Antibacterial triterpenes from Syzygium guineense (Myrtaceae)

Djoukeng, Jules Désiré; Abou-Mansour, Eliane; Tabacchi, Raffaele; Tapondjou, Azefack Léon; Bouda, H.; David, Laurent

doi:10.1016/j.jep.2005.05.008

Cited by 146 publications

(93 citation statements)

References 14 publications

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“…All the isolated compounds however showed antimicrobial activity with at least one microorganism. This finding is therefore not that surprising since some individual xanthones, anthraquinones and triterpenes have shown this type of biological activity (Barre et al, 1997;Ali et al, 2000;Fukai et al, 2005;Djoukeng et al, 2005;Nguemeving et al, 2006;Tala et al, 2007;Wabo et al, 2007).…”

Section: (Figure 2)mentioning

confidence: 78%

Chemistry and biology of genusVismia

Hussain

Al‐Harrasi

Saleem

et al. 2012

Pharmaceutical Biology

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Section: (Figure 2)mentioning

confidence: 78%

Chemistry and biology of genusVismia

Hussain

Al‐Harrasi

Saleem

et al. 2012

Pharmaceutical Biology

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“…From the ethyl acetate residue of methanolic extract of root bark from S. densiflora were characterized five novel hydrolysable tannins named ellagic acid 4 (5), along with the identification of the well known substances ellagic acid 4-O-α-L-4"-O-acetylrhamnopyranoside (7), 2 ellagic acid 4-O-α-L-rhamnopyranoside or eschweilenol C (8), 3 gallic acid (9), 4 syringic acid (10), 5 sitosterol (11), 6 sitosterol 3-O-β-D-glucopyranoside or daucosterol (12), 7 ellagic acid (13), 8 rhamnose (14), casuarinin (15) 9 and castalagin (16). 10 The fractionation of the ethyl acetate residue of the methanolic extract of leaves led to the isolation of the new triterpenoid 28-β-D-glucopyranosyl-6β-hydroxymaslinate or β-D-glucopyranosyl-2α,3β,6β-trihydroxyolean-12-en-28-ate (6), as well as six known compounds: syringic acid (10), 5 quercetin (17), quercitrin (18), quercetin-3-O-α-L-arabinopyranoside or guiajaverin (19), quercetin-3-O-β-D-xylopyranoside or reynoutrin (20), 11 and chebuloside II (21).…”

Section: Resultsmentioning

confidence: 99%

“…The occurrence of triterpenes in leaves of Myrtaceae is high and frequent, 21 but terminolic (25) and madecassic (26) acids have only been recently reported in Syzygium, 14 and compound 25 in Myrtus. 22 Chebuloside II (21), a pentacyclic triterpene glucoside, has been previously isolated from Terminalia chebula (Combretaceae), 12 but this is the first report of this compound from the family Myrtaceae.…”

Section: Resultsmentioning

confidence: 99%

New natural products from Siphoneugena densiflora Berg (Myrtaceae) and their chemotaxonomic significance

Gallo¹,

Silva²,

Vieira³

et al. 2006

J. Braz. Chem. Soc.

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Siphoneugena Berg (Myrtaceae) é um pequeno gênero eugenióide segregado de Eugenia por Berg. A investigação fitoquímica de Siphoneugena densiflora foi realizada com o objetivo de se descobrir metabólitos secundários que possam ser considerados marcadores quimiotaxonômicos e auxiliar na distinção entre os dois gêneros. Cinco taninos hidrolisáveis inéditos foram isolados do extrato metanólico da casca da raiz e caracterizados como 4-O-α-L-2"-O-e seu isômero 4-O-α-L-3"-O-acetilramnopiranosídeo do ácido elágico, siphoneugenina, constituído por uma nova aglicona de estrutura dibenzo-1,4-dioxínica, 4-O-β-D-6"-e 4-O-β-D-3",6"-di-O-acetilglucopiranosídeo do ácido 3,4'-di-O-metilelágico, juntamente com o 4-O-α-L-4"-O-acetilramnopiranosídeo do ácido elágico, eschweilenol C, sitosterol, daucosterol, ramnose, casuarinina, castalagina e ácidos elágico, gálico e siríngico. Do extrato metanólico das folhas, além dos compostos conhecidos como a quercetina, quercitrina, guiajaverina, reinoutrina, chebulosídeo II, ácidos terminólico, madecássico e asiático, lupeol, α-e β-amirina, foi isolado um novo triterpeno pentacíclico nomeado como 2α,3β,6β-triidroxiolean-12-en-28-ato de β-D-glucopiranosila. Todas as substâncias foram identificadas através da análise dos dados espectrais e químicos obtidos, além da comparação com dados relatados na literatura.Siphoneugena Berg (Myrtaceae) is a small eugenioid genus segregated from Eugenia by Berg. The phytochemical survey of Siphoneugena densiflora was carried out in order to find secondary metabolites which may be considered as chemotaxonomic characters and help to distinguish between the two genera. Five novel hydrolysable tannins were isolated from the methanolic extract of root bark and were characterized as ellagic acid 4-O-α-L-2"-O-and its isomer 4-O-α-L-3"-O-acetylrhamnopyranoside, siphoneugenin, that supports a new aglycone with a dibenzo-1,4-dioxin structure, 3,4'-di-O-methylellagic acid 4-O-β-D-6"-O-and 4-O-β-D-3",6"-diacetylglucopyranoside, accompanied by ellagic acid 4-O-α-L-4"-O-acetylrhamnopyranoside, eschweilenol C, sitosterol, daucosterol, rhamnose, casuarinin, castalagin, ellagic, gallic and syringic acids. From methanolic extract of leaves, in addition to the well known compounds quercetin, quercitrin, guiajaverin, reynoutrin, chebuloside II, terminolic, madecassic and asiatic acids, lupeol, α-and β-amyrin, a new pentacyclic triterpene was isolated and named as β-D-glucopyranosyl-2α,3β,6β-trihydroxyolean-12-en-28-ate. Structures were established on the basis of spectroscopic and chemical evidence, along with the comparison of the data reported in the literature. Keywords:Siphoneugena densiflora, Myrtaceae, chemotaxonomy, hydrolysable tannin, pentacyclic triterpene IntroductionThe genus Siphoneugena comprises only eight species and belongs to Myrtaceae family. It is one of the specialized genera segregated from Eugenia by Berg. 1 Siphoneugena densiflora Berg, commonly known as Uvatinga, occurs in montane grasslands ("campos rupestres"), deciduous forests ("cerradões") and gall...

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“…Arjunolic acid (2,3,23-trihydroxyolean-12-en-28-oic acid, AA), a natural pentacyclic triterpenoid saponin isolated from the bark of Terminalia arjuna, is well known to display various biological functions, including antioxidative [165], antifungal [166], hepatoprotective [167], and antibacterial activities [168]. AA plays a protective role against hepatotoxicity induced by environmental toxins such as drugs and chemicals.…”

Section: Plant-derived Agents With Anti-glycation Activity 239mentioning

confidence: 99%