Zur Kenntnis der Triterpene. (83. Mitteilung). Zum oxydativen Abbau der Ringe A und B des Hederagenins

Růžička, L.; Norymberski, J.; Jeger, O.

doi:10.1002/hlca.19430260717

Cited by 10 publications

(4 citation statements)

References 3 publications

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“…The structure which has been defended most staunchly (72,73) and which admittedly explains a greater number of experimental facts than any other is that first proposed by R. D. Haworth (4) and shown in detail in formula I and in condensed 1. Oleanolic acid Ia form in formula Ia with the numbering of the carbon atoms and designation of the rings.…”

Section: Determination Of Structurementioning

confidence: 93%

“…The decision to locate the carboxyl group at C-17 and the double bond between C-12 and C-13 re ' sts methyl acetyloleanolate with selenium dioxide in boiling acetic acid solu tion gave two compounds, Cs3HS004 and CSSH4606 (70). The latter compound on the basis of the absorption spectrum (Amax, = 275 mIl, log E = 4.1) is formulated as a diendione (X) (76). Whereas methyl oleanolate is resistant to hydrolysis, the ester group of the diendione can be saponified with alcoholic potassium hydroxide, presumably because it is a vinylogue of a �-ketoacid, and the acid so obtained (XI) on heating in xylene loses carbon dioxide.…”

Section: Determination Of Structurementioning

confidence: 99%

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The Chemistry of the Triterpenes

Noller¹

1945

Annu. Rev. Biochem.

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Section: Determination Of Structurementioning

confidence: 93%

Section: Determination Of Structurementioning

confidence: 99%

The Chemistry of the Triterpenes

Noller¹

1945

Annu. Rev. Biochem.

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“…Protected amides of GL (44)(45)(46)(47)(48)(49)(50)(51)(52)(53)(54)(55)(56) were synthesized by the reaction of penta-O-acetyl GL trichloride (43) with amines R N H 2 with 52-90% yields [68,69]. Heterocyclic and aromatic amides (57)(58)(59)(60)(61)(62)(63)(64)(65)(66) were prepared by the condensation of GL with bioactive amines, quinolines, uracils and sulfanylamides using DCC [70][71][72].…”

Section: Synthesis Of Glycyrrhizic Acid Amidesmentioning

confidence: 99%

“…The structure of GLA (2) was established by Ruzicka, Djerassi and Beaton [55][56][57], and they have shown, that GLA was a triterpene acid related to the series of β-oleanene and having the structure of 3β-hydroxy-11-oxo-18β-H,20β-olean-12-en-30-oic acid (2). Lithgoe and Trippett investigated the structure of GL carbohydrate chain, and they established that it consisted of two molecules of glucuronic acid [58].…”

Section: Isolation Of Glycyrrhizic Acid From Raw Materials and Its Stmentioning

confidence: 99%

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Балтина

2003

CMC

223

160

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Glycyrrhizic Acid (GL) is the major bioactive triterpene glycoside of licorice root (Glycyrrhiza Radix) extracts possessing a wide range of pharmacological properties (anti-inflammatory, anti-ulcer, anti-allergic, anti-dote, anti-oxidant, anti-tumor, anti-viral etc.). Official sources of GL are Glycyrrhiza glabra L. and Gl. uralensis Fish. (Leguminosae). The content of GL in licorice root is 2-24% of the dry weight. GL is one of the leading natural compounds for clinical trials of chronic active viral hepatitis and HIV infections (preparation Stronger Neo-Minophagen C, SNMC), and its monoammonium salt (glycyram, tussilinar) is used as an anti-inflammatory and anti-allergic remedy. The synthetic transformations of GL on carboxyl and hydroxyl groups were carried out to produce new bioactive derivatives for medicine. GL esters were produced containing fragments of bioactive acids (4-nitrobenzoic, cinnamic, salycilic, acetylsalycilic, nicotinic, isonicotinic). Bioactive amides of GL were synthesized using chloroanhydride technique and N,N'-diciclohexylcarbodiimide (DCC) method. The synthesis of acylthioureids and semicarbazones was carried out via the reaction of triacylisothiocianate of penta-O-acetyl-GL with primary amines and hydrazines. The chain of transformations of trichloranhydride of penta-O-acetyl-GL was made with the introduction of diazoketone groups in the molecule. A new group of GL derivatives to be triterpene glycopeptides was prepared by the activated esters method (N-hydrohysuccinimide-DCC or N-hydroxybenzotriazol-DCC) using alkyl (methyl, ethyl, propyl, butyl, tert-butyl) or benzyl (4-nitrobenzyl) esters of amino acids. The glycyrrhizyl analogs of the known immunostimulator, N-acetyl-muramoyldipeptide (MDP), were synthesized using Reagent Woodward K. A series of ureids and carbamates of GL was synthesized containing 5-amino-5-desoxy-D-xylopyranose units. The synthesis of 4-nitro-4-desoxy-glycosides, modified analogs of GL, was carried out by the oxidative splitting of the carbohydrate part of GL with NaIO(4). Triterpene 2-desoxy-D-glycosides, analogs of GL, were prepared by the glycal method in the presence of iodine-containing promoters or sulfonic acid cation-exchange resin KU-2-8 (H+) and LiBr. New anti-inflammatory and anti-ulcer agents were found among GL derivatives such as esters, amides, ureids, carbamates, thioureids and glycopeptides. GL glycopeptides are of interest as immunomodulators. Some of the chemically modified GL derivatives (salts, amides, glycopeptides) were potent HIV-1 and HIV-2 inhibitors in vitro. Preparation niglizin (penta-O-nicotinate of GL) was studied clinically as an anti-inflammatory agent and is of interest for studies as hepatoprotector and HIV inhibitor.

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Zur Kenntnis der Triterpene. (84. Mitteilung). Neuer Beweis für die verschiedene Lage der Carboxylgruppe bei der Oleanolsäure und der Glycyrrhetinsäure

Růžička

Jeger

Ingold

1943

Helvetica Chimica Acta

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R] , = t 101,SO (c = 0,933 in Chloroform) 3,633 mg Subst. gaben 10,191 mg CO, und 3,305 mg H,O C,,H,,O, Ber. C 76,62 H 10,07% Gef. ,, 76,55 ,, lO,lS% A 2 O j 22-2 1 -0 x y -n o r -a110c h olens Bur e -l a c t o n (VIII). Auf die Isolierung des 20-Oxy-lactons wurde verzichtet. Diejenigen Praktionen, die einen positiven LegaZ-Test zeigten, wurden aus Methanol umkrystallisiert, wobei ein Praparat vom konstanten Smp. 170O erhalt en wurde. [.ID = f1,3 (c = 0,920 in Chloroform) 3,630 mg Subst. gaben 10,711 mg CO, und 3,234 mg H,O CP3H3402 Ber. C 80,65 H l O , O l % Gef. ,, 80,52 ,, 9,97% Die Analysen wurden in unserer mikroanalytischen Abteilung von Herrn W. Nanser ausgefuhrt.

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Zur Kenntnis der Triterpene. (83. Mitteilung). Zum oxydativen Abbau der Ringe A und B des Hederagenins

Cited by 10 publications

References 3 publications

The Chemistry of the Triterpenes

The Chemistry of the Triterpenes

Chemical Modification of Glycyrrhizic Acid As A Route to New Bioactive Compounds for Medicine

Zur Kenntnis der Triterpene. (84. Mitteilung). Neuer Beweis für die verschiedene Lage der Carboxylgruppe bei der Oleanolsäure und der Glycyrrhetinsäure

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