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 d...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.展开更多
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-...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.展开更多
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 ...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.展开更多
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 ...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.展开更多
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...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.展开更多
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-...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.展开更多
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 t...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.展开更多
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 pl...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.展开更多
Phenylethanoid glycosides(PhGs)are a group of important natural products widely distributed in medicinal plants and known for their remarkable pharmacological properties.Uridine diphosphate(UDP)glycosyltransferase 79G...Phenylethanoid glycosides(PhGs)are a group of important natural products widely distributed in medicinal plants and known for their remarkable pharmacological properties.Uridine diphosphate(UDP)glycosyltransferase 79G15(UGT79G15)from Rehmannia glutinosa catalyzes the conversion of osmanthuside A to osmanthuside B,a key intermediate in the PhG biosynthetic pathway,through the formation of a(1→3)glycosidic bond.In this study,we present the crystal structures of UGT79G15 in its apo form,UDP-bound form,and,notably,its ternary complex containing UDP and a mimic acceptor,forsythiaside A,within its active site.Structural and comparative analyses revealed that UGT79G15 possesses a distinctive funnel-shaped acceptor-binding pocket with a small auxiliary cavity capable of accommodating the 4′-hydroxycinnamoyl group of PhGs,explaining the enzyme’s regiospecificity toward the 3′-OH of the acceptor.Additional structural examination and site-directed mutagenesis identified key residues that recognize and stabilize UDP-rhamnose and the sugar acceptor.Among the variants generated,I204W exhibits enhanced catalytic efficiency for osmanthuside A conversion,reaching up to 2.2-fold higher activity than the wild type.This study provides mechanistic insight into the donor specificity and acceptor regioselectivity of PhG 1,3-rhamnosyltransferase and expands the structural understanding of plant UGTs.展开更多
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 wiede...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.展开更多
文摘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.
基金supported by funding from Jilin Province (No.20060904-1 and 20071102).
文摘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.
基金supported by National Natural Science Foundation of China(No.30800835)National Key Project of Scientific and Technical Supporting Programs funded by Ministry of Science & Technology of China(No. 2006BAD31B05)
文摘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.
基金supported by the Key Science-Technology Project of the National '11th Five-Year Plan' of China(No.2006BAI06A15-3).
文摘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.
基金National Key R&D Program of China(Grant Nos.2017YFC1702400,2018YFC1707300 and 2018YFC1707904)
文摘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.
基金supported financially by the NSFC(Nos.30772637 to H.D.Sun,and 30830119 to S.J.Chen)the NSFC-Joint Foundation of Yunnan Province(No.U0832602 to H.D.Sun)+2 种基金the Major State Basic Research Development Program of China(No.2009CB522300 and 2009CB940900)the Natural Science Foundation of Yunnan Province(No.2008CD162)the Science and technology plan project of Yunnan Province(No. 2008IF010)
文摘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.
基金funded by the National Natural Science Foundation of China (81760776)the Natural Science Foundation of Inner Mongolia Autonomous Region (2018ZD13)+2 种基金the Natural Science Foundation of Inner Mongolia Autonomous Region (2020MS08070)Science and technology development projects in key areas of Baotou science and technology plan (2020Z1016-3)Natural Science Foundation Project of Inner Mongolia Autonomous Region (2021MS03025)。
文摘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.
文摘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.
基金supported by the National Key Research and Development Program(2020YFA0907800)the Innovation Fund of Haihe Laboratory of Synthetic Biology(22HHSWSS00023)+3 种基金the Science and Technology Program of Tianjin(24ZYJDSS00300)the National Natural Science Foundation of China(31970065)the Tianjin Synthetic Biotechnology Innovation Capacity Improvement Project(TSBICIP-PTJJ-007-07)the Competitive Support Program of the Tianjin Institute of Industrial Biotechnology,Chinese Academy of Sciences(JZ2024-037).
文摘Phenylethanoid glycosides(PhGs)are a group of important natural products widely distributed in medicinal plants and known for their remarkable pharmacological properties.Uridine diphosphate(UDP)glycosyltransferase 79G15(UGT79G15)from Rehmannia glutinosa catalyzes the conversion of osmanthuside A to osmanthuside B,a key intermediate in the PhG biosynthetic pathway,through the formation of a(1→3)glycosidic bond.In this study,we present the crystal structures of UGT79G15 in its apo form,UDP-bound form,and,notably,its ternary complex containing UDP and a mimic acceptor,forsythiaside A,within its active site.Structural and comparative analyses revealed that UGT79G15 possesses a distinctive funnel-shaped acceptor-binding pocket with a small auxiliary cavity capable of accommodating the 4′-hydroxycinnamoyl group of PhGs,explaining the enzyme’s regiospecificity toward the 3′-OH of the acceptor.Additional structural examination and site-directed mutagenesis identified key residues that recognize and stabilize UDP-rhamnose and the sugar acceptor.Among the variants generated,I204W exhibits enhanced catalytic efficiency for osmanthuside A conversion,reaching up to 2.2-fold higher activity than the wild type.This study provides mechanistic insight into the donor specificity and acceptor regioselectivity of PhG 1,3-rhamnosyltransferase and expands the structural understanding of plant UGTs.
文摘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.
