Investigation of Rhubarbs. III. New Purgative Constituents, Sennosides E and F

Oshio, Haruji; Imai, Shunji; Fujioka, Shoji; Sugawara, Tohru; Miyamoto, Masaomi; Tsukui, Makoto

doi:10.1248/cpb.22.823

Cited by 37 publications

(16 citation statements)

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“…Although only six sennosides have been reported from Rheum species°(sennosides°A-F)°so°far° [24],°a°total°of°28 analogs (S1-S28) were identified in this study by LC/MS from Sect. Palmata species, i.e., R. officinale, R. palmatum, and R. tanguticum.…”

Section: Identification Of Sennosides In Rhubarbsmentioning

confidence: 74%

Analysis of phenolic compounds in rhubarbs using liquid chromatography coupled with electrospray ionization mass spectrometry

Han

Chen

et al. 2007

J. Am. Soc. Mass Spectrom.

227

157

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Rhubarb is an important herbal medicine for the treatment of constipation, inflammation, and cancer. In this study, a facile method based on liquid chromatography coupled with electrospray ionization tandem mass spectrometry has been established for the analysis of bioactive phenolic compounds in rhubarbs. From six rhubarb species, official (Rheum officinale, R. palmatum, and R. tanguticum) and unofficial (R. franzenbachii, R. hotaoense, and R. emodi), a total of 107 phenolic compounds were identified or tentatively characterized based on their mass spectra. These compounds include sennosides, anthraquinones, stilbenes, glucose gallates, naphthalenes, and catechins. Ion chromatograms for the identified compounds of different rhubarbs were then compared. Consistent with previous reports, sennosides and rhein were only detected in official rhubarbs. Unexpectedly, we found that R. officinale contained very different phenolic compounds from the other two official species. Sennoside A, which has been considered as the major purgative component of rhubarb, was only detected in R. officinale, while its close isomers were observed in R. palmatum and R. tanguticum. In addition, the predominant anthraquinone glycosides in R. officinale were found to be rhein 8-O-glucoside and emodin 1-O-glucoside, whereas those in R. palmatum and R. tanguticum were rhein 1-O-glucoside and emodin 8-O-glucoside. Stilbenes, which are the major constituents of unofficial rhubarbs, were also different among the species. Our results clarify the chemical composition of rhubarbs comprehensively for the first time. Due to the significant differences in chemical components of rhubarbs, we suggest that different Rheum species be used separately in clinical practice. (J Am Soc Mass Spectrom 2007, 18, 82-91)

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Section: Identification Of Sennosides In Rhubarbsmentioning

confidence: 74%

Analysis of phenolic compounds in rhubarbs using liquid chromatography coupled with electrospray ionization mass spectrometry

Han

Chen

et al. 2007

J. Am. Soc. Mass Spectrom.

227

157

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“…Standard Compounds Anthraquinones (1-5), anthraquinone glucosides (6-10), dianthrones (11,12), phenylbutanones (13,14), stilbenes (15, 16), flavan-3-ols (17, 18), procyanidins (19,20), galloylglucoses (21)(22)(23)(24), acylglucoses (25)(26)(27) and gallic acid (28) were isolated from the rhubarb sample (TMPW no. 19929), and are listed in Fig.…”

Section: Methodsmentioning

confidence: 99%

“…[23][24][25][26][27][28][29][30][31][32][33][34][35] Purification of RG-Tannin (29) and Rhatannin (30) Rhubarb powder (1 kg) was extracted with 8 l of acetone-water (4 : 1, v/v) three times at room temperature. Combined extracts were evaporated in vacuo and lyophilized to get the final extract (345 g).…”

Section: Methodsmentioning

confidence: 99%

Development of a High Performance Liquid Chromatographic Method for Systematic Quantitative Analysis of Chemical Constituents in Rhubarb

et al. 2006

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Rhei Rhizoma (rhubarb), called Daio in Japanese, is one of the important herbal drugs. To date, qualitative analysis of its typical laxative components, anthraquinone derivatives including sennoside A, has been used for the qualitative evaluation of rhubarb by means of several analytical methods. 1)However, such evaluation is incomplete because rhubarb has been used for the treatment of "Oketsu" (various syndromes caused by the obstruction of blood circulation such as dysmenorrhoea, hypermenorrhea, hematemesis, lower abdominal pain, etc.), jaundice, diarrhea and food poisoning, in addition to constipation. Although various individual pharmacological effects related to the above treatments, such as purgative activity, 2,3) anti-bacterial and anti-fungal activities, 4) anti-tumor activity, 5) anti-inflammatory and analgesic activities, 6,7) improvement of renal disorders, [8][9][10][11] improvement of nitrogen metabolism, 12,13) psychotropic activity, 14) anti-allergic effects, 15,16) anti-cholera toxin activity, 17,18) promoting blood circulation and removing blood stasis, 19) and the various involved active compounds have been reported, comprehensive chemical study of the composition of bioactive constituents of rhubarb has been rare. Kashiwada et al. 20) set up a HPLC method to analyze almost all the phenolic compounds simultaneously, and reported that the majority of the compounds could be separated by a 0.05 M H 3 PO 4 solution-acetonitrile gradient elution system. However, several compounds, i.e. procyanidin B-1 3-Ogallate and 1,2,6-trishowed overlapping peaks. In addition, polymeric procyanidins, i.e. RG-tannin and rhatannin, showed serious band broadening and tailing. Therefore, it is still necessary to develop a HPLC method which can be used for the effective separation and quantitative determination of the active components, which would then be used to evaluate the quality of rhubarb samples.In this study, we developed new HPLC methods to analyze 30 compounds (1-30, Fig. 1) in rhubarb, quantitatively, and the contents of the active components were compared in rhubarb samples of different botanical origins. ExperimentalMaterials Three Rhei Rhizoma samples derived from the following species were quantitatively examined: rhizomes of R. tanguticum (Huangnan County, Qinghai Prov., TMPW no. 20065), R. palmatum (Jiulong County, Sichuan Prov., TMPW no. 20216) and R. officinale (Wanyuan County, Sichuan Prov., TMPW no. 20267). The botanical origins of each sample were correctly identified by the molecular biological methods previously reported. 21,22) The rhubarb sample (Qinghai Prov., TMPW no. 19929) used for the isolation of standard compounds was purchased from Uchida Wakanyaku Co., Ltd. (Japan). Voucher specimens have been deposited in the Museum of Materia Medica, Institute of Natural Medicine, University of Toyama (TMPW).Chemicals and Reagents Sephadex LH-20 (Amersham Biosciences, Sweden) and reversed phase gel MCI CHP-20P (70-150 mesh, Mitsubishi Chemical Co., Japan) were used for column chromatography. A...

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“…The isolated compounds were identified by comparison of their NMR and mass spectral data with those reported in the literature. [11][12][13][14][15][16][17][18][19][20][21][22][23][24] All chemicals were of analytical grade and chromatographic solvents HPLC grade.…”

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confidence: 99%