Pentagalloylglucose, isolated from the leaf extract ofAnacardium occidentaleL., could elicit rapid and selective cytotoxicity in cancer cells

Background: The leaf of Anacardium occidentale L. has been a component of many herbal recipes in South-Western Nigeria. The work reported herein, therefore, explored the phytochemical composition of this plant and the potential anti-cancer activity of an isolated chemical constituent. Methods: Phytochemical methods (including chromatographic analysis) combined with spectroscopic and spectrometric analyses (IR, HRMS and NMR (1D and 2D)) were used to identify chemical constituents. Cytotoxic effects were determined using the MTT viability assay and bright-field imaging. Induction of oxidative stress was determined using the fluorescence-based 2′,7′-dichlorofluorescein diacetate (DCFDA) assay. Results: For the first time in the plant, Compound 1 was isolated from the leaf extract and identified as pentagalloylglucose. Compound 1 was significantly cytotoxic against the cancer cell lines HeLa (human cervical adenocarcinoma cell line) and MRC5-SV2 (human foetal lung cancer cell line), with IC50 of 71.45 and 52.24 μg/ml, respectively. The selectivity index (SI) for Compound 1 was 1.61 (IC50 against the normal human foetal lung fibroblast cell line MRC-5 was 84.33μg/ml), demonstrating better cancer cell-selectivity compared to doxorubicin with a SI of 1.28. The cytotoxic activity of Compound 1 in HeLa cells was also rapid, as shown by its concentration- and time-dependent 3 h and 6 h cytotoxicity profiles, an effect not observed with doxorubicin. Generation of reactive oxygen species at high concentrations of pentagalloylglucose to induce oxidative stress in cancer cells was identified as a mechanistic event that led to or resulted from its cytotoxicity. Conclusions: We suggest that pentagalloylglucose is selectively cytotoxic to cancer cells, and at high concentrations could exhibit pro-oxidant effects in those cells, as opposed to its general anti-oxidant effects in cells. Also, the presence of Compound 1 (pentagalloylglucose) in the plant and its cancer cell-selective cytotoxicity provide some rationale for the ethno-medicinal use of the plant’s leaf extract for treating diseases associated with excessive cell proliferation. Further studies are required to dissect the molecular mechanisms and players differentially regulating the biphasic anti-oxidant and pro-oxidant effects of pentagalloylglucose in normal and cancer cells

Identification of compounds with cytotoxic activity from the leaf of the Nigerian medicinal plant, Anacardium occidentale L. (Anacardiaceae)

Cancer is now the second-leading cause of mortality and morbidity, behind only heart disease, necessitating urgent development of (chemo)therapeutic interventions to stem the growing burden of cancer cases and cancer death. Plants represent a credible source of promising drug leads in this regard, with a long history of proven use in the indigenous treatment of cancer. This study therefore investigated Anacardium occidentale, one of the plants in a Nigerian Traditional Medicine formulation commonly used to manage cancerous diseases, for cytotoxic activity. Bioassay-guided fractionation, spectroscopy, Alamar blue fluorescence-based viability assay in cultured HeLa cells and microscopy were used. Four compounds, zoapatanolide A (1), agathisflavone (2), 1,2-bis(2,6-dimethoxy-4-methoxycarbonylphenyl)ethane (anacardicin, 3) and methyl gallate (4), were isolated, with the most potent being zoapatanolide A with an IC50 value of 36.2 ± 9.8 µM in the viability assay. To gain an insight into the likely molecular basis of their observed cytotoxic effects, Autodock Vina binding free energies of each of the isolated compounds with seven molecular targets implicated in cancer development (MAPK8, MAPK10, MAP3K12, MAPK3, MAPK1, MAPK7 and VEGF), were calculated. Pearson correlation coefficients were obtained with experimentally-determined IC50 in the Alamar blue viability assay. While these compounds were not as potent as a standard anticancer compound, doxorubicin, the results provide reasonable evidence that the plant species contains compounds with cytotoxic activity. This study provides some evidence of why this plant is used ethnobotanically in anticancer herbal formulations and justifies investigating Nigerian medicinal plants highlighted in recent ethnobotanical surveys

Ceibinin, a new positional isomer of mangiferin from the inflorescence of Ceiba pentandra (Bombacaceae), elicits similar antioxidant effect but no anti-inflammatory potential compared to mangiferin

Ceiba pentandra (L.) Gaertn. (Bombacaceae) is popular for the quality of its wood. However, its leaf, stem bark and root bark have been popular in ethnomedicine and, apart from the inflorescence, have been subject of extensive phytochemical investigations. In this study, two compounds were isolated from the crude methanol extract of the inflorescence. Through data from UV, NMR, MS, electrochemical studies, differential scanning calorimetry, and thermogravimetric analysis, the structures were elucidated as 3-C-β-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (1) and 2-C-β-D-glucopyranosyl-1,3,6,7-tetrahydroxyxanthone (mangiferin, 2). They were assessed for antioxidant efficacy (DCFDA assay) and for anti-inflammatory efficacy using the lipopolysaccharide (LPS)-induced inflammation model in the RAW 264.7 macrophages (nitrite levels quantified, using Griess Assay, as surrogate for nitric oxide (NO)). Compound 1 (named ceibinin) was established as a novel positional isomer of mangiferin (2). While both 1 and 2 were antioxidant against basal and hydrogen peroxide (100 μM)-induced oxidative stress (6.25 μg/ml abrogated peroxide-induced oxidative stress), ceibinin (1) demonstrated no anti-inflammatory potential, unlike mangiferin (2) which, as previously reported, showed anti-inflammatory effect. Our work reports a positional isomer of mangiferin for the first time in C. pentandra and demonstrates how such isomerism could underlie differences in biological activities and thus the potential for development into therapeutics

Glandular Odontogenic Cyst: Report of Two Cases and Review of Literature

Glandular odontogenic cyst (GOC) is an uncommon jaw bone cyst of odontogenic origin described in 1987 by Gardner et al. It is a cyst having an unpredictable and potentially aggressive behaviour. It also has the propensity to grow to a large size and tendency to recur with only 111 cases having been reported thus far. The first case occurred in a 42-year-old female and presented as a localized swelling extending from 19 to 29 regions. There was a history of traumatic injury at the site. There was evidence of bicortical expansion and radiographs revealed a multilocular radiolucency. The second case occurred in a 21-year-old male, as a large swelling in the mandible and radiograph revealed radiolucency in the region. On histopathological examination, these lesions were diagnosed as GOC. It was concluded that, two cases submitted by us correlate with the existing literature that GOC’s affect more commonly in the middle age group, having predilection for mandible and that trauma could be a precipitating factor for its occurrence. The increased recurrence rates can be due to its intrinsic biological behavior, multilocularity of the cyst, and incomplete removal of the lining following conservative treatment

In vitro cytotoxicity of crude alkaloidal extracts of South African Menispermaceae against three cancer cell linese

The cytotoxicity of crude alkaloid extracts obtained from the leaves and rhizomes of all the South African members of the family Menispermaceae (seven genera and 13 species) was tested against MCF7 (breast), UACC62 (melanoma) and TK10 (renal) cancer cell lines. Extracts of ten of the thirteen species showed positive activity against all three cancer cell lines with significant inhibition of cellular growth at TGI (total growth inhibition) values lower than 6.25  g/ml for Albertisia delagoensis and Antizoma angustifolia leaves

South African Helichrysum species: A review of the traditional uses, biological activity and phytochemistry

Aims of the study: In South Africa, the genus Helichrysum is widely used in traditional medicine. The uses are well documented although renaming of species and the resulting confusing taxonomic nomenclature may cause uncertainty as to which specific species was referred to in some reports. The aim of this paper is to present a collated and coherent overview of the documented traditional uses of Helichrysum species and to update the botanical identity of previously studied species. Materials and methods: Databases (Scifinder, ISIWeb of Knowledge) and several bookswere used to collect in information on South African Helichrysum species. Results: The traditional uses, chemistry and biological activity of Helichrysum species have been summarized. It was attempted to give clarity as to exactly which species is refer to in the ethnobotanical literature. Conclusions: Although a largenumber of ethnopharmacological uses have beendocumentedand the chemistry of the genus has been studied extensively, only a few South African species have been investigated for their biological activity

Mycotoxins with a special focus on Aflatoxins, Ochratoxins and Fumonisins

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