Acacic Acid Research Articles

A Minor Acylated Triterpenoid Saponin from the Seeds of Pithecellobium dulce

A novel acylated triterpenoid saponin, designated pithecelloside, is isolated from the seeds of Pithecellobium dulce and characterised as 3- O-[α-L-arabinopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21β- O-[(2' E)-6'-hydroxy-2’,6'-dimethylocta-2’,7'-dienoyl]acacic acid 1.

A Minor Acylated Triterpenoid Saponin from the Seeds of Pithecellobium dulce

A novel acylated triterpenoid saponin, designated pithecelloside, is isolated from the seeds of Pithecellobium dulce and characterised as 3-O-[α-L-arabinopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21β-O-[(2′E)-6′-hydroxy-2′,6′-dimethylocta-2′,7′-dienoyl]acacic acid 1.

A New Isomer of Julibroside J2 from Albizia julibrissin

A new isomer of Julibroside J2 (Chen, S.P., Zhang, R.Y., Ma, L.B. and Tu, G.Z. Acta Pharm. Sinica, 1997, 32, 110–115) was obtained from the cytotoxic fraction of 95% ethanol extracts of stem barks of Albizia julibrissin Durazz, together with Julibroside J2. Its structure was elucidated as 3-O-[β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(6S)-2-trans-2-hydroxymethyl-6-methyl-6-O-[3-O-((6S)-2-trans-2-hydroxymethyl-6-methyl-6-hydroxy-2,7 -octadienoyl)-β-D-quinovopyranosyl]-2,7-octadienoyl} acacic acid 28-O-β-D-glucopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester(1), named as Julibroside J7, based on chemical and spectral methods. Julibroside J2 showed good inhibitory action against KB cell line in vitro.

Four acylated triterpenoid saponins from Albizia procera.

Four new oleanane-type triterpene glycosides, proceraosides A-D (1-4), were isolated from the seeds of Albizia procera. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and a monoterpenic carboxylic acid linked to a monoterpene quinovoside as the acyl moiety at C-21. The common oligosaccharide moiety linked to C-28 in 1-3 was determined as alpha-l-arabino- furanosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha-L-rhamnopyranosy l- (1-->2)-beta-D-glucopyranosyl ester. These compounds differed in the C-3-linked sugar unit or in the configuration of C-6' of the inner monoterpene moiety in the C-21-linked acyl unit. Compound 4 was established as the 16-deoxy analogue of 1.

Three acylated saponins and a related compound from Pithecellobium dulce.

Four new oleanane-type triterpene glycosides, pithedulosides H-K (1-4), were isolated from the seeds of Pithecellobium dulce. Their structures were established by extensive NMR experiments and chemical methods. Compounds 1-3 comprised acacic acid as the aglycon and either monoterpene carboxylic acid and its xyloside or monoterpene carboxylic acid as the acyl moiety at C-21. The oligosaccharide moieties linked to C-3 and C-28 were determined as alpha-L-arabinopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1 -->6)- [beta-D-glucopyranosyl-(1-->2)]-beta-D-glucopyranosyl and alpha-L-arabinofuranosyl-(1-->4)-[beta-D-glucopyranosyl-(1-->3)]-alpha- rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester, respectively. Compound 4 was established as an echinocystic acid 3-O-glycoside having the same sugar sequences as 1-3. Also obtained in this investigation was the known compound 5, which was identified as echinocystic acid 3-O-beta-D-xylopyranosyl- (1-->2)-alpha-L-arabinopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1 -->2)]- beta-D-glucopyranoside.

Isolation and structure elucidation of three triterpenoid saponins from Acacia auriculiformis

Three new triterpenoid saponins, proacaciaside-I, proacaciaside-II and acaciamine isolated from the fruits of Acacia auriculiformis, were identified as acacic acid lactone-3-O-β- d-glucopyranosyl (1 → 6)-β- d-glucopyranoside, acacic acid lactone-3-O-α- l-arabinopyranosyl (1 → 2)-β- d-glucopyranoside and acacic acid lactone-3-O-α- l-arabinopyranosyl (1 → 6)-2-acetamido-2-deoxy-β- d-glucopyranoside based on their spectral properties and some chemical transformations.

Acacia concinna saponins. I. Structures of prosapogenols, concinnosides A-F, isolated from the alkaline hydrolysate of the highly polar saponin fraction.

A highly polar saponin mixture from pods of Acacia concinna (Leguminosae) was hydrolyzed with alkali to yield five new triterpenoidal prosapogenols named concinnosides A (6), B (3), C (7), D (4), and E (8), together with four known glycosides, acaciaside, (2), julibroside A1 (10) julibroside A3 (9), albiziasaponin C (5), and their aglycone, acacic acid lactone (1). The structures of these new prosapogenols were elucidated based on spectroscopic means. A less polar saponin fraction from the pods gave spinasteryl glucoside and its dihydro derivative.

Three New Triterpenoidal Saponins Acylated with Monoterpenic Acid from Albizziae Cortex

Abstract The structures of Julibrosides I, II, and III, isolated from dried stem bark of Albizzia julibrissin DURAZZ (Albizziae Cortex), were characterized as complex triterpenoidal glycosides linked to the monoterpene glycoside dimer, mainly by means of an NMR spectroscopic method. These compounds have a common structure comprising from acacic acid, the (6S)-2-trans-6-hydroxy-2,6-dimethy1-2,7-octadienoyl-6-O-quinovopyranoside dimer, and α-l-arabinofuranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)]-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranoside. The diversity of the oligosaccharides attached to the C-3 hydroxyl group of acacic acid, an oleanane-type triterpene, makes a distinction between Julibrosides I, II, and III.

Saponins from Albizia lebbeck

Three main saponins named albiziasaponins A, B, and C were isolated from the barks of Albizia lebbeck. Their structures were established through spectral analyses as acacic acid lactone 3-O-β- d-xylopyranosyl -(1 → 2)-α- l-arabinopyranosyl -(1 → 6)-β- d-glucopyranoside , 3-O-β- d-glucopyranosyl -(1 → 2)-O-[α- l-arabinopyranosyl -(1 → 6)]-β- d-glucopyranoside and 3-O-β- d-xylopyranosyl -(1 → 2)-α- l-arabinopyranosyl -(1 → 6)-O-[β- d-glucopyranosyl -(1 → 2)]-β- d- glucopyranoside .

Structure of acaciaside, a triterpenoid trisaccharide from Acacia auriculiformis

The structure of a new triterpenoid trisaccharide isolated from the seeds of Acacia auriculiformis has been elucidated as acacic acid lactone-3- O-β- d-glucopyranosyl (1 → 6)-[α- l-arabinopyranosyl (1 → 2)]-β- d-glucopyranoside based on its spectral properties and some chemical transformations.

Studies on the constituents of Leguminous plants. VIII. The structure of a new triterpenoid saponin from the fruits of Gymnocladus chinensis BAILLON.

A new triterpenoid saponin, gymnocladus saponin G (1), having a glycosyl monoterpene carboxyl moiety and a 2-methylbutyloyl group, was isolated from the fruits of Gymnocladus chinensis BAILLON. On the basis of chemical and physicochemical evidence, its structure was characterized as 2β, 23-dihydroxy-3-O- [β-D-xylopyranosyl- (1→2) -α-L-arabinopyranosyl- (1→6) -β-D-glucopyranosyl] -21-O- {(6S) -2-trans-2, 6-dimethyl-6- [3-O- (β-D-glucopyranosyl) -4-O- (2-methylbutyroyl) -α-L-arabinopyranosyloxy] -2, 7-octadienoyl} acacic acid 28-O-β-D-xylopyranosyl- (1→3) -β-D-xylopyranosyl- (1→4) -α-L-rhamnopyranosyl- (1→2) - [α-L-rhamnopyranosyl- (1→6)] -β-D-glucopyranoside.

Studies on the constituents of Leguminous plants. VII. The structure of triterpenoid saponins from fruits of Gymnocladus chinensis Baillon.

A new triterpenoid saponin, gymnocladus saponin G (1), having a glycosyl monoterpene carboxyl moiety and a 2-methylbutyloyl group, was isolated from the fruits of Gymnocladus chinensis BAILLON. On the basis of chemical and physicochemical evidence, its structure was characterized as 2β, 23-dihydroxy-3-O- [β-D-xylopyranosyl- (1→2) -α-L-arabinopyranosyl- (1→6) -β-D-glucopyranosyl] -21-O- {(6S) -2-trans-2, 6-dimethyl-6- [3-O- (β-D-glucopyranosyl) -4-O- (2-methylbutyroyl) -α-L-arabinopyranosyloxy] -2, 7-octadienoyl} acacic acid 28-O-β-D-xylopyranosyl- (1→3) -β-D-xylopyranosyl- (1→4) -α-L-rhamnopyranosyl- (1→2) - [α-L-rhamnopyranosyl- (1→6)] -β-D-glucopyranoside.

Isolation of a new sapogenin fromAlbizzia julibrissin

From the hydrolysate of the strong uterotonic active saponin ofAlbizzia julibrissin a new sapogenin, machaerinic acid methylester together with acacic acid lactone was isolated and characterized.

Sapogenins of acacia concinna DC—IV : Wagner-meerwein rearrangements in acacic acid lactone and some selected triterpenes

Dehydration reactions involving the 3-OH of ring-A in acacic acid lactone ( 1), sapogenin-B ( 2), methyl exhinocystate ( 3) and methyl oleanolate ( 4) have been carried out with different reagents: POCl 3/pyridine, PCl 5/hexane and solvolysis of their 3-tosylates. Structures of the different products obtained have been assigned based on the study of their PMR and mass spectra. Dependence of the conformational strain of the rest of the molecule other than ring-A is felt considerably on the course of dehydration with milder reagents, e.g. POCl 3/pyridine and solvolysis but not with PCl 5.

Structure of acacigenin-B, a novel triterpene ester isolated from Acacia concinna

The structure of acacigenin-B, a novel ester genin from the pods of Acacia concinna was established from its PMR and 13 C NMR spectra. It was identified as the 21-hydroxy ester of acacic acid; the esterifying acid was a hitherto unknown monoterpene acid of tetrahydrofuranoid structure. This appears to be the first report of a higher terpenoid forming an ester with a monoterpene acid

Acacidiol, a new nor-triterpene from the sapogenins of Acacia concinna

From the neutral fraction of the acid hydrolysate of the saponin of Acacia concinna pods, acacic acid lactone 3β-acetate and a new nor-triterpene ‘acacidiol’ have been isolated. The latter is shown to be 28-noroleana-16,18-diene-3β,21β-diol.

ChemInform Abstract: SAPOGENINS OF ACACIA CONCINNA DC.‐ PART II. WAGNER‐MEERWEIN REARRANGEMENT OF ACACIC ACID LACTONE AND ITS ISOMER

Chemischer InformationsdienstVolume 8, Issue 31 Preparative Organic Chemistry ChemInform Abstract: SAPOGENINS OF ACACIA CONCINNA DC.- PART II. WAGNER-MEERWEIN REARRANGEMENT OF ACACIC ACID LACTONE AND ITS ISOMER A. S. R. ANJANEYULU, A. S. R. ANJANEYULUSearch for more papers by this authorM. BAPUJI, M. BAPUJISearch for more papers by this authorL. R. ROW, L. R. ROWSearch for more papers by this author A. S. R. ANJANEYULU, A. S. R. ANJANEYULUSearch for more papers by this authorM. BAPUJI, M. BAPUJISearch for more papers by this authorL. R. ROW, L. R. ROWSearch for more papers by this author First published: August 2, 1977 https://doi.org/10.1002/chin.197731081AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume8, Issue31August 2, 1977 RelatedInformation

Some observations on the structure and conformation of echinocystic acid, machaerinic acid, proceric acid, acacic acid and sapogenin B (coriaceolide B).

The paper deals with the structure and conformation of echniocystic acid, machaerinic acid, proceric acid, acacic acid and sapogenin B (Coriaceolide B). Modifications in the configuration of D/E ring junction from eis to trans have been suggested in case of proceric acid, acacic acid and sapogenin B (Coriaceolide B).

The structure, stereochemistry and conformation of acacic acid

The structure, stereochemistry and conformation of acacic acid

Saponins and sapogenins XXV - the sapogenin of acacia concinna d.c. pods and the constitution of acacic acid

Saponins and sapogenins XXV - the sapogenin of acacia concinna d.c. pods and the constitution of acacic acid