ABSTRACT
Two new compounds, named eudesm-4(15),7-diene-3α,9ß,11-triol (1) and eudesm-4(15),7-diene-1ß,3α,9ß,11-tetraol (2) together with three known sesquiterpene lactones (1S,5R,7R,10R)-secoatractylolactone (3), (1S,5R,7R,10R)-secoatractylolactone-11-O-ß-D-glucopyranoside (4) atractylenolide III (5) were isolated from the rhizomes of Atractylodes macrocephala. Their structures were elucidated by using one-dimensional (1D) and 2D-NMR spectra and high resolution electrospray ionization (HR-ESI)-MS data. Compound 5 exhibited the most active anti-inflammatory activity with IC50 values of 27.5 µM in inhibiting of nitric oxide production. Compounds 1, 2, and 3 showed moderate effects while compound 4 was inactive.
Subject(s)
Atractylodes , Sesquiterpenes , Rhizome/chemistry , Atractylodes/chemistry , Anti-Inflammatory Agents/pharmacology , Magnetic Resonance Spectroscopy , Sesquiterpenes/pharmacology , Sesquiterpenes/chemistry , Lactones/pharmacology , Lactones/chemistryABSTRACT
Three new chromanes, malloapeltas J-L (1-3), and one new flavone C-glycoside, malloflavoside (4), together with four known compounds, apigenin 6-C-ß-D-xylopyranosyl-8-C-α-L-arabinopyranoside (5), apigenin 6-C-ß-D-glucopyranosyl-8-C-α-L-arabinopyranoside (6), apigenin 7-O-ß-D-apiofuranosyl-(1â2)-ß-D-glucopyranoside (7), and acantrifoside E (8) were isolated from the methanol extract of the leaves of Mallotus apelta. Their chemical structures were determined using spectroscopic methods, including 1D, 2D NMR, and HR-ESI-MS methods. All the isolated compounds were evaluated their cytotoxic activity against human prostate cancer (PC-3) and human breast cancer (MCF-7) cells, but none of them showed cytotoxicities on both human cancer cell lines.
Subject(s)
Flavones , Mallotus Plant , Humans , Apigenin , Glycosides/pharmacology , Glycosides/chemistry , Flavones/pharmacologyABSTRACT
A new muurolane-type sesquiterpene, a new flavone arabinofuranoside derivative, and other five known flavone arabinofuranoside derivatives were isolated from the leaves of Fissistigma bicolor (Annonaceae family). Their chemical structures were determined to be (1S,6R,7S)-muurola-4,10(14)-diene-15-ol (1), quercetin 3-O-ß-D-apiofuranosyl-(1â2)-α-L-arabinofuranoside (2), quercetin 3-O-α-L-rhamnopyranosyl-(1â2)-α-L-arabinofuranoside (3), quercetin 3-O-α-L-arabinofuranoside (4), kaempferol 3-O-ß-D-apiofuranosyl-(1â2)-α-L-arabinofuranoside (5), kaempferol 3-O-α-L-rhamnopyranosyl-(1â2)-α-L-arabinofuranoside (6), and kaempferol 3-O-α-L-arabinofuranoside (7) by analyses of HR-ESI-MS and NMR spectral data. Compounds 4 and 7 containing monosaccharide, arabinofuranoside, potentially inhibited NO productions in LPS activated RAW264.7 cells (IC50 13.4 ± 0.5 and 12.6 ± 0.4 µM) in compared to disaccharide derivatives (IC50 ranging from 58.9 ± 3.3 to 65.6 ± 3.8 µM).
Subject(s)
Annonaceae , Flavones , Kaempferols/analysis , Quercetin , Annonaceae/chemistry , Flavones/pharmacology , Flavones/analysis , Glycosides/chemistry , Plant Leaves/chemistry , Molecular StructureABSTRACT
Mallotusapelta(Lour.) Müll.Arg has been used in traditional medicine for the treatment of chronic hepatitis. Six new chromene derivatives, malloapeltas C-H (1-6) and one known compound, malloapelta B (7) were isolated and structured from the leaves of M.apelta. Two pairs of enantiomers (1a/1b and 2a/2b) were successfully separated by chiral high-pressure liquid chromatography (HPLC). The structures and absolute configurations of compounds were determined using spectroscopic methods, including 1D, 2D NMR, and MS and quantum chemical calculation methods. All compounds were evaluated for cytotoxic activity using cell counting kit-8 (CCK-8) assay against ovariancancer cell line (TOV-21G). Compounds 1-5 and 7 exhibited significant growth and viability inhibitory effects with GI50 values ranging from 0.06 to 10.39 µM and IC50 values ranging from 1.62 to 10.42 µM on ovarian cancer cell line, TOV-21G. The most cytotoxic compounds 2, 3, and 7 were chosen for studying in apoptosis mechanism. Compounds 2, 3, and 7-induced apoptosis as evidenced by activated caspase 8, caspase 9, and PARP, increased Bak and Bax, and decreased Bcl-xL and survivin. Moreover, compounds 2, 3, and 7 significantly inhibited the NF-κB signaling pathway. Taken together, our findings propose the potential application of compounds 2, 3, and 7 for treating cancer via modulating NF-κB activity.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Benzopyrans/pharmacology , Mallotus Plant/chemistry , Plant Extracts/pharmacology , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Apoptosis/drug effects , Benzopyrans/chemistry , Benzopyrans/isolation & purification , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Humans , Mice , Molecular Structure , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Leaves/chemistry , RAW 264.7 Cells , Stereoisomerism , Structure-Activity RelationshipABSTRACT
Dihydroartemisinin was converted to its corresponding alkyne-functionalized esters, which were subsequently deployed as substrates for a 'click' chemistry-mediated coupling-with 3'-azido-3'-deoxythydimine (AZT) to furnish novel triazole-artesunate-AZT hybrid compounds. Moreover, various substituted triazole-artemisinin :hybrids were synthesized based on 'click' chemistry between propargyl-substituted derivatives and artemisinin containing a 2-hydroxypropane unit. Fourteen new hybrids were thus successfully prepared and evaluated as cytotoxic agents, revealing an interesting anticancer activity of four triazole-artemisinin derivative hybrids in KB and HepG2 cancer cell lines.