ChemInform Abstract: IRIDOIDS. XXI. THE STEREOCHEMISTRY OF IPOLAMIIDE AND THE STRUCTURE OF ITS NATURAL 8‐O‐ACETYL DERIVATIVE, IPOLAMIIDOSIDE

Alkaline Phosphatase (ALP) Enhancing Iridoid Glucosides from the Indonesian Medicinal Plant Barleria Lupulina

“…On the other hand, the 13 C NMR spectrum of 1 revealed signals of an ester carbonyl (δ C 169.3, C-11), an olefin (δ C 154.0, C-3; δ C 113.5, C-4), a methyl, two methylenes, two methines, and two oxygenated quaternary carbons, together with those of an acetyl (δ C 173.2, 22.0) and a β-glucopyranosyl group (Table 1). These were similar to those of ipolamiidoside ( 5) [23,25], an isolate from the same extract, but the 1 H and 13 C NMR spectra of 1 lacked the signals of the ester methyl (δ H 3.72, s; δ C 50.4) in 5. Thus, compound 1 was considered to be a carboxylic acid corresponding to 5, which was confirmed by the COSY, HMQC, and HMBC spectra (Figure 2a).…”

“…Among the compounds isolated, compound 1 was a new iridoid glucoside, and one of the two mixtures consisted of two new iridoid glucosides (2 and 3). Other compounds identified on the basis of spectroscopic analyses were shown to be the known iridoid glucosides, ipolamiide (4) [23,24], ipolamiidoside (5) [23,25], shanzhiside (8) [26,27], shanzhiside methyl ester (9) [26,28] , an olefin (δ C 154.0, C-3; δ C 113.5, C-4), a methyl, two methylenes, two methines, and two oxygenated quaternary carbons, together with those of an acetyl (δ C 173.2, 22.0) and a β-glucopyranosyl group (Table 1). These were similar to those of ipolamiidoside (5) [23,25], an isolate from the same extract, but the 1 H and 13 C NMR spectra of 1 lacked the signals of the ester methyl (δ H 3.72, s; δ C 50.4) in 5.…”

“…Among the compounds isolated, compound 1 was a new iridoid glucoside, and one of the two mixtures consisted of two new iridoid glucosides ( 2 and 3). Other compounds identified on the basis of spectroscopic analyses were shown to be the known iridoid glucosides, ipolamiide (4) [23,24], ipolamiidoside (5) [23,25], shanzhiside (8) [26,27], shanzhiside methyl ester (9) [26,28] 1). On the other hand, the 13 C NMR spectrum of 1 revealed signals of an ester carbonyl (δ C 169.3, C-11), an olefin (δ C 154.0, C-3; δ C 113.5, C-4), a methyl, two methylenes, two methines, and two oxygenated quaternary carbons, together with those of an acetyl (δ C 173.2, 22.0) and a β-glucopyranosyl group (Table 1).…”

Iridoid Glucosides from the Flowers ofBarleria lupulina

“…Here we report the isolation and structure elucidation of a new iridoid diglucoside, lupulinoside (1), along with eight known iridoid glucosides from the flowers of this plant species. These includes acetylbarlerin (2) [4], ipolamiidoside (3) [7], 6-O-acetylshanzhiside methyl ester (4) [4], barlerin (5) [4], shanzhiside methyl ester (6) [4], mussaenosidic acid (7) [8], 8-O-acetylshanzhiside (8) [9], and shanzhiside (9) [10], the latter three of which have not been reported previously from Barleria species. The known iridoids were identified by comparisons of spectroscopic data with those of reported compounds.…”

Application of capillary-scale NMR for the structure determination of phytochemicals

“…Furthermore, the C-1 resonance was at δ 96.1, which indicated 4 to be a cis-fused iridoid (Krull and Stermitz, 1998). The relative configuration of 4 was also deduced on the basis of NOE correlations in the NOESY spectra, and therefore 4 was confirmed to be ipolamiide (Bianco et al, 1976(Bianco et al, , 1981. The structures of strictoloside (Junior, 1985; 1), lamiide (Scarpati and Guiso, 1969;Bianco et al, 1981; 2), phlomoside A (Maksudov et al, 1995 ; 3), and 8epihastatoside (Foderaro and Stermitz, 1992; 5) were determined by MS and one-and two-dimensional NMR experiments together with the comparison of the literature NMR data.…”