Studies on the Constituents of Clematis Species. VII. Triterpenoid Saponins from the Roots of Clematis terniflora DC. var. robusta TAMURA.

Kawata, Yukio; Kizu, Haruhisa; Tomimori, Tsuyoshi

doi:10.1248/cpb.46.1891

Cited by 32 publications

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“…The β configuration for D-ribose could be established by comparison of the NMR data with those reported in the literatures. 16,17) The sequences and linkage positions of sugar moieties were subsequently deduced from an HMBC experiment. In the HMBC spectrum of 1, the correlations between H-1 (δ H 5.95) of D-ribose and C-3 (δ C 81.1) of L-rhamnose 1 , between H-1 (δ H 6.30) of L-rhamnose 1 and C-2 (δ C 75.8) of L-arabinose, between H-1 (δ H 5…”

Section: Resultsmentioning

confidence: 99%

“…The 50% EtOH and 70% EtOH eluates were further purified by repeated column chromatography over middle chromatogram isolated (MCI) gel, octadecyl silica (ODS), silica gel and preparative HPLC to afford eight new bisdesmosidic triterpenoid saponins (1)(2)(3)(4)(5)(6)(7)(8), named as clematiunicinosides A-H, as well as eleven known ones (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19).…”

Section: Resultsmentioning

confidence: 99%

“…16,17,[19][20][21][22][23] The cytotoxic activities of all the saponins, as well as their aglycones oleanolic acid and hederagenin against Caski cells were evaluated in this study. Aglycones and most of the saponins did not show obvious effects under the higher concentration of 80 µM with the exception of compounds 13, 17 and 19 (Table 3).…”

Section: Resultsmentioning

confidence: 99%

“…The plant Clematis uncinata is mainly distributed in southern China, such as Guizhou, Zhejiang, Fujian, Guangdong and Guangxi provinces. 13) The blank in chemical constituent, the potential medicinal importance and our interest in the chemistry of saponins prompted us to carry out a phytochemical investigation on this plant, which led to the isolation of eight new bisdesmosidic triterpenoid saponins, clematiunicinosides A-H (1-8), together with eleven known ones (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). In addition, the cytotoxic effects of the isolated triterpenoid saponins on Caski cells were evaluated.…”

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Triterpenoid Saponins from the Roots of <i>Clematis uncinata</i>

Huang

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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Eight new bisdesmosidic triterpenoid saponins, clematiunicinosides A-H (1-8), along with eleven known ones (9-19), were isolated from the roots of Clematis uncinata. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence. All the isolated saponins were tested for their cytotoxic activities on human caski cervical cancer (Caski) cells, and compounds 13, 17 and 19 exhibited inhibitory effect on Caski cells. Key words triterpenoid saponin; Clematis uncinata; RanunculaceaeThe genus Clematis, belonging to the family Ranunculaceae, comprises of more than 300 species distributed throughout the world.1) Three plants of this genus (Clematis chinensis OSBECK, C. hexapetala PALL., and C. mandshurica RUPR.) are officially used as "Weilingxian," a traditional Chinese herbal drug, for the treatment of inflammation and cancer in China. 2)Previous phytochemical investigations had demonstrated that triterpenoid saponins are the dominant constituents of this genus.3) Some of them showed significant anti-inflammatory and antitumor activities. [4][5][6][7] During the course of our ongoing program to search for new saponins from traditional Chinese medicine, [8][9][10][11][12] Clematis uncinata was selected as a subject for this study. The plant Clematis uncinata is mainly distributed in southern China, such as Guizhou, Zhejiang, Fujian, Guangdong and Guangxi provinces.13) The blank in chemical constituent, the potential medicinal importance and our interest in the chemistry of saponins prompted us to carry out a phytochemical investigation on this plant, which led to the isolation of eight new bisdesmosidic triterpenoid saponins, clematiunicinosides A-H (1-8), together with eleven known ones (9-19). In addition, the cytotoxic effects of the isolated triterpenoid saponins on Caski cells were evaluated. The present paper reports the isolation, structural elucidation and antiproliferative activities of these compounds. Results and DiscussionThe 70% (V/V) EtOH extract of the roots of C. uncinata was subjected to D101 macroporous resin column eluted successively with H 2 O, 10% EtOH, 30% EtOH, 50% EtOH and 70% EtOH. The 50% EtOH and 70% EtOH eluates were further purified by repeated column chromatography over middle chromatogram isolated (MCI) gel, octadecyl silica (ODS), silica gel and preparative HPLC to afford eight new bisdesmosidic triterpenoid saponins (1-8), named as clematiunicinosides A-H, as well as eleven known ones (9-19).Clematiunicinoside A (1) was obtained as an amorphous powder. It showed positive reactions to the LiebermannBurchard and Molish tests, which suggested that 1 might be a triterpenoid glycoside. The molecular formula of 1 was established as C 70 2, 104.8, 106.8, 102.7, 104.6, 95.6 and 101.3, respectively (Tables 1, 2). Acid hydrolysis of 1 afforded Dglucose, D-ribose, L-arabinose and L-rhamnose, which were identified by HPLC analysis.15) The relative anomeric configurations of the sugar moieties were determined to be β for the D-glucose (J=8.0 Hz) and α for the L-...

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Triterpenoid Saponins from the Roots of <i>Clematis uncinata</i>

Huang

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In the screening for PR inhibition, Clematis heracleifolia (15) showed the most potent inhibition (45.3%, at 100 mg/mL). Clematis species contain oleanolic acid derivatives (Kizu et al, 1995;Kawata et al, 1998), significant inhibitors of HIV protease (Kashiwada et al, 1998). It was suggested that the potent inhibitory activity of 15 might be due to these compounds.…”

Section: Discussionmentioning

confidence: 99%

Inhibitory effects of Korean plants on HIV‐1 activities

Min

Kim

Tomiyama

et al. 2001

Phytotherapy Research

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In the search for novel anti-human immunodeficiency virus type 1 (anti-HIV-1) agents from natural sources, 49 MeOH extracts of Korean plants were screened for their inhibitory effects against RNA-dependent DNA polymerase (RT) and ribonuclease H (RNase H) activities of HIV-1 reverse transcriptase and HIV-1 protease, and anti-HIV-1 activity. Regarding the HIV-1 reverse transcriptase, Agrimonia pilosa (whole plant), Cornus kousa (stem and leaf), Limonium tetragonum (root) and Mallotus japonicus (stem) showed significant inhibitory activity on RT activity with 50% inhibitory activity (IC(50)) of 8.9, 6.3, 7.5 and 11.9 microg/mL, respectively, whereas Agrimonia pilosa was also active against RNase H activity (IC(50) = 98.4 microg/mL). Four plants, namely Agrimonia pilosa (whole plant), Atractylodes japonica (root), Clematis heracleifolia (whole plant) and Syneilesis palmata (whole plant), were appreciably active (<35%) against recombinant HIV-1 protease at a concentration of 100 microg/mL. Crinum asiaticum var. japonicum (root) showed significant anti-HIV-1 activity (ED(50) = 12.5 microg/mL) with a favourable SI value of 16.

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Naturally Occurring Triterpenoid Saponins

Dinda

Debnath²,

Mohanta

et al. 2010

Chemistry & Biodiversity

133

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Naturally occurring new triterpenoid saponins reported from mid-1996 to March, 2007 are reviewed including their physical constants and plant sources, and are compiled in Table 1. New saponins are arranged in Table 1 on the basis of the skeletal structures of their aglycones, e.g., oleanane type, ursane type, lupane type, hopane type, taraxastane type, cycloartane type, lanostane type, tirucallane type, dammarane type, cucurbitane type, and holostane type. The known triterpenoid saponins and prosapogenins of the new saponins, the biological and pharmacological activities of which were published during 1996-2007, are also reviewed together with their plant sources listed in Table 2 according to the skeletal structures of their aglycones in the same fashion as in Table 1. The plant and animal sources of both new and known bioactive triterpenoid saponins are collected in Table 3 in alphabetical order. The biological and pharmacological activities such as antiallergic, antiatherosclerosis and antiplatelet, antibacterial, anticomplementary, antidiabetic, contraceptive, antifungal, anti-inflammatory, antileishmanial, antimalarial/antiplasmodial, anti-obesity, anti-proliferative, antipsoriatic, antispasmodic, antisweet, antiviral, cytotoxic/antitumor, detoxication, gastroprotective, haemolytic, hepatoprotective, immunomodulatory, anti-enzyme, anti-osteoporotic, insecticidal, insulin-like, membrane-porosity, molluscicidal, neuropharmacological, anti-endothelial dysfunction, snake venom antidote, and sweet activities of these saponins or derived prosapogenins are discussed briefly after Table 3.

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Studies on the Constituents of Clematis Species. VII. Triterpenoid Saponins from the Roots of Clematis terniflora DC. var. robusta TAMURA.

Cited by 32 publications

References 0 publications

Triterpenoid Saponins from the Roots of <i>Clematis uncinata</i>

Triterpenoid Saponins from the Roots of <i>Clematis uncinata</i>

Inhibitory effects of Korean plants on HIV‐1 activities

Naturally Occurring Triterpenoid Saponins

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