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Showing papers on "Glucoside published in 1979"


Journal ArticleDOI
TL;DR: This is the first report on the occurrence of a neomenthyl glycoside, and the first evidence implicating glycosylation as an early step in monoterpene catabolism.
Abstract: (−)-Menthone, the major monoterpene component of the essential oil of maturing peppermint (Mentha piperita L.) leaves (6 micromoles per leaf) is rapidly metabolized at the onset of flowering with a concomitant rise in the level of (−)-menthol (to about 2 micromoles per leaf). Exogenous (−)-[G-3H]menthone is converted into (−)-[3H]menthol as the major steam-volatile product in leaf discs in flowering peppermint (10% of incorporated tracer); however, the major portion of the incorporated tracer (86%) resided in the nonvolatile metabolites of (−)-[G-3H]menthone. Acid hydrolysis of the nonvolatile material released over half of the radioactivity to the steamvolatile fraction, and the major component of this fraction was identified as (+)-neomenthol by radiochromatographic analysis and by synthesis of crystalline derivatives, thus suggesting the presence of a neomenthyl glycoside. Thin layer chromatography, ion exchange chromatography, and gel permeation chromatography on Bio-Gel P-2 allowed the purification of the putative neomenthyl glycoside, and these results suggested that the glycoside contained a single, neutral sugar residue. Hydrolysis of the purified glycoside, followed by reduction of the resulting sugar moiety with NaB3H4, generated a single labeled product that was subsequently identified as glucitol by radio gas-liquid chromatography of both the hexatrimethylsilyl ether and hexaacetate derivative, and by crystallization to constant specific radioactivity of both the alditol and the corresponding hexabenzoate. These results, along with studies on the hydrolysis of the glycoside by specific glycosidases, strongly suggest that (+)-neomenthyl-β-d-glucoside is a major metabolite of (−)-menthone in flowering peppermint. This is the first report on the occurrence of a neomenthyl glycoside, and the first evidence implicating glycosylation as an early step in monoterpene catabolism.

75 citations


Journal ArticleDOI
TL;DR: Octyl β- d -glucoside was synthetized from α-acetobromoglucose with an improved method yielding a very pure product with a sharp melting point (108–109°C) and free of intermediate products as judged by IR and NMR spectra.

33 citations


Journal ArticleDOI
TL;DR: The 13 C NMR spectra of acridone, 10-methylacridone and arborinine are presented and discussed in this paper, where gravacridondiol acetonide is used as a glucoside.

31 citations


Journal ArticleDOI
TL;DR: The structure of arjunglucoside III, isolated from Terminalia arjuna, was found to be β-D-glucopyranosyl 2α,3β,19α-trihydroxy-11-oxoolean-12-en-28-oate.
Abstract: The structure of a new triterpene glucoside, arjunglucoside III, isolated from Terminalia arjuna was found to be β-D-glucopyranosyl 2α,3β,19α-trihydroxy-11-oxoolean-12-en-28-oate.

25 citations


Patent
02 Jan 1979
TL;DR: In this paper, the prostaglandin synthetase inhibitor comprising certain sterol glycosides, a fatty acid ester thereof or a spiroketal-steroid glucoside or fatty acid is used.
Abstract: Medicaments are prepared having activity as prostaglandin synthetase inhibitor comprising certain sterol glycosides, a fatty acid ester thereof or a spiroketal-steroid glucoside or fatty acid ester thereof in an amount sufficient to inhibit a prostaglandin synthetase.

23 citations


Journal ArticleDOI
TL;DR: In this paper, the synthesis of 6-O-benzoylarbutin from Protea eximia (Salisb. ex Knight) fourcade is described, and a synthesis of tetra-acetate from arbutin is described.
Abstract: Eximin, obtained from the leaves of Protea eximia(Salisb. ex Knight) Fourcade is shown to be 6-O-benzoylarbutin, and the synthesis of its tetra-acetate from arbutin is described. A synthesis of aryl glucoside esters by glucoside formation between tetra-O-acyl-1-α-D-glucopyranosyl bromides and phenols is shown to succeed only with phenols carrying electron-withdrawing substituents. Under the same conditions phenols with electrondonating substituents promote elimination reactions leading to the corresponding glucals.

16 citations



Journal ArticleDOI
TL;DR: Kinetic parameters are reported and results are compared with the results obtained previously on induced hydrolyses found with lysozyme for the hydrolysis of 3,4-dinitrophenyl and p -nitrophenol β- d -glucosides catalysed by the enzyme EII.

14 citations



Journal ArticleDOI
TL;DR: In this paper, the application of high pressure liquid chromatography to the purification and identification of conjugated gibberellins was examined, and two kinds of reversed phase columns, octadesyl-silanized and dimethyl-silaneized silica gel, were used for the isolation and classification of a 3 glucoside from immature seeds of Quamoclit pennata.

13 citations


Journal ArticleDOI
TL;DR: A novel iridoid glucoside, named globularidin, lacking the typical double bond between C(3) and C(4), has been isolated from the whole plant of Globularia alypum by the combination of open column-and high-performance liquid chromatography.
Abstract: A novel iridoid glucoside, named globularidin, lacking the typical double bond between C(3) and C(4), has been isolated from the whole plant of Globularia alypum by the combination of open column- and high-performance liquid chromatography. The structure of this compound was established by chemical transformation and spectral data.



Journal ArticleDOI
TL;DR: In petals of Silene dioica plants the presence of a glycosyltransferase has been demonstrated, which catalyses the transfer of the rhamnosyl moiety of UDP- l -rhamnose to the glucose of cyanidin 3-O-glucoside.

Journal ArticleDOI
TL;DR: The mass spectral fragmentation pattern, chromatographic charactistics and absorption spectra of the acyl moiety obtained from alkaline hydrolysis were indistinguishable from those of an authentic sample of p-hydroxybenzoic acid [4].


Journal ArticleDOI
TL;DR: The intracellular distribution of bergenin and related compounds was examined in mesophyll cell protoplasts ofSaxifraga stolonifera and it was concluded that bergen in and norbergenin were primarily localized in the vacuoles, but gallic acid was distributed equally in vacuole and chloroplasts.
Abstract: The biosynthesis of bergenin and arbutin in the organs ofSaxifraga stolonifera has been studied by tracer techniques. Among the organs tested, the leaves showed the highest incorporation of label fromd-glucose-U-14C into bergenin and arbutin under continuous light, although every organ is more or less able to synthesize both glucosides. The incorporation rate into bergenin was higher in the young leaves, whereas the synthesis of arbutin became active in the mature leaves. The fact that the addition of unlabeled gallic acid enhanced the incorporation of label into bergenin suggests that gallic acid may be a likely glucosyl acceptor in bergenin biosynthesis.

Journal ArticleDOI
TL;DR: A phytochemical investigation of an ethanolic extract of the whole plant of Echites hirsuta resulted in the isolation and identification of the flavonoids naringenin, aromadendrin, and kaempferol.

Patent
11 Dec 1979
TL;DR: An improved method of preparing mycophenolic acid glucoside is presented in this paper, which comprises contacting mycophensolic acid with glucose in an aqueous medium in the presence of a glucosylating enzyme.
Abstract: An improved method of preparing mycophenolic acid glucoside which comprises contacting mycophenolic acid with glucose in an aqueous medium in the presence of a glucosylating enzyme selected from that produced by Streptomyces candidus NRRL 5449 and that produced by Streptomyces aureofaciens NRRL 2209 until mycophenolic acid glucoside is formed.

Journal ArticleDOI
TL;DR: Using petrol with increasing amounts of C,H, as activity of a synthetic sample was found to be one fourth eluent sitosterol, lupeol, and rand p-amyrin were of that of the isomeric 5.7,4'trihydroxyisoflavone.

Patent
24 May 1979
TL;DR: Hemostatics, vascular stabilizers and anti-shock compositions containing at least one steryl-β-D-glucoside or monopalmitates thereof, of the formula: ##STR1## in which R1 is β-sitosteryl, campesteryl, stigmasteryl or cholesteryl, and R2 is hydrogen or palmitoyl.
Abstract: Hemostatics, vascular stabilizers and anti-shock compositions containing at least one steryl-β-D-glucoside or monopalmitates thereof, of the formula: ##STR1## in which R1 is β-sitosteryl, campesteryl, stigmasteryl or cholesteryl, and R2 is hydrogen or palmitoyl. Methods of use are also described.

Journal ArticleDOI
TL;DR: In this paper, it was shown by 1H and 13C nmr spectroscopy that ethyl 3,4,6-tri-O-acetyl 2,amino-2-deoxy-β-D-glucoside reacts in acetone to yield a Schiff base, not the hemiorthoamide proposed previously.
Abstract: It is shown by 1H and 13C nmr spectroscopy that ethyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucoside reacts in acetone to yield a Schiff base, not the hemiorthoamide proposed previously.

Journal ArticleDOI
TL;DR: All attempts to synthesize the O-glucosides of KMA using maltose as a glucosyl donor have been unsuccessful by enzymes such as purified a- glucosidase from As pergillus niger or Aspergillus oryzae or Rhizopus delemar.
Abstract: Some years ago, glycosyl derivatives of kanatnycin A (KMA) were obtained enzymatically by ENDo et al.') and chemically by PERLMAN et al.'\" Although their chemical and biological properties were partially described, their precise chemical properties and antibacterial activities against drug-resistant bacteria producing specific aminoglucosides-inactivating enzymes were not mentioned. In this study, we have prepared new reduced types of KMAglucosides and their chemical and microbiological properties have been investigated. At first, we tried to prepare the enzymatically-derived compounds by the method of ENDO et a1.\". Utilizing the identical method, we prepared the glucosyl derivative of KMA by transglucosylase activity of ClaraseR. We detected a glucosyl derivative possessing the same properties as described by them. However, this compound could not be regarded as the O-glucoside, reported in the case of neamine\", because analysis in high-voltage paper electrophoresis (pH 1.8, 220 volts/cm, about 40 mA/cm, for 30 minutes, with Model HV 5000-3 of Savant Instruments, Inc.) and in silica gel thin-layer chromatography (using CHC13 MeOH NH4OH, 1:3:2), showed unchanged mobility and failed to detect reducing sugar after hydrolysis of this derivative with purified a-glucosidase from Aspergillus niger or Rhizopus delemar. An additional reason against the existence of an O-glucoside is that boiling the derivative in phenylhydrazine hydrochloride solution has liberated free KMA with the precipitation of phenylglucosazone. All our attempts to synthesize the O-glucosides of KMA using maltose as a glucosyl donor have been unsuccessful by enzymes such as purified a-glucosidase from Aspergillus niger or Aspergillus oryzae or Rhizopus delemar which are found to associate with partial transglucosylase activity and by crude cyclodextrin glycosyltransferase produced by Bacillus macerans. We have tried to prepare different type of glucosides of KMA by the following method: 1.0 g KMA (free base) and 4.0 g glucose were dissolved in 10 ml of 0.02 N NH4OH and after gradual addition of 1.0 g NaBH4 with stirring, the reaction mixture was permitted to stand for 5 hours at 45°C. In order to degrade excess


Journal Article
TL;DR: In this paper, the phase specificity of β-glucosidase coinciding with the maximal accumulation of glucoside-bound and free alcohols is revealed, suggesting that the formation of glucoses may precede the accumulation of corresponding free alcohol of terpenic and aromatic origin.
Abstract: Some data on the dynamics of free and glucoside-bound monoterpenic and aromatic (beta-phenylethyl) ethers content and the changes in the beta-glucosidase activity in rose petals at different stages of the flower development and on the kinetics of enzymatic hydrolysis of these glucosides are presented. The phase specificity of beta-glucosidase coinciding with the maximal accumulation of glucoside-bound and free alcohols is revealed. The data obtained suggest that the formation of glucosides may precede the accumulation of corresponding free alcohols of terpenic and aromatic origin.


Journal ArticleDOI
TL;DR: Eriodictyol-7-glucoside, a flavanone glycoside, was isolated as cream-white needles from the deep-blue fruit skins of Lasianthus japonica.
Abstract: Eriodictyol-7-glucoside, a flavanone glycoside, was isolated as cream-white needles from the deep-blue fruit skins of Lasianthus japonica, and in the same tissue eriodictyol and scopoletin were also found to occur in a small amount by means of paper chromatography.


Journal ArticleDOI
TL;DR: Label appeared in several cell fractions isolated from the cotyledons of pea seeds germinated for 48 hr with mevalonate, and served as an acceptor for glucose from UDP-glucose in the presence of a glucosyltransferase from pea seedling axis tissue.