2006
DOI: 10.1590/s0100-46702006000400008
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Isolation of lignans glycosides from Alibertia sessilis (Vell.) K. Schum. (Rubiaceae) by preparative high-performance liquid chromatography

Abstract: Enantiomeric aglycone lignans contained in a mixture were separated from a fraction of the extract of the stems of Alibertia sessilis (Vell.) K. Schum. (Rubiaceae) by preparative high-performance liquid chromatography. An efficient and fast separation can be achieved with methanol-water (30:70, v/v). Their structures were identified as (+)-lyoniresinol 3alpha-O-beta-glucopyranoside and (-)-lyoniresinol 3alpha-O-beta-glucopyranoside, being reported for the first time in Rubiaceae.

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Cited by 7 publications
(4 citation statements)
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“…Based on the obtained data, the structure was established as threo-7-O-butylguaiacylglycerol and named A. pinnata E (Table 1; Figure 1). The 13 known compounds were identified by comparing their spectroscopic data with those reported in the literatures as (7R,8S,7'R,8'S)-4,9,4',9'-tetrahydroxy-3,3'-dimethoxy-7,7'-epoxylignan 9-O-β-D-glucopyranoside (6), 15 (-)-syringaresinol (7), 16 (-)-isolarisiresinol 3α-O-β-D-glucopyranoside (8), 17 (-)-lyonirenisol-3a-O-β-D-glucopyranoside (9), 18 (+)-lyonirenisol-3a-O-β-glucopyranoside (10), 19 (+)-isolariciresinol 9'-O-β-glucopyranoside (11), 20 cyclo(L-Pro-L-Phe) (12), 21 cyclo(L-Pro-D-Ile) (13), 21 cyclo((S)-Pro-(R)-Leu) ( 14), 22 4-(2-formyl-1H-pyrrol-1-yl)butanoic acid (15), 23 2-formyl-5-(butoxylmethyl)-1H-pyrrole-1-butanoic acid ( 16), 24 butyl 2-pyrrolidone-5-carboxylate (17), 25 4'-hydroxy-N-(4-hydroxy-3-methoxybenzoyl)-3',5'-dimethoxybenzamide (18). 26…”
Section: Introductionmentioning
confidence: 99%
“…Based on the obtained data, the structure was established as threo-7-O-butylguaiacylglycerol and named A. pinnata E (Table 1; Figure 1). The 13 known compounds were identified by comparing their spectroscopic data with those reported in the literatures as (7R,8S,7'R,8'S)-4,9,4',9'-tetrahydroxy-3,3'-dimethoxy-7,7'-epoxylignan 9-O-β-D-glucopyranoside (6), 15 (-)-syringaresinol (7), 16 (-)-isolarisiresinol 3α-O-β-D-glucopyranoside (8), 17 (-)-lyonirenisol-3a-O-β-D-glucopyranoside (9), 18 (+)-lyonirenisol-3a-O-β-glucopyranoside (10), 19 (+)-isolariciresinol 9'-O-β-glucopyranoside (11), 20 cyclo(L-Pro-L-Phe) (12), 21 cyclo(L-Pro-D-Ile) (13), 21 cyclo((S)-Pro-(R)-Leu) ( 14), 22 4-(2-formyl-1H-pyrrol-1-yl)butanoic acid (15), 23 2-formyl-5-(butoxylmethyl)-1H-pyrrole-1-butanoic acid ( 16), 24 butyl 2-pyrrolidone-5-carboxylate (17), 25 4'-hydroxy-N-(4-hydroxy-3-methoxybenzoyl)-3',5'-dimethoxybenzamide (18). 26…”
Section: Introductionmentioning
confidence: 99%
“…Flavonoids and phenolic and polyphenol acids are among the most prominent [ 22 ], in addition to caffeic acids in the Alibertia genus [ 23 , 24 ]. Furthermore, the presence of iridoids [ 25 ], alkaloids [ 26 ], anthraquinones [ 27 ], lignones [ 28 ], flavonoids, phenolic derivatives, triterpenes, and diterpenes [ 20 ] have all been reported in the literature.…”
Section: Introductionmentioning
confidence: 99%
“…Cordiera sessilis (Vell.) Kuntze, or "marmelinho", "marmelo-do-cerrado" and "marmelada-de-cachorro" is a branched shrub with a low canopy, which is widely distributed in Brazil, especially in the states of Ceará, Mato Grosso, Goiás, Minas Gerais and São Paulo (Silva, Silva, Bolzani, & Lopes, 2006;Zappi, Calió, & Pirani, 2014). The species is the synonym for Alibertia sessilis (Vell.)…”
Section: Introductionmentioning
confidence: 99%
“…Leaf and branch portions are commonly employed as cataplasms, compresses or baths in the treatment of skin disorders (Rodrigues & Carvalho, 2001). Some chemical studies reported to the isolation of the constituents from leaves such as triterpenes, iridoids, flavonoids and esters of caffeic acid (Olea, Roque, & Bolzani, 1997;Silva et al, 2006). Silva, Bolzani, Young, and Lopes (2007) reported new antifungal phenolic derivatives, iridoids and lignins from leaves.…”
Section: Introductionmentioning
confidence: 99%