1998
DOI: 10.1021/np9800654
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A Novel Antiprotozoal Aminosteroid from Saracha punctata

Abstract: A new aminosteroid, 3beta-amino-22,26-epiminocholest-5-ene named sarachine (1), and two known flavonoids, eriodictyol (2) and 7-O-beta-D-glucopyranosyl-eriodictyol (3), were isolated from the leaves of Saracha punctata. The alkaloid was found to inhibit the growth of Leishmania braziliensis promastigotes (100% at 25 microM) and of Trypanosoma cruzi epimastigotes in culture (50% at 25 microM) and showed a strong in vitro antiplasmodial activity with an IC50 of 25 nM.

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Cited by 68 publications
(39 citation statements)
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References 21 publications
(40 reference statements)
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“…The water layer was separated first by Sephadex LH-20 column chromatography, 2) and the obtained fraction 1 was subjected to MCI-gel CHP 20P, Chromatorex ODS, and silica gel to afford 3, together with 8 known constituents identified as eriodictyol 7-O-glucoside (4), 18) kaempferol 3-Orhamnoside, quercetin 3-O-rhamnoside, quercetin 3-O-glucoside, 7) myricetin 3-O-rhamnoside, rutin, 19) 3-O-methylellagic acid 4Ј-O-a-L-rhamnopyranoside 20) and tuberonic (12-OHjasmonic) acid glucoside.…”
Section: Resultsmentioning
confidence: 99%
“…The water layer was separated first by Sephadex LH-20 column chromatography, 2) and the obtained fraction 1 was subjected to MCI-gel CHP 20P, Chromatorex ODS, and silica gel to afford 3, together with 8 known constituents identified as eriodictyol 7-O-glucoside (4), 18) kaempferol 3-Orhamnoside, quercetin 3-O-rhamnoside, quercetin 3-O-glucoside, 7) myricetin 3-O-rhamnoside, rutin, 19) 3-O-methylellagic acid 4Ј-O-a-L-rhamnopyranoside 20) and tuberonic (12-OHjasmonic) acid glucoside.…”
Section: Resultsmentioning
confidence: 99%
“…Moreover, the signals of two geminal protons at δ H 3.39 (1H, dd, J=7.6, 10.8 Hz, H-12a) and 3.56 (1H, dd, J=6.7, 10.8 Hz, H-12b), instead of the methyl protons in the isopropyl group of 8, indicated one methyl carbon was oxygenated in 7. The eudesmane skeleton of 7 was unambiguously determined using the combinations of The other compounds were identified as apigenin (9), 29) (−)-eriodictyol (10), 30) p-hydroxybenzoic acid (11), 31) nepetin (12), 32) oplodiol 1-O-β-D-glucopyranoside (8), 28) luteolin 7-O-glucoside (13), 33) linarin (14), 34) syringaresinol β-Dglucoside (15), 29) uridine (16), 35) dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside (17), 36) benzyl 6-O-β-Dapiofuranosyl(1 6)-β-D-glucopyranoside (icariside F 2 ) (18), 37) (Z)-3-hexenyl-O-vicianoside (19), 38) and phenethyl-O-vicianoside (20) 38) on the basis of spectral data and chemical evidence, which were in good agreement with those reported in the literature. Of these, compounds 8, 10-12, and 15-20 were isolated from this plant for the first time.…”
Section: Resultsmentioning
confidence: 99%
“…Each group was further separated using CC over silica gel 60, using a gradient of n-hexane-acetone as eluent. Fraction G-5 yielded catechin [11] (622 mg, 0.27%); fraction G-6 yielded catechin [11] (119 mg, 0.05%), daucasterol [13], and stigmasteryl-β-D-glucopyranoside [14]; and fraction G-7 yielded epigallocatechin [11] (19 mg, 0.008%) and eriodictyol [12] (95 mg, 0.04%).…”
Section: Methodsmentioning
confidence: 99%
“…is a shrub or tree growing up to 3 m high, found throughout the southern states of Mexico, and to our knowledge, no phytochemical investigation has been carried out on this species so far. In this analysis, from the dried leaves fourteen natural products were isolated: triacontanol [3], β-sitosterol palmitate [4], β-sitosterol, squalene [5], nonaprenol [6], meso-2,6,10,14-tetramethylpentadecane (norphytane, 1) [7], lupenone [8], lupeol [9], daphnetin [10], catechin [11], epigallocatechin [11], eriodictyol [12], 3-O-β-D-glucopyranosyl-β-sitosterol (daucasterol) [13], and stigmasteryl-β-D-glucopyranoside [14]. Compound 1 has been obtained from shark liver oil, herring oil, wool wax and zooplankton [15]; however, this is the first occasion that this natural product is isolated from a plant.…”
mentioning
confidence: 99%