Saponins from the stem bark of Filicium decipiens

Lavaud, Catherine; Voutquenne, Laurence; Massiot, Georges; Men‐Olivier, L. Le; Das, Bhupesh C.; Laprévôte, Olivier; Sérani, Laurent; Delaude, Clément; Becchi, Michel

doi:10.1016/s0031-9422(97)00586-4

Cited by 32 publications

(49 citation statements)

References 17 publications

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“…5 (Figure 2) between the signal of the carbonyl at δ C 183.5 (C-23) and the protons at δ H 4.15 (H-3), δ H 1.64 (H-5), and δ H 1.39 (CH 3 -24), and between the signal of ester carbonyl at C-28 (δ C 176.0) and the oxymethine proton H-16 at δ H 4.49 confirm the place of the substituent. [8][9][10] The configuration of the 2β, 3β, 16α-trihydroxy groups, and α-orientation of the COOH at C-4 was confirmed from the ROESY experiments ( Figure 3). The coupling constant (J = 3.2 Hz) between H-2 and H-3 is in accordance with the literature.…”

Section: Resultsmentioning

confidence: 74%

“…The MS/MS of this ion gave other fragment-ion peaks at m/z 647. 6, 25.8, and 32.0, the ethylenic carbons at δ C 121.9 (CH) and 143.5 (C), attributable to an olean-12-ene skeleton [8][9][10] (Table 1), in which three hydroxy groups were located at δ C 69.9, 85.3, and 73.3 together with two carboxylic groups at C 183. 5 (Figure 2) between the signal of the carbonyl at δ C 183.5 (C-23) and the protons at δ H 4.15 (H-3), δ H 1.64 (H-5), and δ H 1.39 (CH 3 -24), and between the signal of ester carbonyl at C-28 (δ C 176.0) and the oxymethine proton H-16 at δ H 4.49 confirm the place of the substituent.…”

Section: Resultsmentioning

confidence: 99%

“…The coupling constant (J = 3.2 Hz) between H-2 and H-3 is in accordance with the literature. [9,10] On this basis, the aglycone moiety of compound 1 was established to be zanhic acid or 2β,3β,16α-trihydroxyolean-12-en-23, 28-dioic acid. Deshielding 13 C NMR chemical shift at δ C 85.3 (C-3) and shielding 13 C NMR chemical shift at δ C 176.0 (C-28) suggested that this saponin was a bidesmosidic saponin with glucosidic linkages at C-3 through an O-heterosidic bond and at C-28 through an ester bond.…”

Section: Resultsmentioning

confidence: 99%

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Leptocarposide: a new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)

Mabou

Tebou

Ngnokam

et al. 2013

Magnetic Reson in Chemistry

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A new triterpenoid bidesmoside (leptocarposide) possessing an acyl group in their glycosidic moiety (1), together with the known luteolin-8-C-glucoside (2) and 1-O-β-D-glucopyranosyl-(2S,3R,8E)-2-[(2'R)-2-hydroxypalmitoylamino]-8-octadecen-1,3-diol (3) was isolated from the n-butanol-soluble fraction of whole plant of Ludwigia leptocarpa (Nutt) Hara (Onagraceae). Structure of compound 1 has been assigned on the basis of spectroscopic data ((1)H and (13)C NMR, (1)H-(1)H COSY, HSQC, HMBC, and ROESY), mass spectrometry, and by comparison with the literature. This compound was further screened for its potential antioxidant properties by using the radical scavenging assay model 2,2-diphenyl-1-picrylhydrazyl and reveals non-potent antioxidant activities, while compound 2 shows SC50 of 0,038 mM.

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Section: Resultsmentioning

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Leptocarposide: a new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)

Mabou

Tebou

Ngnokam

et al. 2013

Magnetic Reson in Chemistry

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“…Sitosterol, kaempferol were identified in n-butanol extract from the methanol extracts from the leaves of Filicium decipiens 6 . Four new saponins were isolated from the stem bark of Filicium decipiens 7 .…”

Section: Introductionmentioning

confidence: 99%

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2013

IJPSR

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This study evaluated methanolic extract of Filicium decipiens (MFD) on reducing hyperglycemia and hyperlipidemia in streptozotocin-induced diabetic rats. MFD was orally administered once a day after 3 days of streptozotocin -induction at 100,200 and 400 mg/kg for 45 day and the results showed that serum fasting blood glucose, Glucose -6 -phosphotase , Fructose 1, 6 -phosphotase in hepatic tissues ,TC, free fatty acids , phospholipids, and TG in serum levels were significantly decreased, whereas Hb and HbCA1in blood and serum HDL, Glucokinase, Glucose -6 -Phosphate Dehydrogenase in hepatic tissues and liver and muscle glycogen level were increased. The dosage of 400 mg/kg is more effective than that of 100, 200 mg/kg. These results suggest that the MFD possesses antidiabetic and hypolipidemic effects in streptozotocin -induced diabetic rats.

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“…An aglycon of compound 4 was obtained according to the method of Lavaud et al (1998). Compound 4 (lO mg) was dissolved in I ml of a mixture containing (1 : 1) 6.5% aq.…”

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confidence: 99%

Isolation and Structure of Antimicrobial Substances from Paprika Seeds.

Yajima¹,

Takayanagi

Matsuo

et al. 2000

FSTR

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Antimicrobial substances were isolated from the 50 % ethanol extract of paprika seeds by ODS open column chromatography and reverse phase HPLC. Ten compounds (1-10) which demonstrated antimicrobial activity against Saccharomyces cerevisiae (MIC= 1.3-2.6 mg/O were isolated. The structure of the major compound, 4 (MIC=2.6 mg/D, was determined to be Paprika is a sweet or mildly pungent substance that belongs to the genus Capsicum. The brilliant red powder obtained from dried paprika fruits is used as a fiavoring and ganrish. We previously found that a water extract from paprika seeds exhibited strong antimicrobial activity towards yeasts (Yajima et al., 1996).The antimicrobial substance partially purified from paprika seeds was very stable at high temperatures, over a wide pH range. Furthermore, several application studies showed that this antimicrobial substance was a good food preservative to prevent yeast growth (Yajima et al., 1997; Yajima et al., 1998a;1998b). However, this antimicrobial substance has not yet been completely purified, nor has its structure been elucidated. We report here the purification and structure of antimicrobial substances from paprika seeds.To extract the antimicrobial substances, paprika seeds (100 g)were ground into a powder using a mechanical coffee grinder. The powder was mixed with 50% ethanol (700 ml) and stirred at room temperature for 3 h. The stirred solution was filtered through a cotton cloth and then centrifuged (1 0.000Xg, 20 min).The filtrate was concentrated to l/2 of its original volume by rotary evaporation at 40'C and then applied to a reverse phase open column (16x300 mm, Cosmosil 140 C18-0PN, NacalaiTesque) that had been equilibrated with 5% ethanol solution.After washing the column with 300 ml of 5 % ethanol solution, antimicrobial substances were eluted using a stepwise gradient of 20% to 80% ethanol. The fraction that eluted at 60% ethanol showed the highest antimicrobial activity. The antimicrobial activity against Saccharomyces cerevisiae W-3 was measured using a 96-well microplate (Yajima et al., 1996). The pre-culture of S. HPLC equipped with a CarboPac PA-I column (4X250 mm, Dionex) and eluted with 15 mM sodium hydroxide. The eluted oligosaccharides were monitored using a pulsed amperometric detector (Hardy et al. , 1988). Compound 4 had a sugar chain consisting of D-glucose (Glc) and D-galactose (Gal) in a proportion of4.3 : I (Glc : Gal).

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Saponins from the stem bark of Filicium decipiens

Cited by 32 publications

References 17 publications

Leptocarposide: a new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)

Leptocarposide: a new triterpenoid glycoside from Ludwigia leptocarpa (Onagraceae)

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Isolation and Structure of Antimicrobial Substances from Paprika Seeds.

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