Synthesis of ent-Kaurane Diterpene Monoglycosides

Chaturvedula, Venkata Sai Prakash; Klucik, Josef; Upreti, Mani; Prakash, Indra
October 2011
Molecules;Oct2011, Vol. 16 Issue 10, p8402
Academic Journal
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-≈-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, namely 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-≈-D-glucopyranosyl ester (10) was performed using the starting material isosteviol and similar synthetic methodology. Synthesis of all three steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR as well as mass spectral (MS) data.


Related Articles

  • A new triterpene glycoside from Premna microphylla. Zha-Jun Zhan; Lan Tang; Wei-Guang Shan // Chemistry of Natural Compounds;Mar2009, Vol. 45 Issue 2, p197 

    A new triterpene glycoside, namely 28- O-α-L-rhamnopyranosyl (1→2)-β- D-glucopyranoside tormentic acid ester, was isolated from the leaves of Premna microphylla, together with two known triterpenes, i.e., arjunolic acid ( 2) and hyptatic acid A ( 3). Its structure was established by...

  • A New Diterpene Glycoside from Stevia rebaudiana. Chaturvedula, Venkata Sai Prakash; Prakash, Indra // Molecules;Apr2011, Vol. 16 Issue 4, p2937 

    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-...

  • New triterpene glycoside from Cyclamen adzharicum tubers. Tabidze, B. V.; Tabatadze, N. A.; Dekanosidze, G. E.; Elias, R.; Faure, R. // Chemistry of Natural Compounds;Sep2009, Vol. 45 Issue 5, p660 

    Nine pure glycosides were isolated from total saponins of Cyclamen adzharicum Pobed. (Primulaceae). The total chemical structure of cyclamen F, 3β- O-[β- D-Xylp(1→2)]-[β- D-Glcp(1→2)]-(β- D-Glcp(1→4)-α-L-Arap)-16α-hydroxy-13,28-epoxy-30,30-dibutoxyolean,...

  • New Cucurbitane Triterpenoids and Steroidal Glycoside from Momordica charantia. Jie-Qing Liu; Jian-Chao Chen; Cui-Fang Wang; Ming-Hua Qiu // Molecules;Dec2009, Vol. 14 Issue 12, p4804 

    Three new cucurbitane triterpenoids 1-3 and one new steroidal glycoside 4, were isolated together with ten known compounds from Momordica charantia. The structures of new compounds were determined to be 19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside...

  • Synthesis and In Vivo Acute Antihyperglycemic Evaluation of Novel Isosteviol Derivatives. Junqing Chen; Xiaoming Zha; Min Sun; Jin Cai; Wen Zhou; Min Ji // Letters in Drug Design & Discovery;Nov2010, Vol. 7 Issue 9, p686 

    No abstract available.

  • 4-Hydroxy-2-quinolones 141. Synthesis and structure of 5R-3-hydroxy-1,5-dihydropyrazolo[4,3- c]quinolin-4-ones. Ukrainets, I.; Kravtsova, V.; Tkach, A.; Sim, G. // Chemistry of Heterocyclic Compounds;Feb2008, Vol. 44 Issue 2, p173 

    Treatment of 1R-4-chloro-3-ethoxycarbonyl-2-oxo-1,2-dihydroquinolines with p-toluenesulfonylhydrazide in refluxing ethanol and in the presence of triethylamine gives the 3-hydroxy-5R-1,5-dihydropyrazolo[4,3-c]quinolin-4-ones. The possible mechanism of formation, features of the steric structure...

  • Metabolism of 18β-glycyrrhetinic acid in Sphingomonas paucimobilis strain G5. Yoshida, Keishiro; Furihata, Kazuo; Yamane, Hisakazu; Omori, Toshio // Biotechnology Letters;Feb2001, Vol. 23 Issue 4, p253 

    Seven strains capable of utilizing 18β-glycyrrhetinic acid (18β-GRA) as a sole carbon and energy source were isolated from soil samples by enrichment culture technique. One of these strains, named strain G5, was identified as Sphingomonas paucimobilis. When this strain grew on 18β-GRA,...

  • Interaction of sodium fullerene derivatives with trimethylchlorosilane. Titova, S.; Domrachev, G.; Gorina, E.; Kalakutskaya, L.; Ob”edkov, A.; Kaverin, B.; Ketkov, S.; Lopatin, M.; Markin, A.; Smirnova, N.; Zhogova, K. // Physics of the Solid State;May2006, Vol. 48 Issue 5, p1000 

    Soluble dimer compounds of the general formula [C60( Me 3Si)n]2 (where n = 3, 5, 7, or 9 and M e = CH3) and a soluble monomer compound, C60( Me 3Si)12, are synthesized by the reaction of the compound C60Nan( THF)x (where n = 4, 6, 8, 10, or 12 and THF = tetrahydrofuran) with...

  • A New Natural Ceramide from Trollius chinensis Bunge. Ru-Feng Wang; Rui-Ning Liu; Tong Zhang; Tao W // Molecules;Oct2010, Vol. 15 Issue 10, p7467 

    A new natural product named trolliamide was isolated from Trollius chinensis Bunge. Its structure was determined as 2-hydroxy-tetracosanoic acid(2,3-dihydroxy-1- hydroxymethyl-heptadec-7-enyl)-amide by spectroscopic methods, including UV, IR, MS and NMR. This is the first report of a ceramide...


Read the Article


Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics