Phenylethanoid glycosides from traditional Mongolian medicine Cymbaria daurica alleviate alloxan-induced INS-1 cells oxidative stress and apoptosis

Cymbaria daurica L. is a well-known traditional Mongolian medicine, which has been used to treat diabetesrelated conditions characterized by persistent thirst and hunger, copious urination, and weight loss. We aimed to investigate the protective effects of C. daurica extracts and phenylethanoid glycosides including verbascoside and isoacteoside on INS-1 cells. We discovered phenylethanoid glycosides from n-butanol extract with large content through extraction and separation. We continue to study the protective effects of phenylethanoid glycosides including verbascoside and isoacteoside on INS-1 cells. INS-1 cells were treated with C. daurica, cell viability assay, RNA-seq technology, superoxide dismutase activity and malonaldehyde content, quantitative real time-PCR and Western blot analysis were used to study the protective effects of C. daurica. Cell viability assay resulted that n-butanol extract and verbascoside, isoacteoside showed protective effects of C. daurica. According to the RNA-seq technology to identify the differentially expressed genes in INS-1 cells, the pathway of gene enrich the protective effect of C. daurica on oxidative stress. SOD activity and the content of MDA indicated that C. daurica could enhance the antioxidant capacity of INS-1 cells. Further investigation indicated C. daurica alleviate oxidative stress by inhibiting INS-1 cell apoptosis. C. daurica may play an anti-diabetic role by inhibiting islet cell apoptosis.

Phenylethanoid Glycosides from Cultivated Cistanche salsa

Introduction The plants of genus Cistanche G. Beck, which belong to Orobanchaceae family, include about twenty species, and there are four species and one variety are distributed in the northwest part of China. The dried fleshy stem of Cistanche genus plant known as ＇Roucongrong＇ in Chinese traditional medicine, has long been used for kidney deficiency, female infertility, morbid leucorrhea, and neurasthenia. Studies on active components and pharmacological activities show that it possesses significant activities in enhancing potency, anti-fatigue, immuno-modulability, etc, and phenylethanoid glycosides are the major active components. Due to excessive exploitation, its natural resources are facing with exhaustion. In order to improve this situation, the plant has been cultivated on a large scale in the northwest part of China. Up to now, the chemical investigations of the cultivated Cistartcbe salsa have not been undertaken. In this paper we report seven phenylethanoid glycosides from the cultivated Cistanche salsa： echinacoside （1）, cistanoside A （2）, acteoside （3）, isoacteoside （4）, 2＇-acetylacteoside （5）, tubuloside B （6）, and eutigoside A （7）. Among them, compound 7 isolated fronl family Orobanchaceae was reported previously, and compounds 1, 2, 3, 4, 5 and 6 from the cultivated Cistanche salsa are reported for the first time.

Verbascoside—A Review of Its Antitumor Activities

Cancer is a set of diseases including abnormal growth of cells that can spread to another tissue. Verbascoside (or acteoside) is a naturally occurring, water-soluble secondary metabolite with significant biological properties, which is distributed widely in plant kingdom. Verbascoside is pharmacologically active compounds with many recent evidences that support its biological activities and safety. This review focuses on the recent studies that concerned with the antitumor activities of verbascoside alone and as a synergistic agent as well as nanoproduct. It also shows the latest advances in its antitumor effects, cytotoxic selectivity and its efficiencies in treating cancer, in vitro and/or vivo.

Isolation and purification of phenylethanoid glycosides from plant extract of Plantago asiatica by high performance centrifugal partition chromatography

Two phenylethanoid glycosides （PhGs） were isolated and purified from the aerial parts of Plantago asiatica for the first time by high performance centrifugal partition chromatography （HPCPC） using ethyl acetate-n-butanol-ethanol-water （0.5：0.5：0.1：1, v/v/v/v）. A total of 45.6 mg of compound 1 and 293.8 mg of compound 2 were purified from 1341 mg of the n-butanol extract of P. asiatica. The structures of the two PhGs were tentatively identified as plantamajoside and aeteoside or isoacteoside by eleetrospray ionization multi stage tandem mass spectrometry （ESI-MS^n） in the negative ion mode.

Two new phenylethanoid glycosides and a new secoiridoid glycoside from the roots of Picrorhiza scrophulariiflora

Two new phenylethanoid glycosides,named scroside H（1）,scroside I（2）,and a new secoiridoid glycoside,named picrogentioside I（3）,have been isolated from the underground parts of Picrorhiza scrophulariiflora.Their structures were elucidated on the basis of spectroscopic evidence.

A new phenylethanoid glycoside from Rabdosia lophanthoides(Buch.-Ham.ex D.Don) Hara.

A new phenylethanoid glycoside, 3-hydroxy-4-methoxy-β-phenylethoxy-O-α-L-rhamnopyranosyl-（1 → 3）-2-O-acetyl-O-β-D- glucopyranoside, named lophanthoside A, was isolated from Rabdosia lophanthoides （Buch.-Ham.ex D.Don） Hara. Its structure was determined by spectroscopic evidences.

Efficacy of verbascoside,echinacoside,crenatoside on altitudeinduced fatigue in rats and possible mechanism

OBJECTIVE:To study the efficacy and mechanism of three phenylethanoid glycosides(PhG s)(verbascoside,echinacoside,and crenatoside)on altitude-induced fatigue in rats.METHODS:Altitude-induced fatigue model rats were established in a large hypobaric chamber.Swimming time,energy storage substances,metabolic enzymes,and metabolites were used to evaluate the anti-fatigue activities and mechanism of three PhG s(verbascoside,echinacoside,and crenatoside)(150 mg/kg,intragastric administration)in the hypoxic environment.RESULTS:The three PhGs,especially verbascoside,could prolong the swimming time of rats,ameliorate the edema and inflammatory infiltration of liver and skeletal muscle,increase the level of energy storage substances,reduce the decomposition of proteins,and exhibit positive effects on the metabolism-related enzyme activity and metabolites.CONCLUSIONS:The PhG s,especially verbascoside,are very potential with anti-fatigue activity in hypoxia.The mechanism may be explained with regulation of energy metabolism and reduction of oxidative stress.

Phenolic glycosides from Boschniakia himalaica

Two new phenylethanoid glycosides,himalosides A（1） and B（2）,were isolated from the whole plant of Boschniakia himalaica, together with four known compounds.Their structures were elucidated on the basis of spectral and chemical evidences.Himaloside A（1） and（＋）-lariciresinol 4＇-O-β-D-glucopyranoside（4） exhibited antibacterial activity with the MIC values at 50 and 25μg/mL against Staphylococcus aureus and S.epidermidis,respectively.

Application of ~1H NMR-based metabolomics for discrimination of different parts and development of a new processing workflow for Cistanche deserticola

Cistanche deserticola(CD) is one of the two authoritative source plants of Cistanches Herba, a well-known medicinal plant. Herein,~1H NMR spectroscopy was employed to characterize the chemical profile and to distinguish the different parts, as well as to propose a new processing workflow for CD.Signal assignment was achieved by multiple one and two dimensional NMR spectroscopic techniques in combination with available databases and authentic compounds. The upper parts of the plant were distinguished from the lower parts by combining ~1H NMR spectroscopic dataset with multivariate statistical analysis. A new processing method that hyphenated steaming with freeze-drying, was demonstrated to be superior to either steaming coupled with oven-drying or direct freeze-drying via holistic ~1H NMR-based metabolomic characterization. Phenylethanoid glycosides, mainly echinacoside and acteoside, were screened out and confirmed as the chemical markers responsible for exhibiting the superiority of the new processing workflow, whereas serial primary metabolites, especially carbohydrates and tricarboxylic acid cycle metabolites, were found as the primary molecules governing the discrimination between the upper and lower parts of the plant. Collectively,~1H NMR spectroscopy was demonstrated as a versatile analytical tool to characterize the chemical profile and to guide the indepth exploitation of CD by providing comprehensive qualitative and quantitative information.

Simultaneous determination of five phenylethanoid glycosides in Cistanches Herba using quantitative analysis of multi-components by single marker

In the present study, a method for the quantitative analysis of multi-components by single marker(QAMS) has been developed and validated for the simultaneous determination of echinacoside(ECH), tubuloside A, acteoside, isoacteoside, and2’-acetylacteoside in Cistanches Herba. ECH was used as the internal standard(IS) to obtain the relative correction factors(RCFs) of the other four phenylethanoid glycosides(PhGs);meanwhile, various influencing factors on RCFs were investigated under different conditions. The content of each component was calculated with RCF. The results were compared with those obtained by the external standard method(ESM) to verify the feasibility and accuracy of the established QAMS method. No significant difference was found in the quantitative results of 10 batches of Cistanches Herba between QAMS and ESM. The proposed QAMS method for simultaneous determination of PhGs in Cistanches Herba is accurate and feasible, providing an efficient and economical approach for the quality control of Cistanches Herba.

Effects of feeding tyrosine and phenylalanine on the accumulation of phenylethanoid glycosides to Cistanche deserticola cell suspension culture

AIM: To investigate the effects of feeding phenylalanine(Phe) and tyrosine(Tyr) on the accumulation of total phenolic compounds and four phenylethanoid glycosides(PeGs) to a cell suspension culture of the parasitic plant Cistanche deserticola. METHOD: A cell suspension culture of C. deserticola was established and precursors of different concentrations were fed. In each group, the cell was sampled at the 24th day after inoculation. The content of total phenolic compounds and four PeGs compounds were determined using the Folin-Ciocalteu method and an HPLC method, respectively. RESULTS: In the Phe fed cells, the maximum PeGs yield was achieved when Phe was fed at 1.5 mmol·L-1 and the yield reached 1.13 times the control cell concentration. In the Tyr fed cells, the maximum yield of PeGs was 1.60 times of control when 0.75 mmol·L-1 Tyr was fed to the cells. Furthermore, it was found that the salidroside yield was 4.01 times of control group when 5 mmol·L-1 Tyr was fed. CONCLUSION: Tyr is a better precursor for PeGs accumulation compared with Phe, and the rate limiting enzymes might be involved in the Tyr branch.

Phenylethanoid Glycosides from Picria felterrae Lour.

Abstract: In our search for bioactive compounds from the whole plant of Picria felterrae Lour., three new phenylethanoid glycosides, picfeosides A-C (1-3), along with five known phenylethanoid glycosides, namely wiedemannioside (4), acteoside (5), acteoside isomer (6), cis-acteoside isomer (7), and cis-acteoside (8), were isolated using several chromatographic purification steps, including semipreparation HPLC on RP-18. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analysis.

A new phenylethanoid glycoside from Isodon sculponeatus

A new phenylethanoid glycoside,seulponisidc（1） was isolated from the aerial parts of Isodon sculponeatus（Vaniot） Kudo, along with six known compounds martynoside（2）,verbascoside（3）,（＋）-hydroxypinoresinol-8-O- β-D-glucoside（4）,cedrusin（5）, 7-megastigmene-3S,5R,6R,7E,9S-tetrol（6） and 4-oxo- β-ionol- β-D-glucopyranoside（7）.Their chemical structures were elucidated from physieochemical data and by acidic hydrolysis.

Forsythosides as Essential Components of Forsythia-based Traditional Chinese Medicines Used to Treat Inflammatory Diseases and COVID-19

The dried fruits of the plant Forsythia suspensa(Forsythia Fructus: Lianqiao in Chinese) are used in many herbal preparations to treat various diseases or the associated symptoms. Forsythia extracts contain phenylethanoid glycosides(Ph Gs) such as the forsythosides(Fst A-to-P). The leading products, Fst-A,-B and-F(arenarioside), can be found also in >90 other plants inventoried here. The pharmacological properties of Fst are reviewed, with emphasis on their anticancer, antiviral, and antibacterial activities, which essentially derive from their anti-inflammatory and antioxidant effects. Fst-B functions as a potential binder of the repressor protein Kelch-like ECH-association protein 1(Keap 1), thus promoting the nuclear translocation of the transcription factor Nuclear factor erythroid 2-related factor 2(Nrf2) implicated in the subsequent activation of the production of antioxidant enzymes and repression of the oxidative stress. The regulation of the Nrf2/Heme oxygenase-1 pathway is the central piece of the multifaceted mechanism of action of Fst-A/B. Their prominent antioxidant and anti-inflammatory effects support the use of these compounds in different inflammation-related diseases and conditions, from sepsis to neuroprotection and many other pathologies discussed here. In addition, these properties contribute to the antiviral action of the compounds. Fst-A/B displays activities against the influenza A virus and different Fst-containing traditional Chinese medicinal(TCMs) have revealed beneficial effects to combat the current COVID-19 pandemic. The mechanisms whereby Fst-A/B could inhibit viral multiplication are discussed. Ph Gs likely contribute to the anti-COVID-19 activities reported with several TCM such as Shuang-Huang-Lian oral liquid, Lianhua-Qingwen capsules, and others. This review highlights the pharmacological profile of Fst and illustrates health benefits associated with the use of Forsythia Fructus.