Research Progress Of Phenylethanol Glycosides in Cistanche

For more information:ali.ma@wecistanche.com

Yan Guihui, Tian Jinhu, Long Wenwen, Li Na (Xinghui Tianli (Hangzhou) Pharmaceutical Co., Ltd., Hangzhou 311100)

Keywords: Cistanche; Phenylethanoids; Extraction and separation

Chinese Library Classification Number: R284 Document Identification Code: A Article Number: 1672-2981 (2012)09-0692-04

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Cistanche

The traditional Chinese medicine Cistanche deserticola YC Ma or Cistanche tubulosa (Schrenk) Wight is a dry fleshy stem with scaly leaves, also known as Dayun. It is a traditional Chinese medicine for invigorating the kidney and yang. It was first recorded in Shennong. "Materia Medica", listed as the top grade, has the effects of nourishing kidney yang, nourishing essence and blood, and moisturizing the intestines. Indications of male impotence, female infertility, blood dryness constipation, and other diseases, have the reputation of "desert ginseng". According to the records in "Meat Clan Paste and Its Artificial Planting" m, 8 species and 1 variety have been found in my country, including Cistanche tubulosa (Schrenk) Wight and C. deserticola (YC Ma). ), salt raw meat from the paste (C.salsa (Camey.) G.Beck), Lanzhou meat girl paste (CZYZhang), sand egg paste (C.szRe such as sfs G. .ambigna (Bge.) G.Beck), deeply cracked eggplant paste (C.fissa (Camey) G.Beck), Ningxia meat hernia paste (C.ningxiaensis DZMa et A.Duan) and 1 variant source ( C.salsa var. albifora PFYU et ZCLou); among them, the largest production of piranha, mainly produced in the Tarim Basin, Xinjiang, has been successfully introduced in a large area and is currently the most important source of the traditional Chinese medicine Cistanche.

Since the 1970s, scholars at home and abroad have begun to systematically study the chemical components and pharmacological activities of the plants of the genus Rhododendron. So far, nearly 100 chemical components and trace elements have been isolated and identified from Cistanche deserticola, mainly including phenylethanoids, cycloalcosides, lignan glycosides, monosaccharides, disaccharides, polysaccharides, amino acids, peptides, and proteins, Three Borrows, Street Alcohol, Polyhydric Alcohol, etc. Among them, the content of phenethyl alcohol glycosides is the highest in the original medicinal materials. It is one of the main active ingredients of the plant of the genus Flesh ash. It is also an index component for identification and content determination under the item of "Rice Congrong" in the Chinese Pharmacopoeia. It has antioxidant and promoting substances. Metabolism, improvement of learning and memory, enhancement of sexual function, etc.PI =In this paper, combined with domestic and foreign literature, the research overview of the chemical structure, extraction and separation methods, and pharmacological effects of the phenethyl alcohol glycosides in the eggplant puree is reviewed.

1 Chemical structure of phenylethanoids

1.1 Structural features

phenylethanoids (phenylethanoids, PhGs) are a type of glycoside compound formed by the combination of phenyl ethanol aglycone and sugar group. Among them, most of the compounds have caffeoyl or feruloyl groups attached to their sugars. Scholars at home and abroad It is also called phenylpropanoid glycosides. Most of the phenoxyethanol glycosides in Cistanche has a general structure (see Figure 1), and its constituent sugars are mostly glucose and rhamnose; the central sugar directly connected to the aglycon is glucose; in addition to aminoglycosides, the central sugar Rhamnose is attached to the 3 positions of glucose; the second glucose in the triglyceride is often connected to the 6 positions of the central glucose; the 4 or 6 positions of the central glucose are often combined with caffeoyl, feruloyl, or coumarin, etc. Acyl forms an ester.

1.2 Representative ingredients

Echinacoside (see Figure 2 for the chemical structure) and verbascoside are the main indicator components in the cistanche. Among them, echinacoside is the first phenethyl alcohol glycoside compound recorded in the literature called Echinacea Angustifolia (Ec. area Angus Joshua) isolated and purified, and it is also one of the index components in Echinacea extract. Since the 2005 edition of the Chinese Pharmacopoeia, echinacoside and verbascoside have been used as the index components of Cistanche to control the quality of medicinal materials.

Fig 1 Structure of phenylethanoid

1.3 Identified ingredients

Since the 1970s, scholars at home and abroad have conducted a large number of studies on the chemical components of the traditional Chinese medicine Cistanche. Among them, the research on desert and Cistanche is more in-depth and systematic, and other species have also been reported so far, and they are separated from Cistanche. Nearly 40 kinds of phenylethanoid have been identified.

Pengfei Tu’s research group at Peking University has done a lot of work in this area. In 2003, Lei Li et al. 151 summarized and reported that domestic and foreign scholars have isolated 22 phenylethanoids from Cistanche, including 1 monosaccharide back. 14 diglycosides and 7 triglycerides. In 2008, Jiang Yong et al. carried out a further systematic introduction and concluded that more than 30 phenethanol glycosides have been isolated and identified from Cistanche plants, including 12 species of Cistanche, 19 species of Cistanche striata, and 10 of Cistanche salina. There are 13 species of Sha Huanrong. In addition, the total phenyl ethanol glycosides derived from Cistanche Tubula have been developed, with echinacoside and verbascoside as the main components. The phenylethanoid content is >90% and the echinacoside content is >40%.

Song Hailong et al. also reported that 19 phenylethanoids were isolated from domestic pipe flower and eggplant paste. Later, another four phenylethanoids were isolated and identified from Cistanche deserticola, namely kankanosides Jl, J2, K1, and K2.

Cistanche

2 Extraction and separation process

Phenylethanoids are mostly amorphous powders, with good water solubility and hygroscopicity, easily soluble in methanol and acetone, and their properties are relatively stable. The extraction and separation methods that have been researched and reported include ethanol reflux extraction, macroporous resin adsorption, multiple organic solvent extractions, microwave extraction, ultrasonic extraction, and flocculation water extraction. Among them, the application of macroporous resin adsorption is used. The most extensive and the most reported.

2.1 Ethanol reflux method

Meng Qingyan et al. 1141 used a multi-index comprehensive scoring orthogonal design method to screen the ethanol reflux extraction process of phenethyl alcohol glycosides from the squash of the tube flower flesh, and the best extraction process was: 20 times the amount of 40% ethanol was used for 1 extraction. 2h, the extract was concentrated under reduced pressure until it had no ethanol taste, and the concentrated solution was dried at 60°C to obtain the crude phenylethanoids of Cistanche Tubulosa.

Wu Haihong et al. [15] investigated the various factors of the ethanol reflux extraction process of phenethyl alcohol glycosides in salted raw meat nuggets and found that the reaction temperature was 40~70°C, which had no significant effect on the extraction of phenethyl alcohol glycosides. However, when the extraction temperature exceeds 70 °C, as the reaction temperature rises, the concentration of phenylethanoid in the extract decreases significantly. It is recommended that the extraction temperature be 70 °C.

2.2 Macroporous resin adsorption method

Macroporous adsorption resin has multiple advantages such as strong selectivity, large adsorption capacity, simple regeneration, rapid adsorption, and easy desorption. In recent years, it has been favored in the separation of effective components of traditional Chinese medicine. It has been widely used in the separation of phenethyl alcohol glycosides in Cistanche deserticola. Application, and has been industrialized. According to the polar characteristics of the phenylethanoid in the meat ash paste, Ren Lu et al. adsorbed 7 kinds of macroporous resins, including D290, D3520, NKA, AB-8, D-100, NKA-II, and S-8. A performance comparison study found that AB-8 has a larger adsorption capacity for phenylethanoids. Chen Xinping et al. [, 7] selected an adsorbent suitable for separating echinacoside and verbascoside by comparing the adsorption and analysis performance of 8 kinds of resins, and from the perspective of adsorption rate, resolution rate, adsorption time, acidity control, reproducibility, etc. Various comparative studies are carried out to provide an important reference basis for industrial production.

2.3 Organic solvent extraction and separation method

Zhang Kaisi selected ethanol to crudely extract meat hernia and then extracted it with ethyl acetate and n-butanol to obtain higher concentrations of phenethyl alcohol glycosides. He also investigated the influence of various factors in the ethanol extraction process and found that The order of influence of each factor is: extraction time>crushing degree>ethanol dosage>ethanol concentration, and the optimal extraction process conditions are obtained.

2.4 Flocculation water extraction method

Wang Yingzi et al. [91 used echinacoside, p-sitfluorol, total sugars, and dry extract yields as indicators. Under the premise of the same conditions as the size of the medicinal materials, the number of medicinal materials, filtration, and concentration, the ultrasonic extraction Method (USE), Flocculation Water Extraction (WFE), Alcohol Extraction (AE) 3 methods are compared and studied. The experimental results show that the flocculation water extraction method is superior to the other two methods, and it is the phenethyl alcohol glycoside compound of scallion paste. Provides yet another better extraction and separation process.

2.5 Other extraction methods

In the early days, the phenethanol glycosides in the meat from the puree were often separated and prepared by silica gel or dextran gel column chromatography. However, because these compounds contain phenolic hydroxyl groups in their molecules, they are easily adsorbed on solid chromatographic columns. Therefore, the yield of preparing such compounds by column chromatography is relatively low, and a large number of organic solvents are consumed 1201 O Lei Li 1211 used high-speed counter-current chromatography to extract the phenylethanoid from A. floribunda and made a separation and identification, which provides a simple and fast method for the separation of phenethanol glycosides.

Cistanche

3 pharmacological effects

At present, many scholars at home and abroad have conducted a lot of research on the pharmacological activities of the phenethyl alcohol glycosides in meat hernia, mainly focusing on the total phenethyl alcohol glycosides, echinacoside, and verbascoside. The pharmacological activities of other ingredients are rarely reported. Studies have found that the phenylethanoids in Cistanche have various pharmacological activities in improving memory, anti-aging, immune regulation, anti-neuronal cell apoptosis, myocardial ischemia protection, and improving sexual function.

3.1 Anti-aging effect

The gavage of the total glycosides of Cistanche can significantly increase the activity of superoxide dismutase (SOD) in subacutely aging mice induced by D-galactose, and significantly reduce the lipid peroxide content in the brain and liver. The anti-oxidant and anti-aging effects four.

Kuang Rong et al. used the H202-injured PCI2 cell model to study the protective effects of echinacea on survival, apoptosis, necrosis, and lactate dehydrogenase (LDH) leakage of PCI2 cells injured by H202. A study of its mechanism from the perspective of mitochondrial pathways provides an important theoretical basis for the development and utilization of echinacoside in the prevention and treatment of neurodegenerative diseases such as Alzheimer's disease (AD).

3.2 Improve memory

Studies have shown that this type of ingredient not only has the function of improving learning and memory in both amnesia model mice and normal mice. Park Jinghua et al. (iv) Studies have found that mullein glycosides can antagonize the increase in cerebral cortex acetylcholinesterase and the decrease in the maximum binding capacity of the cortex and striatum M receptors caused by opine, and it can improve the memory impairment caused by scotropine.

Hu Yuming and others used the water maze experiment, platform jumping method, and dark avoidance method to observe the effect of the total glycosides of Rhizoma Rhizome on the learning and memory function of normal mice. The experimental results all show that the total glycosides of Congrong can significantly reduce the time to reach the end of the water maze experiment, and the number of animals to the end within 2 minutes is significantly increased; it can significantly extend the incubation period of the platform jumping, and the number of errors within 5 minutes is significantly reduced. It shows that the total glycosides of Solanum lucidum can improve the learning and memory function of normal mice, and provide a basis for its development as a new resource for healthy people to help improve memory.

3.3 Immune regulation

phenylethanoids of Cistanche in mice can enhance delayed-type hypersensitivity after 60C0-Y irradiation, increase thymus index, increase T lymphocyte proliferation response and increase the activity of interleukin 2 (IL-2). Oral administration can significantly increase the ability of macrophages in the blood of mice and the weight of immune organs, showing that the total glycosides of Solanaceae can promote immune regulation [27].

3.4 Improve sexual function

Cistanche is a traditional Chinese medicine for invigorating the kidney and yang. Verbascoside, polysaccharides, and betaine are some of the main active components of cistanche to produce androgen-like effects.

A functional test showed that the ergot luciferin (that is, verbascoside) in Cistanche tubulosa can shorten the erectile latency of the penis in castrated rats, increase the weight and index of accessory organs such as the foreskin gland and seminal vesicle gland in castrated rats, and increase the normal The weight of the sex organs and accessory sex organ index of rats show androgen-like effects, which can improve sexual function (iv). Domestic scholars have studied the pharmacological effects of Cistanche for nourishing the kidney yang, and the results show that the water extracts of two kinds of cistanche (C. cistanche and Cistanche cistanche) can make the mice with kidney yang deficiency caused by hydrocortisone obvious cold tolerance time Prolonged, the effect of nourishing kidney yang is significant, and it is suggested that the ingredients that have been proven to produce nourishing kidney and yang include polysaccharides and betaine.

3.5 Myocardial ischemia protection

The experimental study found that the coronary artery was ligated 5 minutes after the intravenous administration of the total glycosides of Solanum solani. Compared with the non-administered group, the total glycosides of Solanum lanolin can significantly improve the ischemic electrocardiogram and reduce the area of myocardial infarction. It improves the activity of creatine phosphokinase (CPK) in the myocardial tissue and shows a network of actions to protect the ischemic myocardium. Wang Xiaowen D'S 36] and other studies have shown that the total glycosides of Rourongrong can remove free radicals in vitro, produce anti-oxidant effects, and thus have cardioprotective effects.

3.6 Central Nervous System Protection

Pu Xiaoping’s research has found that the phenethyl alcohol glycosides of Cistanche Tubula inhibit the activity of caspase-3, and have an anti-apoptotic effect on midbrain nerve cells. Administration of total glycosides of Cistanche can significantly reduce the scope of cerebellar infarction in rats with focal cerebral ischemia, increase the activity of brain tissue SOD and glutathione peroxidase (GSH-Px), and significantly reduce malondialdehyde (MDA). ) Content, has a neuroprotective effect

3.7 Other

Experimental studies have shown that verbascoside has a significant protective effect on liver damage caused by chloroform. In addition, domestic scholars have concluded that echinacoside has a variety of pharmacological effects such as neuroprotection, prevention of liver damage, anti-inflammatory, anti-tumor, anti-aging, immune regulation, and memory improvement.

4 Conclusion

Cistanche is a precious traditional Chinese medicine in my country. It has been used most frequently in the prescriptions for invigorating kidney yang in the past. It is also a precious wild resource. It has been listed as a secondary protected species in my country and included in the "International Wild Plant Protection List". At present, it has been successfully planted in large areas in Xinjiang, Inner Mongolia, and other regions of my country. Among them, the main component, phenethyl alcohol total alfalfa, has been confirmed and developed to be used in the treatment of senile dementia and other aspects.

With the continuous development of science and technology and the deepening of research, the new pharmacological activities of phenethyl alcohol glycosides and their components will gradually be discovered, which will lay the foundation for the modernization research and development of traditional Chinese medicines of phenethyl alcohol glycosides in Roujingrong. Solid foundation.

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