Triterpenoid saponins from stem bark of Pentaclethra macroloba

Viana, Francisco Arnaldo; Braz-Filho, Raimundo; Pouliquen, Yvone B.M.; Net, Manoel Andrade; Santiago, Gilvandete Maria Pinheiro; Rodrigues‐Filho, Edson

doi:10.1590/s0103-50532004000400024

Cited by 19 publications

(20 citation statements)

References 6 publications

(6 reference statements)

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“…Triterpenic monodesmoside saponins have already been found as major compounds in this species (Viana et al, 2004b). These compounds have shown anti-hemorrhagic activity, justifying the use of P. macroloba against bites from snakes .…”

Section: Introductionmentioning

confidence: 98%

Pentaclethra macroloba tannins fractions active against methicillin-resistant staphylococcal and Gram-negative strains showing selective toxicity

Leal¹,

Júnior²,

Pereira³

et al. 2011

Rev. bras. farmacogn.

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Abstract:The ethanol extract of the vegetal species Pentaclethra macroloba (Willd.) Kuntze, Fabaceae, was fractioned and the antibacterial activity was determined. The active ethyl acetate (ea) fraction showed activity against Gram-positive (Staphylococcus spp. and Enterococcus spp.) and Gram-negative (Pseudomonas aeruginosa, Acinetobacter spp. and Klebsiella pneumoniae) multiresistant bacteria. Gallic acid derivatives were identified as the main compounds in inactive subfractions from the ea fraction, while the active one afforded ellagic acid as the major constituent when submitted to acid hydrolysis reaction, which suggests the presence of hydrolysable tannins. The minimum bactericidal concentration analysis showed a bactericide mechanism of action for the tannin subfraction found. The antibacterial mechanism of action of the active tannin subfraction against S. aureus reference strains (ATCC 29213 e 33591) was proposed adopting an in vitro assay of protein synthesis inhibition. For this, bacterial cells were labeled with [ 35 S] methionine in the presence of the subfraction. The protein synthesis inhibition was observed at 256 μg/mL of this subfraction. At this concentration it did not present cytotoxicity in eukaryotic cells by the neutral red technique, suggesting selective toxicity. The present study is the first in vitro investigation of the antibacterial properties of tannin fractions obtained from a polar extract of P. macroloba.

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Section: Introductionmentioning

confidence: 98%

Pentaclethra macroloba tannins fractions active against methicillin-resistant staphylococcal and Gram-negative strains showing selective toxicity

Leal¹,

Júnior²,

Pereira³

et al. 2011

Rev. bras. farmacogn.

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“…The up-fielded carbon signals at δ 73.2 and 74.5 for C-3‵ and C-4‵ of rhamnose-2, confirmed that the rhamnose-2 is terminal and not attached to another sugars (Wang et al, 2014). The up-fielded carbon signal at δ 61.9 for C-6‵ of glucose-1 confirmed that its C-6‵ is free, while the down-fielded carbon signal at δ 69.7 for C-6‵ of glucose-2 confirmed the attachment of glucose-2 to rhamnose-2 in the C-6‵ position of glucose-2 (Fu et al, 2006; Viana et al, 2004; Voutquenne et al, 2003; Wang et al, 2014). Acid hydrolysis of 1 gave the aglycon hederagenin along with xylose, glucose and rhamnose.…”

Section: Resultsmentioning

confidence: 73%

New triterpenoidal saponins from Koelreuteria paniculata

Mostafa

El‐Hela

Mohammad

et al. 2016

Phytochemistry Letters

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Bioassay guided fractionation and chemical investigation of the ethanolic extract of the aerial parts of Koelreuteria paniculata Laxm. (Sapindaceae), resulted in the isolation and identification of three new triterpenoid saponins 1–3 named Paniculatosoid A–C, along with eleven known compounds. The structures of the isolated compounds were elucidated using 1D and 2D NMR experiments, HRESIMS, and comparison with literature data. The occurrence of tridesmosidic saponin is reported for the first time from family Sapindaceae, as well as it is rarely found in natural saponins. Compounds 4–13 were evaluated for their antibacterial, antifungal, antimalarial and antileishmanial activities. Compound 12 showed weak antibacterial activity against Escherichia coli with an IC50 value of 101 μM. Compounds 12 and 13 showed antimalarial activity against chloroquine-sensitive (D6) Plasmodium falciparum protozoan with IC50 values of 6.46 and 6.95 μM, and against chloroquine-resistant (W2) Plasmodium falciparum protozoan with IC50 values of 9.34 and 4.18 μM.

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“…this position is glycosylated. Further, the moderate deviation in the H-23 value of genin in the 1 H NMR ( 3.92, 4.04) from the expected value is attributed to the stereoelectronic effect of the OH-3 sugar chain (Arnaldo Viana, et al, 2004;Finar, 1989;Khalik, Miyase, El-Ashaal, & Melek, 2000;Mahato & Kundu, 1994;Voutquenne, Guinot, Thoison, Sevenet, & Lavaud, 2003). In the 13 C NMR spectrum of saponin, the signals attributed to the aglycon (genin) range from 10 to 50, except those of C-23, C-3, C-12, C-13 and C-28 (Table 1).…”

Section: Resultsmentioning

confidence: 98%

Isolation and structure determination of acetylated triterpenoid saponins from the seeds ofCentratherum anthelminticum

Mehta

Itoriya

2010

Natural Product Research

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Phytochemical investigation of Centratherum anthelminticum seeds resulted in the isolation of two novel glycosides. The pentacyclic triterpenoid saponins were shown to contain hederagenin and sugar residues forming two glycosyl chains. The structural analysis of its acetylated derivative was determined using a combination of homo- (1D 1H NMR, 13C NMR and 13C NMR-DEPT) and heteronuclear 2D NMR techniques (1H-1H-COSY, total correlated spectroscopy (TOCSY), heteronuclear multiple quantum coherence (HMQC)), heteronuclear multiple bond correlation (HMBC) and chemical methods. The structure of the saponins were established to be 3-O-[beta-D-glucopyranosyl-(1 --> 2)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-xylopyranosyl-(1 --> 4)-alpha-L-rhamnopyranosyl-(1 --> 3)-beta-D-glucopyranosyl]-23-hydroxyolean-12-en-28-oic acid and 3-O-[beta-D-glucopyranosyl-(1 --> 2)-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl]-28-O-[beta-D-glucoyranosyl-(1 --> 3)-beta-D-glucopyranosyl]-23-hydroxyolean-12-en-28-oic acid. Different extracts and compounds were also tested for antifilarial and antimicrobial activities. Methanolic, acetone and aqueous extracts of seeds exhibited some pronounced pharmacological activity under study.

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Triterpenoid saponins from stem bark of Pentaclethra macroloba

Abstract: 3)-alpha-L-rhamnopyranosyl-(1->2)],beta-D- glucopyranosyl-(1->4)}-alpha-L-arabinopyranosylhederagenin (3) and 3beta-O-{[beta-D-glucopyranosyl-(1->4)-beta-D-glucopyranosyl-(1->3)-alpha-L-rhamnopyranosyl- (1->2)],beta-D- glucopyranosyl(1->4)}-alpha-L-arabinopyranosyloleanolic acid (4).]]>

Cited by 19 publications

References 6 publications

Pentaclethra macroloba tannins fractions active against methicillin-resistant staphylococcal and Gram-negative strains showing selective toxicity

Pentaclethra macroloba tannins fractions active against methicillin-resistant staphylococcal and Gram-negative strains showing selective toxicity

New triterpenoidal saponins from Koelreuteria paniculata

Isolation and structure determination of acetylated triterpenoid saponins from the seeds ofCentratherum anthelminticum

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