Limonoids from Aphanamixis polystachya Leaves and Their Interaction with Hsp90

Abstract

A phytochemical study of -hexane, CHCl, and CHCl-MeOH extracts of leaves led to the isolation of 10 compounds. Five of them turned out to be new natural compounds, including two mexicanolide-type (1, 2: ) and three polyoxyphragmalin-type (3: -5: ) limonoids, together with two known andirobin-type limonoids (6, 7: ) and three phenolic derivatives. The structures of the new compounds were established on the basis of spectroscopic methods to be 8-hydro-14,15-en-cabralin (1: ), 3-deacetyl-8-hydro-cabralin-14,15-en-3-one (2: ), 20,22-dihydroxy-21,23-dimethoxytetrahydrofuran khayanolide A (3: ), 1-deacetyl-3-dehydroxy-3-oxokhaysenelide E (4: ), and meliaphanamixin A (5: ). All compounds were isolated for the first time from this species. The ability of the isolated limonoids to interact with the molecular chaperone Hsp90 was tested. Compounds 6: and 7: were the most active.

Protective Effects of Bergamot (Citrus bergamia Risso & Poiteau) Juice in Rats Fed with High-Fat Diet

“…Its UV spectrum was characterized by 2 strong absorptions at 253 e 347 nm, while the full mass spectrum showed a deprotonated molecule [M -H] − at m/z 397, which generated product ions in MS/MS experiments at m/z 235 [M -H -162] − and 191 [M -H -206] − due to the loss of quinic and synapoyl acids, respectively. On the contrary, the limonoid limonin glucoside, reported by Da Pozzo et al [8], was not herein detected, while the aglycones nomilinic acid (22) and limonin (23) were observed as previously reported [7,9]. In addition, a higher number of phenolics were identified considering a very recent study on C. bergamia juice chemical content [9].…”

“…Among phenolics, the following constituents were identified: 1 phenolic acid, 5-synapoylquinic acid (7); 4 flavone Cglucosides, vicenin-2 (2), lucenin-2 4′-methyl ether (3), apigenin 8-C-glucoside or apigenin 6-C-glucoside (6), and diosmetin 8-Cglucoside (8); 5 flavanone 7-O-glycosides, eriocitrin (4), neoeriocitrin (5), luteolin 7-O-neohesperidoside (9), naringin (12), and neohesperidin (14); 6 3-hydroxy-3-methyl-glutaryl flavanone O-glycosides, 3-hydroxy-3-methyl-glutaryl-neoeriotricin (or eriocitrin) hexoside (10), bergamjuicin (11), 3-hydroxy-3-methyl-glutarylneohesperidin dihexoside (13), 3-hydroxy-3-methyl-glutaryl-neoeriotricin (16), melitidin (18), and brutieridin (19); 1 flavone O-glycoside, neodiosmin, or chrysoeriol 7-O-neohesperidoside (15); 1 furanocoumarin, bergapten (21). In addition, 3 limonoids, nomilinic acid glucoside (20), nomilinic acid (22), and limonin (23), were identified. Limonoids, tetranortriterpenes characterized by a wide variety of structures and biological activities [22], contribute to the bitter juice taste.…”

“…In addition, 3 limonoids, nomilinic acid glucoside (20), nomilinic acid (22), and limonin (23), were identified. Limonoids, tetranortriterpenes characterized by a wide variety of structures and biological activities [22], contribute to the bitter juice taste. Compared to our previous work [8], the bergamot juice herein analyzed showed the presence of 5-synapoylquinic acid (7, t R = 21.6 min), previously reported by Russo et al [7].…”

Characterization and Antifungal Activity of Limonoid Constituents Isolated from Meliaceae Plants Melia dubia, Aphanamixis polystachya, and Swietenia macrophylla against Plant Pathogenic Fungi In Vitro

“…polystachya grows abundantly in India, China, and Southeast Asia and has been used as medicinal materials in traditional medicine. e structural characterization and bioactivities of various limonoids from the fruits of A. polystachya were investigated in previous studies [3,23,24]. Especially, the reports of the antifungal activity of limonoids from this plant have been rare until now.…”

Synergistic Anti Leukemia Effect of a Novel Hsp90 and a Pan Cyclin Dependent Kinase Inhibitors

“…Surface plasmon resonance (SPR), which is an optical analytic technique for measuring the kinetic and thermodynamic parameters of ligand−protein complexes’ formation and affinity, is widely used to investigate enzyme/inhibitor interactions [ 30 , 31 , 32 ]. Recently this approach was successfully applied to study the binding of small molecules to Hsp90 [ 33 , 45 , 46 , 47 ]. SPR experiments were performed in this study as described elsewhere [ 33 ].…”