中药天葵子的化学成分研究进展*

1 Introduction

Radix Semiaquilegiae (Tiankuizi in Chinese), the root of Semiaquilegia adoxoides belongs to the genus Ranunculaceae plant. [1]

This plant is distributed in the subtropical area of the Yangtze River in China, according to the investigations in phytochemistry on Radix Semiaquilegiae, various biologically active compounds have been founded. In addition, in TCM, the plant is mainly applied for the treatment of tumor and mastitis in clinical practice. This review aims to systematically summarise the published literatures related to the chemical constituents of S. Radix and to provide information as a basis of further development and utilization of this herbal resource.

Clinically used to treat acute mastitis with honey sometimes[2-8], Radix Semiaquilegiae contains a variety of chemical compositions and cyanoglycosides as the main components shows significant medicinal activity.[9].

Monomeric compounds from Radix Semiaquilegiae can inhibit the activity of cholinesterase [10], and have the anti-inflammatory[11] and anti-tumor activity in vitro [12-15]. Alkaloid fractions of Radix Semiaquilegiae have inhibitory effect on mouse sarcoma S180[16], while the water layer and the n-butanol layerer of Radix Semiaquilegiae have antioxidaive activity[17].

丰田纺织拥有强大的技术储备，并致力于在电池技术上实现突破。在过滤器制造过程中，用于处理微细纤维的技术其实也可以用于在锂电池的隔膜上。基于此技术，丰田纺织开发了一种无纺布型分离器，与常见的隔膜相比，具有三维结构的无纺布多孔结构在锂离子通过隔板时容易保持较低的离子电阻。极大地提高了锂电池的功率密度。丰田纺织开发的电池单元是层压型，容量约为15Wh。将数十个电池单元组合成模块，再有多个模块组合成电池包。该产品的最大特点是输出密度高，其输出密度是普通混合动力汽车（HEV）电池输出密度的1.5～2倍。

To date, four alkaloids have been isolated and identified from Radix Semiaquilegiae (Table 1， Figure 1)， namely thalifendine (1), semiaquilegine A (2), magnoflorine (3), and berberine (4), respectively. The structures of Thalifendine and Semiaquilegine A have been elucidated by NMR spectroscopic analysis.

2 Phytochemistry

The advancement of analysis technologies has allowed many studies on Semiaquilegia adoxoides to reveal numbers of phytochemicals, including alkaloids, diterpenes, cyano compounds and nitro compounds, lactones, coumarins, lignins, glycosides, sterols and others.

2.1 Alkaloids

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Cyano compounds and nitro compounds are the main characteristic components of Radix Semiaquilegiae. Up to now, 11 compounds with cyano and nitro have been obtained and identified from this herb. These compounds have the similar molecular configuration(Table 3). Their chemical structures are shown in Figure 3.

Table 1 Alkaloids

  

No．NameMolecularFormulaPhysicalstate1ThalifendineC19H16NO4Yellowneedle[18]2SemiaquilegineAC19H24NO4Whitepowder[19]3MagnoflorineC20H24NO4+Yellowamorphouspowder[20]4BerberineC20H18NO4Yellowneedle[21]

  

Figure 1 Structures of compounds from Radix Semiaquilegiae (Alkaloids)

2.2 Diterpenes

Lactones and a coumarins compounds were found in Radix Semiaquilegiae(Table 4). Their structures are shown in Figure 4.

Table 2 Diterpenes

  

No．NameMolecularFormulaPhysicalstate4E semiaquileginC38H46O9Whiteamorphouspowder[22]5Z semiaquileginC38H46O9Whiteamorphouspowder[23]6SemiaquilegosideAC26H38O9Colorlessneedlecrystal[24]

 

Figure 2 Structures of compounds from Radix Semiaquilegiae (diterpenes)

2.3 Cyano compounds and nitro compounds

在特定的生态区域中不可能只生长一种作物。不同种类的作物很可能会出现病虫害交叉生长的状况，使得作物在生长过程中会发生相互制约。很多专家认为，针对这种情况，需要转变病虫害治理方式，由原来的根据作物进行防治，转变为整体上对某一类作物进行防治。这种防治方式主要是通过不同作物之间的抵抗特征来实现，推进了防治技术的发展。在应用此技术的过程中，需要注意土壤、技术、作物等因素的影响。

2.4 Lactones and coumarins

Two diterpenes have been isolated from EtOH extraction fraction of the root of Semiaquilegia adoxoides, namely E-semiaquilegin and Z-semiaquilegin, respectively(Table 2, Figure 2).

图6为空载工况下车辆的轮重减载率都超过了0.65，尤其是在曲线轨道上主被动头车都频繁超标。曲线轨道上，刚性轮和弹性轮的轮重减载率都达到1，弹性轮超过限值0.65的最大作用时间为23 ms，略小于刚性轮的25 ms。直线轨道上，刚性轮和弹性轮的轮重减载率最大值分别为1和0.95，超过限值0.65的最大作用时间分别为11 ms和8 ms，相比于刚性轮，弹性轮的轮重减载率最大值减少5%，超过限值的作用时间降低27.27%。

 

Table 3 Cyano compounds and nitro compounds

  

No．NameMolecularFormulaPhysicalstate7lithospermosideC14H19NO8Whiteamorphouspowder[25]8(Z) 6α ( D glucosyloxy) 4α，5α dihydroxy 2 cyclohexene 1，α acetonitrileC14H19NO8Whiteamorphouspowder[20]9MenisdauriC14H19NO7Whiteamorphouspowder[20]

 

(续表)

  

No．NameMolecularFormulaPhysicalstate10ehretiosideC14H17NO7Colorlessneedlecrystal[26]11thalictricosideC19H27NO12Colorlessneedlecrystal[26]124 [ D apiofuranosyl (1→6) O D glicopyranosyloxy]phenylacetonitrileC19H25NO10[26]13(1E，4α，5，6α) 4，5，6 trihydroxy 2 cyclohexen 1 ylideneacetonitrileC8H9NO3Whiteamorphouspowder[26]142 ( D glucopyranosyloxy) 4 hydroxybenzeneacetonitrileC14H17NO7whiteneedles[27]15 4 Hydroxy 1 (2 nitroethyl)benzene4 O (6′ O D xylopyranosyl) D sitosterolC19H27NO12Whitepowderedcrystal[23]164 hydroxy 2 D glucopyranosyloxyphenylacetonitrileC14H17NO7EhretiosideB[26]174 [ D xylopyranosyl (1→6) O D glucopyranosyloxy] 1 (2 nitroethy1)benzeneWhiteamorphouspowder[28]

  

Figure 3 Structures of compounds from Radix Semiaquilegiae (cyanos and nitros)

 

Table 4 Lactones and coumarins

  

No．NameMolecularFormulaPhysicalstate18GriffonilideC8H8O4Colorlessprismycrystal[25]19AquilegiolideC8H8O3whiteneedles[22]20MenisdaurilideC8H8O3whiteneedles[22]214，6 dimethoxy 5 methyl 2H Pyran 2 oneC8H10O4whiteneedles[11]

  

Figure 4 Structures of compounds from Radix Semiaquilegiae (lactones and coumarins)

2.5 Others chemical constituents

Radix Semiaquilegiae contains organic acids, including octanedioic acid, fumaric acid and palmitic acid. The root of this plant contains a lot of phenolic acids, such as hexanoic acid, octanoic acid, nonanoic acid, myristic acid, pentadecanoic acid and heptadecanoic acid(Table 5). Their structures are shown in following Figure 5.

There are also some lignins, glycosides[30-31], sterols and others in the plant. Genistein, an active ingredient, can increase the activity of gemcitabine in vivo and in vitro against pancreatic cancer[32].

 

Table 5 Phenolic acids

  

No．NameMolecularFormulaPhysicalstate244 hydroxybenzaldehydeC7H6O2Colorlesscrystal[24]254 hydroxybenzoicacidC7H6O3Colorlesscrystal[24]263 hydroxy 4 methoxybenzoicacidC8H8O4Colorlesscrystal[28]272，4 dihydroxybenzoicacidC7H6O4Colorlesscrystal[22]28Bis(2 ethylhexyl)phthalateC24H38O4Yellowsyrup[28]29DibutylterephthalateC16H22O4Yellowishneedles[28]30Methyl2 (2，4 dihydroxyphenyl)acetateC9H10O4Colorlesscrystal[22]31FerulicacidC10H10O4Lightyellowcrystallinepowder[29]322 propenoicacid，3 (4＇ hydroxyphenyl) (4＇＇ carboxyl) phenylesterC16H12O5Colorlessneedles[24]334 (bromomethyl) 2 hydroxybenzoicacidC8H7BrO3Brownredneedlecrystal[24]345 (2 hydroxyethyl) 2 O glucosylohenolC14H20O8Colorlessneedles[29]35SalidrosideC14H20O7Colorlessneedles[24]36p HydroxyphenethylalcoholC8H10O2Whtiecrystal[22]373，4 dihyroxybenzoicacidC7H6O4Whitetomicro brownneedle[11]38p D glucosyloxybenzoicacidC13H16O8Whtieneedle[11]39MonordicophenoideAC18H24O12Browngum likesubstance[26]

 

Figure 5 Chemical Compositions of Phenolic Acids from Radix Semiaquilegiae

3 Conclusion

Modern pharmacological studies have shown that Radix Semiaquilegiae has anti-inflammatory, cytotoxic and other activities, with thegreat potential in the pharmaceutical field. The results of phytochemistry indicated that the major components of Radix Semiaquilegiae are phenolic acids, cyano compounds and nitro compounds which exhibit multiple pharmacological effects. In addition, the bioactive components and their corresponding pharmacological activities should be investigated systematically in order to optimize the development and utilization of this herbal resource.

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