Synthesis and n.m.r. spectral properties of grape monoterpenyl glycosides

Voirin, Ste ́phane; Baumes, Raymond; Bayonove, Claude; M'Bairaroua, Oubadjim.; Tapiéro, C.

doi:10.1016/0008-6215(90)80004-m

Cited by 50 publications

(34 citation statements)

References 32 publications

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“…The 1 H-and 13 C-NMR spectra of 5 and 6 displayed the signals due to glucopyranose and an (E)-caffeoyl group in addition to the signal due to each aglycone. The similarity of the 13 C-NMR spectral data of 5 to those of myzodendrone 7) and dracunculifoside I 1) let us to guess that the aglycone of 5 was 4-(3,4-dihydroxyphenyl)-butan-2-one. Similarly, comparison of the 1 H-and 13 C-NMR spectral data of 6 with those of dracunculifoside J 1) indicated the presence of dracunculifoside J and the (E)-caffeoyl group in 6.…”

Section: -O-(e)-caffeoyl]-b-d-glucopyranosidementioning

confidence: 95%

“…The similarity of the 13 C-NMR spectral data of 5 to those of myzodendrone 7) and dracunculifoside I 1) let us to guess that the aglycone of 5 was 4-(3,4-dihydroxyphenyl)-butan-2-one. Similarly, comparison of the 1 H-and 13 C-NMR spectral data of 6 with those of dracunculifoside J 1) indicated the presence of dracunculifoside J and the (E)-caffeoyl group in 6. Production of myzodendrone and (E)-caffeic acid from 5, and dracunculifoside J and (E)-caffeic acid from 6 by mild alkaline hydrolysis confirmed the above presumption.…”

Section: -O-(e)-caffeoyl]-b-d-glucopyranosidementioning

confidence: 95%

“…The molecular formulae of dracunculifosides K (5) and L (6) were expected to be C 25 H 28 O 11 and C 28 H 30 O 13 by the HR-FAB-MS. The 1 H-and 13 C-NMR spectra of 5 and 6 displayed the signals due to glucopyranose and an (E)-caffeoyl group in addition to the signal due to each aglycone.…”

Section: -O-(e)-caffeoyl]-b-d-glucopyranosidementioning

confidence: 99%

“…The J value of the anomeric proton signal of glucopyranose (Jϭ8.0 Hz) and GC analysis after acid hydrolysis indicated that this glucopyranose had a b-D-configuration. With regard to the aglycone moiety, fifteen carbon signals were observed in the 13 C-NMR spectra, so the aglycone of 7 was deduced to be a sesquiterpene derivative. C-NMR spectral data of this aglycone were in good agreement with those of 1b,4b,7a-trihydroxyeudesumane 8) except for the data of C-1, C-2 and C-10.…”

Section: -O-(e)-caffeoyl]-b-d-glucopyranosidementioning

confidence: 99%

“…Concerning the aglycone moiety, the 13 C-NMR spectrum showed twenty carbon signals including twelve aromatic carbon signals and the methoxyl carbon signals, and in the 1 H-NMR spectrum, the AMX type-[d 7.05 (1H, d, Jϭ8.0 Hz), 6.96 (1H, d, Jϭ2.0 Hz), 6.70 (1H, dd, Jϭ8.0, 2.0 Hz)] and AAЈX type-aromatic proton signals [d 6.78 (2H, br s), 6.93 (1H, br s)]. Therefore, the aglycone of 4 was deduced to be a lignan derivative.…”

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Studies on the Constituents from the Aerial Part of Baccharis dracunculifolia DC. II.

2002

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In the course of our research on the constituents of Brazilian plants, we started investigation of the glycosides from Baccharis dracunculifolia DC. (Compositae); we previously reported the structures of dracunculifosides A-J from the aerial part of this plant.1) Recently, ten new glycosides were isolated along with five known compounds identified by their NMR spectral data [1: 3,4-O-dicaffeoylquinic acid methyl ester, 2) 2:]. This paper also describes the isolation and structural elucidation of these new compounds.The extraction of the constituents from B. dracunculifolia DC. was described in a previous paper.1) The adsorbed material on the Mitsubishi Diaion HP-20 column was eluted with 50% MeOH in water, 70% MeOH in water and MeOH, continuously. The residues of the 50% and 70% MeOH eluates gave compounds 1-15.Compound 4 was suggested to have the molecular formula, C 35 (d 149.7, 147.0, 127.8, 123.0, 116.7, 115.3) and six carbon signals due to the sugar moiety (d 102.6, 77.9, 75.6, 74.9, 72.2, 64.7) along with the signal due to the aglycone moiety. Thus, compound 4 was believed to consist of an aglycone, one monosaccharide and an (E)-caffeoyl group.Concerning the aglycone moiety, the 13 C-NMR spectrum showed twenty carbon signals including twelve aromatic carbon signals and the methoxyl carbon signals, and in the 1 H-NMR spectrum, the AMX type- [d 7.05 (1H, d, Jϭ8. Mild alkaline hydrolysis of compound 4 afforded 4a which was identified as pinoresinol O-b-D-glucopyranoside (2) 3,6) by the HPLC analysis and The molecular formulae of dracunculifosides K (5) and L (6) were expected to be C 25 H 28 O 11 and C 28 H 30 O 13 by the HR-FAB-MS. The 1 H-and 13 C-NMR spectra of 5 and 6 displayed the signals due to glucopyranose and an (E)-caffeoyl group in addition to the signal due to each aglycone. The similarity of the 13 C-NMR spectral data of 5 to those of myzodendrone 7) and dracunculifoside I 1) let us to guess that the aglycone of 5 was 4-(3,4-dihydroxyphenyl)-butan-2-one. Similarly, comparison of the 1 H-and 13 C-NMR spectral data of 6 with those of dracunculifoside J 1) indicated the presence of dracunculifoside J and the (E)-caffeoyl group in 6. Production of myzodendrone and (E)-caffeic acid from 5, and dracunculifoside J and (E)-caffeic acid from 6 by mild alkaline hydrolysis confirmed the above presumption. Consistency of the 1 H-and 13 C-NMR spectral data of the sugar and ester moieties in 5 and 6 with those in 4 suggested that the (E)-caffeoyl group was attached to the C-6 position of b-D-glucopyranose. Accordingly, the structures of dracunculifosides K (5) and L (6) were determined as shown in Chart 1.Dracunculifoside M (7) had the molecular formula, . The 1 H-and 13 C-NMR spectra of 7 also showed the signals due to glucopyranose and an (E)-caffeoyl group. The J value of the anomeric proton signal of glucopyranose (Jϭ8.0 Hz) and GC analysis after acid hydrolysis indicated that this glucopyranose had a b-D-configuration. With regard to the aglycone moiety, fifteen carbon signals were observed in the 1...

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