Isolation of Some Glycosides as Aroma Precursors in Young Leaves of Japanese Pepper (Xanthoxylum piperitum DC.)

Abstract

To clarify the formation mechanism for the major alcoholic aroma compounds in young leaves of Japanese pepper, the glycosides were isolated as aroma precursors. The presence of glycosides of the main alcoholic aroma constituents was indirectly determined by enzymatic hydrolysis and trifluoroacetylation (TFA) of the glycoside-containing fraction. After Amberlite XAD-2 column chromatography, ODS flash chromatography, and high-performance liquid chromatography (HPLC), two new compounds, namely, (3S,6S)-cis-linalool-3,7-oxide beta-D-glucopyranoside and 2-methylpropanyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, were isolated. In addition, (3S,6R)-cis-linalool-3,6-oxide beta-D-glucopyranoside, which absolute configuration was the first determined, and six known glycosides, citronellyl beta-D-glucopyranoside, linalyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, (Z)-3-hexenyl beta-D-glucopyranoside, benzyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside, dendranthemoside A, and 3,6-dihydroxy-5,6-dihydro-beta-ionol 9-beta-D-glucopyranoside, were isolated. All of these glycosides were isolated for the first time from the leaves of Japanese pepper. Their structures were established on the basis of spectral data and chemical evidence. The ratios of stereoisomers of the aglycon moieties of citronellyl beta-D-glucopyranoside and linalyl 6-O-beta-D-apiofuranosyl-beta-D-glucopyranoside were investigated by a chiral GC analysis and compared with those of free citronellol and linalool in the aroma concentrate.

Sulfated Glucosides of an Aliphatic Alcohol and Monoterpenes, and Megastigmanes from the Leaves of <i>Meliosma pinnata</i> spp. <i>arnottiana</i>

“…arnottiana, seven new compounds, i.e., sulfated glucosides of oct-1-en-3-ol (1) and monoterpenes (2)(3)(4)(5), and megastigmanes (6, 7), together with four known ones, (3S,6S)-cis-linalool-3,7-oxide β-D-glucopyranoside (8), 6) (3S,5R,6S,9R)-3,6-dihydroxy-5,6-dihydro-β-ionol (9), 7) alangionoside A (10), 8) and (2R,3R,5R,6S,9R)-3-hydroxy-5,6-epoxy-β-ionol 2-O-β-D-glucopyranoside (11) 9) ( Fig. 1) were isolated using various kinds of chromatographic techniques.…”

“…The three degrees of unsaturation required a mono-cyclic structure, probably due to an oxyran ring between two oxygenated tertiary carbons. From this evidence, 2 was expected to be a sulfated analogue of (3S,6S)-cis-linalool-3,7-oxide β-D-glucopyranoside (8) isolated from Zanthoxylum piperitum, 6) which co-occurred in this plant. The sulfated position was deduced be the same as that in 1 and 8 from the sugar ring signals in the 13 C-NMR spectrum superimposable with those of 1 (Table 1).…”

Thermal decomposition study of menthyl-glycoside by TGA/SDTA, DSC and simultaneous Py-GC–MS analysis

“…The volatility limited its wider application in the high temperature processing. Glycosides are sugar derivatives, an overwhelming number of them occuring in nature [1,2]. Many studies on fruits and vegetables had shown that a significant portion of volatile flavor compounds including menthol might occur in many plants by enzymatic hydrolysis of glycosidic bond flavor precursors.…”

Application of the Extract of Zanthoxylum piperitum DC to Manufacturing Eco-friendly Antimicrobial Interior Fabric Blind Materials

“…초피에서 분리 동정된 화합물로는 초피잎에서 protocatechuic acid [12], 향기관련 물질로 과피 정유로부터 geranyl acetate, citronellol, alpha-terpineol, citronellal, linalool 과 isopulegol [15][16][17], polymeric procyanidin [20], aliphatic acid amide [8], hydroxyl-alpha-sanshool [19], quercetin과 kaempferol [7], 그리고 2종류의 세레토인 유도체인 N,N-dimethylserotonin 5-O-β-glucoside (1a)와 N-methylser- Retension index on a HP-5MS column. Retension index on a HP-5MS column.…”