ABSTRACT
Five new cytochalasins, diaporchalasins A-E (1-5), together with 14 known congeners (6-19) were isolated from the endophytic fungus Diaporthe sp. BMX12, which was isolated from the branches of Aquilaria sinensis. The structures of the new compounds were elucidated by extensive spectroscopic analyses including high-resolution electron spray ionization mass spectrometry (HR-ESI-MS) and nuclear magnetic resonance (NMR). Their absolute configurations were assigned by theoretical electronic circular dichroism (ECD) calculations. Compounds 11 and 12 featuring a keto carbonyl at C-21 displayed cytotoxicity toward K562, BEL-7402, SGC-7901, A549, and HeLa cell lines with IC50 values ranging from 4.4 to 47.4â µM.
Subject(s)
Ascomycota , Cytochalasins , Drug Screening Assays, Antitumor , Thymelaeaceae , Cytochalasins/chemistry , Cytochalasins/pharmacology , Cytochalasins/isolation & purification , Humans , Thymelaeaceae/chemistry , Thymelaeaceae/microbiology , Ascomycota/chemistry , Ascomycota/metabolism , Cell Line, Tumor , Antineoplastic Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Molecular Structure , Cell Proliferation/drug effects , Structure-Activity Relationship , Dose-Response Relationship, Drug , Molecular Conformation , Cell Survival/drug effectsABSTRACT
In this study, analysis of the chemical constituents and bioactivities of the unpolar fractions [petroleum ether (PE) and chloroform (C)] of fruits and leaves of Alpinia oxyphylla Miq. were carried out, as well as the bioactivities of the main compounds nootkatone and valencene. From PE and C fractions of the fruits, and PE fraction of the leaves, 95.80%, 59.30%, and 82.11% of the chemical constituents respectively were identified by GC-MS. Among these identified compounds, nootkatone was the main compound in all of three fractions, while valencene was the second main compound in the PE fractions of the fruits and leaves. The bioactivities results showed that all of the fractions and the major compound nootkatone showed tyrosinase inhibitory, as well as inhibitory effect on NO production in LPS-stimulated RAW264.7 cells. While valencene only presented inhibitory activity on NO production in RAW264.7 cells. The critical genes involved in nootkatone biosynthesis in A. oxyphylla were identified from the public transcriptome datasets, and protein sequences were preliminarily analyzed. Our studies develop the usage of the unpolar fractions of A. oxyphylla, especially its leaves as the waste during its production, and meanwhile provide the gene resources for nootkatone biosynthesis.
Subject(s)
Alpinia , Polycyclic Sesquiterpenes , Sesquiterpenes , Alpinia/chemistry , Plant Extracts/pharmacologyABSTRACT
Phytochemical investigation on the stems of Strophanthus divaricatus led to the isolation of four undescribed cardiac glycosides and one undescribed C21 pregnane, together with eleven known steroids. Their structures were elucidated by a comprehensive analysis of HRESIMS, 1D and 2D NMR spectra. The absolute configuration of 16 was determined by comparison of the experimental and computed ECD spectra. Compounds 1-13 and 15 displayed potent to significant cytotoxicity against human cancer cell lines K562, SGC-7901, A549 and HeLa with IC50 values of 0.02-16.08, 0.04-23.13, 0.06-22.31 and 0.06-15.13 µM, respectively.
Subject(s)
Antineoplastic Agents , Strophanthus , Humans , Glycosides/chemistry , Pregnanes/pharmacology , Pregnanes/chemistry , Cell Line, Tumor , Molecular StructureABSTRACT
Six new 2-(2-phenylethyl)chromone dimers (1-6) were isolated from ethyl ether extract of red soil agarwood of Aquilaria crassna from Vietnam by LC-MS-guided fractionation procedure. Their structures were unambiguously elucidated based on HRESIMS, 1D and 2D NMR spectra. The absolute configuration of 2-(2-phenylethyl)chromone dimers was determined by comparison of the experimental and computed ECD spectra. Compound 6 displayed cytotoxicity against the human myeloid leukemia cell line (K562) with an IC50 value of 39.49 µM.
Subject(s)
Chromones , Thymelaeaceae , Chromatography, Liquid , Chromones/chemistry , Flavonoids/chemistry , Humans , Molecular Structure , Soil , Tandem Mass Spectrometry , Thymelaeaceae/chemistry , Wood/chemistryABSTRACT
Three new 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones and one new dimeric 2-(2-phenylethyl)chromone were isolated from the agarwood of Aquilaria crassna Pierre ex Lecomte in Laos. The structures of the isolates were elucidated by spectroscopic methods, and their configurations were determined via ROESY correlations, 3 J H-H coupling constants analyses, comparisons of chemical shifts and specific rotations with known compounds, and ECD calculation in the case of 1. Compounds 1-4 were evaluated for their cytotoxicity. Compounds 1 and 2 exhibited weak cytotoxicity toward HeLa cell line (IC50: 49.8 ± 1.2 µM) and K562 cell line (IC50: 42.66 ± 0.47 µM), respectively.
Subject(s)
Flavonoids/isolation & purification , Thymelaeaceae/chemistry , Wood/chemistry , Carbon-13 Magnetic Resonance Spectroscopy , Cell Line, Tumor , Flavonoids/chemistry , Humans , Laos , Proton Magnetic Resonance SpectroscopyABSTRACT
Fourteen compounds were isolated from the ethanol extract of Dalbergiae Odoriferae Lignum by various chromatographic techniques, including column chromatographies on silica gel, Sephadex LH-20 and semi-preparative HPLC. Their structures were determined by spectroscopic techniques as S-3'-hydroxy-7,2',4'-trimethoxyisoxane(1), 2-(2',4'-dimethoxyphenyl)-6-hydroxybenzofuran(2), 2-(2'-hydroxy-4'-methoxyphenyl)-6-methoxybenzofuran(3), 7,2',4'-trimethoxydihydroisoflavone(4), sativanone(5), 3,9-dimethoxy-6H-benzofuro[3,2-c]chromen-6-one(6),(6 aS,11 aS)-homopterocarpin(7),(6 aS,11 aS)-8-hydroxy-3,9-dimethoxypterocarpan(8),(6 aS,11 aS)-3,8,9-trimethoxypterocarpan(9), isodalbergin(10), isoliquiritigenin(11), butein(12), butin(13) and 3,7,4'-trihydroxyflavone(14). Among them, compound 1 was a new compound, while 2 and 3 were new natural products, 6, 8, 9 and 14 were isolated for the first time from Dalbergiae Odoriferae Lignum. Compounds 1-14 were tested for their cytotoxic activity against human hepatoma cell line BEL-7402, human gastric cancer cell line SCG-7901, human lung cancer cell line A549, human chronic myeloid leukemia cell line K562 and HeLa human cervical cancer cellline by MTT method. Compound 1 exhibited significant cytotoxicity with IC_(50) values ranging from 2.85 to 11.62 µg·mL~(-1). In addition, 2, 11 and 12 showed weak cytotoxic activities.
Subject(s)
Antineoplastic Agents , Chromatography, High Pressure Liquid , HeLa Cells , HumansABSTRACT
Two new sesquiterpenoids (1 and 2), together with two known sesquiterpenoids (3 and 4), were isolated from agarwood originated from Aquilaria sp. Their structures were elucidated by extensive spectroscopic methods including 1D and 2D NMR, IR, HRESIMS, and comparison with the literatures. All compounds were evaluated for cytotoxicity against five human cancer cell lines, but none of them displayed significant activity. [Formula: see text].
Subject(s)
Sesquiterpenes , Thymelaeaceae , Humans , Molecular Structure , WoodABSTRACT
Six 8,12-epoxyguaiane sesquiterpenes (1-6), together with two known 2-(2-phenylethyl)chromone derivatives (7-8) were isolated from agarwood originating from Aquilaria filaria. Their structures were established by spectroscopic methods including IR, HRESIMS, 1D, and 2D NMR, and comparison with the published data. The absolute configuration of compound 1 was unambiguously determined by quantum chemical calculation of the electronic circular dichroism (ECD) spectrum. All compounds were tested for their α-glucosidase inhibitory activity and cytotoxicity. Compound 5 showed significant α-glucosidase inhibitory activity with IC50 value of 253.2⯱â¯9.7⯵M (Acarbose, 743. 4⯱â¯3.3⯵M). Compounds 2-4 displayed weak cytotoxicity against K562 tumor cell lines.
Subject(s)
Glycoside Hydrolase Inhibitors/pharmacology , Sesquiterpenes, Guaiane/pharmacology , Sesquiterpenes/pharmacology , Thymelaeaceae/chemistry , Cell Survival/drug effects , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , K562 Cells , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes, Guaiane/chemistry , Sesquiterpenes, Guaiane/isolation & purification , Wood/chemistryABSTRACT
Six compounds were isolated from the aerial part of cultivated Clerodendranthus spicatus in Hainan with various chromatographic techniques,and their structures were determined as:1-dehydroxy-1-oxo-rupestrinol(1),N-trans-feruloyltyramine(2),methyl 3,4-dihydroxyphenyllactate(3),caffein acid(4),methyl caffeate(5) and ethyl caffeate(6),via analysis of physicochemical properties and spectroscopic evidence.Compound 1 was a new compound,while compounds 2 and 3 were isolated from C.spicatus for the first time.Biological activity results showed that compounds 2-4 exhibited α-glucosidase inhibitory activity with different inhibition ratio.
Subject(s)
Glycoside Hydrolase Inhibitors/pharmacology , Lamiaceae/chemistry , Sesquiterpenes, Eudesmane/pharmacology , China , Glycoside Hydrolase Inhibitors/isolation & purification , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Sesquiterpenes, Eudesmane/isolation & purificationABSTRACT
Three new flavanoids, (2R)-7,4'-dihydroxy-8-methylflavan (1), (2R)-7,4'-dihydroxy-6-methylflavan (2), and (3R)-7,3',4'-trihydroxyhomoisoflavan (3), together with seven known compounds (4-10), were isolated from artificially induced dragon's blood of Dracaena cambodiana, and their structures were determined based on HR-ESI-MS and extensive spectroscopic techniques (UV, IR, 1D-, and 2D-NMR). Compound 2 exhibited weak cytotoxicity against BEL-7402 cells line with the IC50 value of 39.2 µM. In addition, compound 3 showed significant acetylcholinesterase (AChE) inhibitory activity.
Subject(s)
Cholinesterase Inhibitors/isolation & purification , Cholinesterase Inhibitors/pharmacology , Dracaena/chemistry , Flavonoids/isolation & purification , Cholinesterase Inhibitors/chemistry , Flavonoids/chemistry , Flavonoids/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Extracts/chemistryABSTRACT
Three new2-(2-phenylethyl)chromone derivatives (1-3) and a new2-(2-phenylethenyl)chromone derivative (4), together with two known 2-(2-phenylethyl)chromone derivatives (5-6), were isolated from agarwood originating from Gyrinops salicifolia Ridl. The structures of compounds 1-4 were elucidated by comprehensive spectroscopic techniques (UV, IR, 1D and 2D-NMR) and MS analysis, as well as by comparison with the literature. Compounds 1, 2, and 5 showed moderate cytotoxicity against human tumor K562, BEL-7402, and SGC-7901 cell lines with IC50 values of 5.76 to 20.1 µM.
Subject(s)
Antineoplastic Agents/chemistry , Chromones/chemistry , Flavonoids/chemistry , Magnoliopsida/chemistry , Plant Extracts/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Chromones/isolation & purification , Chromones/pharmacology , Flavonoids/pharmacology , Humans , K562 Cells , Molecular StructureABSTRACT
Six new sesquiterpenoids (1-6) and six known sesquiterpenoids (7-12) were isolated from agarwood originated from Gyrinops salicifolia Ridl. Most of them gave off aromatic odor, and all the compounds were isolated from this genus for the first time. The structures of 1-6 were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR) and MS analysis, as well as by comparison with literature data. Compounds 1, 6 and 11-12 showed moderate acetylcholinesterase (AChE) inhibitory activity.
Subject(s)
Cholinesterase Inhibitors/chemistry , Sesquiterpenes/chemistry , Thymelaeaceae/chemistry , Acetylcholinesterase/metabolism , Cholinesterase Inhibitors/isolation & purification , Molecular Structure , Sesquiterpenes/isolation & purification , Wood/chemistryABSTRACT
Phytochemical investigation on the stems of C. tabularis (Meliaceae) led to the isolation of two new phragmalin-type limonoids, named tabularisins S and T (1-2), along with five known ones (3-7). The structures of the new limonoids were established by spectroscopic methods including UV, IR, HRESIMS, and 1D and 2D NMR. All the compounds were evaluated for α-glucosidase inhibitory activity in vitro. Compounds 2 and 3 exhibited significant inhibitory activity against α-glucosidase with IC50 values of 0.15 and 0.03 mM, respectively (acarbose as positive control, IC50 0.95 mM).
Subject(s)
Drugs, Chinese Herbal , Glycoside Hydrolase Inhibitors , Limonins , Meliaceae/chemistry , alpha-Glucosidases/drug effects , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Glycoside Hydrolase Inhibitors/pharmacology , Limonins/chemistry , Limonins/isolation & purification , Limonins/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Bark/chemistry , Plant Stems/chemistryABSTRACT
Seven new 2-(2-phenylethyl)chromone derivatives (1-7) including a chlorinated one (4), together with eight known ones (8-15), were isolated from the EtOAc extract of artificial agarwood originating from Aquilaria sinensis (Lour.) Gilg. All structures including the absolute configurations were unambiguously elucidated by spectroscopic (NMR, UV, IR, MS) methods, Mosher's method, and comparison with reported data in the literatures. Among those, compounds 8, 12, and 14 exhibited significant inhibition against α-glucosidase in vitro with IC50 values of 0.15, 0.05, and 0.09 mM, respectively (with acarbose as the positive control; IC50: 0.98 mM). In addition, compounds 3, 9, 11, and 14 showed weak inhibitory activity against AChE; and compounds 12 and 13 displayed weak cytotoxicity against human gastric cell line (SGC-7901) among three types of tested human cancer cell lines (BEL-7402, K562, and SGC-7901).
Subject(s)
Flavonoids/chemistry , Thymelaeaceae/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line, Tumor , Cholinesterase Inhibitors/chemistry , Cholinesterase Inhibitors/isolation & purification , Flavonoids/isolation & purification , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , Inhibitory Concentration 50 , Molecular Structure , Plant Extracts/chemistry , Wood/chemistry , alpha-GlucosidasesABSTRACT
Phytochemical investigation on the stems of C. tabularis led to the isolation of five new phragmalin-type limonoids and six known ones. The structures of the new compounds 1-5, named chukbularisins A-E, were elucidated by spectroscopic techniques (IR, HRESIMS, 1D and 2D NMR) and comparisons with published data. All the compounds were evaluated for in vitro α-glucosidase inhibitory activity. Compounds 2, 3, 4, 5, and 8 exhibited inhibitory activity against α-glucosidase with IC50 values of 0.06 ± 0.008, 0.04 ± 0.002, 0.52 ± 0.039, 1.09 ± 0.040, and 0.20 ± 0.057 mM, respectively (using acarbose as positive control, IC50 0.95 ± 0.092 mM).
Subject(s)
Enzyme Inhibitors/chemistry , Limonins/chemistry , Meliaceae/chemistry , alpha-Glucosidases/chemistry , Enzyme Inhibitors/isolation & purification , Limonins/isolation & purification , Liquid-Liquid Extraction/methods , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Stems/chemistry , Structure-Activity RelationshipABSTRACT
A new triterpenoid (1) with apotirucallane skeleton was isolated from the ethanol extract of the roots of Atalantia buxifolia (Poir.) Oliv. The complete structural assignment of the new compound was elucidated by a combination of 1D, 2D NMR (HMQC, HMBC, COSY, and NOESY), and HR-ESI-MS analysis. Moreover, this new compound was evaluated in vitro for its cytotoxic, antimicrobial and enzymes inhibitory activities.
