Venkata Sai Prakash Chaturvedula

Technical Advisor/Consulatant

Novel Mogrosides, Compositions and Their Purification

Compositions used for sweetened substances

Edible sweetened substances

Solubilized steviol glycoside compositions

A new diterpene glycoside with six β-D-glucopyranosyl units was isolated from the extract of the leaves of Stevia rebaudiana Bertoni, which was identified as 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[2-O-β-D-glucopyranosyl-3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyrano-syl -β-D-glucopyranosyl) ester (1) based on...

A new minor diterpene glycoside has been isolated from a commercial extract of the leaves of Stevia rebaudiana and its structure was identified as 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[2-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyranosyl-3-O-b-D-glucopyranosyl-β-D-glucopyranosyl] ester (1) based on extensive NMR...

Rebaudioside D3, a novel steviol glycoside, is produced by specific UDP-glycosyltransferase of rebaudioside E, a minor steviol glycoside of Stevia rebaudiana Bertoni. The complete proton and carbon NMR spectral assignments of rebaudioside D3, 13-[(2-O-β-D-glucopyranosyl-6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) oxy] ent-kaur-16-en-19-oic acid-(2-O...

Steviol glycosides are a group of highly sweet diterpene glycosides isolated in only a few plant species of the Paraguayan shrub Stevia rebaudiana. Stevioside and rebaudioside A are the most abundant steviol glycosides which are responsible for its sweet taste and have commercial value all over the world as sugar substitute in foods, beverages, or...

A systematic phytochemical study of the commercial extract of Luo Han Guo (Siraitia grosvenorii) resulted in the isolation of an additional minor new cucurbitane glycoside, mogroside V Al (1). The structure of the new compound was characterized on the basis of 1D (1H and 13C NMR) and 2D (COSY, HMQC, HMBC and NOESY) NMR and high resolution mass spec...

High Performance Liquid Chromatography (HPLC) studies were performed on the nine sweet steviol glycosides reported in Joint Expert Committee on Food Additives (JECFA) namely rebaudioside A, steviolbioside, stevioside, rubusoside, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside F, and dulcoside A isolated from the leaves of Stevia rebau...

Controlled hydrolysis studies of the two sweet diterpene glycosides of Stevia rebaudiana Bertoni namely 13-[(2-O- β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(2-O-β-Dglucopyranosyl- β-D-glucopyranosyl) ester (rebaudioside D, 1) resulted in the formation of rebaudioside A, whereas 13-[(2-O-β-D-glucop...

Four new minor diterpene glycosides with a rare α-glucosyl linkage were isolated from a cyclodextrin glycosyltransferase glucosylated stevia extract containing more than 98% steviol glycosides. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-(4-O-α-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-o...

From the commercial extract of the leaves of the sweet plant Stevia rebaudiana Bertoni obtained from Sinochem Qingdao Co. Ltd., a new diterpene glycoside having three β-D-glucopyranosyl units of which two of them were connected in a relatively rare linkage of 3-β-D-glucobiosyl substitution at C-19 position of the aglycone steviol. The structure of...

Continuous phytochemical studies of the crude extract of Luo Han Guo (Siraitia grosvenorii) furnished three additional new cucurbitane triterpene glycosides, namely 11-deoxymogroside V, 11-deoxyisomogroside V, and 11-deoxymogroside VI. The structures of all the isolated compounds were characterized on the basis of extensive NMR and mass spectral da...

Degradation of rebaudioside M, a minor sweet component of Stevia rebaudiana Bertoni, under conditions that simulated extreme pH and temperature conditions has been studied. Thus, rebaudioside M was treated with 0.1 M phosphoric acid solution (pH 2.0) and 80 °C temperature for 24 h. Experimental results indicated that rebaudioside M under low pH and...

Additional High Performance Liquid Chromatography (HPLC) studies were performed on the nine sweet steviol glycosides reported in Joint Expert Committee on Food Additives (JECFA) namely rebaudioside A, steviolbioside, stevioside, rubusoside, rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside F, and dulcoside A isolated from the leaves of S...

From the commercial extract of the leaves of Stevia rebaudiana Bertoni, a minor steviol glycoside, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(2-O-(3-O-β-D-glucopyranosyl-α-L-rhamnopyranosyl)-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester] (1); also known as rebaudioside O having seven s...

Aminoglycoside antibiotics of the formula are disclosed. The compounds are useful for treating bacterial infections, particularly infections resistant to known antibiotics.

From the extract of the leaves of Stevia rebaudiana Bertoni, a diterpene glycoside was isolated which was identified as 13-[(2-O-beta-D-glucopyranosyl-3-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O-beta-D-glucopyranosyl-3-O-beta-D-glucopyranosyl-D-glucopyranosyl) ester (1). The complete 1H and 13C NMR assignmen...

Catalytic hydrogenation of the exocyclic double bond present between C16 and C17 carbons of the four ent-kaurane diterpene glycosides namely rebaudioside A, rebaudioside B, rebaudioside C, and rebaudioside D isolated from Stevia rebaudiana has been carried out using Pt/C, Pd(OH)2, Rh/C, Raney Ni, PtO2, and 5% Pd/BaCO3 to their corresponding dihydro...

Chemical examination of the ethyl acetate extract of the soft coral Sinularia gibberosa, collected from the Diglipur Island of the group of A & N Islands, furnishes eight pure compounds (1-8) besides a mixture of monohydroxysterols. Two of these are new compounds, one a steroid glycoside, (24S)-24-methylcholest-5-ene-3β, 16β-diol-3-O-α-L-fucopyrano...

A review of the chemistry of the constituents reported from all the Tinospora species (family : Menispermaceae) has been presented under the chemical groups (a) alkaloids (b) diterpenoids (c) steroids (d) flavonoids (e) lignans and (f) miscellaneous. Pharmacological properties of the isolated components and crude extracts are discussed.

The genus Camellia sinensis belongs to the family of Theaceae of the flowering plants. The leaves and leaf buds of C. sinensis are used to produce tea. The chemical composition of tea leaves has been thoroughly studied and the main constituents belong to the polyphenol group accounting for 25 to 35% on a dry weight basis. C. sinensis also contains...

A new diterpenoid glycoside, 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19- oic acid-(4-O-(2-O-α-D-glucopyranosyl)-a-D-glucopyranosyl-β-D-glucopyranosyl) ester (1) was isolated from the commercial extract of the leaves of Stevia rebaudiana along with the known steviol glycosides including stevioside, rebaudiosides A-G, rubus...

Stability of rebaudioside A, a sweet component of Stevia rebaudiana was studied covering a typical pH range 2.8–4.2 that simulated both relevant and extreme beverage storage conditions. Thus, rebaudioside A was evaluated in mock beverage solutions by simulating formulations used in commercial cola soft drinks (pH 2.8 and pH 3.2), lemon–lime soft dr...

Nineteen compounds including taxumairol R (1), taxinine M (2), taxacin (3), paclitaxel (4), 10‐deacetyltaxol A (5), 10‐deacetyl‐7‐epi‐taxol (6), 7‐epi‐taxol (7), taxol C, 10‐deacetyltaxol C, 7β‐xylosyl‐10‐deacetyltaxol (8), taxamairin A (9), taxinine A, 14β‐hydroxytaxusin (10), 5α‐hydroxy‐7β,9α,10β, 13α‐tetraacetoxy‐4(20), 11‐taxadiene, 1‐dehydroxy...

The complete proton and carbon NMR spectral assignments of a diterpene glycoside isolated from the commercial extract of the leaves of Stevia rebaudiana Bertoni, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] entkaur-16-en-19-oic acid-[(2-O-α-L-rhamnopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester] (1); also k...

Hydrolysis of the diterpene glycoside, rebaudioside M isolated from Stevia rebaudiana Bertoni was performed using acid and base conditions. Acid hydrolysis was carried out using H2SO4 and HCl, whereas base hydrolysis was performed using NaOH. This is the first report of the synthesis of isosteviol and rebaudioside B from the diterpene steviol glyco...

Systematic phytochemical studies of the dichloromethane (CH2Cl2) fraction of the aqueous extract of Astragalus propinquus on a C-18 column using a Biotage Flash Chromatography system yielded three flavonoids namely 5-hydroxy-4′, 6, 7 trimethoxyflavone (salvigenin), 4′, 5, 7-trihydroxyflavone (apigenin), and 3′, 4′, 5, 7-tetrhydroxyflavone (luteolin...

Catalytic hydrogenation of the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana, namely rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)₂ and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemis...

Catalytic hydrogenation of rebaudioside B, rebaudioside C, and rebaudioside D; the three ent-kaurane diterpene glycosides isolated from Stevia rebaudiana was carried out using Pd(OH)(2). Reduction of steviol glycosides was performed using straightforward synthetic chemistry with the catalyst Pd(OH)(2) and structures of the corresponding dihydro der...

Purification of the dichloromethane (CH2Cl2) fraction of the aqueous extract of Rubus suavissimus resulted in the isolation of two sterols namely stigmasterol and β-sitosterol. The structures of the isolated compounds were characterized on the basis of extensive spectral data (1D and 2D NMR; and MS) and in comparison with their literature data.

Photostability of rebaudioside A, a sweet constituent of Stevia rebaudiana was studied under fluorescent light exposure at 25 o C in mock beverages at pH 3.8 using International Conference on Harmonization (ICH) technical requirements covering the stability testing of new drug substances and products. Experimental results indicated that rebaudiosid...

Aim: To study NMR spectral analysis and hydrolysis products of Rebaudioside A (1) that has been isolated from Stevia rebaudiana. Study Design: Acquiring NMR and high resolution mass spectral (HRMS) data of Rebaudioside A for structural characterization, and identification of hydrolysis products. Methodology: The 1D (1 H & 13 C) and 2D (COSY, HSQC,...

Systematic phytochemical study of the n -BuOH fraction of the aqueous extract of Rubus suavissimus resulted in the isolation of three diterpene glycosides namely rubusoside, suavioside-A and sugeroside; a phenolic glycoside quercetrin; and a lignan glycoside arctiin. The structures of the isolated compounds were characterized on the basis of extens...

The objective is to identify the Infra-Red (IR) spectral analysis of the diterpene glycosides present in the commercial extracts of Stevia rebaudiana was achieved by PerkinElmer Spectrum 400 Fourier Transform (FT) spectrometer employing a PerkinElmer Universal Attenuated Total Reflection (ATR) accessory. Using this technique the IR spectral pattern...

Hydrolysis of the diterpene glycoside rebaudioside F isolated from Stevia rebaudiana was performed using enzymatic and acid conditions. Acid hydrolysis was carried out using H 2SO 4 and HCl whereas enzymatic hydrolysis was performed using pectinase. Utilizing these methods, aglycone moieties of rebaudioside F and its sugar residues were identified....

The complete NMR spectral assignments for the two diterpenes, steviol obtained from the hydrolysis of stevioside that was isolated from Stevia rebaudiana and its monoacetylated product were achieved by the extensive 1D (1H and 13C) and 2D NMR (COSY, HSQC, and HMBC) as well as mass spectral data.

From the commercial extract of the leaves of Stevia rebaudiana, a new diterpene glycoside was isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compound was identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O...

Three novel diterpene glycosides were isolated for the first time from the commercial extract of the leaves of Stevia rebaudiana, along with several known steviol glycosides, namely stevioside, rebaudiosides A-F, rubusoside and dulcoside A. The new compounds were identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)ox...

Synthesis of two ent-kaurane diterpene glycosides, steviol 19-O-β-D-glucopyranosiduronic acid (steviol glucuronide, 5), and 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7) has been achieved from a common starting material, steviol, using phase transfer catalyst. Also, synthesis of an additional 17-nor-ent-kaurane glycoside, namel...

The complete 1 H and 13 C NMR assignments for the two diterpene glycosides 13-[(2-O-α-L-rhamnopyranosyl --D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid -D-glucopyranosyl ester (Dulcoside A) and 13-[(2-O-α-L-rhamnopyranosyl-3-O--D-glucopyranosyl--D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester (Dulcoside B) isolated...

Three new minor diterpene glycosides were isolated from the commercial extract of the leaves of Stevia rebaudiana and their structures were identified as 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent -kaur-15-en-19-oic acid β-D-glucopyranosyl ester (1),13-[(2-O-β-D-glucopyranosyl-3-O-β-Dglucopyranosyl-β β β β-D-glucopyranosyl)oxy] ent -ka...

Hydrolysis studies of the two diterpene glycosides stevioside and rebaudioside A that were isolated from Stevia rebaudiana were performed using acid and alkaline conditions. Acid hydrolysis was carried out using H2SO4 whereas alkaline hydrolysis was performed using NaOH. Using these methods, partial hydrolyzed glycosides of stevioside and rebaudios...

From the commercial extract of the leaves of Stevia rebaudiana, two additional new diterpenoid glycosides were isolated and their structures were characterized as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-xylopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester (1) and 13-[(2-O-β-D-xylopyranosyl-β-D-glucopyranosyl)oxy] en...

Two additional novel minor diterpene glycosides were isolated from the commercial extract of the leaves of Stevia rebaudiana Bertoni. The structures of the new compounds were identified as 13-{beta-D-glucopyranosyl-(1 -> 2)-O-[beta-D-glucopyranosyl-( 1 -> 3)-beta-D-glucopyranosyl-oxy} ent-kaur-16-en-19-oic acid {beta-D-xylopyranosyl-(1 -> 2)-O-[ be...

Photostability of a mixture of steviol glycosides was studied under fluorescent light exposure at 25 °C in mock beverages at pH 3.8 using International Conference on Harmonization (ICH) technical requirements covering the stability testing of new drug substances and products. Experimental results indicated that steviol glycoside mixture did not und...

From the commercial extract of the leaves of Stevia rebaudiana, two new minor diterpene glycosides having α-glucosyl linkage were isolated besides the known steviol glycosides including stevioside, steviolbioside, rebaudiosides A-F, rubusoside and dulcoside A. The structures of the two compounds were identified as 13-[(2-O-(3-α-O-d-glucopyranosyl)-...

From the commercial extract of the leaves of Stevia rebaudiana, two new diterpenoid glycosides were isolated besides the known steviol glycosides including stevioside, rebaudiosides A-F, rubusoside, and dulcoside A. The structures of the two new compounds were identified as 13-[(2-O-6-deoxy-β-d-glucopyranosyl-β-d-glucopyranosyl)oxy] ent-kaur-16-en-...

Two new new diterpene glycosides, 13-[(2-O-(6-O-β-D-glucopyranosyl)-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid β-D-glucopyranosyl ester (1) and 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-fructofuranosyl-β-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid β-D-glucopyranosyl ester (2) were isolated from the leaves of Stevia rebaudiana, alo...

Two new new diterpene glycosides, 13-[(2-O-(6-O-beta-D-glucopyranosyl)-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid beta-D-glucopyranosyl ester (1) and 13-[(2-O-beta-D-glucopyranosyl-3-O-beta-D-fructofuranosyl-beta-D-glucopyranosyl)oxy] kaur-16-en-18-oic acid beta-D-glucopyranosyl ester (2) were isolated from the leaves o...

Systematic phytochemical studies of the extract of Luo Han Go (Siraitia grosvenorii) furnished six known cucurbitane glycosides, namely, mogrosides IVa, mogrosides V and VI, isomogroside V, 11-oxomogroside V, and siamenoside I. The structures of all the isolated compounds were characterized on the basis of extensive spectral and chemical studies. T...

Stability of a mixture of steviol glycosides was studied under a variety of conditions covering a typical pH range and various temperatures that simulated both relevant and extreme beverage storage conditions. Thus, steviol glycosides was evaluated in mock beverage solutions by simulating formulations used in commercial cola soft drinks (pH 2.8 and...

Two kaempferol glycosides were isolated from the purification of the commercial extract of Luo Han Go (Siraitia grosvenorii) on a C-18 column using a Biotage Flash Chromatography system. The structures of the isolated compounds were characterized as kaempferol-3-O-α-L- rhamnoside and kaempferol-3,7-O-α-L-dirhamnoside on the basis of extensive spect...

From the commercial extract of the leaves of Stevia rebaudiana, a diterpene glycoside was isolated which was identified as 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-Dglucopyranosyl) oxy] ent-kaur-16-en-19-oic acid-(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester (1); also known as rebaudioside D. The complete 1H and 13C NMR assignment o...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Bioassay-directed fractionation of an extract of the root and bark of Podocarpus madagascariensis resulted in the isolation of a new totarol diterpenoid (1) in addition to the three known cytotoxic diterpenoids 19-hydroxytotarol (2), totaradiol (3), and 4beta-carboxy-19-nor-totarol (4). The structure of the new compound 1 was established as methyl-...

Bioassay-directed fractionation of ethanol extracts of the roots and leaves of the plant Cassipourea madagascariensis resulted in the isolation of the two new terpenoids cassipourol (1) and cassipouryl acetate (2) in addition to the three known compounds, 3beta,30-dihydroxylup-20(29)-ene (3), 30-hydroxylup-20(29)-en-3-one (4), and combretol (5). Th...

Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase β, resulted in the isolation of the four new lupane triterpenoids 1–4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, α-amyri...

Bioassay-guided fractionation of an EtOAc extract of the leaves of Melampodium camphoratum using an assay for inhibitors of the degradation of hemin resulted in the isolation of six new eudesmane sesquiterpenes (1-6) and the known 6-epi-beta-verbesinol coumarate (7). The structures of compounds 1-6 were established as 6alpha-(4'-O-methyl-7'E-coumar...

Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, alph...

Using an assay to detect inhibitors of the lyase activity of DNA polymerase β, bioassay-directed fractionation of a CHCl3 extract of an unidentified sponge of the family Demospongiae resulted in the isolation of the new diterpenoid 1, the new bis-norditerpenoids 2–3, and the two known compounds spongia-13(16),14-dien-19-oic acid (4), and methylspon...

Five new and uncommon aromatic derivatives and the red pigment caulerpin have been reported from the CHCl3 extract of Caulerpa racemosa. The structures of the new derivatives have been elucidated as 1,5-diphenyl-1,4-pentadiene {1}, trans-cinnamyl-1-phenyl-2-propenyl ether {2}, dicinnamyl ether {3}, cinnamyl-3-phenyl-1-propenyl ether {4}, and cinnam...

Bioassay-directed fractionation of a methyl ethyl ketone extract of the roots of Endlicheria aff. resulted in the isolation of four new neolignans (1-4) and eight known compounds, namely, canellin A (5), canellin C (6), 3'-methoxyguianin (7), (7S,8R,1'S,5'S,6'R)-Delta(2',8')-3',6'-dihydroxy-5'-methoxy-3,4-methylenedioxy-4'-oxo-8.1',7.5'-neolignan (...

Continuation of the chemical examination of the cytotoxic constituents of the wood of Vepris punctata resulted in the isolation of the two new terpenoids 1 and 2 and eight known compounds, glechomanolide (3), isogermafurenolide, (E,E)-germacra-1(10),4,7(11)-triene, alpha-amyrin, lupeol, lupeyl acetate, taraxerol, and 3-epi-taraxerol, in addition to...