ABSTRACT
Four new flavonoids, artoheteroids A-D (1-4), together with six known ones (5-10), were isolated from the roots of Artocarpus heterophyllus. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR, UV, IR, CD, and HR-ESI-MS. All isolated compounds were screened for their inhibitory abilities against cathepsin K (CatK). Among them, compounds 1-2, 4-6, and 10 were found to have suppression capabilities against CatK with IC50 values ranging from 1.4 to 93.9µM.
Subject(s)
Artocarpus/chemistry , Cathepsin K/antagonists & inhibitors , Flavonoids/chemistry , Plant Roots/chemistry , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/isolation & purification , Flavonoids/isolation & purification , Molecular StructureABSTRACT
OBJECTIVE: To study the chemical constituents from root of Artocarpus styracifolius. METHODS: Tne constituents were isolated from the root of Artocarpus styracifolius by column chromatography over silica gel, RP-18 silica gel, MCI GEL CHP-20P, macroporous resin HP-20, Sephadex LH-20, Toyopearl HW-40C and by preparative HPLC. Their structures were elucidated by analysis of physical and chemical properties and spectral data. RESULTS: Nine compounds were isolated and their structures were identified as p-hydroxy benzoic acid (1), syringic acid (2), 2,4-dihydroxy benzaldehyde (3), (+)-lyoniresinol (4), 5,5'-dimethoxysecoisolariciresinol (5), (+)- syringaresinol (6), scopoletin (7), xylarolide (8) and trans-oxyresveratrol (9). CONCLUSION: Compounds 2, 5, 6 and 8 are isolated from Moraceae for the first time. Compounds 1, 4 and 7 are firstly characterized in the genus Artocarpus, compounds 3 and 9 are characterized in Artocarpus styracifolius for the first time.
Subject(s)
Artocarpus/chemistry , Phytochemicals/analysis , Plant Roots/chemistry , Chromatography, High Pressure Liquid , Furans , Gallic Acid/analogs & derivatives , Lignans , Plant Extracts , Scopoletin , StilbenesABSTRACT
CONTEXT: Searching for polymorphonuclear neutrophils (PMNs) respiratory burst inhibitors is an important topic in the treatment of human diseases associated with inflammation. OBJECTIVE: To investigate the inhibitory effects of phenolics isolated from Artocarpus styracifolius Pierre (Moraceae) on respiratory burst induced by phorbol myristate acetate (PMA). MATERIALS AND METHODS: The anti-respiratory burst activities of eight phenolics (20 µM) were assessed by determining luminol-dependent chemiluminiscence in rat PMNs. Cytotoxicity of active compounds (1-1000 µM) was assayed by Trypan blue dye exclusion method. Cell-free models were employed to evaluate scavenging capacity of active compounds (20 µM) against reactive oxygen species. RESULTS: The PMA-induced respiratory burst was significantly inhibited (p < 0.05) by six isoprenylated phenolics (AS1-6) at the concentration of 20 µM (below the toxic concentration) with the inhibition rate ranging from 25.0 to 99.6%. The inhibitory potency estimated by IC50 was in the order of AS1 (3.1 µM) >AS6 (5.9 µM) >AS2 (9.1 µM) >AS3 (10.0 µM) >AS5 (29.7 µM) >AS4 (57.7 µM). AS1-4, four isoprenylated flavones, potently quenched superoxide anion, hydroxyl radical, and hydrogen peroxide at the concentration of 20 µM with their scavenging rates in the range of 30.1-78.1%, 35.4-69.7%, and 65.5-86.3%, respectively. In contrast, AS5-6, two isoprenylated 2-arylbenzofurans, showed less effect than that exhibited by AS1-4. CONCLUSION AND DISCUSSION: The isoprenylated phenolics from A. styracifolius can potently inhibit PMA-induced respiratory burst in rat neutrophils without showing cytotoxicity. The inhibitory effects of these isoprenylated phenolics on the respiratory burst might depend on their different types of structure.
