A new dihydrophenanthrene from Cymbidium finlaysonianum and structure revision of cymbinodin-A.

1-(4-Hydroxybenzyl)-4,6-dimethoxy-9,10-dihydrophenanthrene-2,7-diol (13), a new dihydrophenanthrene, was isolated along with ferulic acid esters (1), eight phenanthrene derivatives (2, 3, 6-11) and three bibenzyls (4, 5, 12) from an epiphytic orchid, Cymbidium finlaysonianum. The molecular structure of cymbinodin-A (2) was revised based on spectroscopic data and comparison with the literature. Compounds 2, 3, and 6-13 were evaluated and shown to be cytotoxic against human small cell lung cancer (NCI-H187) cell line. Cymbinodin-A displayed the highest cytotoxicity with an IC50 value of 3.73 µM.

Cytotoxic stilbenes from the roots of Paphiopedilum godefroyae.

Two new stilbenes, 2-(3',5'-dimethoxyphenyl)-6-hydroxy-5-methoxybenzofuran (1) and 3'-hydroxy-2,5'-dimethoxystilbene (2), together with seven known stilbenes (3, 5-10) and one flavanone (4), were isolated from the roots of Paphiopedilum godefroyae. Their chemical structures were determined on the basis of their spectroscopic data. These isolated compounds were evaluated for their cytotoxicity against human small cell lung cancer (NCI-H187) cell lines and an arylbenzofuran derivative, 5,6-dimethoxy-2-(3-hydroxy-5-methoxyphenyl)benzofuran (6), was shown to be strongly cytotoxic with an IC50 value of 5.10 µM.

Film seeds coating with hexane extracts from Illicium verum Hook.f. and Syzygium aromaticum (L.) Merrill & Perry for controlling Callosobruchus maculatus (F.) and Callosobruchus chinensis L.

BACKGROUND: The application of film seed coating with some plant extracts against stored insect pests was an alternative approach for insect protection instead of using chemical insecticides. The overuse of insecticides has contributed to both human health and environmental problems. The hexane extracts of Illicium verum (HS) and Syzygium aromaticum (HC) were evaluated against bruchid beetles (Callosobruchus maculatus and Callosobruchus chinensis). The insecticidal activities and enhancing seed germination after being coated by various concentrations of extracts, purified fraction (PF) of extracts, standard chemicals of PF, fipronil insecticide (FI), and coating agent groups were evaluated after stored. RESULTS: Both HS and HC at 3% concentrations were more effective against C. maculatus than C. chinensis with LT50 values of 1.60-1.90 and 3.44-3.62 h, respectively. They could also kill those insects with a higher number than that of standards. The HS and HC could inhibit the progeny population of those insects over 95.6% with no significant difference compared to the FI group. The eugenol standard was the most effective and completely inhibited the emergence compared with trans-anethol standard and PFs. The seed that was coated with 1% of HS and stored at 4 °C for 6 months showed no effect on seed germination with no significant difference between FI and control groups. CONCLUSION: The application of 1% of HS incorporated in the film seed coating against bruchid beetles and did not affect seed germination quality after 6 months. © 2021 Society of Chemical Industry.

Anti-adipogenic effect of flavonoids from Chromolaena odorata leaves in 3T3-L1 adipocytes.

OBJECTIVE: The leaves of Chromolaena odorata, a highly invasive shrub found growing wild worldwide, are traditionally used for wound healing. Due to its high flavonoid contents, we aimed to find a new application for this plant. Preliminary tests using its ethanolic leaf extract showed that it could suppress the accumulation of lipids in adipocytes. We therefore studied the anti-adipogenic effect of several C. odorata leaf extracts and the relationship between molecular structure and bio-activity of its isolated flavonoid constituents using 3T3-L1 preadipocytes/adipocytes as a model. METHODS: Three leaf extracts and thirteen flavonoids isolated from C. odorata were tested for their effect on lipid accumulation in 3T3-L1 adipocytes using AdipoRed reagent, with quercetin as the positive control. The effects of active flavonoids on the adipocytes were confirmed by oil red O staining and visualized under a light microscope. RESULTS: n-Hexane and ethyl acetate extracts of C. odorata leaves displayed anti-adipogenic activity. The latter extract was the more potent one, especially at 40 µg/mL. Four flavonoids, pectolinarigenin, kaempferide, 4,2'-dihydroxy-4',5',6'-trimethoxychalcone and dillenetin, exhibited significant, concentration-dependent inhibitory effects on lipid accumulation in 3T3-L1 adipocytes. The most potent flavonoid obtained in this study was 4,2'-dihydroxy-4',5',6'-trimethoxychalcone, which caused 75% and 90% inhibition of cellular lipid accumulation at 30 and 50 µmol/L, respectively. Both kaempferide and 4,2'-dihydroxy-4',5',6'-trimethoxychalcone were major constituents in the ethyl acetate extract of this plant. CONCLUSION: C. odorata leaves contained several flavonoids with anti-adipogenic effects against lipid accumulation in 3T3-L1 adipocytes. The plant, normally considered a useless weed, may actually provide an abundant source of biologically active flavonoids.

Benzophenones and xanthone derivatives from Garcinia schomburgkiana-induced P-glycoprotein overexpression in human colorectal Caco-2 cells via oxidative stress-mediated mechanisms.

BACKGROUND: Up-regulation of P-gp is an adaptive survival mechanism of cancer cells from chemotherapy. Three new phytochemicals including two benzophenones, guttiferone K (GK) and oblongifolin C (OC), and a xanthone, isojacaruebin (ISO), are potential anti-cancer agents. However, the capability of these compounds to increase multidrug-resistance (MDR) through P-gp up-regulation in cancer cells has not been reported. PURPOSE: This study was to investigate the effects of GK, OC and ISO on P-gp up-regulation in colorectal adenocarcinoma cells (Caco-2 cells). In addition, the mechanisms underlying their inductive effect were also determined. METHODS: The inductive effect of GK, OC and ISO on P-gp expression at transcription level was measured by real-time reverse transcription polymerase chain reaction. The reactive oxygen species production was determined by 2', 7'-dichlorofluorescin diacetate assay. The protein content of P-gp and involvement of mitogen-activated protein kinases (MAPK) pathway was evaluated by western blot analysis. RESULTS: GK, OC and ISO (50 µM, 24 h) were able to increase the amount of MDR1 mRNA and protein in Caco-2 cells. The presence of N-acetyl-l-cysteine significantly prevented the inductive effect of GK, OC and ISO on MDR1 mRNA level. Moreover, MAPK inhibitors including U0126 (an ERK1/2/MAPK inhibitor) and SB202190 (p38/MAPK inhibitor) suppressed an increase of MDR1 mRNA levels in the cells treated with benzophenones (GK, OC) and xanthone ISO, respectively. These findings were in agreement with the increase of phosphorylated form of either ERK1/2 (p-ERK1/2) or p38 (p-p38) upon treatment of the cells with these three compounds. In addition, OC and ISO, but not GK, increased mRNA of c-Jun level. CONCLUSION: The benzophenones GK, OC and xanthone ISO are likely MDR inducers through up-regulation of P-gp expression at transcription level. Their molecular mechanisms involve oxidative stress-mediated activation of MAPK signaling pathway.