Antiplasmodial Phenolic compounds from <i>Piptadenia pervillei</i>

Ramanandraibe, Voahangy; Grellier, Philippe; Martin, Marie‐Thérèse; Deville, Alexandre; Joyeau, Roger; Ramanitrahasimbola, David; Mouray, Elisabeth; Rasoanaivo, Philippe; Mambu, Lengo

doi:10.1055/s-2008-1034328

Cited by 47 publications

(25 citation statements)

References 24 publications

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“…As noted previously, compound 8 was reported to moderately inhibit the proliferation of B16F10 [8], HeLa [8], and MK-1 [8] cells and to be a moderately cytotoxic compound to HepG2 [9] and MRC-5 cells [11]. Compounds 6−10 exhibited significantly lower activity compared to 3,5-digalloyl-(-)-epicatechin (4 (-)-epigallocatechin (10), in which the number of hydroxyl groups on the B-ring was greater than that in 4, did not efficiently inhibit cell proliferation.…”

Section: Inhibitory Activity Against Cervical Epithelioid Carcinoma Csupporting

confidence: 62%

“…Since its first isolation from Sanguisorba officinals [4], there have been several reports regarding the isolation and biological activities of compound 8 as a minor constituent of Paeoniae obovate [7]; a moderate antiproliferation constituent against B16F10 [8], HeLa [8], and MK-1 [8]; a cytotoxic constituent against HepG2 [9] isolated from the seeds of Rhynchosia volubilis; and an antioxidant isolated from Acacia nilotica [10]. In addition, synthesis of 8 from a catechol-protected-(+)-catechin derivative, moderate antiplasmodial activity against FcB1, and cytotoxicity against MRC-5 cells were reported [11].…”

Section: Synthesismentioning

confidence: 99%

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Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

Hojima¹,

Komeda²,

Higashino³

et al. 2017

Nat Prod Chem Res

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Flavan-3-ol derivatives are common plant-derived bioactive compounds with strong various biological activities. In particular, (-)-epigallocatechin-3-O-gallate exhibits a variety of moderate biological activities without severe toxicity. Its health-promoting effects have been widely studied because it is a main ingredient in green tea and is commercially available at low cost. In general, the galloyl moieties of flavan-3-ol derivatives are thought to be essential to their strong biological activities. However, it is not clear which position is most effective for modification with the galloyl moiety to strengthen the biological activities because various galloylated analogs are difficult to obtain in pure form in a quantity large enough for assays. Therefore, we synthesized various galloylated flavan-3-ol derivatives in a stereoselective and regioselective manner. We reported in a previous paper that 3,5-digalloyl-(-)-epicatechin displayed much stronger inhibitory activity than 3,5-digalloyl-(+)-catechin did against HeLa S3 cell proliferation. In this study, we describe synthetic studies of 7-galloyl-and 3,7-digalloyl-modified (-)-epicatechin and (+)-catechin and compared their biological activities, HeLa S3 cell proliferation inhibitory activity and DPPH radical scavenging activity with those of 3,5-digalloyl-(-)-epicatechin. The results indicated that 3,7-digalloyl derivative did not inhibit HeLa S3 cell proliferation. Furthermore, 3,5-digalloyl-(-)-epigallocatechin was synthesized to evaluate the importance of the number of phenolic hydroxyl groups on the B-ring. Contrary to our expectations, 3,5-digalloyl-(-)-epigallocatechin exhibited a weaker inhibition of HeLa S3 cell proliferation than 3,5-digalloyl-(-)-epicatechin did. The DPPH radical scavenging activity of the synthesized compounds suggested that the galloyl-modified position and the number of phenolic hydroxyl groups on B-ring affected to the radical scavenging ability. In conclusion, we found that 3,5-digalloyl-(-)-epicatechin exhibited a superlative HeLa S3 cell proliferation inhibitory effect among the galloylated flavan-3-ol derivatives we synthesized and DPPH radical scavenging activity was affected by the galloyl-moiety-introduced position and the number of phenolic hydroxyl groups on the B-ring.

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Section: Inhibitory Activity Against Cervical Epithelioid Carcinoma Csupporting

confidence: 62%

Section: Synthesismentioning

confidence: 99%

Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

Hojima¹,

Komeda²,

Higashino³

et al. 2017

Nat Prod Chem Res

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“…A preliminary structure activity relationship study of benzoic acid and gallate derivatives, including several synthesized de novo for this study, indicate that free hydroxyl groups on the aromatic ring for gallic acid and gallate esters are essential for their antimalarial effect. Gallic acid and protocatechuic acid have both previously been shown to moderate antimalarial activities against chloroquine-resistant P. falciparum strain W2 (Garcia-Alvarez et al, 2013) with an additional study using ethyl gallate reporting an in vitro antiplasmodial effect of IC 50 between 9 -35 µM (Ramanandraibe et al, 2008). Results from these previous studies were in agreement with our own, with our study further suggesting that alkyl gallates, in particular lauryl gallate, have a greater antiplasmodial activity than gallic acid itself (Table 1).…”

Section: Discussionmentioning

confidence: 99%

A characterization of the antimalarial activity of the bark of Cylicodiscus gabunensis Harms

Aldulaimi

Uche

Hameed

et al. 2017

Journal of Ethnopharmacology

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Ethnopharmacological relevance and aim: A decoction of the bark of Cylicodiscus gabunensis Harms is used as a traditional medicine in the treatment of malaria in Nigeria. This study aims to validate the antimalarial potency of this decoction in vitro against Plasmodium falciparum and define potential bioactive constituents within the C. gabunensis bark. Materials and methods:A bioassay-guided separation and fractionation protocol was applied to C. 4

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“…The presence of these compounds indicates that the examined extracts could be used as templates for the development of new antimalarial or antibiotic medicines. The biological function of these compounds against the plasmodium parasite has been reported (Dolabela et al, 2008;Ngouamegne et al, 2008;Murata et al, 2008;Likhiwitayawuid et al, 1997;Ramanandraibe et al, 2008;Ajaiyeoba et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

Antimicrobial activity and phytochemical fingerprints of five crude extracts obtained from indigenous medicinal plants of Uganda

Katuura¹,

Bossa²,

Waako³

et al. 2017

Res. Pharm. Biotech.

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Five crude extracts from four Ugandan plants were screened in vitro for their antimicrobial activity and phytochemical composition. They included the chloroform extracts of Bothliocline longipes, Maesa lanceolata, Trimeria bakeri, Rhus natalensis and the petroleum ether extract of T. bakeri. The plant crude extracts were tested against Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 49619) and Entamoeba sp. Antimicrobial activities of the plants were determined by using the agar well diffusion and agar well dilution methods. The plant extracts showed activity against all the tested organisms with the zones of inhibition ranging from 4 to 19 mm. All the extracts inhibited the growth of S. aureus while the strongest activity was found for T. bakeri against S. aureus and Entamoeba sp. at 19 mm. Other plant extracts that induced strong antimicrobial activity were the chloroform extract of R. natalensis with an inhibition diameter of 13 mm against both S. aureas and P. aeruginosa and 9 mm diameter inhibition against E. coli. Only T. bakeri showed growth inhibition of S. aureus (4 mm). The minimum inhibitory concentration (MIC) was observed against S. aureus at 0.25 g/ml by the T. bakeri and B. longipes plant extracts. Sterol and triterpenes, fatty acids, flavanoids, coumarins and alkaloids were determined in T. bakeri, B. longipes, R. natalensis and M. lanceolata. The presence of these compounds indicates that the plants may contain an active compound or one that can be used as a template for the development of a new antimalarial or antibiotic medicine.

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Antiplasmodial Phenolic compounds from Piptadenia pervillei

Cited by 47 publications

References 24 publications

Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

Role of 3,5-Digalloyl and 3’,4’-Dihydroxyl Structure of (–)-Epicatechin- 3,5-Digallate in Inhibition of Hela S3 Cell Proliferation

A characterization of the antimalarial activity of the bark of Cylicodiscus gabunensis Harms

Antimicrobial activity and phytochemical fingerprints of five crude extracts obtained from indigenous medicinal plants of Uganda

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