Two New Biologically Active Triterpenoidal Saponins Acylated with Salicylic Acid from <i>Albizia adianthifolia</i>

Haddad, Mohamed; Miyamoto, Tomofumi; Laurens, Véronique; Lacaille‐Dubois, Marie‐Aleth

doi:10.1021/np020391q

Cited by 77 publications

(91 citation statements)

References 24 publications

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“…The best combination was found to be with ginsenosides isolated from Achyranthes bidentata. 54 Similar effects have also been observed for saponins isolated from Albizia adianthifolia, 55,56 for which the reported effects have been found to be highly structure-dependent. This was illustrated for Muraltia heisteria, where only two of four isolated saponins exhibited toxicity-enhancing properties.…”

Section: Tumor-suppressive Effects Of Saponinssupporting

confidence: 64%

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Thakur¹,

Melzig²,

Fuchs³

et al. 2011

BTAT

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Saponins are bioactive compounds produced mainly by plants but also by some marine organisms and insects. In the recent past, there has been unforeseen interest in the clinical utilization of saponins as chemotherapeutic agents. The research on saponins in various forms as a treatment for cancer has generated a lot of potential. The advent of nanotechnology and the cytotoxicity enhancing properties of saponins are some of the highlights of the current decade. This review gives an updated overview of the clinical potential that saponins hold as cytotoxic agents, and covers the literature for 1957-2011, with the main focus on research conducted in the last decade. It is conceivable that saponins hold a lot of therapeutic potential and could be a lead for identification of synthetic or semisynthetic molecules for the treatment of cancer via membrane-mediated or transport-mediated pathways.

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Section: Tumor-suppressive Effects Of Saponinssupporting

confidence: 64%

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Thakur¹,

Melzig²,

Fuchs³

et al. 2011

BTAT

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“…2. Compared with the NMR data of the compounds reported previously, the aglycon of compound 1 was the same as Platycogenic acid C. 9,10) In the nuclear Overhauser effect spectrosocpy (NOESY) spectrum, the β configuration of the hydroxyl group at H-21 was identified from the correlations as follows: H-21 (δ 3.42) with H-29 (δ 1.21); β configuration of the hydroxyl group at C-16 was identified from the correlation between H-16 (δ 4.34) and H-27 (δ 1.26). Therefore, the aglycon of 1 was established as 2β,3β,16 β,21β-tetrahydroxyolean-12-ene-28-oic acid.…”

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confidence: 55%

“…Furthermore, the absolute configurations of the sugars were determined by gas chromatography according to a method previously described. 9,15) In this method, l-cysteine methyl ester hydrochloride (0.06 mol/L) and hexamethyldisilazane-trimethylchlorosilane (HMDS-TMCS, 3 : 1) were added to the aqueous residue for derivatization. The solution was then centrifuged and the precipitate was removed.…”

Section: )mentioning

confidence: 99%

Two New Triterpenoid Saponins from the Root of <i>Platycodon grandiflorum</i>

Guo

Li-zi

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…16) After this period, the reaction mixture was diluted with H 2 O (15 ml) and extracted with CHCl 2 (3ϫ5 ml). Then, the aqueous layer was repeatedly evaporated to dryness with MeOH until neutral.…”

Section: Methodsmentioning

confidence: 99%

Four New Phenones from the Cortexes of Polygala tenuifolia

Jiang

2005

Chem. Pharm. Bull.

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Previous reports described that many saponins, saccharide esters and xanthones had been isolated from Polygala tenuifolia, [1][2][3][4][5][6] whose cortex is used widely in China, Korea and Japan as a tonic, sedative, expectorant and anti-inflammation agent. In the process of our studying the chemical constituents of P. tenuifolia, phenones were also isolated from this plant besides the above mentioned compounds. So in this paper, we describe the isolation and structural identification of four new phenones, tenuiphenones A-D. This is the second report of phenones isolated from the genus of Polygala, besides the former report of benzophenones from P. telephioides. 7) Results and DiscussionThe CHCl 3 and n-BuOH soluble parts of 95% EtOH extract of P. tenuifolia were subjected to silica gel, Sephadex LH-20 column chromatographies and HPLC purification to give compounds 1-6.Compound 1 was obtained as a yellow amorphous powder and its molecular formula was deduced as C 26 ). On acid hydrolysis, 1 afforded glucose and rhamnose, and the GC analyses of their L-cysteine derivatives showed their retention times were identical with those of D-glucose and L-rhamnose, respectively. The 13 C-NMR spectrum (Table 1) displayed 24 carbon signals in total, among which twelve were assigned to the sugar moiety, one for a methoxyl and the remaining eleven were reminiscent of a benzopheonone or a xanthone skeleton. The chemical shift of carbonyl signal (d 194.5) indicated 1 was a benzophenone compound. C-NMR spectrum data of 2 were comprised of six sugar moiety carbon signals (d 75.2, 72.7, 77.8, 69.0, 81.0, 59.9) assigned to be those of the C-glucosyl by comparing with the reported values (d 74.7, 72.1, 77.8, 69.2, 81.1, 60.0), 7,10) and the configuration of the glucosyl residue was deduced to be b from the J value (10.0 Hz) of the anomeric proton. Besides the sugar carbon signals, there were eleven benzophenone skeleton carbon signals in the 13 C-NMR.7) The 1 H-NMR spectrum of 2 showed a ABCX-system aromatic protons at (tenuiphenone A, 1), 3,5-di-C-b b-glucopyranosyl-2,4,6,3-tetrahydroxybenzophenone (tenuiphenone B, 2), 2,4,6-trihydroxyphenyl-(24Z)-triacontene-1-one (tenuiphenone C, 3), 2,4,6-trihydroxyphenyl-(26Z)-dotriacontene-1-one (tenuiphenone D, 4) respectively, on the basis of spectroscopic analyses. The isolation of 1 and 2 supplied an evidence for the hypothesis that xanthone was biosynthesized from benzophenone in the plants.

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Two New Biologically Active Triterpenoidal Saponins Acylated with Salicylic Acid from Albizia adianthifolia

Cited by 77 publications

References 24 publications

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Chemistry and pharmacology of saponins: special focus on cytotoxic properties

Two New Triterpenoid Saponins from the Root of <i>Platycodon grandiflorum</i>

Four New Phenones from the Cortexes of Polygala tenuifolia

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