Synthesis and high-resolution NMR spectra of A-nor-derivatives of 11-deoxyglycyrrhetic acid

Михайлова, Л. Р.; Балтина, Л. А.; Кондратенко, Р. М.; Kunert, Olaf; Спирихин, Л. В.; Галин, Ф. З.; Толстиков, Г. А.

doi:10.1007/s10600-006-0212-5

Cited by 15 publications

(8 citation statements)

References 10 publications

(3 reference statements)

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“…Assignments for the protons associated with GA are given as the protons associated with a particular carbon atom, as shown in Figure 6, which are based on assignments given by Mikhailova and co-workers. [72] Bands characteristic of both the antimony and arsenic moiety and the GA moiety are present consistent with the proposed structure. Similar results are found for the triphenybismuth product.…”

Section: Nmr Spectroscopy Resultssupporting

confidence: 83%

“…Assignments are in agreement with those cited in the literature. [72][73][74] Results appear in Table 4 for the products from triphenylantimony dichloride and GA, and triphenylarsenic dichloride and GA. Assignments for the protons associated with GA are given as the protons associated with a particular carbon atom, as shown in Figure 6, which are based on assignments given by Mikhailova and co-workers.…”

Section: Nmr Spectroscopy Resultsmentioning

confidence: 99%

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Synthesis of organoarsenic, organoantimony, and organobismuth poly(ether esters) from reaction with glycyrrhetinic acid and their preliminary activity against pancreatic cancer cell lines

Carraher

Truong

Roner

et al. 2013

Journal of the Chinese Advanced Materials Society

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Section: Nmr Spectroscopy Resultssupporting

confidence: 83%

Section: Nmr Spectroscopy Resultsmentioning

confidence: 99%

Synthesis of organoarsenic, organoantimony, and organobismuth poly(ether esters) from reaction with glycyrrhetinic acid and their preliminary activity against pancreatic cancer cell lines

Carraher

Truong

Roner

et al. 2013

Journal of the Chinese Advanced Materials Society

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“…Resonances in NMR spectra were assigned using COSY and HSQC correlation spectroscopy and by comparison with literature data for GLA and its derivatives [9,10]. Molecular ions were determined by LC/MS on a Shimadzu LCMS-2010 using CI at atmospheric pressure as solutions in methanol or acetonitrile.…”

Section: Methodsmentioning

confidence: 99%

“…The methyl ester of 11-desoxo-GLA (3) was prepared by treating a solution of 1 in MeOH with an ether solution of diazomethane as described before [10], mp 248-250°C (CHCl 3 :CH 3 OH), lit. [13] mp 248-249°C.…”

Section: Methodsmentioning

confidence: 99%

Ozonolysis of 11-desoxoglycyrrhetic acid and its derivatives

et al. 2007

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12-Oxo derivatives of 11-desoxolycyrrhetic acid and its derivatives were produced by oxidative transformation using ozone. acid was produced for the first time by exhaustive ozonolysis of 11-desoxoglycyrrhetic acid at -60°C.Oxidative transformations of bioactive plant triterpenoids is of great interest for preparing new oxygenated derivatives, seeking selective oxidizing reagents, and studying structure-activity relationships of derivatives of natural compounds. Introduction of additional oxygenated functional groups into triterpenoids can significantly affect their biological activity [1][2][3].Ozone is an effective and ecologically clean oxidant that has been used in various studies to prepare oxygenated derivatives of oleanolic acid and 18β-glycyrrhetic acid (GLA), the principal triterpenoid from licorice roots (Glycyrrhiza glabra L. and G. uralensis Fisher). It had been thought that the C12=C13 olefinic bond does not react with O 3 due to steric hindrance [4][5][6]. Prolonged (50 h) ozonation of GLA methyl ester acetate produced the methyl ester of 3-acetoxy-12,13-epoxy-18β-olean-11-on-30-oic acid in 40% yield [5].The goal of our work was to study transformations of 11-desoxo-GLA (1) and its derivatives 2 and 3 that were caused by ozone. 1: R = R 1 = H; 2: R = H, R 1 = Ac; 3: R = Me, R 1 = H Ozonolysis of 11-desoxo-GLA (1) in CH 2 Cl 2 at -60°C until ozone appeared at the outlet from the flask (until the solution turned blue) and subsequent reduction of the reaction products with Zn powder in CH 3 COOH for 1 h at 0°C produced a mixture of products that was separated by column chromatography (CC) over silica gel (SG). Compound 4 (36% yield), which was identified by its PMR and 13 C NMR spectra as olean-3,12-dion-30-oic acid (Scheme 1), and starting 1, the TLC and PMR spectrum of which agreed with a known sample, were isolated pure from the oxidation products.The PMR spectrum of 4 had seven singlets for methyls and a resonance for proton β-H13 at 2.8 ppm with spin-spin coupling constant 4 Hz. This was typical of derivatives of β-amyrin triterpenoids with oxygenated functional groups on C12 [4,7]. The 13 C NMR spectrum of 4 had resonances for 30 C atoms including typical resonances for C3=O and C12=O at 216.9 and 212.7 ppm, respectively. The chemical shifts for C12 and C13 (50.2 ppm) in 13β-H ketone 4 were similar to those of 13β-H-12-oxo-derivatives of oleanolic acid [8] and confirmed its configuration.

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“…Partial ozonolysis of 177 gave the epoxide 178 as product, and oxidation of 179 with RuO 4 gave 180 and 181 as a mixture (2:1) of products, while partial ozonolysis of 179 gave only 180 as product. 29 derivative and DCC as coupling promoter (Scheme 23), leading to the respective amides 183 and 185, which were reacted with KOH in order to generate the un-protected derivatives 184 and 186, respectively.…”

Section: Modifications At Rings a And Cmentioning

confidence: 99%

Glycyrrhizin and glycyrrhetic acid: scaffolds to promising new pharmacologically active compounds

Graebin¹,

Verli²,

Guimarães³

2010

J. Braz. Chem. Soc.

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O ácido glicirrizínico (GL), também conhecido como glicirrizina, é uma saponina triterpênica, um produto natural encontrado na raiz de Glycyrrhyza glabra L. ("licquorice" ou "alcaçuz"), utilizada mundialmente como edulcorante e também na medicina tradicional do Oriente. Este artigo de revisão enfoca os novos compostos sintetizados usando GL ou sua aglicona, o ácido glicirretínico (GLA), como materiais de partida e as atividades farmacológicas descritas para os mesmos e seus derivados.Glycyrrhizinic acid (GL), also known as glycyrrhizin, is a triterpene saponin, a natural product found on the root of Glycyrrhyza glabra L. ("licquorice"), used worldwide as sweetener and in the traditional eastern medicines. This review is focused on a series of new derivatives synthesized using GL and its aglycon, glycyrrhetinic acid (GLA), as starting materials, the pharmacological activities described for those compounds, as well as new activities reported for GL and GLA themselves.

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Synthesis and high-resolution NMR spectra of A-nor-derivatives of 11-deoxyglycyrrhetic acid

Cited by 15 publications

References 10 publications

Synthesis of organoarsenic, organoantimony, and organobismuth poly(ether esters) from reaction with glycyrrhetinic acid and their preliminary activity against pancreatic cancer cell lines

Synthesis of organoarsenic, organoantimony, and organobismuth poly(ether esters) from reaction with glycyrrhetinic acid and their preliminary activity against pancreatic cancer cell lines

Ozonolysis of 11-desoxoglycyrrhetic acid and its derivatives

Glycyrrhizin and glycyrrhetic acid: scaffolds to promising new pharmacologically active compounds

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