ABSTRACT
Three new secolignans were found in the detailed chemical study of Peperomia blanda (Jacq.) Kunth collected from China. Detailed NMR data analysis, especially 1H NMR, 13C NMR and 2 D NMR, elucidates the structures of the three new secolignans.
Subject(s)
Peperomia , Peperomia/chemistry , Magnetic Resonance Spectroscopy , ChinaABSTRACT
Seven undescribed polyketide compounds (1-4, 9-11) and six known polyketide compounds (5-8,12, 13) were isolated from Rhodiola tibetica endophytic Penicillium sp. HJT-A-10. The structural of seven undescribed polyketides metabolites were established on the basis of spectroscopic methods. The results of anti-inflammatory activity showed that compounds 1-8ï¼10-13 had significant inhibitory effects on LPS-induced NO production in RAW 264.7 cells.
Subject(s)
Penicillium , Polyketides , Rhodiola , Penicillium/chemistry , Molecular Structure , Anti-Inflammatory Agents/chemistryABSTRACT
Six new polyketone metabolites, compounds (1-6) and seven known polyketone compounds (7-13) were isolated from Rhodiola tibetica endophytic fungus Alternaria sp. The structural elucidation of five new polyketone metabolites were elucidated on the basis of spectroscopic including 2D NMR and HRMS and spectrometric analysis. Inhibition rate evaluation revealed that compounds 1(EC50 = 0.02 mM), 3(EC50 = 0.3 mM), 6(EC50 = 0.07 mM), 8(EC50 = 0.1 mM) and 9(EC50 = 0.04 mM) had inhibitory effect on the SARS-CoV-2 virus.
Subject(s)
Alternaria/chemistry , Antiviral Agents/isolation & purification , Antiviral Agents/pharmacology , Ketones/isolation & purification , Ketones/pharmacology , Polymers/isolation & purification , Polymers/pharmacology , SARS-CoV-2/drug effects , Antiviral Agents/chemistry , Humans , Ketones/chemistry , Molecular Structure , Polymers/chemistryABSTRACT
Artemisinin (ART) is the most effective component in malaria treatment, however, the extremely low content restricts its clinical application. Therefore, it is urgent to increase the yield of ART. ART gradually accumulates with aging, small RNA (sRNA) and transcriptome analysis were applied on the leaves of 2-week-old (2 w) and 3-month-old (3 m) A. annua respectively. Among all the annotated sRNAs, 125 were upregulated and 128 downregulated in the 3 m sample compared to the 2 w one. Whereas 2183 genes were upregulated and 2156 downregulated. Notably, the level of miR156 and several annotated miRNAs gradually decreased while SPLs increased. In addition, the genes on ART biosynthesis pathway were significantly upregulated including ADS, CYP71AV1, ADH1, DBR2 and ALDH1, and so were the positive transcription factors like AaERF1, AaORA and AaWRKY1 indicating that age influences the ART biosynthesis by activating the expression of the synthesizing genes as well as positive transcription factors. This study contributes to reveal the regulatory effects of age on ART biosynthesis both in sRNA and transcription levels.
Subject(s)
Artemisia annua/metabolism , Artemisinins/metabolism , Artemisinins/pharmacology , Age Factors , Antimalarials/metabolism , Antimalarials/pharmacology , Biosynthetic Pathways/genetics , Gene Expression/genetics , Gene Expression Profiling/methods , Gene Expression Regulation, Plant/genetics , MicroRNAs/genetics , Plant Leaves/metabolism , Plant Proteins/genetics , Transcription Factors/metabolism , Transcriptome/geneticsABSTRACT
Two isopentenyl resorcinols, peperobtusin B and peperobtusin C, have been isolated from Peperomia tetraphylla. Their structures were determined on the basis of spectroscopic methods, especially 1H NMR, 13C NMR, 2D NMR, and HR-TOF-MS. Two compounds were evaluated for cytostatic activity against G2, A 549, Hela and HCT 116 cells, but cytostatic activity of both compounds is weak.
Subject(s)
Peperomia , HeLa Cells , Humans , Magnetic Resonance Spectroscopy , Molecular Structure , Resorcinols/pharmacologyABSTRACT
It is reported that dihydroartemisinin could reduce the expression of phosphorylated adhesion kinase and matrix metalloproteinase-2, inhibit the growth, migration and invasion of ovarian cancer cells, promote the formation of Treg cells through TGF-beta/Smad signaling pathway, and play an immunosuppressive role; dihydroartemisinin could also inhibit the growth of lung cancer cells by inhibiting the expression of vascular endothelial growth factor(VEGF) receptor KDR. However, there are few studies on dihydroartemisinin in hepatocellular carcinoma cells. In order to preliminarily explore the effect of dihydroartemisinin on invasion and metastasis of hepatocellular carcinoma cells, CCK-8 method and crystal violet staining were used to detect the effect of dihydroartemisinin on the growth of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H. The effects of dihydroartemisinin on the invasion and metastasis of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H were studied by using cell wound healing and Transwell. Western blot was used to detect the protein expression of epidermal growth factor receptor(EGFR) and its downstream signaling pathway in cells treated with dihydroartemisinin for 48 hours. The results showed that dihydroartemisinin could inhibit the growth of hepatocellular carcinoma cell 7402 and highly metastatic hepatocellular carcinoma cell MHCC97 H at 25 µmol·L~(-1). As compared with the control group, the number of cell clones was significantly reduced, and the ability of cell migration and invasion was weakened. Western blot results showed that as compared with the control group, dihydroartemisinin group could down-regulate the protein expression of EGFR and its downstream signaling pathways p-AKT, p-ERK, N-cadherin, Snail and Slug, and up-regulate the expression of E-cadherin protein, thus affecting the migration, invasion and metastasis of hepatocellular carcinoma cells 7402 and MHCC97 H.
Subject(s)
Artemisinins/pharmacology , Carcinoma, Hepatocellular/pathology , Liver Neoplasms/pathology , Neoplasm Invasiveness , Neoplasm Metastasis , Carcinoma, Hepatocellular/drug therapy , Cell Line, Tumor , Cell Movement , ErbB Receptors/metabolism , Humans , Liver Neoplasms/drug therapy , Signal TransductionABSTRACT
Two new secolignans, 3,4-trans-3-hydroxymethyl-4-[bis(4-hydroxy-3- methoxyphenyl)methyl]butyrolactone (1) and 3,4-trans-3-hydroxymethyl-4- [bis(3,4-dimethoxyphenyl)methyl]butyrolactone (2) have been isolated from the roots of Urtica fissa E.Pritz. Their structures were determined on the basis of spectroscopic methods, especially 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS. The inhibitory effects on N1 and N2, two subtypes of neuraminidases (NAs), of these two compounds were assayed.
Subject(s)
Lignans/chemistry , Plant Roots/chemistry , Urticaceae/chemistry , Molecular StructureABSTRACT
Euphorbia maculata is a medicinal plant of the Euphorbiaceae family, which can produce anti-inflammatory and cancer chemopreventive agents of triterpenoids. The present study reports on the bioactive triterpenoids of this plant. Two new lanostane-type triterpenoids, named (3S,4S,7S,9R)-4-methyl-3,7-dihydroxy-7(8â9) abeo-lanost-24(28)-en-8-one (1) and 24-hydroperoxylanost-7,25-dien-3ß-ol (2), together with 15 known triterpene derivatives, were isolated from Euphorbia maculata. The structures of the new compounds were determined on the basis of extensive spectroscopic data (UV, MS, ¹H and 13C-NMR, and 2D NMR) analysis. All tetracyclic triterpenoids (1â»11) were evaluated for their anti-inflammatory effects in the test of TPA-induced inflammation (1 µg/ear) in mice. The triterpenes exhibited significant anti-inflammatory activities.
Subject(s)
Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Euphorbia/chemistry , Plant Extracts/chemistry , Plant Extracts/pharmacology , Triterpenes/chemistry , Animals , Disease Models, Animal , Edema/drug therapy , Edema/pathology , Female , Magnetic Resonance Spectroscopy , Mice , Molecular StructureABSTRACT
Three new amino acid derivatives, oxalamido-L-phenylalanine methyl ester (1), oxalamido-L-leucine methyl ester (2), and lumichrome hydrolyzate (3), together with nine known compounds (4-12), were isolated from the solid culture of edible mushroom Pleurotus ostreatus. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations of 1 and 2 were established by the chiral synthesis and confirmed by circular dichroism (CD) analysis of their total synthesis products and natural isolates. All new compounds were evaluated for their antioxidant effects, antimicrobial activities, and cytotoxic activity. Compounds 1-3 showed weak antifungal activities against Candida albicans with minimum inhibitory concentration (MIC) value of 500 µg/ml.
Subject(s)
Agaricales/chemistry , Antioxidants/isolation & purification , Pleurotus/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Candida albicans/drug effects , Flavins/chemistry , Flavins/isolation & purification , Leucine/analogs & derivatives , Leucine/chemistry , Leucine/isolation & purification , Microbial Sensitivity Tests , Molecular Structure , Phenylalanine/analogs & derivatives , Phenylalanine/chemistry , Phenylalanine/isolation & purification , Phenylalanine/pharmacologyABSTRACT
Two new bisindolylbenzenoid alkaloids asterriquinol E (1) and asterriquinol F (2), together with four known compounds (3-6) were isolated from the fermentation products of the fungus Aspergillus sp. CBS-P-2. Their structures were established on the basis of extensive spectroscopic analysis, including HR-ESI-MS, UV, IR, 1D, and 2D NMR (HSQC, HMBC, and NOESY) methods. The stereochemical structure of 2 was confirmed via the CD data of the in situ formed [Rh2(OCOCF3)4] complex method. All of the isolated compounds were tested for inhibitory activity against LPS (lipopolysaccharide)-induced nitric oxide production in microglia.
Subject(s)
Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Aspergillus/chemistry , Indole Alkaloids/isolation & purification , Indole Alkaloids/pharmacology , Anti-Inflammatory Agents/chemistry , China , Indole Alkaloids/chemistry , Inhibitory Concentration 50 , Lipopolysaccharides/pharmacology , Microglia/drug effects , Molecular Structure , Nitric Oxide/biosynthesis , Nuclear Magnetic Resonance, Biomolecular , Soil MicrobiologyABSTRACT
Five new polyketides including three new butenolides (1-3), one new diphenyl ether (4), and one new benzophenone (5), together with eleven known compounds (6-16) were isolated from a wetland fungus Aspergillus flavipes PJ03-11. Their structures were elucidated on the basis of detailed spectroscopic analysis. All the isolated compounds were tested for their α-glucosidase inhibitory activities. The results showed that compounds 1-3, 6, 7, 11, 15 and 16 exhibited stronger inhibitory activities than acarbose. And the preliminary structure-activity relationships of aspulvinone and diphenyl ether compounds on the α-glucosidase inhibitory activity were reported.
Subject(s)
4-Butyrolactone/analogs & derivatives , Aspergillus/chemistry , Benzophenones/chemistry , Glycoside Hydrolase Inhibitors/chemistry , Phenyl Ethers/chemistry , Polyketides/chemistry , 4-Butyrolactone/chemistry , 4-Butyrolactone/isolation & purification , 4-Butyrolactone/pharmacology , Benzophenones/isolation & purification , Benzophenones/pharmacology , Glycoside Hydrolase Inhibitors/isolation & purification , Glycoside Hydrolase Inhibitors/pharmacology , Phenyl Ethers/isolation & purification , Phenyl Ethers/pharmacology , Polyketides/isolation & purification , Polyketides/pharmacology , Saccharomyces cerevisiae/enzymology , alpha-Glucosidases/metabolismABSTRACT
Two new compounds, (22E)-25-carboxy-8ß,14ß-epoxy-4α,5α-dihydroxyergosta-2,22-dien-7-one (1) and fusidione (3), along with two known compounds, 5α,8α-epidioxy ergosta-6,22-diene-3ß-ol (2) and microperfuranone (4), were isolated from the fermentation products of the marine-sourced fungus Acremonium fusidioides RZ01. The structures of compounds 1 and 3 were elucidated by extensive spectroscopic methods, especially 2D NMR, and their absolute configurations were suggested on the basis of the circular dichroism spectral analysis and the NOESY data. Both new compounds showed inhibitory activity against HL-60 cells with IC50 values being16.6 and 44.9 µmol·L-1, respectively.
Subject(s)
Acremonium/chemistry , Seawater/microbiology , Acremonium/classification , Acremonium/isolation & purification , Acremonium/metabolism , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Cell Proliferation/drug effects , Fermentation , HL-60 Cells , Humans , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
From the EtOH extract of the flowers of Camellia nitidissima Chi, a new acylated flavonoid glycoside, quercetin 7-O-(6"-O-E-caffeoyl)-ß-D-glucopyranoside (1), has been isolated, together with three known flavonoids: quercetin (2), quercetin 3-O-ß-D-glucopyranoside (3), and quercetin 7-O-ß-D-glucopyranoside (4). Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was shown to inhibit proliferation and to induce apoptosis of human lymphoma U937 cells.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Antineoplastic Agents, Phytogenic/pharmacology , Camellia/chemistry , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Glucosides/isolation & purification , Glucosides/pharmacology , Quercetin/analogs & derivatives , Antineoplastic Agents, Phytogenic/chemistry , Apoptosis/drug effects , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Flowers/chemistry , Glucosides/chemistry , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Quercetin/chemistry , Quercetin/isolation & purification , Quercetin/pharmacology , Stereoisomerism , U937 CellsABSTRACT
Three new secolignan glycosides {3,4-trans-4-[bis(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (1), {3,4-trans-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (2) and {3,4-cis-4-[(3-methoxy-4-hydroxyphenyl)(3,4-dimethoxyphenyl)methyl]-2-oxotetrahydrafuran-3-yl}methyl-O-ß-glucopyranoside (3) were isolated from the roots of Urtica fissa E. Pritz. Their structures were identified by spectral methods including 1D NMR, 2D NMR and HR-EI-MS.
Subject(s)
Glycosides/chemistry , Plant Roots/chemistry , Urticaceae/chemistry , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Two new 3-oxo-α-ionol glucoside isomers, (6R,9R)-3-oxo-α-ionol-9-O-ß-D-glucopyranosyl (1 â 2)-ß-D-glucopyranoside (1) and (6S,9R)-3-oxo-α-ionol-9-O-ß-D-glucopyranosyl (1 â 2)-ß-D-glucopyranoside (2) were isolated from the aerial parts of Urtica laetevirens Maxim. Their structures, including stereochemistry, were established by spectral analyses (HR-ESI-MS, NMR and CD). Also, 3-oxo-α-ionol glucosides were isolated from Urtica species for the first time.
Subject(s)
Glucosides/isolation & purification , Urticaceae/chemistry , Circular Dichroism , Glucosides/chemistry , Magnetic Resonance Spectroscopy , Spectrometry, Mass, Electrospray Ionization , StereoisomerismABSTRACT
Seven sinapine analogs (6a-6g) were synthesized using cinnamon acid or benzoic acid and their derivatives as starting materials, which obtained from substituted benzaldehyde and malonate. The structures of target compounds were characterized by IR, 1H NMR and elemental analysis. The effects of compounds 6a-6g on the smooth muscle of intestine isolated from rabbit were studied, and the experimental results showed that compounds 6a, 6d and 6g had diastolic action, while 6f had contractile action.
Subject(s)
Choline/analogs & derivatives , Intestines/physiology , Muscle Tonus/drug effects , Muscle, Smooth/physiology , Animals , Choline/chemical synthesis , Choline/chemistry , Choline/pharmacology , In Vitro Techniques , Molecular Structure , Muscle Contraction/drug effects , RabbitsABSTRACT
Continuous research on the ethyl acetate extract of the fermentation broth of the marine fungus Y26-02 (Penicillium sp.) led to the purification of one known and three new compounds. Their structures were elucidated, respectively, as butyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (1), 4-hydroxyphenethyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (2), 3-hydroxybenzyl 2-(4-oxo-5,6-dihydro-2H-pyran-3-yl) acetate (3), and desoxypatulinic acid (4) on the basis of their spectroscopic and physico-chemical properties.
Subject(s)
Penicillium/chemistry , Pyrans/isolation & purification , Marine Biology , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Pyrans/chemistryABSTRACT
From the dried aerial parts of Acanthopanax senticosus, two new diketopiperazines, eleutherazines A (1) and B (2), were isolated. Their structures were elucidated on the basis of chemical and spectroscopic methods.
Subject(s)
Diketopiperazines/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Eleutherococcus/chemistry , Diketopiperazines/chemistry , Drugs, Chinese Herbal/chemistry , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
Two new aurantiamides named as cordyceamides A and B were isolated from the culture liquid of Cordyceps sinensis (BERK.) SACC., along with one known compound, aurantiamide acetate. Their structures were elucidated as N-benzoyl-L-tyrosinyl-L-phenylalaninol acetate and N-benzoyl-L-tyrosinyl-L-p-hydroxyphenylalaninol acetate by 1D, 2D-NMR techniques and comparison with literatures.