Norcarotenoids of Rehmannia glutinosa var. Hueichingensis

Sasaki, Hiroshi; Morota, Takashi; Nishimura, Hiroaki; Ogino, Tatsunori; Katsuhara, Takao; Sugama, Ko; Chin, Masao; Mitsuhashi, Hiroshi

doi:10.1016/0031-9422(91)85055-5

Cited by 41 publications

(26 citation statements)

References 11 publications

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“…On the other hand, the results obtained are in good accordance with the other references. The compound showed a significant dose dependent immunosuppressive activity in the spleen of mice (Sasaki et al, 1989). Also, the change in the cell structure of lymphocytes (Inoue et al, 1998a) and the decrease in the phagocytic activity of human neutrophilic granulocytes (Molnar et al, 1989) by in vitro studies as well as its cytotoxic (Saracoglu et al, 1995) and antioxidant (Miyase et al, 1991) activities confirm that verbascoside has a modulatory effect in the immune system.…”

Section: Resultsmentioning

confidence: 76%

In vitro Immunomodulatory activity of verbascoside from Nepeta ucrainica L.

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Ündeğer

et al. 2002

Phytotherapy Research

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Nepeta ucrainica L. is used as a herbal tea in Kazakhistan. Phytochemical investigations of the aerial parts of the plant resulted in the isolation of verbascoside (1) and 1,5,9-epi-deoxyloganic acid (2). The structures of the compounds were elucidated by spectral (UV, IR, (1)H-NMR and (13)C-NMR) methods and HPLC analysis. The in vitro immunomodulatory activity of verbascoside was investigated by assessing neutrophil function; chemotaxis and intracellular killing activity. Verbascoside showed an increased chemotactic activity in all doses applied compared with the medium used as a negative control and had a positive effect on respiratory burst of neutrophils, but there was an opposite effect with increasing doses, pointing to a possible suppression of neutrophil intracellular killing activity.

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Section: Resultsmentioning

confidence: 76%

In vitro Immunomodulatory activity of verbascoside from Nepeta ucrainica L.

Akbay

Çalış

Ündeğer

et al. 2002

Phytotherapy Research

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“…Resent investigations have demonstrated that chyrogi has anti-anoxia action (1), inhibitory action on hyarulonidase activity (2) and immunosuppressive action (3).…”

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confidence: 99%

Acteoside, a Component of Stachys Sieboldii MIQ, May Be a Promising Antinephritic Agent: Effect of Acteoside on Crescentic-Type Anti-GBM Nephritis in Rats.

et al. 1994

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ABSTRACT-Effectsof acteoside (ACT) on crescentic-type anti-GBM nephritis in rats were investigated. When rats were treated with ACT from the 1st day after i.v. injection of anti-GBM serum, ACT inhibited the elevation of protein excretion into urine. In the ACT-treated rats, cholesterol and creatinine contents and antibody production against rabbit r-globulin in the plasmas were lower than those of the nephritic control rats. Histological observation demonstrated that this agent suppressed hypercellularity and the incidence of crescent formation, adhesion of capillary wall to Bowman's capsule and fibrinoid necrosis in the glomeruli. Furthermore, rat-IgG and C3 deposits on the GBM were significantly less in the ACT-treated group than in the control nephritic group. When the treatment was started from the 20th day after i.v. injec tion of anti-GBM serum, by which the disease had been established, ACT resulted in a similar effect on the nephritic rats as stated above. These results suggest that ACT may be a useful medicine against rapidly pro gressive glomerulonephritis, which is characterized by severe glomerular lesions with diffuse crescents.

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“…2,3) A number of chemical constituents with diverse structures, including iridoids, [4][5][6][7][8][9][10][11][12][13] ionone glucosides, 14,15) sesquiterpenes, 16,17) phenylethanoid glycosides, 18,19) norcarotenoids, 20,21) cerebrosides, 12) carbohydrates, and others, [22][23][24][25][26] have been isolated from this plant. During our ongoing studies of bioactive constituents used in traditional Chinese medicines, we characterized the 70% EtOH extracts of the roots of Paeonia lactiflora [27][28][29][30][31] and Astragalus membranaceus, [32][33][34][35] and the aerial parts of Lonicera japonica, [36][37][38][39][40][41] and several constituents have been isolated and characterized from these extracts.…”

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confidence: 99%

“…Therefore, the aglycon should be aeginetic acid. 20,21,[52][53][54][55] Acid hydrolysis of 2 with 5% HCl gave an aglycon, aeginetic acid, 21) and D-quinovose as the sugar component identified on TLC and GC analyses by comparison with authentic sample. Given the above ob- C-NMR spectra of the compound suggested the presence of aeginetic acid quinovoside and an ajugol moiety of a 6-O-acylated ajugol derivative, 6-O-(4Љ-O-a-L-rhamnopyranosyl)vanilloyl ajugol, which was also isolated from the same plant, suggesting that 3 is an aeginetoyl ajugol quinovoside.…”

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confidence: 99%

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A New Polyoxygenated Triterpene and Two New Aeginetic Acid Quinovosides from the Roots of Rehmannia glutinosa

et al. 2011

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Rehmanniae Radix is the fresh or dry root of Rehmannia glutinosa LIBOSCH. (Scrophulariaceae). As officially listed in the Korean Pharmacopoeia, this herbal drug is to be used in dried form or after processing.1) The dry roots of R. glutinosa have been used in traditional Chinese medicine as an antipyretic and hemostatic.2,3) A number of chemical constituents with diverse structures, including iridoids, [4][5][6][7][8][9][10][11][12][13] ionone glucosides, 14,15) sesquiterpenes, 16,17) phenylethanoid glycosides, 18,19) norcarotenoids, 20,21) cerebrosides, 12) carbohydrates, and others, [22][23][24][25][26] have been isolated from this plant. During our ongoing studies of bioactive constituents used in traditional Chinese medicines, we characterized the 70% EtOH extracts of the roots of Paeonia lactiflora [27][28][29][30][31] and Astragalus membranaceus, [32][33][34][35] and the aerial parts of Lonicera japonica, [36][37][38][39][40][41] and several constituents have been isolated and characterized from these extracts. In the continuing search for new chemical and biomarkers from the medicinal plant R. glutinosa for quality control studies of related herbal medicines, a new polyoxygenated triterpene and two aeginetic acid quinovosides, together with other known components, were isolated. In the present investigation, we report the isolation and structure elucidation of a minor polyoxygenated triterpene named glutinolic acid (1) and two new aeginetic acid quinovosides (2, 3) from the roots of R. glutinosa cultivated in Korea. Results and DiscussionThe dried roots of R. glutinosa were crushed and extracted with 70% EtOH. The concentrated extract was suspended in H 2 O and successively extracted with EtOAc and BuOH. The EtOAc extract was added to 90% aqueous MeOH and extracted with hexane to give hexane and 90% MeOH extracts. The 90% MeOH extract was subjected to sequential column chromatography over silica gel, MCI gel and RP-18 gel to yield a new minor polyoxygenated triterpene named glutinolic acid (1) and two new aeginetic acid quinovosides (2, 3).Glutinolic acid (1) C-NMR data for 1 revealed the presence of one oxymethine carbon at d 71.3, two oxymethylene carbons at d 68.7 and 66.3, two oxygenated quaternary carbons at d 74.9 and 76.6, a carboxylic acid carbon at d 183.0, and an olefinic double bond (d 129.5, 139.5) supporting a pentahydroxy-urs-12-en-oic acid skeleton bearing an a-hydroxyl at C-19. Regarding the two hydroxyl groups and a carboxylic acid group on the D/E rings, two methyl groups on the D/E rings were transformed into the COOH and one CH 2 OH group, respectively. The latter group and the remaining hydroxyl group on the D/E rings were assigned at C-20 due to its quaternary nature. A comparison of the 13 C-NMR spectra of 1 and 3b,19a,23,30-tetrahydroxyurs-12-en-28-oic acid (30-hydroxyrotundic acid) 28-O-glucoside 44) showed the expected downfield shifts for absorption due to C-20 (ϩ28.4 ppm) and C-30 (ϩ3.8 ppm), and upfield shifts for C-18 (Ϫ4.8 ppm), C-22 (Ϫ5.0 ppm), and C-29 (Ϫ4.7 ppm) due to t...

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Norcarotenoids of Rehmannia glutinosa var. Hueichingensis

Cited by 41 publications

References 11 publications

In vitro Immunomodulatory activity of verbascoside from Nepeta ucrainica L.

In vitro Immunomodulatory activity of verbascoside from Nepeta ucrainica L.

Acteoside, a Component of Stachys Sieboldii MIQ, May Be a Promising Antinephritic Agent: Effect of Acteoside on Crescentic-Type Anti-GBM Nephritis in Rats.

A New Polyoxygenated Triterpene and Two New Aeginetic Acid Quinovosides from the Roots of Rehmannia glutinosa

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