两种金粟兰属植物的化学成分及相关生物活性的研究
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摘要
银线草Chloranthus japonicus Sieb.和多穗金粟兰Chloranthus multistachys Pei属于金粟兰科Chloranthaceae金粟兰属Chloranthus多年生草本植物,全草或根入药。具有抗菌消炎、散瘀活血等功效。在民间是治疗跌打损伤、瘀血肿痛、风湿痛、毒蛇咬伤、疖疮肿毒的良药,具有很高的药用价值。长期以来,由于缺乏对银线草和多穗金粟兰的生物活性物质基础及其作用机制的研究,限制了对它们的开发与利用。本课题应用植物解剖学、组织化学、植物化学、药理学和毒理学等方法,从形态结构、化学成分和生物活性三个方面对银线草和多穗金粟兰进行了研究,为进一步开发利用金粟兰属植物奠定基础。论文的主要结果如下：
1.银线草和多穗金粟兰营养器官形态结构研究。两种植物营养器官形态结构具有很多相同点,主要表现在：根中皮层宽广,内皮层明显,维管组织的初生木质部和初生韧皮部均属外始式发育；茎断面中空,具较大的髓腔,根状茎中皮层宽广,内皮层不明显,韧皮部狭窄；叶为异面叶,栅栏组织和海绵组织分化明显,叶的气孔长椭圆形,韧皮部较窄,木质部发达；叶片上、下表皮均无任何毛被,细胞近多边形或不规则形,只有下表皮分布有气孔器,为不规则型。除此之外,两种植物营养器官形态结构具有明显的不同点,主要表现在：银线草的根皮层细胞排列整齐,细胞间隙较小,韧皮部较窄,维管组织中导管数目较多；茎皮层细胞排列整齐,在韧皮部外方包围有多层束状纤维束；根茎木质部导管数目较少；叶的海绵组织由各种形状的细胞组成,具有较小的胞间隙,厚角组织内为形状不规则的薄壁组织细胞,细胞间隙较大,排列不整齐；主叶脉角质膜不具有乳状突起；多穗金粟兰的根皮层细胞排列不整齐,细胞间隙较大,韧皮部宽广,维管组织中导管数目较少；茎皮层细胞排列不整齐,在韧皮部外方仅包围有少数几层束状纤维束；根茎木质部导管数目较多。叶的海绵组织多以近圆形细胞组成,且具有较大的胞间隙；厚角组织内为类圆形薄壁组织细胞,细胞间隙较小,排列整齐；主叶脉角质膜具有明显乳状突起。
2.萜类和黄酮类化合物在银线草和多穗金粟兰不同营养器官中的组织化学定位结果类似,均主要分布在根的皮层、茎的皮层及韧皮部细胞中。但二者在含量上有所区别。萜类化合物在银线草茎中皮层的薄壁组织细胞以及韧皮部细胞被染为淡红色,而在多穗金粟兰中被染成淡红棕色,提示多穗金粟兰中含有的萜类化合物含量较多。黄酮类化合物在银线草根的皮层细胞中显示绿色荧光,在茎中,皮层和韧皮部细胞呈现绿色荧光；而在多穗金粟兰根的皮层细胞中显示强烈的绿色荧光,在茎中,皮层和韧皮部细胞呈现蓝绿色荧光,提示多穗金粟兰中黄酮类化合物的含量较银线草中多。该结果与植物化学研究结果相一致。
3.通过水蒸气蒸馏法并采用气相色谱-质谱联用技术提取、鉴定银线草和多穗金粟兰全草的挥发性成分。共分离鉴定出59个成分,两种植物中相同的成分有28种。其中,银线草全草中分离鉴定出48种成分,占挥发油色谱峰面积的95.56%,多穗金粟兰全草中分离鉴定出39种成分,占挥发油色谱峰面积的94.58%。已鉴定的化合物中,绝大部分是萜类化合物,其中以单萜和倍半萜及其含氧类化合物为主。银线草挥发性成分中单萜及含氧单萜类化合物为77.04%,倍半萜及含氧倍半萜类化合物为16.37%；多穗金粟兰挥发性成分中单萜及含氧单萜类化合物为46.64%,倍半萜及含氧倍半萜类化合物为14.20%。乙酸龙脑酯是银线草和多穗金粟兰全草挥发性成分中的主要成分,分别占30.98%和35.99%。银线草和多穗金粟兰全草挥发性成分中最显著的区别是多穗金粟兰中还含有较大比例的肉豆蔻醚。
4.采用索氏提取法和气相色谱-质谱联用技术(GC-MS)对银线草和多穗粟兰的脂溶性成分进行分离和鉴定。银线草脂溶性成分中共鉴定出24种化合物,占检出物总质量分数的99.03%。包括14种脂肪酸,其中饱和脂肪酸9种,占总质量分数的22.32%,不饱和脂肪酸5种,占总质量分数的70.02%。多穗金粟兰脂溶性成分中共鉴定出15种化合物,占检出物总质量分数的92.59%。包括12种脂肪酸,其中饱和脂肪酸7种,占总质量分数的15.73%,不饱和脂肪酸6种,占总质量分数的54.71%。
5.采用Phenomenex C18色谱柱(250mm×4.6mm,5μm),以甲醇-0.1%甲酸水溶液梯度洗脱,波长分别为254nm和323nm,光电二极管阵列检测器和电喷雾质谱同时在线检测,全离子扫描模式扫描,通过质谱分析及文献对照,鉴定出没食子酸、咖啡酸、异秦皮啶和迷迭香酸,并测定其含量。结果显示多穗金粟兰中没食子酸、咖啡酸、迷迭香酸的含量均高于银线草。银线草中的含量分别为0.372 mg/g,0.111 mg/g和2.073 mg/g,多穗金粟兰中的含量分别为1.173 mg/g,0.173 mg/g和7.228 mg/g。银线草和多穗金粟兰中香豆素类异秦皮啶的含量分别为0.507 mg/g和0.292 mg/g。
银线草和多穗金粟兰中不同部位的酚类和香豆素类含量差异也较大。没食子酸在银线草和多穗金粟兰不同部位的含量均为茎>根>叶,且多穗金粟兰茎中的含量明显高于银线草。咖啡酸和迷迭香酸在银线草和多穗金粟兰不同部位中的含量为根>叶>茎,迷迭香酸在银线草和多穗金粟兰不同部位中的含量差异很大,在银线草根中含量为34.623 mg/g、叶中含量为1.432mg/g；在多穗金粟兰根中含量为4.582 mg/g、叶中含量为23.572 mg/g。异秦皮啶在银线草和多穗金粟兰不同部位中的含量也表现为根>茎>叶,但含量差异很大,在银线草根中为0.601mg/g,而在多穗金粟兰中仅为0.094 mg/g。
6.利用超声技术提取银线草和多穗金粟兰中的总黄酮,同时应用响应面分析法优化其提取工艺参数,得到银线草总黄酮提取的最佳工艺条件：甲醇浓度57%,料液比1：17,提取时间6 min,提取温度60℃。多穗金粟兰总黄酮提取的最佳工艺条件：甲醇浓度70%,料液比1：8,提取时间28min,提取温度27℃,模型预测结果和实验检测结果基本吻合
7.采用微波消解-火焰原子吸收法测定秦岭山区两种金粟兰属药用植物银线草和多穗金粟兰中铁、锌、铜、锰、钙、镁、钠、钾的含量。结果显示：银线草和多穗金粟兰中含有丰富的大量和微量元素,银线草中所测元素含量依次为K>Ca>Na>Mg>Fe>Zn>Mn>Cu,多穗金粟兰为K>Ca>Mg>Na>Fe>Mn>Zn>Cu;所测得的8种元素中,银线草中的含量均高于多穗金粟兰。
8.采用滤纸片法和96孔板法分别检测银线草和多穗金粟兰全草挥发性成分的抑菌活性。结果显示银线草和多穗金粟兰挥发油对8种革兰氏阳性菌、3种革兰氏阴性菌和4种真菌均有抑制和灭活作用,对所试菌种的作用强度依次为革兰氏阳性菌>真菌>革兰氏阴性菌。其中银线草挥发油对蜡状芽孢杆菌的抑制效果最强,抑菌圈直径为22.2 mm,与盐酸四环素的抑菌效果21.4 mm相当,最小抑菌浓度MIC为0.39 mg/mL,最小杀菌浓度MBC为0.78mg/ml;多穗金粟兰挥发油的抑菌效果总体比银线草弱,但表现出相同的趋势,对蜡状芽孢杆菌和解脂假丝酵母菌的抑制效果最强,抑菌圈直径分别为18.8 mm和17.8 mm,最小抑菌浓度MIC为0.78 mg/mL,最小杀菌浓度MBC为1.56 mg/ml;另外,银线草挥发油对蜡状芽孢杆菌、凝结芽孢杆菌和藤黄八叠球菌的效果优于多穗金粟兰挥发油,而对粘红酵母的抑制效果低于多穗金粟兰挥发油。
9.建立了银线草和多穗金粟兰提取物体外抗氧化评价体系。采用DPPH-自由基清除活性、超氧自由基清除、β-胡萝卜素-亚油酸漂白以及DNA损伤保护活性等4种方法对银线草和多穗金粟兰不同提取物的体外抗氧化能力进行了综合评价。结果显示银线草和多穗金粟兰甲醇总提取物具有优于其它提取部位的较强抗氧化活性。
10.采用改良寇氏法、组织学和免疫组织化学方法进行银线草和多穗金粟兰提取物对小鼠的急性毒性试验。结果显示,银线草和多穗金粟兰甲醇提取物对小鼠的半数致死量LDso分别为50.91g/kg和45.74g/kg,LD50的95%可信区间分别为42.25-61.34 g/kg和42.60-49.04g/kg。为临床推荐生药用量的124-318和112-286倍。参照中药毒性分级标准,银线草和多穗金粟兰分属于小毒和有毒中药。小鼠中毒表现呈剂量依赖性加剧,死亡率亦随之增高。中毒损害是全身性的,靶器官与组织主要是肝、肾、心、脾和全身血管。
11.对银线草和多穗金粟兰甲醇提取物进行镇痛抗炎活性的研究。采用醋酸扭体法、热板法和福尔马林法确定银线草和多穗金粟兰甲醇提取物的镇痛效应和类型；采用二甲苯致小鼠耳廓肿胀、醋酸致小鼠腹腔毛细血管通透性变化探讨它们的抗炎效应。结果显示,两种甲醇提取物中、高剂量对化学物质(醋酸)和热刺激引发的疼痛反应均有显著的抑制作用,且还可对抗由福尔马林诱发的第二相疼痛,其镇痛作用机制可能通过外周与中枢两种机制介导。银线草和多穗金粟兰甲醇提取物浸膏对小鼠的多种急性炎症具有明显的抗炎作用,且其效果与浓度呈正相关。
Chloranthus japonicus Sieb. and Chloranthus multistachys Pei, which belong to the genus Chloranthus in Chloranthaceae family are two perennial herbaceous plants. As folklore medicines native to the Qinling Mountains of China, the whole plants and their roots have been traditionally used for hundreds of years to treat boils, dermatopathia, enteric fever, detumescence, snake bite, bone fractures, cough, and rheumatic pain. Their various bioactivities have now gained attention from researchers because of their antifungal, cytotoxic, hepatoprotective, and tyrosinase-inhibitory properties. However, the active constituents and the mechanism for their function still remain unclear. In this study, we used anatomical, histochemical, phytochemical, pharmacological and toxicological methods were used to investigate structure, chemical composition and biological activities of C. japonicus and C. multistachys. The research will be beneficial to the further exploitation and utilization of the Chloranthus plants. The main results are as follows:
1. The morphological structure of vegetative organs of C. japonicus and C. multistachys were analyzed and compared. The main similarities were as follows:cortexs in the root and the rhizome were broad; stems got large hollow pith cavities; leaves had the bifacial structure, palisade tissue and sponge tissue were clearly differentiated, and leaf veins had a narrow phloem and a developed xylem; there were no hairs on the upper and lower epidermis of the leaf, the stomatal apparatuses fell into anomocytic type and occurs only on the lower epidermis. In addition, there were some obvious differences in the structures of two species. In C. japonicus, the root cortex cells were arranged in order and had smaller intercellular spaces, and the root phloem was narrow; the stem cortex cells were also arranged in order, and the stem phloem was surrounded by strands of fiber; the leaf sponge tissue of were composed of cells with various shapes, which had a small intercellular space, there were parenchyma cells with irregular shapes, which have large intercellular spaces inside collenchyma of main leaf vein, and the epidermis cells of the main vein had no papilla. In C. multistachys, however, the root cortex cells got arranged irregularly and had large intercellular spaces, the root phloem was broad as well; the stem cortex cells were misaligned, with its phloem surrounded by a few layers of fiber; the leaf sponge tissue was composed of round-like cells which had large intercellular space; there were nearly round parenchyma cells which had small intercellular space inside the collenchyma of main leaf vein, and the epidermis cells of the main vein had obvious papilla.
2. The histochemistry results of terpenoids and flavonoids localization were similar in different vegetative organs in C. japonicus and C. multistachys, both of which were mainly distributed in the cortex of root, the cortex of stem and phloem cell. Otherwise, the only difference just lied in their contents in two species. Terpenoids were dyed reddish in the cortex parenchyma stem cells and phloem cells in C. japonicus, and was dyed reddish brown in C. multistachys, which indicated that C. multistachys. contained more terpenoids than those in C. japonicus. Flavonoids showed strong yellow-green fluorescence in the cortex cells of root and displayed yellow-green fluorescence in stem cortex and phloem cells in C. japonicus. On the contrary, in C. multistachys, strong green fluorescence was shown in the cortex cells and blue-green fluorescence in stem cortex and phloem cells. From the above, the conclusion could be drawn that the contents of flavonoids in C. multistachys were more than those in C. japonicus, which was consistent with the phytochemical results.
3. The essential oils of C.japonicus and C. multistachys were obtained by hydrodistillation and analyzed by GC and GC-MS. In all of them,48 and 39 compounds were identified, accounting for 95.56% and 94.58% of all constituents in the oil from C.japonicus and C. multistachys, respectively. Up to 28 compounds were found in common between the two oils, which featured a high relatively content of monoterpenes and their oxygenated monoterpenes (77.04%,46.64%). Bornyl acetate was the most abundant compound in these oils, which ranged from 30.98% to 35.99%. In addition, the telling distinguishing feature was that there was a high proportion of myristicin in C. multistachys.
4. The fat-soluble components in C. japonicus and C. multistachys were extracted by soxlet extraction, and then esterified and analyzed by GC-MS. There were twenty-four fat-soluble components detected and identified in C. japonicus, amounting to 99.03% of the total contents, among which the saturated fatty acid and unsaturated fatty acid were 22.32% and 70.02%, respectively. There are fifteen fat-soluble components detected and identified in C. multistachys, amounting to 92.59% of the total contents, among which the saturated fatty acid and unsaturated fatty acid were 15.73% and 54.71%, respectively.
5. The sample solution were analyzed by a Phenomenex C18 column (250mm×4.6mm,5μm) with a gradient mobile phase composed of methanol and 0.1% formic acid solution. Both DAD and mass spectrometry detector were used simultaneously, full-scan detection mode was evaluated for the identification of LC peaks. As a result, gallic acid, caffeic acid, isofraxidin and rosmarinic acid were identified; in addition, the contents of gallic acid, caffeic acid, and rosmarinic acid were higher in the methanol extract of C. multistachys (0.372mg/g, 0.111mg/g, and 2.073mg/g) than those of C. japonicus (1.173mg/g,0.173mg/g, and 7.228mg/g). The amount of isofraxidin in C.japonicus and C. multistachys were 0.507 mg/g and 0.292mg/g, respectively.
Significant difference was found in contents of phenols and counarins in the different parts of C. japonicus and C. multistachys. The contents of gallic acid in C. japonicus and C. multistachys were both stems>roots>leaves, and the content in the stems of C. multistachys were much more than those in C. japonicus. The contents of caffeic acid and rosmarinic acid in C. japonicus and C. multistachys were both roots>leaves>stems, and the rosmarinic acid content were 34.623 mg/g and 1.432 mg/g in the roots and lesves of C. japonicus, respectively, but 4.582 mg/g and 23.572 mg/g in C. multistachys. The contents of isofraxidin in C. japonicus and C. multistachys were both roots>stems >leaves,0.601mg/g and 0.094 mg/g in the roots of the two plants, respectively.
6. Ultrasound-assisted extraction response surface method (RSM) was applied to optimize the extraction condition of the total flavonoids in both C. japonicus and C. multistachys. The influence factors of methanol concentration, extraction temperature, extraction time, and ratio of material to solvent were evaluated using a fractional factorial design. The experimental data were disposed by Design-Expert 7.1.3 program. The optimum extraction conditions were confirmed as follows:In C. japonicus, methanol concentration 57%, ratio of material to solvent 1:17, extraction time 6 min, extraction temperature 60℃; In C. multistachys, methanol concentration 70%, ratio of material to solvent 1:8, extraction time 28 min, extraction temperature 27℃. The extraction rate of flavonoids under this condition agreed with the experimental values.
7. The microwave digestion and flame atomic absorption spectrophotometry (FAAS) were employed to determine the macro and trace elements (iron, zinc, copper, manganese, calcium, potassium, sodium and magnesium) in C. japonicus and C. multistachys. The results revealed that the order of concentrations of macro and trace elements in C. japonicus and C. multistachys were K>Ca>Na>Mg>Fe>Zn>Mn>Cu and K>Ca>Mg>Na>Fe>Mn>Zn>Cu, respectively. On the whole, the contents of these elements in C. japonicus were higer than those in C.multistachys.
8. Antimicrobial properties of the essential oils of C. japonicus and C. multistachys were evaluated in vitro via disc-diffusion and microbroth dilution assays. Activities were strong against 15 tested microorganisms (8 gram-positive bacteria,3 gram-negative bacteria,3 yeasts). Oil from C. japonicus was generally more efficient for inhibiting bacterial growth. MIC and MBC determinations indicated that gram-positive bacteria and yeasts were more sensitive to both oils than were gram-negative bacteria. The oil of C. japonicus showed the strongest bactericidal activity against B. cereus, as evidenced by the lowest values for MIC (0.39 mg/mL) and MBC (0.78 mg/mL). In contrast, oil from C. multistachys exerted the strongest bactericidal activity against B. cereus and Candida lipolytica, with the lowest MIC (0.78 mg/mL) and MBC (1.56 mg/mL), respectively. C. japonicus oil was stronger against B. cereus, B. coagulans, and Sarcina lutea than was C. multistachys, but the former oil was weaker against Rhodotorula glutinis.
9. The antioxidant activities of different extracts of C. japonicus and C. multistachys were evaluated with several antioxidant testing systems such as DPPH radical scavenging assay, superoxide radical scavenging assay,β-carotene-linoleic acid assay (β-CLA), and a plasmid DNA damage protection potential assay. The results revealed that the methanol extracts of the two plants showed higher antioxidant activity than other extracts.
10. Karber's method, histological and immunohistochemical method were used to explore the acute toxicity of the methanol extracts of C. japonicus and C. multistachys in mice. The results showed that the 50% lethal dose (LD50) were 50.91g/kg (42.25-61.34g/kg) and 45.74 g/kg (42.60-49.04 g/kg), respectively. According to the toxicity grading criteria, C. japonicus and C. multistachys were slightly and moderately poisonous medicinal plants. The main acute toxic effects were enhanced in a dose-dependent manner. The methanol extracts of C. japonicus and C. multistachys acted on target organs and tissues including kidney, liver, heart, spleen and systemic blood-vessel.
11. To investigate the analgesic and anti-inflammatory activity of the methanol extracts of C. japonicus and C. multistachys, the researcher used the acetic acid induced writhing test, hot p late test and formalin test to determine this effect and its analgesic type. The anti-inflammatory effect was determined by using the model of xylene-induced mice ear edema and increased vascular permeability induced by histamine phosphate in mice. The results showed that oral administration of extraction from C. japonicus and C. multistachys could improve the mice's pain threshold, significantly inhibit the inflammatory edema induced by various inflammatory agents and reduce the times of body writhing induced by acetic acid in mice. In addition, the extraction was remarkably active in the second phase of formalin-induced pain. C. japonicus and C. multistachys might have peripheral and central analgesic properties and have marked anti-inflammatory activity both on the acute phase.
1.银线草和多穗金粟兰营养器官形态结构研究。两种植物营养器官形态结构具有很多相同点,主要表现在：根中皮层宽广,内皮层明显,维管组织的初生木质部和初生韧皮部均属外始式发育；茎断面中空,具较大的髓腔,根状茎中皮层宽广,内皮层不明显,韧皮部狭窄；叶为异面叶,栅栏组织和海绵组织分化明显,叶的气孔长椭圆形,韧皮部较窄,木质部发达；叶片上、下表皮均无任何毛被,细胞近多边形或不规则形,只有下表皮分布有气孔器,为不规则型。除此之外,两种植物营养器官形态结构具有明显的不同点,主要表现在：银线草的根皮层细胞排列整齐,细胞间隙较小,韧皮部较窄,维管组织中导管数目较多；茎皮层细胞排列整齐,在韧皮部外方包围有多层束状纤维束；根茎木质部导管数目较少；叶的海绵组织由各种形状的细胞组成,具有较小的胞间隙,厚角组织内为形状不规则的薄壁组织细胞,细胞间隙较大,排列不整齐；主叶脉角质膜不具有乳状突起；多穗金粟兰的根皮层细胞排列不整齐,细胞间隙较大,韧皮部宽广,维管组织中导管数目较少；茎皮层细胞排列不整齐,在韧皮部外方仅包围有少数几层束状纤维束；根茎木质部导管数目较多。叶的海绵组织多以近圆形细胞组成,且具有较大的胞间隙；厚角组织内为类圆形薄壁组织细胞,细胞间隙较小,排列整齐；主叶脉角质膜具有明显乳状突起。
2.萜类和黄酮类化合物在银线草和多穗金粟兰不同营养器官中的组织化学定位结果类似,均主要分布在根的皮层、茎的皮层及韧皮部细胞中。但二者在含量上有所区别。萜类化合物在银线草茎中皮层的薄壁组织细胞以及韧皮部细胞被染为淡红色,而在多穗金粟兰中被染成淡红棕色,提示多穗金粟兰中含有的萜类化合物含量较多。黄酮类化合物在银线草根的皮层细胞中显示绿色荧光,在茎中,皮层和韧皮部细胞呈现绿色荧光；而在多穗金粟兰根的皮层细胞中显示强烈的绿色荧光,在茎中,皮层和韧皮部细胞呈现蓝绿色荧光,提示多穗金粟兰中黄酮类化合物的含量较银线草中多。该结果与植物化学研究结果相一致。
3.通过水蒸气蒸馏法并采用气相色谱-质谱联用技术提取、鉴定银线草和多穗金粟兰全草的挥发性成分。共分离鉴定出59个成分,两种植物中相同的成分有28种。其中,银线草全草中分离鉴定出48种成分,占挥发油色谱峰面积的95.56%,多穗金粟兰全草中分离鉴定出39种成分,占挥发油色谱峰面积的94.58%。已鉴定的化合物中,绝大部分是萜类化合物,其中以单萜和倍半萜及其含氧类化合物为主。银线草挥发性成分中单萜及含氧单萜类化合物为77.04%,倍半萜及含氧倍半萜类化合物为16.37%；多穗金粟兰挥发性成分中单萜及含氧单萜类化合物为46.64%,倍半萜及含氧倍半萜类化合物为14.20%。乙酸龙脑酯是银线草和多穗金粟兰全草挥发性成分中的主要成分,分别占30.98%和35.99%。银线草和多穗金粟兰全草挥发性成分中最显著的区别是多穗金粟兰中还含有较大比例的肉豆蔻醚。
4.采用索氏提取法和气相色谱-质谱联用技术(GC-MS)对银线草和多穗粟兰的脂溶性成分进行分离和鉴定。银线草脂溶性成分中共鉴定出24种化合物,占检出物总质量分数的99.03%。包括14种脂肪酸,其中饱和脂肪酸9种,占总质量分数的22.32%,不饱和脂肪酸5种,占总质量分数的70.02%。多穗金粟兰脂溶性成分中共鉴定出15种化合物,占检出物总质量分数的92.59%。包括12种脂肪酸,其中饱和脂肪酸7种,占总质量分数的15.73%,不饱和脂肪酸6种,占总质量分数的54.71%。
5.采用Phenomenex C18色谱柱(250mm×4.6mm,5μm),以甲醇-0.1%甲酸水溶液梯度洗脱,波长分别为254nm和323nm,光电二极管阵列检测器和电喷雾质谱同时在线检测,全离子扫描模式扫描,通过质谱分析及文献对照,鉴定出没食子酸、咖啡酸、异秦皮啶和迷迭香酸,并测定其含量。结果显示多穗金粟兰中没食子酸、咖啡酸、迷迭香酸的含量均高于银线草。银线草中的含量分别为0.372 mg/g,0.111 mg/g和2.073 mg/g,多穗金粟兰中的含量分别为1.173 mg/g,0.173 mg/g和7.228 mg/g。银线草和多穗金粟兰中香豆素类异秦皮啶的含量分别为0.507 mg/g和0.292 mg/g。
银线草和多穗金粟兰中不同部位的酚类和香豆素类含量差异也较大。没食子酸在银线草和多穗金粟兰不同部位的含量均为茎>根>叶,且多穗金粟兰茎中的含量明显高于银线草。咖啡酸和迷迭香酸在银线草和多穗金粟兰不同部位中的含量为根>叶>茎,迷迭香酸在银线草和多穗金粟兰不同部位中的含量差异很大,在银线草根中含量为34.623 mg/g、叶中含量为1.432mg/g；在多穗金粟兰根中含量为4.582 mg/g、叶中含量为23.572 mg/g。异秦皮啶在银线草和多穗金粟兰不同部位中的含量也表现为根>茎>叶,但含量差异很大,在银线草根中为0.601mg/g,而在多穗金粟兰中仅为0.094 mg/g。
6.利用超声技术提取银线草和多穗金粟兰中的总黄酮,同时应用响应面分析法优化其提取工艺参数,得到银线草总黄酮提取的最佳工艺条件：甲醇浓度57%,料液比1：17,提取时间6 min,提取温度60℃。多穗金粟兰总黄酮提取的最佳工艺条件：甲醇浓度70%,料液比1：8,提取时间28min,提取温度27℃,模型预测结果和实验检测结果基本吻合
7.采用微波消解-火焰原子吸收法测定秦岭山区两种金粟兰属药用植物银线草和多穗金粟兰中铁、锌、铜、锰、钙、镁、钠、钾的含量。结果显示：银线草和多穗金粟兰中含有丰富的大量和微量元素,银线草中所测元素含量依次为K>Ca>Na>Mg>Fe>Zn>Mn>Cu,多穗金粟兰为K>Ca>Mg>Na>Fe>Mn>Zn>Cu;所测得的8种元素中,银线草中的含量均高于多穗金粟兰。
8.采用滤纸片法和96孔板法分别检测银线草和多穗金粟兰全草挥发性成分的抑菌活性。结果显示银线草和多穗金粟兰挥发油对8种革兰氏阳性菌、3种革兰氏阴性菌和4种真菌均有抑制和灭活作用,对所试菌种的作用强度依次为革兰氏阳性菌>真菌>革兰氏阴性菌。其中银线草挥发油对蜡状芽孢杆菌的抑制效果最强,抑菌圈直径为22.2 mm,与盐酸四环素的抑菌效果21.4 mm相当,最小抑菌浓度MIC为0.39 mg/mL,最小杀菌浓度MBC为0.78mg/ml;多穗金粟兰挥发油的抑菌效果总体比银线草弱,但表现出相同的趋势,对蜡状芽孢杆菌和解脂假丝酵母菌的抑制效果最强,抑菌圈直径分别为18.8 mm和17.8 mm,最小抑菌浓度MIC为0.78 mg/mL,最小杀菌浓度MBC为1.56 mg/ml;另外,银线草挥发油对蜡状芽孢杆菌、凝结芽孢杆菌和藤黄八叠球菌的效果优于多穗金粟兰挥发油,而对粘红酵母的抑制效果低于多穗金粟兰挥发油。
9.建立了银线草和多穗金粟兰提取物体外抗氧化评价体系。采用DPPH-自由基清除活性、超氧自由基清除、β-胡萝卜素-亚油酸漂白以及DNA损伤保护活性等4种方法对银线草和多穗金粟兰不同提取物的体外抗氧化能力进行了综合评价。结果显示银线草和多穗金粟兰甲醇总提取物具有优于其它提取部位的较强抗氧化活性。
10.采用改良寇氏法、组织学和免疫组织化学方法进行银线草和多穗金粟兰提取物对小鼠的急性毒性试验。结果显示,银线草和多穗金粟兰甲醇提取物对小鼠的半数致死量LDso分别为50.91g/kg和45.74g/kg,LD50的95%可信区间分别为42.25-61.34 g/kg和42.60-49.04g/kg。为临床推荐生药用量的124-318和112-286倍。参照中药毒性分级标准,银线草和多穗金粟兰分属于小毒和有毒中药。小鼠中毒表现呈剂量依赖性加剧,死亡率亦随之增高。中毒损害是全身性的,靶器官与组织主要是肝、肾、心、脾和全身血管。
11.对银线草和多穗金粟兰甲醇提取物进行镇痛抗炎活性的研究。采用醋酸扭体法、热板法和福尔马林法确定银线草和多穗金粟兰甲醇提取物的镇痛效应和类型；采用二甲苯致小鼠耳廓肿胀、醋酸致小鼠腹腔毛细血管通透性变化探讨它们的抗炎效应。结果显示,两种甲醇提取物中、高剂量对化学物质(醋酸)和热刺激引发的疼痛反应均有显著的抑制作用,且还可对抗由福尔马林诱发的第二相疼痛,其镇痛作用机制可能通过外周与中枢两种机制介导。银线草和多穗金粟兰甲醇提取物浸膏对小鼠的多种急性炎症具有明显的抗炎作用,且其效果与浓度呈正相关。
Chloranthus japonicus Sieb. and Chloranthus multistachys Pei, which belong to the genus Chloranthus in Chloranthaceae family are two perennial herbaceous plants. As folklore medicines native to the Qinling Mountains of China, the whole plants and their roots have been traditionally used for hundreds of years to treat boils, dermatopathia, enteric fever, detumescence, snake bite, bone fractures, cough, and rheumatic pain. Their various bioactivities have now gained attention from researchers because of their antifungal, cytotoxic, hepatoprotective, and tyrosinase-inhibitory properties. However, the active constituents and the mechanism for their function still remain unclear. In this study, we used anatomical, histochemical, phytochemical, pharmacological and toxicological methods were used to investigate structure, chemical composition and biological activities of C. japonicus and C. multistachys. The research will be beneficial to the further exploitation and utilization of the Chloranthus plants. The main results are as follows:
1. The morphological structure of vegetative organs of C. japonicus and C. multistachys were analyzed and compared. The main similarities were as follows:cortexs in the root and the rhizome were broad; stems got large hollow pith cavities; leaves had the bifacial structure, palisade tissue and sponge tissue were clearly differentiated, and leaf veins had a narrow phloem and a developed xylem; there were no hairs on the upper and lower epidermis of the leaf, the stomatal apparatuses fell into anomocytic type and occurs only on the lower epidermis. In addition, there were some obvious differences in the structures of two species. In C. japonicus, the root cortex cells were arranged in order and had smaller intercellular spaces, and the root phloem was narrow; the stem cortex cells were also arranged in order, and the stem phloem was surrounded by strands of fiber; the leaf sponge tissue of were composed of cells with various shapes, which had a small intercellular space, there were parenchyma cells with irregular shapes, which have large intercellular spaces inside collenchyma of main leaf vein, and the epidermis cells of the main vein had no papilla. In C. multistachys, however, the root cortex cells got arranged irregularly and had large intercellular spaces, the root phloem was broad as well; the stem cortex cells were misaligned, with its phloem surrounded by a few layers of fiber; the leaf sponge tissue was composed of round-like cells which had large intercellular space; there were nearly round parenchyma cells which had small intercellular space inside the collenchyma of main leaf vein, and the epidermis cells of the main vein had obvious papilla.
2. The histochemistry results of terpenoids and flavonoids localization were similar in different vegetative organs in C. japonicus and C. multistachys, both of which were mainly distributed in the cortex of root, the cortex of stem and phloem cell. Otherwise, the only difference just lied in their contents in two species. Terpenoids were dyed reddish in the cortex parenchyma stem cells and phloem cells in C. japonicus, and was dyed reddish brown in C. multistachys, which indicated that C. multistachys. contained more terpenoids than those in C. japonicus. Flavonoids showed strong yellow-green fluorescence in the cortex cells of root and displayed yellow-green fluorescence in stem cortex and phloem cells in C. japonicus. On the contrary, in C. multistachys, strong green fluorescence was shown in the cortex cells and blue-green fluorescence in stem cortex and phloem cells. From the above, the conclusion could be drawn that the contents of flavonoids in C. multistachys were more than those in C. japonicus, which was consistent with the phytochemical results.
3. The essential oils of C.japonicus and C. multistachys were obtained by hydrodistillation and analyzed by GC and GC-MS. In all of them,48 and 39 compounds were identified, accounting for 95.56% and 94.58% of all constituents in the oil from C.japonicus and C. multistachys, respectively. Up to 28 compounds were found in common between the two oils, which featured a high relatively content of monoterpenes and their oxygenated monoterpenes (77.04%,46.64%). Bornyl acetate was the most abundant compound in these oils, which ranged from 30.98% to 35.99%. In addition, the telling distinguishing feature was that there was a high proportion of myristicin in C. multistachys.
4. The fat-soluble components in C. japonicus and C. multistachys were extracted by soxlet extraction, and then esterified and analyzed by GC-MS. There were twenty-four fat-soluble components detected and identified in C. japonicus, amounting to 99.03% of the total contents, among which the saturated fatty acid and unsaturated fatty acid were 22.32% and 70.02%, respectively. There are fifteen fat-soluble components detected and identified in C. multistachys, amounting to 92.59% of the total contents, among which the saturated fatty acid and unsaturated fatty acid were 15.73% and 54.71%, respectively.
5. The sample solution were analyzed by a Phenomenex C18 column (250mm×4.6mm,5μm) with a gradient mobile phase composed of methanol and 0.1% formic acid solution. Both DAD and mass spectrometry detector were used simultaneously, full-scan detection mode was evaluated for the identification of LC peaks. As a result, gallic acid, caffeic acid, isofraxidin and rosmarinic acid were identified; in addition, the contents of gallic acid, caffeic acid, and rosmarinic acid were higher in the methanol extract of C. multistachys (0.372mg/g, 0.111mg/g, and 2.073mg/g) than those of C. japonicus (1.173mg/g,0.173mg/g, and 7.228mg/g). The amount of isofraxidin in C.japonicus and C. multistachys were 0.507 mg/g and 0.292mg/g, respectively.
Significant difference was found in contents of phenols and counarins in the different parts of C. japonicus and C. multistachys. The contents of gallic acid in C. japonicus and C. multistachys were both stems>roots>leaves, and the content in the stems of C. multistachys were much more than those in C. japonicus. The contents of caffeic acid and rosmarinic acid in C. japonicus and C. multistachys were both roots>leaves>stems, and the rosmarinic acid content were 34.623 mg/g and 1.432 mg/g in the roots and lesves of C. japonicus, respectively, but 4.582 mg/g and 23.572 mg/g in C. multistachys. The contents of isofraxidin in C. japonicus and C. multistachys were both roots>stems >leaves,0.601mg/g and 0.094 mg/g in the roots of the two plants, respectively.
6. Ultrasound-assisted extraction response surface method (RSM) was applied to optimize the extraction condition of the total flavonoids in both C. japonicus and C. multistachys. The influence factors of methanol concentration, extraction temperature, extraction time, and ratio of material to solvent were evaluated using a fractional factorial design. The experimental data were disposed by Design-Expert 7.1.3 program. The optimum extraction conditions were confirmed as follows:In C. japonicus, methanol concentration 57%, ratio of material to solvent 1:17, extraction time 6 min, extraction temperature 60℃; In C. multistachys, methanol concentration 70%, ratio of material to solvent 1:8, extraction time 28 min, extraction temperature 27℃. The extraction rate of flavonoids under this condition agreed with the experimental values.
7. The microwave digestion and flame atomic absorption spectrophotometry (FAAS) were employed to determine the macro and trace elements (iron, zinc, copper, manganese, calcium, potassium, sodium and magnesium) in C. japonicus and C. multistachys. The results revealed that the order of concentrations of macro and trace elements in C. japonicus and C. multistachys were K>Ca>Na>Mg>Fe>Zn>Mn>Cu and K>Ca>Mg>Na>Fe>Mn>Zn>Cu, respectively. On the whole, the contents of these elements in C. japonicus were higer than those in C.multistachys.
8. Antimicrobial properties of the essential oils of C. japonicus and C. multistachys were evaluated in vitro via disc-diffusion and microbroth dilution assays. Activities were strong against 15 tested microorganisms (8 gram-positive bacteria,3 gram-negative bacteria,3 yeasts). Oil from C. japonicus was generally more efficient for inhibiting bacterial growth. MIC and MBC determinations indicated that gram-positive bacteria and yeasts were more sensitive to both oils than were gram-negative bacteria. The oil of C. japonicus showed the strongest bactericidal activity against B. cereus, as evidenced by the lowest values for MIC (0.39 mg/mL) and MBC (0.78 mg/mL). In contrast, oil from C. multistachys exerted the strongest bactericidal activity against B. cereus and Candida lipolytica, with the lowest MIC (0.78 mg/mL) and MBC (1.56 mg/mL), respectively. C. japonicus oil was stronger against B. cereus, B. coagulans, and Sarcina lutea than was C. multistachys, but the former oil was weaker against Rhodotorula glutinis.
9. The antioxidant activities of different extracts of C. japonicus and C. multistachys were evaluated with several antioxidant testing systems such as DPPH radical scavenging assay, superoxide radical scavenging assay,β-carotene-linoleic acid assay (β-CLA), and a plasmid DNA damage protection potential assay. The results revealed that the methanol extracts of the two plants showed higher antioxidant activity than other extracts.
10. Karber's method, histological and immunohistochemical method were used to explore the acute toxicity of the methanol extracts of C. japonicus and C. multistachys in mice. The results showed that the 50% lethal dose (LD50) were 50.91g/kg (42.25-61.34g/kg) and 45.74 g/kg (42.60-49.04 g/kg), respectively. According to the toxicity grading criteria, C. japonicus and C. multistachys were slightly and moderately poisonous medicinal plants. The main acute toxic effects were enhanced in a dose-dependent manner. The methanol extracts of C. japonicus and C. multistachys acted on target organs and tissues including kidney, liver, heart, spleen and systemic blood-vessel.
11. To investigate the analgesic and anti-inflammatory activity of the methanol extracts of C. japonicus and C. multistachys, the researcher used the acetic acid induced writhing test, hot p late test and formalin test to determine this effect and its analgesic type. The anti-inflammatory effect was determined by using the model of xylene-induced mice ear edema and increased vascular permeability induced by histamine phosphate in mice. The results showed that oral administration of extraction from C. japonicus and C. multistachys could improve the mice's pain threshold, significantly inhibit the inflammatory edema induced by various inflammatory agents and reduce the times of body writhing induced by acetic acid in mice. In addition, the extraction was remarkably active in the second phase of formalin-induced pain. C. japonicus and C. multistachys might have peripheral and central analgesic properties and have marked anti-inflammatory activity both on the acute phase.
引文
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