Antifungal dimeric chalcone derivative kamalachalcone E from Mallotus philippinensis

• Published in: Natural product research 2014-02, Vol.28 (4), p.245-250
• Main Authors: Kulkarni, Roshan R., Tupe, Santosh G., Gample, Suwarna P., Chandgude, Macchindra G., Sarkar, Dhiman, Deshpande, Mukund V., Joshi, Swati P.
• Format: Article
• Language: English
• Subjects: 4′-hydroxyrottlerin; antifungal; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; Aspergillus fumigatus; Aspergillus fumigatus - drug effects; Chalcone - analogs & derivatives; Chalcone - chemistry; Chalcone - isolation & purification; Chalcone - pharmacology; Chalcones; Cryptococcus neoformans; Cryptococcus neoformans - drug effects; dimeric chalcone; Drug Screening Assays, Antitumor; Euphorbiaceae - chemistry; Fruit - chemistry; Fungi - drug effects; Humans; India; Inhibitory Concentration 50; kamalachalcone E; Leukemia - drug therapy; Mallotus; Mallotus philippinensis; Microbial Sensitivity Tests; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Plant Extracts - chemistry; rottlerin; Yeasts - drug effects
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2013.843178

From the red coloured extract (Kamala) prepared through acetone extraction of the fresh whole uncrushed fruits of Mallotus philippinensis, one new dimeric chalcone (1) along with three known compounds 1-(5,7-dihydroxy-2,2,6-trimethyl-2H-1-benzopyran-8-yl)-3-phenyl-2-propen-1-one (2), rottlerin (3) and 4′-hydroxyrottlerin (4) were isolated. The structure of compound 1 was elucidated by 1D and 2D NMR analyses that included HSQC, HMBC, COSY and ROESY experiments along with the literature comparison. Compounds 1-4 were evaluated for antifungal activity against different human pathogenic yeasts and filamentous fungi. The antiproliferative activity of the compounds was evaluated against Thp-1 cell lines. Compounds 1 and 2 both exhibited IC 50 of 8, 4 and 16 μg/mL against Cryptococcus neoformans PRL518, C. neoformans ATCC32045 and Aspergillus fumigatus, respectively. Compound 4, at 100 μg/mL, showed 54% growth inhibition of Thp-1 cell lines.