Bioactive constituents from Flacourtia vogelii Hook.f. (Flacourtiaceae).

The chemical investigation of the methanolic root extract of Flacourtia vogelii led to the isolation of a new arylbenzoate derivative, vogelinal (1), together with thirteen known compounds (2-14). The structures of the isolates were elucidated by extensive spectroscopic and spectrometric analyses (1D and 2D NMR, ESI-MS) and by comparison with previously reported data. All the compounds were tested for their antioxidant, antifungal and antibacterial activities. Compound 7 exhibited the highest antioxidant potential, with RSa50of 11.80 ± 2.13 µg/mL, RSa50of 42.60 ± 6.32 µg/mL and RC50 of 51.60 ± 7.71 µg/mL for the DPPH, ABTS and FRAP assay, respectively. Compound 13 displayed weak antifungal effect with MIC value of 125 µg/mL against Candida parapsilosis. Compound 8 showed weak antibacterial effect with MIC value of 125 µg/mL, against Shigella dysenteria. The present study, conclude that this species could be a promising source of antioxidant and antibacterial constituents.

Rukamtenol, a new spiro compound isolated from Flacourtia rukam Zoll. & Moritzi growing in Vietnam.

Chemical investigation of chloroform extract of Flacourtia rukam Zoll. & Moritzi stems led to the isolation of one new compound namely rukamtenol together with four known compounds, viz., chaulmooric acid, flacourtin, 3,4,5-trimethoxyphenyl ß-D-glucopyranoside, and daucosterol. Their structures and relative stereochemistry have been determined by 1D and 2D NMR analysis, high resolution mass spectroscopy, and compared with those in literatures. Rukamtenol represented the first 2-oxaspiro[4.4]non-8-en-3-one in nature. The relative configuration of rukamtinol was defined using DFT-NMR chemical shift calculations and subsequent DP4 probability method. Rukamtenol, flacourtin, and 3,4,5-trimethoxyphenyl ß-D-glucopyranoside were tested for cytotoxic activity toward three MDA-MB-231, HepG2, and RD cancer cell lines. However, they failed to reveal any activity (IC50 > 100 µM) on these cell lines.

Four new phenolics and antiparasitic secondary metabolites from Flacourtia rukam Zoll. & Mortizi.

Phytochemical investigation of Flacourtia rukam Zoll. & Mortizi (F. rukam) leaves and bark led to the isolation and characterization of seventeen compounds of which four phenolics were not previously described; 2-[(benzoyloxy)methyl]-phenyl-O-ß-xylosyl-(1→2)-ß-glucopyranoside (1), 2-[(benzoyloxy)methyl]-4-hydroxyphenyl-O-ß-xylosyl-(1→2)-ß-D-glucopyranoside (2), 2-hydroxy-5-(2-hydroxyphenoxy)phenoxy-ß-glucopyranoside (3) and biphenyl-1,1',2,2'-tetraol (5). Interestingly, the later compound is known as a synthetic but this is the first report for its isolation from nature. Chemical structures were established using extensive analysis of spectroscopic data (1 D and 2 D NMR and HRESIMS). Biphenyl-1,1,2,2'-tetrol (5) exhibited a good activity against Trypanosoma brucei trypomastigotes with IC50= 6.66 ug/mL. Compounds 2, 5, 9, 10, 11 and 12 showed a good in-vitro anti-inflammatory activity using proteinase inhibitory assay. On the contrary, all tested compounds were inactive as antileishmanial or antimalarial.

Phenyl glycosides from the leaves of Flacourtia indica (Burm. f.) Merr (Salicaceae).

Thirteen phenolic glycosides, together with fourteen various known compounds, were isolated from the methanolic extract of leaves of Flacourtia indica. Twelve of these were composed of gentisyl or salicyl alcohols, glycosylated on the phenol and acylated on the primary alcohol with various more or less oxidized forms of pyrocatechuic acid. A number of positions on the glucose or on the acid were further acylated by benzoic or cinnamic acid. In addition to these, a glucoside of a phenyl propanoid was also isolated. The gross structures were elucidated by spectroscopic means including 1D and 2D NMR experiments and HR-ESI-MS analyses. Several of these structures, for example, xylosmin, were previously described but it proved extremely difficult to conclude on their exact identity with the absence of clear data on absolute configuration in the literature.

Oxidative stress mediated cytotoxicity in leukemia cells induced by active phyto-constituents isolated from traditional herbal drugs of West Bengal.

ETHNOPHARMACOLOGICAL RELEVANCE: In search of safe and effective therapeutic agents as alternative to synthetic chemotherapeutics for the treatment of leukemia, the herbal drugs (Leaf of Madhuca longifolia, leaf of Prosopis cineraria and bark of Flacourtia indica) with long traditional use in West Bengal have received our attention. AIM OF THE STUDY: Present work was conducted to isolate and identify the active compounds of the selected herbal drugs using bio-assay guided fractionation and also to investigate their anticancer mechanism in leukemia cell lines. MATERIALS AND METHODS: Bio-assay guided fractionation was used for the isolation of active constituents such as myricitrin, vitexin and vanillin from the aqueous extracts of M. longifolia, P. cineraria and F. indica, respectively using liquid partitioning and column chromatography and the compounds were characterized by HPLC, MS and NMR. Dose and time-dependent cytotoxicity of isolated compounds were studied against leukemia cells and their anticancer mechanism such as cell wall damage, nuclear damage, ROS and NO generation, SOD level, LDH release and lipid peroxidation were investigated. RESULTS: Aqueous extract of M. longifolia, P. cineraria and F. indica exhibited maximum anti-proliferative activity against HL-60 (Acute myeloid leukemia, AML, 72.06%), K-562 (Chronic myeloid leukemia, CML, 42.14%) and Jurkat (Acute lymphoblastic leukemia, ALL, 51.71%) cells. Myricitrin, vitexin and vanillin exhibited dose-dependent (IC-50 values 164.4, 147 & 29.22 µg/ml) and time-dependent activity with maximum cytotoxicity at 48 h. All these three compounds caused apoptosis in leukemia cells by inducing free radicals such as ROS (1.33-2.65 Arbitrary units) and NO (11.17-18.53 µM), cell membrane damage and nuclear condensation which were evidenced by increased release of LDH (1326-1439 U/L), improved lipid peroxidation (10.19-14.41 nM/mg protein) and reduced SOD level (6.2-9.21 U/mg protein) in leukemia cells. CONCLUSIONS: Based on anti-proliferative activity, the isolated phyto-compounds myrcitrin, vitexin and vanillin from M. longifolia, P. cineraria and F. indica could be developed as natural drugs for treating AML, CML and ALL leukemia types, respectively.

Internal transcribed spacer 2 (ITS2) molecular morphometric analysis based species delimitation of foliar endophytic fungi from Aglaia elaeagnoidea, Flacourtia inermis and Premna serratifolia.

Molecular morphometrics is an emerging third dimensional aspect of fungal species delimitation. They have been demonstrated to be more informative than conventional barcoding methods. Hence in this study, foliar endophytic fungal (FEF) assemblages in three Magnoliopsida plants were delimited using nuclear ribosomal internal transcribed spacer 2 (ITS2) sequence-secondary structural features based phylogenetic analysis, also known as molecular morphometrics. A total of 392 FEF isolates were obtained from the Aglaia elaeagnoidea, Flacourtia inermis, and Premna serratifolia leaves and grouped into 98 morphotypes. Among these host plants, P. serratifolia showed the maximum percentage of colonization frequency. Representatives of each morphotype was sequenced and subjected to further molecular characterization. The results revealed that morphotypes were belonged to the phylum of Ascomycota, distributed over two classes (Sordariomycetes (68.59%) and Dothideomycetes (31.41%)), 6 orders and 19 genera. Based on compensatory base changes (CBC) analysis and absolute identity of ITS2 structure, 21, 20 and 23 species were recognized from A. elaeagnoidea, F. inermis, and P. serratifolia respectively. Diversity indices were higher in A. elaeagnoidea, despite it accounted for a modest 16.8% of total isolates recorded in this study. The genus Colletotrichum was predominant in A. elaeagnoidea (39%) and P. serratifolia (48%). Similarly, Diaporthe (43%) was dominant in F. inermis. Several host-specific species were also observed. This study concludes that these plants host diverse species of Ascomycota. To the best of our knowledge, this is the first detailed report on FEF diversity from these plants. Also, the inclusion of ITS2 secondary structure information along with the sequence provides a further dimension to resolve the inherent problems in identification of fungal species.

Physicochemical Characterization, Antioxidant Potential and Sensory Quality of Wine from Wild Edible Fruits of Flacourtia montana J. Graham

Abstract The objective of the present study was to produce wine from wild edible fruits of Flacourtia montana J. Graham. The various physicochemical attributes including total phenolic content and total flavonoid content were analyzed. Further, the prepared wine was evaluated for the antioxidant potential using four different assays, viz., 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS), 1,1-diphenyl-2-picrylhydrazyl (DPPH), reducing power assay and total antioxidant activity. Finally, the wine was subjected for the sensory evaluation. Experimental results revealed that wine had an alcohol content of 7.20%, total phenolic content of 0.776±0.032 mg GAE/ml and total flavonoids of 0.121±0.012 mg QE/ml. High performance liquid chromatography analysis revealed the presence of four major phenolic acids, viz., gallic acid (0.009±0.0005 mg/ml), chlorogenic acid (0.623±0.091 mg/ml), catechin (0.063±0.011 µg/ml) and epicatechin (0.060±0.009 mg/ml). In vitro antioxidant analysis of wine was able to successfully scavenge the free radicals in a dose dependent manner. Sensory scores indicated wine to be good in overall acceptability. Thus, present study highlighted the therapeutic nature of wine prepared from this underutilized fruit which could provide possibilities for enhancing socio-economic benefits among rural communities.