种资源性成分进行了LC-MS/MS定量分析。
益智不同部位的资源性成分含量分布情况不同,研究证实,在果实整个生长周期,萜类、二苯基庚烷类资源性成分主要富集在益智果实中,而黄酮类资源性成分基本均匀分布在益智果实、茎叶和根茎中。益智在结果45天时果实中各种资源性成分含量处于最高峰,果实最佳采收时间定在结果45天基本合理,结果45天后,圆柚酮、益智酮甲和杨芽黄素三种功效成分的蓄积量均有所提高,一般益智3月上旬开始结果,益智果实最佳采收时间定在4月底至5月初,传统应用中益智采收期定在5-6月基本合理：益智根茎和茎叶在益智结果后亦有一定量以上成分蓄积,证实了益智根茎和茎叶潜在的药用价值待挖掘。
益智果实最佳采收期及益智果实、根茎和茎叶之间资源性成分的转运规律有待进一步研究确定。
3益智果实中核苷与碱基类资源性成分评价
对于不同产地益智果实中核苷及其碱基含量测定结果表明：各产地药材所含主要核苷及其碱基的种类基本相同,但是各类核苷和碱基含量差异较大,这可能是由于地理环境、气候、温度、采收期等因素所造成的。对于不同采收期益智果实中核苷及其碱基含量测定结果表明：14批益智果实中几乎都富含待测十种核苷和碱基,但含量有极大的差别。2’-脱氧胸苷含量最多,在益智果实整个生长周期内变化明显(36.79-310.58gg/g)；次黄嘌呤含量最低,在果实形成后期甚至未检测到。此外,随着益智果实成熟度增加,单个核苷和碱基以及它们的总量都随之减少,表明核苷及其碱基的合成与果实的生长发育密切相关。
4益智果实、根茎及茎叶中无机元素分布及动态累积研究
研究结果表明,益智果实中锌、铁、锰、钙及镁五种营养元素含量相对于根茎、茎叶更丰富,除重金属镉元素益智果实含量高于根茎、茎叶,果实中另外四种重金属砷、汞、铅和铜含量均相对较低。
据国家商务部2001年颁发的《药用植物及制剂进出口绿色行业标准》有关药材重金属元素含量限量标准,我国云南省、广西省、广东省及海南省的20个益智果实样品的砷、汞、铅、镉含量均符合绿色行业标准；海南省琼中长兴、琼中毛阳、屯昌乌坡和屯昌南吕四产地的益智果实铜含量符合绿色行业标准,但采自云南西双版纳、广西南宁、广东2产地及海南省其它12个市县益智果实的铜含量超标。需要今后进一步深入研究,同时,需要考察这些产区大气、土壤及灌溉用水的重金属含量情况。
20个产地益智果实重金属和营养元素含量的检测结果显示,海南产的益智安全性最好,突出表现为以下四个产地海南琼中长兴村、琼中毛阳镇、屯昌乌坡镇和屯昌南昌镇；广西南宁产的益智果实营养元素的含量最丰富。
从益智不同生长期果实、根茎和茎叶重金属元素和营养元素的含量分布情况看,益智果实、根茎中重金属含量与茎叶相比较低,而营养元素含量相对较高；益智果实如在结果45天时采收,除镉元素,其它四种重金属元素含量均相对较低,锌、铁、锰、钙和镁五种营养元素含量均较高,即在益智结果45天时采收益智果实营养元素含量较高,而重金属含量相对较低。
三、益智温脾止泻和补肾缩尿功效的活性评价研究
(一)益智不同提取分离部位的制备
为了明确益智符合其传统功效的有效作用部位,本文制备了益智挥发油部位、非挥发油部位95%乙醇提取物、大孔树脂50%乙醇洗脱物和大孔树脂90%乙醇洗脱物四个部位,并采用HPLC进行了初步定性。
(二)益智不同提取分离部位温脾止泻功效的活性评价研究
为了研究益智传统温脾止泻功效的活性部位,选择番泻叶致小鼠急性腹泻和大黄引起小鼠脾虚泻下两种模型,对从益智中分离获得的4个提取部位进行止泻活性评价。研究结果表明：益智非挥发油部位95%乙醇提取物和益智大孔树脂90%乙醇洗脱物能够延长番泻叶致急性腹泻小鼠的腹泻潜伏期和降低稀便比重,具有良好的止泻活性,大孔树脂50%乙醇洗脱物对小鼠急性腹泻无影响,益智果实挥发油能够显著的延长小鼠腹泻潜伏期,但是对稀便个数及稀便比重均无影响；通过上述活性的筛选结果,进一步对益智非挥发油部位95%乙醇提取物、大孔树脂90%乙醇洗脱物及大孔树脂50%乙醇洗脱物进行化学分析,结果显示脂溶性大的成分可能是益智止泻的活性部位。进一步研究表明益智非挥发油部位95%乙醇提取物和益智大孔树脂90%乙醇洗脱物能够显著地影响脾虚小鼠的胃残留率和小肠推进率,对胃肠运动影响显著,且能够一定程度改善脾虚小鼠的脾虚状态。
研究结果亦证实益智大孔树脂90%乙醇洗脱物改善脾虚状态与升高血浆中LDH水平相关,同时其抑制胃肠运动主要与升高血浆中NO和降低胃肠激素MOT和SS有关；该部位通过升高血浆中LDH水平,同时降低血浆中SDH水平改善脾虚泻下小鼠的脾虚状态,其影响小鼠的胃肠运动能力主要与升高NO有关,同时与降低血浆中胃肠激素MOT和SS的水平密切相关。
(三)益智不同提取与分离部位缩尿功效的活性评价研究
为了明确益智的缩尿作用活性,本节对不同益智提取部位及单体化合物进行缩尿作用药效学筛选,确定益智挥发油部位、非挥发油部位乙醇提取物、大孔树脂50%乙醇洗脱物和大孔树脂90%乙醇洗脱物四个部位对卡巴胆碱诱导的离体膀胱逼尿肌收缩均有一定的抑制作用；筛选了伊砂黄素、山柰素、益智醇、益智酮乙、诺卡酮、杨芽黄素、白杨素等7个益智中分离出来的单体化合物,发现伊砂黄素抑制卡巴胆碱EC50=3.50±0.05μmol/L。
四、中药益智的质量标准研究
为了完善现有中药益智的质量标准,本文采用薄层色谱法及高效液相色谱法等先进技术对于中药益智进行了质量标准研究。即建立了薄层鉴别、显微鉴别项；建立了圆柚酮、杨芽黄素、益智酮甲三种功效成分同时测定含量检测项；完善了水分、灰分及酸不溶性灰分等项的建立。为今后益智原料药材、饮片及其产品开发质量标准的建立奠定科学基础。
五、益智资源开发与产业化
益智属药食同源品种,常间种于槟榔、橡胶的树下,海南省目前益智的种植面积达2万亩。益智广泛的药理作用和其药食同源的特性决定了更适合于研制平时就可以食用的普通食品。
在海南省中药现代化专项基金的支助下,项目组研发了益智椰子粉、益智木瓜粉固体饮料,以上产品可丰富现有旅游产品的种类,提升我省旅游产品的层次,带动相关益智种植业及我省旅游业的发展。
This research paper, referring to the project "Research on establishment of standardized planting base and the SOP of Alpinia oxyphylla Miq.", which is contained in the regional base project "Optimization and upgrading of standardized planting base and the SOP of7kinds of traditional Chinese medicines" financially supported by the national12th five-year plan regional base project (2011BA101B07). Besides, a part of research contents are from "Establishment of quality control on crude drugs and decoction pieces of the fruits of A. oxyphylla from standardized planting base in Hainan" supported by Hainan special plan for the modernization of traditional Chinese medicines.
This dissertation involves five chapters.
Chapter1Literature research
In this part, mainly through summarizing relevant literature, the pharmaceutical usages of the plants belong to Zingiberacea family, the research progress in the plants of Alpinia genus, traditional applications and research advances of chemistry and pharmacology of the fruits of A. oxyphylla were reviewed systematically. Based on the preliminary work, the research ideas and experimental design were put forward.
Chapter2Studies on the chemical resources of A. oxyphylla
This chapter is further divided into two sections.
Section one includes three parts.
In part1, studies on the chemical constituents from the fruits of A. oxyphylla were included. The objective of this study is to further develop and exploit the rich resources of Hainan famous-region drug-A. oxyphylla, clarify the pharmacological substances based on its traditional efficacy and find its new effective fractions and components. For this reason, the chemical investigation on the fruits of A. oxyphylla were carried out with the combined methods of silica gel column chromatography, preparative TLC, gel permeation chromatography, ODS column chromatography and recrystallization. The structures of the isolated compounds were elucidated on the grounds of their physicochemical constants and NMR spectral data analysis.11compounds were isolated and their structures were determined as9-hydroxy epinootkatol (1), pinocembrin (2), nookatone (3), tectochrysin (4),β-sitosterol (5), yakuchinone A (6), izalpinin (7), β-daucosterol (8),β-sitosterol palmitate (9),(S)-2-pentanol-2-O-β-D-glucopyranoside (10) and protocatechuic acid (11). Compounds1and10were new natural products and compound2was isolated from the fruits of A. oxyphylla for the first time. This study provided scientific basis for the further research and exploitation of the resources of the fruits of A. oxyphylla in the future.
In part2, investigation on the chemical constituents from the rhizomes of A. oxyphylla was referred to. Based on the pharmacological substances exploited that were discovered from the rhizomes of A. oxyphylla, the chemical investigation on the rhizomes of A. oxyphylla was carried out with the methods of silica gel column chromatography and polyamide column chromatography. The structures of the isolated compounds were elucidated according to the physicochemical constants and NMR spectral data analysis.14compounds were isolated from the ethanol extract from the rhizomes of A. oxyphylla and their structures were determined as doacontanol (1), izalpinin (2), tectochrysin (3), kaempferol-7,4'-dimethyl mester (4), β-sitosterol (5),p-hydroxylcinnamic acid (6), dihydrokaempferol (7), yakuchinone A (8), chrysin (9), pinocembrin (10), kaempferol-4'-methylmester (11), myristic acid (12), pinostrobin (13). All the compounds were isolated from the rhizomes of A. oxyphylla for the first time. This study lays scientific basis for the exploitation of the resources of rhizomes of A. oxyphylla in the future.
In part3, research into the chemical constituents from the stems and leaves of A. oxyphylla was discussed. To study the effective substances in the stems and leaves of A. oxyphylla further, their chemical constituents were isolated and purified by silica column chromatography and polyamide column chromatography. The structures of those compounds were identified and determined based on their physicochemical constants and spectral data analysis. Consequently,16compounds were obtained, and they were elucidated as izalpinin (1), tectochrysin (2), apigenin-7,4'-dimethyl ester (3), kaempferol-4'-methyl mester (4),(E)-p-hydroxy cinnamic acid (5), chrysin (6), pinocembrin (7), apigenin-4'-methyl ester (8), myristic acid (9), docosanoic acid (10), octacosanoic acid (11), septadecanoic acid (12), eicosanoic acid (13), n-hexadecanoic acid (14), pinostrobin (15),5,7,4'-trimethyl flavone (16). All the compounds were isolated from the stems and leaves of A. oxyphylla for the first time. This study provides scientific basis for the exploitation of the resources of stems and leaves of A. oxyphylla in the future.
In section two, the chemical resources evaluation of A. oxyphylla was studied. This chapter consists of five parts.
In part1, the volatile components in the fruits of A. oxyphylla were tested and analyzed. Chemical compositions in the volatile oils from the fruits of A. oxyphylla collected from different provinces and regions in China, including Yunnan, Guangxi, Guangdong and Hainan, were studied by GC-MS. The results showed that there was a large variation in the components and content of volatile oils among the drugs from different regions. Among the components in the volatile oil, β-panasinsene and humulene are two major compounds. In addition, hierarchical cluster analysis (HCA) was performed to classify all the samples according to the contents of the investigated analytes. The samples from Baisha, Qiongzhong and Tunchang (Hainan province) can be classified into one cluster, which indicates that these regions are similar in the environment, while the samples from Guandong, Guangxi and Yunnan were classified into another cluster, whose contents of volatile oils were different from the three regions mentioned above.
In part2, the variation rule about the contents of the constituents in the fruits, rhizomes, stems and leaves of A. oxyphylla at different growth time was studied. Nine compounds, i.e., nootkatone, yakuchinone A, yakuchinone B, nootkatol, tectochysin, izalpinin, chrysin and7,4'-dimethyl apigenin were analyzed by LC-MS/MS.
The contents of the resource constituents in the different parts of A. oxyphylla are different. The result shows that the resource constituents of terpenoids, diarylheptanoids are mainly rich in the fruits of A. oxyphylla, while the flavonoids is evenly distributed in the fruits, stems and leaves, and rhizomes of A. oxyphylla in the whole growth period of the fruits.
The results showed that the contents of all the compounds in the fruits reached the highest at45-day harvest time. Thus, it is reasonable that the best harvest time for the fruits is set at45days after it bears fruits. With the maturation of the fruits, most of the chemical components accumulated in the fruits at45days. This indicates that it is reasonable for the fruits of A. oxyphylla traditionally used as a medicinal part. At45days, a large quantity of flavonoids and a small amount of terpenoids and diary lheptanoids also accumulated in the stems and leaves of A. oxyphylla, which shows that the stems and leaves can be used as new resources in the future.
The best harvest time of the fruits and the transfer rule of the resource constituents among the fruits, rhizomes, stems and leaves, need to be verified.
In part3, the assay of nucleobases and nucleosides in the fruits of A. oxyphylla was done. Nucleobases and nucleosides were quantitatively determined in the fruits of A. oxyphylla collected from different cultivation regions. Almost all the samples were rich in nucleobases and nucleosides, but there was a large variation in the content, which might attribute to the factor of harvest time. Nucleobases and nucleosides were also quantitatively determined in the fruits of A. oxyphylla collected at different harvest time. The results showed that the content of thymidine is much higher during the whole research period than that of others, which is in the range of36.79-310.58μg/g. Hypoxanthine is observed to be the least in all the analytes, and its contents in some samples cannot be detected. Additionally, the total amount of both total and individual nucleosides and nucleobases in the fruits of A. oxyphylla decreased with the increase of maturity degree, which indicates that the synthesis of such components is closely relevant to the growth cycle.
In part4, the contents of inorganic elements in the fruits, rhizomes, stems and leaves and flowers at different growth stages were assayed. The results showed that the contents of nutrient elements such as Zn、Fe、Mn、Ca and Mg in the fruits of A. oxyphylla were higher than those in the rhizomes or stems and leaves. In the fruits of A. oxyphylla, the contents of heavy metals, i.e., As、Hg、Pb and Cu (except Cd) are lower than those in the rhizomes or stems and leaves.
As we all known,"Green trade standards of importing&exporting medicinal plants&preparations", which was awarded by the state department of commerce in2001, has set the lowest content of heavy metals in medicinal plants. The contents of As、Hg、Pb、Cd in the20samples of the fruits of A. oxyphylla, which were collected from different regions, such as Yunnan, Guangxi, Guangdong and Hainan, are in line with the standards. The contents of Cu in the samples from some regions, such as the samples from Changxing village and Maoyang village in Qiongzhong County, Wupo village and Nanlv village in Tunchang County, Hainan province, are in accordance with the standards. While the contents of Cu in the samples from other regions collected from Xishuangbanna, Yunnan province, Nanning, Guangxi, Guangdong and other areas in Hainan province are higher than the limitation set in the standards. The exact content of heavy metals need farther research on atmosphere, soil and irrigate water.
It is concluded from the results of the contents of heavy metals and nutrient elements in the20samples that, the sample from Hainan province is the best in the security of medicinal plants, especially from Changxing village and Maoyang village in Qiongzhong county, Wupo village and Nanlv village in Tunchang county in Hainan province. The contents of nutrient elements in the samples from Nanning and Guangxi are the highest of all.
A conclusion can be drawn from the changes in the contents of heavy metals and nutrient elements in the different parts of A. oxyphylla at different growth time:the contents of heavy metals in the fruits and rhizomes are lower than those in the stems and leaves, while the contents of nutrient elements in the fruits and rhizomes are higher. The contents of heavy metals are the lowest and the contents of nutrient elements are the highest when the fruit of A. oxyphylla is the45th day.
Chapter3Bioactive studies on the extracts and compounds from A. oxyphylla
In Chapter3, spleen warming, anti-diarrhea, kidney-tonifying and anti-polyuria bioactivities of the fruits of A. oxyphylla were studied. This chapter can be divided into three sections.
In Section1, preparation of different extracts of A. oxyphylla was studied. To clarify the bioactive fraction, the volatile oil, the95%ethanol extract, the50%ethanol eluate and the90%ethanol eluate from the fruits of A. oxyphylla were prepared for the bioactive assay. The quality of the four fractions was controlled by HPLC.
In Section2, the preliminary research focused on the active fractions from the fruits of A. oxyphylla and the mechanism of spleen warming and anti-diarrhea was included. Acute diarrhea induced by senna-leaf and the mouse model of diarrhea of spleen deficiency induced by rhubarb were used to study the anti-diarrhea effect of the active fractions from the fruits of A. oxyphylla. Four fractions were prepared to study the anti-diarrhea effect of the fruits of A. oxyphylla. The experiment results suggested that the95%ethanol extract and the90%ethanol eluate could prolong the onset time of diarrhea and reduce the wet faeces proportion, however, the50%ethanol eluate had no effect on diarrhea. The volatile oil prolonged the onset time of diarrhea, but showed no effects on the wet faeces proportion and the number of wet faeces. Chemical analysis results displayed that fat-soluble components may be the active ingredients for curing diarrhea. The further research showed the95%ethanol extract and the90%ethanol eluate affect the gastric residual rate and the intestinal propulsion rate, and improve the spleen asthenia syndrome to some extent.
The results indicated the95%ethanol extract could improve the spleen asthenia syndrome by increasing the level of plasma LDH, inhibit gastrointestinal motility by increasing plasma NO and reducing gastrointestinal hormone MOT and SS. The90%ethanol eluate can improve the spleen asthenia by increasing the level of plasma LDH and reducing SDH, while its inhibitory effect on gastrointestinal motility is primarily related with the increase in the level of NO and the decrease in the level of gastrointestinal hormone MOT and SS.
In Section3, pharmacodynamic screening of different fractions and compounds from A. oxyphylla to ensure the urination reducing activity was investigated. The volatile oil, the95%ethanol extract (non-volatile oil), the eluate of50%ethanol and the eluate of90%ethanol prepared by macroporous resin column chromatography inhibit the bladder detrusor contraction that induced by carbachol.7compounds isolated from A. oxyphylla, i.e., izalpinin, kaempferide, oxyphyllacinol, yakuchinone B, nootkatone, tectochrysin, chrysin were screened for the activity, and found that izalpinin showed inhibitory effect on the bladder detrusor contraction induced by carbachol with a mean EC50(concentration for50%of maximal effect) as0.35±0.05μM.
Chapter4Quality standard of the fruits of A. oxyphylla
In this chapter, the quality standard of the fruits of A. oxyphylla was studied and established. Based on the quality standard of the fruits of A. oxyphyllae in Chinese Pharmacopoeia2010th edition, TLC and HPLC methods were adopted to improve its quality standard. The moisture, total ash, acid-insoluble ash of A. oxyphylla fruits were measured according to the procedures recorded in the Chinese Pharmacopoeia. The contents of nootkatone, tectochrysin and yakuchinone A were determined by HPLC. All these work will establish a solid foundation for the quality standard of new products.
Chapter5Exploitation and industrialization of A. oxyphylla
The fruits of A. oxyphylla are commonly used as herbal medicine and food, which is called "the same source of medicine and food" according to the principle of traditional Chinese medicine. As one of undergrowth vegetation, A. oxyphylla is commonly planted under the trees, such as Areca catechu and Hevea brasiliensis, and the cultivated area is about66.7km2in Hainan province. Therefore, the common foods are more suitable for the exploitation and industrialization for the fruits of A. oxyphylla. We have developed two new powdered drink products (i.e., Yizhi-Yezi tea and Yizhi-Mugua tea) containing the fruits of A. oxyphylla with the financial support from the Hainan provincial special fund for the modernization of traditional Chinese medicines. These products may play important roles in the Hainan provincial tourism service trade and promote the plant industry development of A. oxyphylla.
本论文的研究工作以益智的文献为起点,综合了益智的资源化学研究、资源化学评价研究和传统功效的诠释研究,基本阐述了益智的资源内涵及其功效基础。以此为基础进行了益智的质量标准研究和产业化开发研究,为益智资源的合理高效利用奠定科学基础。
一、文献研究
文献是科学研究的起点,为了全面准确的提挈益智的资源现状,本文系统综述了姜科植物药用概况、姜科山姜属植物研究进展、益智历史应用沿革及其现代化学药理研究基础,并藉此凝练出本论文的研究思路和整体实验方案。
二、益智的资源化学研究
(一)益智各部位的资源性成分研究
1益智果实资源性成分研究
为了全面阐述益智果实的资源化学分布,阐明其基于传统功效的药效物质基础,促进益智资源的合理使用,本文采用硅胶柱层析、制备薄层层析、凝胶柱色谱及反相柱色谱等色谱技术对益智果实所含资源性成分进行分离、纯化和结构鉴定。从益智果实中共分离得到了11个化合物,分别鉴定为9-羟基表圆柚醇(1)、乔松素(2)、圆柚酮(3)、杨芽黄素(4)、β-谷甾醇(5)、益智酮甲(6)、伊砂黄素(7)、p-胡萝卜苷(8)、p-谷甾醇棕榈酸酯(9)、(S)-2-戊醇-2-O-β-D-吡喃葡萄糖苷(10)、原儿茶酸(11)。其中化合物1和化合物10为新天然产物,化合物2为首次从益智中分离得到。以上研究为益智的进一步深入研究奠定了基础。
2益智根茎资源性成分研究
为了探索益智根茎废弃资源的可利用价值,本文采用硅胶柱层析及聚酰胺柱层析等色谱技术对益智根茎所含资源性成分进行分离、纯化,根据所分离化学成分的理化性质及波谱数据鉴定其结构。结果从益智根茎乙醇提取物中共分离鉴定13个化合物,分别鉴定为三十二烷醇(1)、伊砂黄素(2)、杨芽黄素(3)、山奈酚-7,4'-O-二甲醚(4)、p-谷甾醇(5)、对羟基桂皮酸(6)、双氢山奈素(7)、益智酮甲(8)、白杨素(9)、乔松素(10)、山奈酚-4'-o-甲醚(11)、肉豆蔻酸(12)、球松素(13),所有化合物均为首次从益智根茎中分离得到。以上研究为今后益智根茎的资源利用奠定科学基础。
3益智茎叶资源性成分研究
基于发现与挖掘益智茎叶可利用的物质基础,本文采用硅胶柱层析及聚酰胺柱层析等色谱技术对益智茎叶所含资源性成分进行分离、纯化,根据其理化性质及波谱数据鉴定其结构。结果从益智茎叶乙醇提取物中共分离鉴定了11个化合物,分别鉴定为伊砂黄素(1)、杨芽黄素(2)、芹菜素-4',7-O-二甲醚(3)、山奈素-4'-o-甲醚(4)、反式对羟基桂皮酸(5)、白杨素(6)、乔松素(7)、刺槐素(8)、棕榈酸(9)、球松素(10)、5,7,4'-三甲氧基黄酮(11),所有化合物均为首次从益智根茎中分离得到。以上研究为今后益智茎叶的资源利用奠定科学基础。
(二)益智资源化学评价
1益智果实挥发性成分分析
通过对来自我国云南省、广西省、广东省及海南省(包括来自白沙县、琼中县、万宁市及屯昌县)等共21份益智果实挥发油中资源性成分进行比较研究。研究证实：各产地益智挥发油所含成分种类及含量差异较大,其中β-panasinsene和humulene两种成分含量较高。采用系统聚类分析方法对该21批益智果实进行聚类分析,结果表明：海南省白沙县、琼中县和屯昌县三个县的益智挥发油中所含成分相似,说明这些地区的区域环境相似；广东阳江、广西和云南三个省份的益智挥发油中所含成分接近,但是与上述三个县的益智药材有所差别。
2不同生长期益智果实、根茎及茎叶中资源性成分动态累积研究
本研究对不同生长期益智不同部位中圆柚酮、益智酮甲、益智酮乙、益智醇、杨芽黄素、伊砂黄素、白杨素、山奈素和芹菜素二甲醚9种资源性成分进行了LC-MS/MS定量分析。
益智不同部位的资源性成分含量分布情况不同,研究证实,在果实整个生长周期,萜类、二苯基庚烷类资源性成分主要富集在益智果实中,而黄酮类资源性成分基本均匀分布在益智果实、茎叶和根茎中。益智在结果45天时果实中各种资源性成分含量处于最高峰,果实最佳采收时间定在结果45天基本合理,结果45天后,圆柚酮、益智酮甲和杨芽黄素三种功效成分的蓄积量均有所提高,一般益智3月上旬开始结果,益智果实最佳采收时间定在4月底至5月初,传统应用中益智采收期定在5-6月基本合理：益智根茎和茎叶在益智结果后亦有一定量以上成分蓄积,证实了益智根茎和茎叶潜在的药用价值待挖掘。
益智果实最佳采收期及益智果实、根茎和茎叶之间资源性成分的转运规律有待进一步研究确定。
3益智果实中核苷与碱基类资源性成分评价
对于不同产地益智果实中核苷及其碱基含量测定结果表明：各产地药材所含主要核苷及其碱基的种类基本相同,但是各类核苷和碱基含量差异较大,这可能是由于地理环境、气候、温度、采收期等因素所造成的。对于不同采收期益智果实中核苷及其碱基含量测定结果表明：14批益智果实中几乎都富含待测十种核苷和碱基,但含量有极大的差别。2’-脱氧胸苷含量最多,在益智果实整个生长周期内变化明显(36.79-310.58gg/g)；次黄嘌呤含量最低,在果实形成后期甚至未检测到。此外,随着益智果实成熟度增加,单个核苷和碱基以及它们的总量都随之减少,表明核苷及其碱基的合成与果实的生长发育密切相关。
4益智果实、根茎及茎叶中无机元素分布及动态累积研究
研究结果表明,益智果实中锌、铁、锰、钙及镁五种营养元素含量相对于根茎、茎叶更丰富,除重金属镉元素益智果实含量高于根茎、茎叶,果实中另外四种重金属砷、汞、铅和铜含量均相对较低。
据国家商务部2001年颁发的《药用植物及制剂进出口绿色行业标准》有关药材重金属元素含量限量标准,我国云南省、广西省、广东省及海南省的20个益智果实样品的砷、汞、铅、镉含量均符合绿色行业标准；海南省琼中长兴、琼中毛阳、屯昌乌坡和屯昌南吕四产地的益智果实铜含量符合绿色行业标准,但采自云南西双版纳、广西南宁、广东2产地及海南省其它12个市县益智果实的铜含量超标。需要今后进一步深入研究,同时,需要考察这些产区大气、土壤及灌溉用水的重金属含量情况。
20个产地益智果实重金属和营养元素含量的检测结果显示,海南产的益智安全性最好,突出表现为以下四个产地海南琼中长兴村、琼中毛阳镇、屯昌乌坡镇和屯昌南昌镇；广西南宁产的益智果实营养元素的含量最丰富。
从益智不同生长期果实、根茎和茎叶重金属元素和营养元素的含量分布情况看,益智果实、根茎中重金属含量与茎叶相比较低,而营养元素含量相对较高；益智果实如在结果45天时采收,除镉元素,其它四种重金属元素含量均相对较低,锌、铁、锰、钙和镁五种营养元素含量均较高,即在益智结果45天时采收益智果实营养元素含量较高,而重金属含量相对较低。
三、益智温脾止泻和补肾缩尿功效的活性评价研究
(一)益智不同提取分离部位的制备
为了明确益智符合其传统功效的有效作用部位,本文制备了益智挥发油部位、非挥发油部位95%乙醇提取物、大孔树脂50%乙醇洗脱物和大孔树脂90%乙醇洗脱物四个部位,并采用HPLC进行了初步定性。
(二)益智不同提取分离部位温脾止泻功效的活性评价研究
为了研究益智传统温脾止泻功效的活性部位,选择番泻叶致小鼠急性腹泻和大黄引起小鼠脾虚泻下两种模型,对从益智中分离获得的4个提取部位进行止泻活性评价。研究结果表明：益智非挥发油部位95%乙醇提取物和益智大孔树脂90%乙醇洗脱物能够延长番泻叶致急性腹泻小鼠的腹泻潜伏期和降低稀便比重,具有良好的止泻活性,大孔树脂50%乙醇洗脱物对小鼠急性腹泻无影响,益智果实挥发油能够显著的延长小鼠腹泻潜伏期,但是对稀便个数及稀便比重均无影响；通过上述活性的筛选结果,进一步对益智非挥发油部位95%乙醇提取物、大孔树脂90%乙醇洗脱物及大孔树脂50%乙醇洗脱物进行化学分析,结果显示脂溶性大的成分可能是益智止泻的活性部位。进一步研究表明益智非挥发油部位95%乙醇提取物和益智大孔树脂90%乙醇洗脱物能够显著地影响脾虚小鼠的胃残留率和小肠推进率,对胃肠运动影响显著,且能够一定程度改善脾虚小鼠的脾虚状态。
研究结果亦证实益智大孔树脂90%乙醇洗脱物改善脾虚状态与升高血浆中LDH水平相关,同时其抑制胃肠运动主要与升高血浆中NO和降低胃肠激素MOT和SS有关；该部位通过升高血浆中LDH水平,同时降低血浆中SDH水平改善脾虚泻下小鼠的脾虚状态,其影响小鼠的胃肠运动能力主要与升高NO有关,同时与降低血浆中胃肠激素MOT和SS的水平密切相关。
(三)益智不同提取与分离部位缩尿功效的活性评价研究
为了明确益智的缩尿作用活性,本节对不同益智提取部位及单体化合物进行缩尿作用药效学筛选,确定益智挥发油部位、非挥发油部位乙醇提取物、大孔树脂50%乙醇洗脱物和大孔树脂90%乙醇洗脱物四个部位对卡巴胆碱诱导的离体膀胱逼尿肌收缩均有一定的抑制作用；筛选了伊砂黄素、山柰素、益智醇、益智酮乙、诺卡酮、杨芽黄素、白杨素等7个益智中分离出来的单体化合物,发现伊砂黄素抑制卡巴胆碱EC50=3.50±0.05μmol/L。
四、中药益智的质量标准研究
为了完善现有中药益智的质量标准,本文采用薄层色谱法及高效液相色谱法等先进技术对于中药益智进行了质量标准研究。即建立了薄层鉴别、显微鉴别项；建立了圆柚酮、杨芽黄素、益智酮甲三种功效成分同时测定含量检测项；完善了水分、灰分及酸不溶性灰分等项的建立。为今后益智原料药材、饮片及其产品开发质量标准的建立奠定科学基础。
五、益智资源开发与产业化
益智属药食同源品种,常间种于槟榔、橡胶的树下,海南省目前益智的种植面积达2万亩。益智广泛的药理作用和其药食同源的特性决定了更适合于研制平时就可以食用的普通食品。
在海南省中药现代化专项基金的支助下,项目组研发了益智椰子粉、益智木瓜粉固体饮料,以上产品可丰富现有旅游产品的种类,提升我省旅游产品的层次,带动相关益智种植业及我省旅游业的发展。
This research paper, referring to the project "Research on establishment of standardized planting base and the SOP of Alpinia oxyphylla Miq.", which is contained in the regional base project "Optimization and upgrading of standardized planting base and the SOP of7kinds of traditional Chinese medicines" financially supported by the national12th five-year plan regional base project (2011BA101B07). Besides, a part of research contents are from "Establishment of quality control on crude drugs and decoction pieces of the fruits of A. oxyphylla from standardized planting base in Hainan" supported by Hainan special plan for the modernization of traditional Chinese medicines.
This dissertation involves five chapters.
Chapter1Literature research
In this part, mainly through summarizing relevant literature, the pharmaceutical usages of the plants belong to Zingiberacea family, the research progress in the plants of Alpinia genus, traditional applications and research advances of chemistry and pharmacology of the fruits of A. oxyphylla were reviewed systematically. Based on the preliminary work, the research ideas and experimental design were put forward.
Chapter2Studies on the chemical resources of A. oxyphylla
This chapter is further divided into two sections.
Section one includes three parts.
In part1, studies on the chemical constituents from the fruits of A. oxyphylla were included. The objective of this study is to further develop and exploit the rich resources of Hainan famous-region drug-A. oxyphylla, clarify the pharmacological substances based on its traditional efficacy and find its new effective fractions and components. For this reason, the chemical investigation on the fruits of A. oxyphylla were carried out with the combined methods of silica gel column chromatography, preparative TLC, gel permeation chromatography, ODS column chromatography and recrystallization. The structures of the isolated compounds were elucidated on the grounds of their physicochemical constants and NMR spectral data analysis.11compounds were isolated and their structures were determined as9-hydroxy epinootkatol (1), pinocembrin (2), nookatone (3), tectochrysin (4),β-sitosterol (5), yakuchinone A (6), izalpinin (7), β-daucosterol (8),β-sitosterol palmitate (9),(S)-2-pentanol-2-O-β-D-glucopyranoside (10) and protocatechuic acid (11). Compounds1and10were new natural products and compound2was isolated from the fruits of A. oxyphylla for the first time. This study provided scientific basis for the further research and exploitation of the resources of the fruits of A. oxyphylla in the future.
In part2, investigation on the chemical constituents from the rhizomes of A. oxyphylla was referred to. Based on the pharmacological substances exploited that were discovered from the rhizomes of A. oxyphylla, the chemical investigation on the rhizomes of A. oxyphylla was carried out with the methods of silica gel column chromatography and polyamide column chromatography. The structures of the isolated compounds were elucidated according to the physicochemical constants and NMR spectral data analysis.14compounds were isolated from the ethanol extract from the rhizomes of A. oxyphylla and their structures were determined as doacontanol (1), izalpinin (2), tectochrysin (3), kaempferol-7,4'-dimethyl mester (4), β-sitosterol (5),p-hydroxylcinnamic acid (6), dihydrokaempferol (7), yakuchinone A (8), chrysin (9), pinocembrin (10), kaempferol-4'-methylmester (11), myristic acid (12), pinostrobin (13). All the compounds were isolated from the rhizomes of A. oxyphylla for the first time. This study lays scientific basis for the exploitation of the resources of rhizomes of A. oxyphylla in the future.
In part3, research into the chemical constituents from the stems and leaves of A. oxyphylla was discussed. To study the effective substances in the stems and leaves of A. oxyphylla further, their chemical constituents were isolated and purified by silica column chromatography and polyamide column chromatography. The structures of those compounds were identified and determined based on their physicochemical constants and spectral data analysis. Consequently,16compounds were obtained, and they were elucidated as izalpinin (1), tectochrysin (2), apigenin-7,4'-dimethyl ester (3), kaempferol-4'-methyl mester (4),(E)-p-hydroxy cinnamic acid (5), chrysin (6), pinocembrin (7), apigenin-4'-methyl ester (8), myristic acid (9), docosanoic acid (10), octacosanoic acid (11), septadecanoic acid (12), eicosanoic acid (13), n-hexadecanoic acid (14), pinostrobin (15),5,7,4'-trimethyl flavone (16). All the compounds were isolated from the stems and leaves of A. oxyphylla for the first time. This study provides scientific basis for the exploitation of the resources of stems and leaves of A. oxyphylla in the future.
In section two, the chemical resources evaluation of A. oxyphylla was studied. This chapter consists of five parts.
In part1, the volatile components in the fruits of A. oxyphylla were tested and analyzed. Chemical compositions in the volatile oils from the fruits of A. oxyphylla collected from different provinces and regions in China, including Yunnan, Guangxi, Guangdong and Hainan, were studied by GC-MS. The results showed that there was a large variation in the components and content of volatile oils among the drugs from different regions. Among the components in the volatile oil, β-panasinsene and humulene are two major compounds. In addition, hierarchical cluster analysis (HCA) was performed to classify all the samples according to the contents of the investigated analytes. The samples from Baisha, Qiongzhong and Tunchang (Hainan province) can be classified into one cluster, which indicates that these regions are similar in the environment, while the samples from Guandong, Guangxi and Yunnan were classified into another cluster, whose contents of volatile oils were different from the three regions mentioned above.
In part2, the variation rule about the contents of the constituents in the fruits, rhizomes, stems and leaves of A. oxyphylla at different growth time was studied. Nine compounds, i.e., nootkatone, yakuchinone A, yakuchinone B, nootkatol, tectochysin, izalpinin, chrysin and7,4'-dimethyl apigenin were analyzed by LC-MS/MS.
The contents of the resource constituents in the different parts of A. oxyphylla are different. The result shows that the resource constituents of terpenoids, diarylheptanoids are mainly rich in the fruits of A. oxyphylla, while the flavonoids is evenly distributed in the fruits, stems and leaves, and rhizomes of A. oxyphylla in the whole growth period of the fruits.
The results showed that the contents of all the compounds in the fruits reached the highest at45-day harvest time. Thus, it is reasonable that the best harvest time for the fruits is set at45days after it bears fruits. With the maturation of the fruits, most of the chemical components accumulated in the fruits at45days. This indicates that it is reasonable for the fruits of A. oxyphylla traditionally used as a medicinal part. At45days, a large quantity of flavonoids and a small amount of terpenoids and diary lheptanoids also accumulated in the stems and leaves of A. oxyphylla, which shows that the stems and leaves can be used as new resources in the future.
The best harvest time of the fruits and the transfer rule of the resource constituents among the fruits, rhizomes, stems and leaves, need to be verified.
In part3, the assay of nucleobases and nucleosides in the fruits of A. oxyphylla was done. Nucleobases and nucleosides were quantitatively determined in the fruits of A. oxyphylla collected from different cultivation regions. Almost all the samples were rich in nucleobases and nucleosides, but there was a large variation in the content, which might attribute to the factor of harvest time. Nucleobases and nucleosides were also quantitatively determined in the fruits of A. oxyphylla collected at different harvest time. The results showed that the content of thymidine is much higher during the whole research period than that of others, which is in the range of36.79-310.58μg/g. Hypoxanthine is observed to be the least in all the analytes, and its contents in some samples cannot be detected. Additionally, the total amount of both total and individual nucleosides and nucleobases in the fruits of A. oxyphylla decreased with the increase of maturity degree, which indicates that the synthesis of such components is closely relevant to the growth cycle.
In part4, the contents of inorganic elements in the fruits, rhizomes, stems and leaves and flowers at different growth stages were assayed. The results showed that the contents of nutrient elements such as Zn、Fe、Mn、Ca and Mg in the fruits of A. oxyphylla were higher than those in the rhizomes or stems and leaves. In the fruits of A. oxyphylla, the contents of heavy metals, i.e., As、Hg、Pb and Cu (except Cd) are lower than those in the rhizomes or stems and leaves.
As we all known,"Green trade standards of importing&exporting medicinal plants&preparations", which was awarded by the state department of commerce in2001, has set the lowest content of heavy metals in medicinal plants. The contents of As、Hg、Pb、Cd in the20samples of the fruits of A. oxyphylla, which were collected from different regions, such as Yunnan, Guangxi, Guangdong and Hainan, are in line with the standards. The contents of Cu in the samples from some regions, such as the samples from Changxing village and Maoyang village in Qiongzhong County, Wupo village and Nanlv village in Tunchang County, Hainan province, are in accordance with the standards. While the contents of Cu in the samples from other regions collected from Xishuangbanna, Yunnan province, Nanning, Guangxi, Guangdong and other areas in Hainan province are higher than the limitation set in the standards. The exact content of heavy metals need farther research on atmosphere, soil and irrigate water.
It is concluded from the results of the contents of heavy metals and nutrient elements in the20samples that, the sample from Hainan province is the best in the security of medicinal plants, especially from Changxing village and Maoyang village in Qiongzhong county, Wupo village and Nanlv village in Tunchang county in Hainan province. The contents of nutrient elements in the samples from Nanning and Guangxi are the highest of all.
A conclusion can be drawn from the changes in the contents of heavy metals and nutrient elements in the different parts of A. oxyphylla at different growth time:the contents of heavy metals in the fruits and rhizomes are lower than those in the stems and leaves, while the contents of nutrient elements in the fruits and rhizomes are higher. The contents of heavy metals are the lowest and the contents of nutrient elements are the highest when the fruit of A. oxyphylla is the45th day.
Chapter3Bioactive studies on the extracts and compounds from A. oxyphylla
In Chapter3, spleen warming, anti-diarrhea, kidney-tonifying and anti-polyuria bioactivities of the fruits of A. oxyphylla were studied. This chapter can be divided into three sections.
In Section1, preparation of different extracts of A. oxyphylla was studied. To clarify the bioactive fraction, the volatile oil, the95%ethanol extract, the50%ethanol eluate and the90%ethanol eluate from the fruits of A. oxyphylla were prepared for the bioactive assay. The quality of the four fractions was controlled by HPLC.
In Section2, the preliminary research focused on the active fractions from the fruits of A. oxyphylla and the mechanism of spleen warming and anti-diarrhea was included. Acute diarrhea induced by senna-leaf and the mouse model of diarrhea of spleen deficiency induced by rhubarb were used to study the anti-diarrhea effect of the active fractions from the fruits of A. oxyphylla. Four fractions were prepared to study the anti-diarrhea effect of the fruits of A. oxyphylla. The experiment results suggested that the95%ethanol extract and the90%ethanol eluate could prolong the onset time of diarrhea and reduce the wet faeces proportion, however, the50%ethanol eluate had no effect on diarrhea. The volatile oil prolonged the onset time of diarrhea, but showed no effects on the wet faeces proportion and the number of wet faeces. Chemical analysis results displayed that fat-soluble components may be the active ingredients for curing diarrhea. The further research showed the95%ethanol extract and the90%ethanol eluate affect the gastric residual rate and the intestinal propulsion rate, and improve the spleen asthenia syndrome to some extent.
The results indicated the95%ethanol extract could improve the spleen asthenia syndrome by increasing the level of plasma LDH, inhibit gastrointestinal motility by increasing plasma NO and reducing gastrointestinal hormone MOT and SS. The90%ethanol eluate can improve the spleen asthenia by increasing the level of plasma LDH and reducing SDH, while its inhibitory effect on gastrointestinal motility is primarily related with the increase in the level of NO and the decrease in the level of gastrointestinal hormone MOT and SS.
In Section3, pharmacodynamic screening of different fractions and compounds from A. oxyphylla to ensure the urination reducing activity was investigated. The volatile oil, the95%ethanol extract (non-volatile oil), the eluate of50%ethanol and the eluate of90%ethanol prepared by macroporous resin column chromatography inhibit the bladder detrusor contraction that induced by carbachol.7compounds isolated from A. oxyphylla, i.e., izalpinin, kaempferide, oxyphyllacinol, yakuchinone B, nootkatone, tectochrysin, chrysin were screened for the activity, and found that izalpinin showed inhibitory effect on the bladder detrusor contraction induced by carbachol with a mean EC50(concentration for50%of maximal effect) as0.35±0.05μM.
Chapter4Quality standard of the fruits of A. oxyphylla
In this chapter, the quality standard of the fruits of A. oxyphylla was studied and established. Based on the quality standard of the fruits of A. oxyphyllae in Chinese Pharmacopoeia2010th edition, TLC and HPLC methods were adopted to improve its quality standard. The moisture, total ash, acid-insoluble ash of A. oxyphylla fruits were measured according to the procedures recorded in the Chinese Pharmacopoeia. The contents of nootkatone, tectochrysin and yakuchinone A were determined by HPLC. All these work will establish a solid foundation for the quality standard of new products.
Chapter5Exploitation and industrialization of A. oxyphylla
The fruits of A. oxyphylla are commonly used as herbal medicine and food, which is called "the same source of medicine and food" according to the principle of traditional Chinese medicine. As one of undergrowth vegetation, A. oxyphylla is commonly planted under the trees, such as Areca catechu and Hevea brasiliensis, and the cultivated area is about66.7km2in Hainan province. Therefore, the common foods are more suitable for the exploitation and industrialization for the fruits of A. oxyphylla. We have developed two new powdered drink products (i.e., Yizhi-Yezi tea and Yizhi-Mugua tea) containing the fruits of A. oxyphylla with the financial support from the Hainan provincial special fund for the modernization of traditional Chinese medicines. These products may play important roles in the Hainan provincial tourism service trade and promote the plant industry development of A. oxyphylla.
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