Novel, Complex Flavonoids from Mallotus philippensis (Kamala Tree)

Abstract

One new flavanone, 4'-hydroxyisorottlerin (2), and two new chalcone derivatives, kamalachalcones C (3) and D (4), were isolated from Mallotus philippensis (kamala tree). The largest compound (4; M r 1098 g/mol) was shown to possess a unique, fused-ring system made of two hydroxy-chalcone units, giving rise to eight fused benzene/pyran units. From the same plant, the following six known compounds were also isolated: kamalachalcone A (5) and B (6), isoallorottlerin (7), isorottlerin (8), 5,7-dihydroxy-8-methyl-6-prenylflavanone (9); 6,6-dimethylpyrano(2'',3'': 7,6)-5-hydroxy-8-methylflavanone (10), and rottlerin (1). The structures of the new compounds were confirmed by in-depth spectral analyses, including 2D-NMR techniques, and the full 13 C-NMR assignments of the known flavanones 1 and 7 ± 10 are published for the first time.

Characteristic Fingerprint Analysis of Mallotus philippinensis by Ultra Performance Liquid Chromatography Electrospray Ionization Mass Spectrometry

“…The major phytoconstituent of M. philippinensis is rottlerin (peak 10), which elute at t R 2.89, exhibit a [M+H] + peak at m/z 517.1 [1,[18][19][20] M. philippinensis fruits were collected from the plants grown in western ghats of Maharashtra region, India in the month of February. A voucher specimen of M. philippinensis (RAAMAP3) was deposited in the Botanical Survey of India, Western Region Centre, Pune, India.…”

Efficient Synthesis of Biologically Interesting Natural Pyranochalcones from Mallotus Philippensis and Their Unnatural Derivatives

“…1 Extracts from the fruits and bark of the plant have been shown to possess antioxidant, 2 antiulcer, 2 anti-tumor, 3 cytotoxic, 4 and antiallergic 5 activities. Kamara, a red powder consisting of the glandular hairs from this plant, has been used in traditional medicines as an anthelmintic and cathartic.…”

“…To a solution of 28 (0.100 g, 0.34 mmol) in ethanol (2 mL) was added KOH (0.096 g, 1.71 mmol) and aldehyde 18 (0.068 g, 0.41 mmol). The reaction mixture was stirred at room temperature for 48 h. Evaporation of ethanol, addition of water (10 mL) and 1N HCl (2 mL), extraction with EtOAc (3 × 20 mL), washing with brine (20 mL), and removal of the solvent followed by flash column chromatography on silica gel using hexane/EtOAc (10:1) gave 33 Red Compound (4). To a solution of 29 (0.100 g, 0.26 mmol) in methanol (8 mL) was added 3M HCl (2 ml) and the reaction mixture was refluxed for 0.5 h. The reaction mixture was diluted with saturated NaHCO 3 solution (12 mL) and extracted with EtOAc (3 × 30 mL).…”

Novel Flavonoids in Dragon's Blood of Daemonorops draco

“…The structures were elucidated by extensive 1D-and 2D-NMR spectroscopic analysis. In our successive research of the phytochemicals in secretes, we have isolated secobiflavonoids in farinose exudate of Pentagramma triangularis [10] and kamalachalcones in glandular hair of Mallotus philippensis [11], and the chemical constituents in the red resin originated from D. draco were investigated. Herein, the structures of three novel secobiflavonoids, daemonorols A -C 1 ) (1 -3), a novel 2-flavene, daemonorol D…”