New apiose-containing triterpenoid saponins from Conyza blinii

Su, Yi; Koike, Kazuo; Guo, Dan; Satou, Tadaaki; Liu, Jiansheng; Zheng, Jie; Nikaido, Tamotsu

doi:10.1016/s0040-4020(01)00632-9

Cited by 34 publications

(23 citation statements)

References 4 publications

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“…T5 has the same aglycone as T4 and on the basis of chemotaxonomic considerations the structure of bayogenin disaccharide was proposed for T5 . The foregoing data in conjunction to those found in the literature allowed the identification of T5 structure as conyzasaponin G (chemical name: bayogenin 3‐ O ‐β‐ d ‐xylopyranosyl‐(1 → 3)‐β‐ d ‐glucopyranoside) formerly obtained from Conyza blini (Su et al, ). Two further fragments to support the proposed structure were obtained at m/z 631.3828 (C 36 H 55 O 9 − ) and 439.3218 (C 29 H 43 O 3 − ) resulting to the loss of (C 5 H 8 O 4 and H 2 O) and (C 5 H 8 O 4 , C 6 H 10 O 5 , H 2 O and H 2 CO), respectively (Fig.…”

Section: Resultssupporting

confidence: 77%

ESI‐MS² and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS² Search of Related Metabolites from Donella ubanguiensis

Sandjo

Nascimento

Silva

et al. 2016

Phytochemical Analysis

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Section: Resultssupporting

confidence: 77%

ESI‐MS² and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS² Search of Related Metabolites from Donella ubanguiensis

Sandjo

Nascimento

Silva

et al. 2016

Phytochemical Analysis

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“…7,8) A b-configuration of the anomeric center of the apiose was determined by the comparison of the 13 C-NMR data for 1 with those for a-and b-D-apiofuranosides, 9) and the J H-1,H-2 coupling constant of the apiose was similar to the reported data of b-D-apiofuranoside. 10) The sugar sequences of the oligosaccharide chains as well as the glycosidic sites were subsequently determined by a combination of HSQC and HMBC experiments ( In the HMBC spectrum of 1 (Fig. 2), the correlations could be achieved between the anomeric proton of apiose at d H 6.07 (d, Jϭ4.5 Hz) and C-3ٞ of rhamnose at d 82.2, as well as between H-3ٞ (d H 4.67) of rhamnose and the anomeric carbon of apiose at d 111.6, which supported the terminal apiose attached to C-3ٞ of rhamnose.…”

mentioning

confidence: 99%

Two New Triterpenoid Saponins Isolated from Polygala japonica

Wang

Gao

Zhu

et al. 2006

CHEMICAL & PHARMACEUTICAL BULLETIN

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Polygala japonica HOUTT. (Polygalaceae) widely distributes in Asian, primarily in eastern China. It has long history of using P. japonica in traditional Chinese medicines for the treatment of various inflammatory disorders, such as acute tonsillitis, pharyngitis, myelitis and nephritis. 1) Our bioassay guided investigation of P. japonica has showed that the methanol (MeOH) extract have significant anti-inflammation effect against carrageenan-induced mouse paw edema, and the ethyl acetate (EtOAc) and n-butanol (n-BuOH) fractions from it are the main active fractions. Our efforts further extended to isolate and identify the bioactive compounds in these fractions, which will support the wide utility of P. japonica in traditional Chinese medicines. We have isolated and elucidated two new triterpenoid saponins (1, 2), along with four known triterpenoid saponins, 4) and tenuifolin (6). 5) The structures of the known compounds were elucidated by comparison of their physical and spectral data with literature values. We report herein the isolation and structure elucidation of two new triterpenoid glycosides as well as the anti-inflammatory activity using the carrageenan-induced mouse paw edema for all the isolated saponins ( Fig. 1).Saponin 1 was obtained as a white amorphous powder, and assigned a molecular formula of C 58 H 92 O 28 , as deduced from HR-ESI-MS and 13 C-NMR (Table 1) (d H 5.43, t-like). Additionally, the 13 C-NMR spectra displayed six methyl groups, five anomeric carbons, and two olefinic carbons. A detailed comparison between 1 and the reference data of medicagenic acid, 6) a major aglycone present in this plant, implied that 1 possessed of the aglycone of medicagenic acid.

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“…isolated from the aerial parts of Conyza blinii exhibited moderate cytotoxicities against the cancer cell line HL-60 with IC 50 values of 3.8 and 3.9 mm, respectively, compared with the positive control drugs, etoposide (IC 50 0.28 mm) and CP DD (IC 50 0.20 mm) [252]. The aerial parts of the plant is used in Chinese folk medicine for treatment of inflammatory diseases like chronic bronchitis [504].…”

Section: Acacia Concinnamentioning

confidence: 99%

Naturally Occurring Triterpenoid Saponins

Dinda

Debnath²,

Mohanta

et al. 2010

Chemistry & Biodiversity

132

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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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New apiose-containing triterpenoid saponins from Conyza blinii

Cited by 34 publications

References 4 publications

ESI‐MS² and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS² Search of Related Metabolites from Donella ubanguiensis

ESI‐MS² and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS² Search of Related Metabolites from Donella ubanguiensis

Two New Triterpenoid Saponins Isolated from Polygala japonica

Naturally Occurring Triterpenoid Saponins

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New apiose-containing triterpenoid saponins from Conyza blinii

Cited by 34 publications

References 4 publications

ESI‐MS2 and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS2 Search of Related Metabolites from Donella ubanguiensis

ESI‐MS2 and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS2 Search of Related Metabolites from Donella ubanguiensis

Two New Triterpenoid Saponins Isolated from Polygala japonica

Naturally Occurring Triterpenoid Saponins

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Product

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ESI‐MS² and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS² Search of Related Metabolites from Donella ubanguiensis

ESI‐MS² and Anti‐inflammatory Studies of Cyclopropanic Triterpenes. UPLC‐ESI‐MS and MS² Search of Related Metabolites from Donella ubanguiensis