ABSTRACT
Three undescribed alkaloids (+)-9-hydroxy-N-acetylnordicentrine (1), illigeparvinine (2), and deca-(2E,4Z)-2,4-dienoic acid 4-hydroxy-2-phenethyl amide (3), along with 19 known analogues (4-22), were isolated from the ethnic medicinal plant Illigera parviflora. Their structures were established using NMR, MS, and other spectroscopic analyses as well as X-ray diffraction. Moderate inhibition of human gastric carcinoma (MGC-803) and breast adenocarcinoma (T-47D) cell lines proliferation was observed for actinodaphnine (4) with IC50 values of 28.74 and 11.65 µM, respectively. These findings contribute new anticancer potential compounds and expand the chemical diversity known from the valuable traditional medicinal plant I. parviflora.
Subject(s)
Alkaloids , Aporphines , Hernandiaceae , Plants, Medicinal , Humans , Molecular Structure , Alkaloids/pharmacology , Alkaloids/metabolism , Aporphines/pharmacology , Plants, Medicinal/chemistry , Magnetic Resonance Spectroscopy , Hernandiaceae/chemistry , Hernandiaceae/metabolismABSTRACT
Ten dimeric and two monomeric Erythrina alkaloids, all of them are undescribed, were isolated from the bark of Erythrina variegata L. and named as erythrivarines O-Z. Their structures were determined on the basis of NMR and UV-spectroscopy and mass spectrometry. Dimeric Erythrina alkaloids with a C-10/11' linkage in erythrivarine O and a C-7/10' connectivity in erythrivarines P-U are not yet reported. The two identified monomeric alkaloids may be the precursors of the described dimeric derivatives. These co-occurring dimeric and monomeric alkaloids enabled us to propose a possible biosynthetic pathway leading to these dimers. Their effects of preventing hearing loss were additionally evaluated and erythrivarine T showed as a potential protector of the House Ear Institute-Organ of Corti 1 (HEI-OC-1) cells against neomycin.
Subject(s)
Alkaloids , Erythrina , Alkaloids/chemistry , Alkaloids/pharmacology , Erythrina/chemistry , Magnetic Resonance Spectroscopy , Mass SpectrometryABSTRACT
Caulis Trachelospermi, the stems with leaves of Trachelospermum jasminoides, is a well-known herbal drug of the Apocynaceae family recorded in the Chinese pharmacopeia and used for the treatment of inflammation-related diseases by ethnic minorities of China. The mechanism of anti-inflammatory activity and responsible constituents of T. jasminoides have not been well elucidated in previous studies. Preliminary investigation showed that both the water and the ethyl ester extracts of T. jasminoides exhibited potent inhibitory activity on nitric oxide (NO) production using lipopolysaccharide (LPS)-stimulated murine macrophages. Phytochemical investigation on these extracts afforded 23 compounds, including three new compounds (1: â-3: ) identified on the basis of spectroscopic and mass spectrometric data. Anti-inflammatory bioassay showed that compounds 17, 18, 22: , and 23: inhibited significantly the production of NO in a concentration-dependent manner. Further studies indicated that compound 23: inhibited significantly TNF-α and IL-6 produced by LPS-stimulated RAW 264.7 cells with good selectivity, as well as protein expression of iNOS in RAW 264.7 cells. These chemical constituents may contribute to the anti-inflammatory potential of T. jasminoides.
Subject(s)
Anti-Inflammatory Agents , Apocynaceae , Plant Extracts , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Apocynaceae/chemistry , Inflammation/drug therapy , Lipopolysaccharides , Macrophages/metabolism , Mice , Nitric Oxide/metabolism , Nitric Oxide Synthase Type II/metabolism , Plant Extracts/chemistry , Plant Extracts/pharmacology , RAW 264.7 Cells , Tumor Necrosis Factor-alpha/metabolismABSTRACT
Five dimeric Erythrina alkaloids, named erythrivarines J-N, were isolated from the barks of Erythrina variegata L. (Fabaceae). The erythrivarines J-L featured a 6/6/5/6/6/5/6/6/6 ring system and super conjugated double bond systems, causing intense color from blue to wine red, while erythrivarines M-N looked orange. The structures of the isolated compounds were elucidated by 1D and 2D NMR experiments combined with MS and confirmed by the X-ray crystal diffraction technique. The performed bioassay using HEI-OC-1 cells revealed neuroprotective properties of erythrivarine N against the hearing loss causing antibiotics, neomycin.
Subject(s)
Alkaloids , Erythrina , Indolizines , Neuroprotective Agents , Alkaloids/pharmacology , Neuroprotective Agents/pharmacology , X-Ray DiffractionABSTRACT
One new long-chain ester derivative of trans-ferulic acid 1 and one natural tirucallane-type triterpenoid 2, together with forty known compounds (3-42), were isolated from the barks of Melia azedarach. Their structures were established on the basis of spectroscopic data interpretation. Compounds 7, 9, 10, 12, 13 showed significant inhibitory activities against PTP1B with IC50 values of 13.82 ± 1.29 µM, 13.29 ± 2.26 µM, 20.27 ± 0.52 µM, 24.36 ± 1.25 µM, 15.23 ± 0.6 µM, respectively.
Subject(s)
Melia azedarach , Protein Tyrosine Phosphatase, Non-Receptor Type 1ABSTRACT
A decoction of Plumeria rubra flowers has been used traditionally for the treatment of diabetes in China and Mexico. Chemical investigations on the bioactive constituents of these flowers led to the isolation of 30 compounds, including the four new compounds, one iridoiod (1), two triterpenoids (4, 5), and a long-chain δ-lactone (16). In addition, 26 known compounds (2, 3, 6-15, 17-30) are also reported. All of these compounds were identified on the basis of spectroscopic data interpretation and the absolute configurations of compound 4, 5, 16 were determined by Mosher's method. Compounds 1-4, 7, 8 and 16 showed moderate to significant inhibitory activities against α-glucosidase and protein tyrosine phosphatase 1B, with 4 having IC50 values of 19.45 µM and 0.21 µM, respectively.
Subject(s)
Apocynaceae/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Lactones/pharmacology , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Terpenes/pharmacology , China , Flowers/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Lactones/isolation & purification , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Terpenes/isolation & purificationABSTRACT
A new natural product, 3α,19-dihydroxyl-ent-pimara-8(14),15-diene (1), which possesses an α-orientation hydroxymethyl at C-4 and ∆8,14 groups, as well as eight known compounds, was isolated from the rhizomes of Ricinus communis. The structure of 1 was elucidated by extensive spectroscopic methods and its absolute configurations were confirmed by X-ray crystallographic analysis. The inhibitory rate of 1 against protein tyrosine phosphatase 1B (PTP1B) was 49.49% at the concentration of 6.58 × 10-5 mol/L.
Subject(s)
Diterpenes/chemistry , Diterpenes/pharmacology , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Protein Tyrosine Phosphatase, Non-Receptor Type 1/antagonists & inhibitors , Ricinus/chemistry , Animals , Crystallography, X-Ray , Hypoglycemic Agents/chemistry , Hypoglycemic Agents/pharmacology , Mice , Molecular Conformation , Molecular Structure , Rhizome/chemistryABSTRACT
Six compounds, benzyl 3-O-ß-D-glucopyranosyl-7-hydroxybenzoate (1), spathulenol (2), 1,7,8-trihydroxy-2-naphtaldehyde (3), quercetin (4), astragalin (5) and 2-methoxy-4-(2-propenyl)phenyl ß-D-glucoside (6), were isolated from the leaves of Melia azedarach L. The structure elucidation of compound 1 was discussed in detail based on its 2D-NMR data. Compound 1 showed weak cytotoxicity against the cell lines of T-24, NCI-H460, HepG2, SMMC-7721, CNE, MDA-MB-231 and B16F10 with the inhibition rates from 10.01% to 34.05% at the concentration of 80 µM.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Melia azedarach/chemistry , Plant Leaves/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Line , Cell Line, Tumor , Drug Screening Assays, Antitumor , Glucosides/chemistry , Glucosides/isolation & purification , Glucosides/pharmacology , Hep G2 Cells , Humans , Kaempferols/chemistry , Kaempferols/isolation & purification , Kaempferols/pharmacology , Magnetic Resonance Spectroscopy , Molecular Structure , Quercetin/chemistry , Quercetin/isolation & purification , Quercetin/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Sesquiterpenes/pharmacologyABSTRACT
Seven terpenoids and three sterols were isolated from the methanol extracts of the aerial parts of Ricinus communis by chromatography methods and their structures were identified by spectra analysis as ficusic acid( 1), phytol(2), callyspinol(3) , lupeol(4), 30-norlupan-3beta-ol-20-one(5) , lup-20(29)-en-3beta,15alpha-diol(6) , acetylaleuritolic acid( 7), stigmast4-en-3-one(8) , stig-mast-4-en-6beta-ol-3-one(9) , and stigmast4-en-3,6-dione(10). Compounds 1-3 and 5-10 were obtained from this species for the first time and 5 and 6 showed significant inhibitive activity and good selectivity against 11beta-HSD of mouse and human in vitro. [Key words] Ricinus communis; terpenoids; sterols; 11beta-HSD
Subject(s)
Diabetes Mellitus/drug therapy , Hypoglycemic Agents/pharmacology , Ricinus/chemistry , Sterols/pharmacology , Terpenes/pharmacology , 11-beta-Hydroxysteroid Dehydrogenase Type 1/antagonists & inhibitors , 11-beta-Hydroxysteroid Dehydrogenase Type 2/antagonists & inhibitors , Animals , Diabetes Mellitus/enzymology , Humans , Hypoglycemic Agents/therapeutic use , Inhibitory Concentration 50 , Mice , Sterols/therapeutic use , Terpenes/therapeutic useSubject(s)
Limonins/chemistry , Animals , Drug Evaluation, Preclinical , Humans , Limonins/pharmacologyABSTRACT
Three new sterols (1-3) including an unprecedented ring A-seco natural product (1), five new terpenoids (4-8), and 15 known compounds were isolated from the bark of Melia azedarach. Their structures were elucidated by means of spectroscopic data, and the structure of 1 was confirmed by X-ray crystallography.
Subject(s)
Drugs, Chinese Herbal/isolation & purification , Melia azedarach/chemistry , Sterols/isolation & purification , Terpenes/isolation & purification , Crystallography, X-Ray , Drugs, Chinese Herbal/chemistry , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Bark/chemistry , Stereoisomerism , Sterols/chemistry , Terpenes/chemistryABSTRACT
Eight new monoterpenoid indole alkaloids, alstoyunines A-H (1-8), along with 17 known analogues, were isolated from Alstonia yunnanensis. The structures of the new alkaloids were established by means of extensive spectroscopic methods. Alstoyunines C (3), E (5), and F (6) showed selective inhibition of Cox-2 (>75%). Alstoyunine F (6) showed weak cytotoxicity against the human myeloid leukemia HL-60 (IC50 = 3.89 microM) and hepatocellular carcinoma SMMC-7721 (IC50 = 21.73 microM) cell lines.
Subject(s)
Alstonia/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Secologanin Tryptamine Alkaloids/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Secologanin Tryptamine Alkaloids/chemistry , Secologanin Tryptamine Alkaloids/pharmacologyABSTRACT
An unprecedented cage-like alkaloid, scholarisine A was isolated from the leaves of Alstonia scholaris and its structure determined on the basis of 1D and 2D NMR, FTIR, UV, and high-resolution mass spectroscopic data. This alkaloid might be derived from picrinine via oxygenation, rearrangement, and lactonization.