ABSTRACT
Two new limonoids, 12-ethoxynimbolinins G and H (compounds 1 and 2), and one known compound, toosendanin (Chuanliansu) (compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin (3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.
Subject(s)
Humans , Cell Line, Tumor , Cell Proliferation , Limonins , Melia , Chemistry , Molecular Structure , Plant Bark , Chemistry , Plant Extracts , Chemistry , Pharmacology , X-Ray DiffractionABSTRACT
Two new limonoids, 12-ethoxynimbolinins G and H (compounds 1 and 2), and one known compound, toosendanin (Chuanliansu) (compound 3), were isolated from the bark of Melia toosendan. Their structures were elucidated by spectroscopic analysis and X-ray techniques. The absolute configuration of toosendanin (3) was established by single-crystal X-ray diffraction. Compounds 1-3 were evaluated for their cytotoxicity against five tumor cell lines.
Subject(s)
Humans , Cell Line, Tumor , Cell Proliferation , Limonins , Melia , Chemistry , Molecular Structure , Plant Bark , Chemistry , Plant Extracts , Chemistry , Pharmacology , X-Ray DiffractionABSTRACT
In the present study, two new limonoids, 1α, 7α-dihydroxyl-3α-acetoxyl-12α-ethoxylnimbolinin (1) and 1α-tigloyloxy-3α-acetoxyl-7α-hydroxyl-12β-ethoxylnimbolinin (2), together with other four known limonoids (3-6), were isolated from the fruits of Melia toosendan. Their structures were elucidated by means of extensive spectroscopic analyses (NMR and ESI-MS) and comparisons with the data reported in the literature. The isolated compounds were evaluated for their antibacterial activities. Compound 4 exhibited significant antibacterial activity against an oral pathogen, Porphyromonas gingivalis ATCC 33277, with an MIC value of 15.2 μg·mL(-1). Compound 2 was also active against P. gingivalis ATCC 33277, with an MIC value of 31.25 μg·mL(-1). In conlcusion, our resutls indicate that these compounds may provide a basis for future development of novel antibiotics.
Subject(s)
Anti-Bacterial Agents , Chemistry , Pharmacology , Drugs, Chinese Herbal , Chemistry , Fruit , Chemistry , Limonins , Chemistry , Magnetic Resonance Spectroscopy , Melia , Chemistry , Molecular Structure , Porphyromonas gingivalis , Spectrometry, Mass, Electrospray IonizationABSTRACT
The present study was designed to isolate and evaluate the antibacterial activity of the compounds from the whole plant of Euphorbia helioscopia L.. Various chromatographic techniques were used to isolate and purify the compound. The structure of the compound was elucidated on basis of spectral data ((1)H NMR, (13)C NMR, (1)H-(1)H COSY, HSQC, HMBC, NOESY, IR, and HR-ESI-MS). A new jatrophone-type diterpenoid (14α,15β-diacetoxy-3β-benzoyloxy-7β-nicotinoyloxy-9-oxo-jatropha-5E,11E-diene), named euphoheliosnoid E (1), was isolated from the whole plant of E. helioscopia L. Compound 1 showed significant anti-microbial activity against oral pathogens.
Subject(s)
Anti-Infective Agents , Pharmacology , Diterpenes , Chemistry , Pharmacology , Euphorbia , Chemistry , Molecular Structure , Mouth Diseases , Microbiology , Niacin , Chemistry , Pharmacology , Plant Extracts , Chemistry , PharmacologyABSTRACT
To study the chemical constituents of the fruits of Melia toosendan, three limonoids were isolated and purified by repeated silica gel column chromatography and preparative HPLC from the EtOAc extract of M. toosendan. Their structures were determined by their physico-chemical properties and spectroscopic data (1D-NMR, 2D-NMR) as: 24, 25, 26, 27-tetranorapotirucalla-(apoeupha)-1alpha-tigloyloxy-3alpha, 7alpha-dihydroxyl-12alpha-acetoxyl-14, 20, 22-trien-21, 23-epoxy-6, 28-epoxy (1), nimbolinin B (2), and trichilinin D (3), separately. Compound 1 is a new compound, and compound 2 is obtained from this plant for the first time.
Subject(s)
Fruit , Chemistry , Limonins , Chemistry , Melia , Chemistry , Molecular Structure , Plants, Medicinal , ChemistryABSTRACT
<p><b>OBJECTIVE</b>To study the constituents of the whole herbs of Vernonia cinerea. by bio-activity guided isolation with PC-12 model.</p><p><b>METHOD</b>The constituents were separated by column chromatography and the structures were elucidated by spectroscopic methods.</p><p><b>RESULT</b>Four compounds were identified to be (+)-lirioresinol B (1), stigmasterol (2), stigmasterol-3-O-beta-D-glucoside (3), 4-sulfo-benzocyclobutene (4), and their NGF inducing activity were also investigated.</p><p><b>CONCLUSION</b>Compounds 1, 3, 4 were isolated from this genus for the first time, and compound 4 was identified as a new natural product. Compounds 1, 3, 4 showed cytotoxicity on PC-12, and compounds 2, 3, 4 showed inhibition activity. Compound 4 showed a specific effect on the survival of TrkA fibroblasts, and resulted in the inducing NGF activity.</p>
Subject(s)
Animals , Rats , Drugs, Chinese Herbal , Chemistry , Glucosides , Chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , PC12 Cells , Polycyclic Compounds , Chemistry , Pharmacology , Stigmasterol , Chemistry , Vernonia , ChemistryABSTRACT
In order to look for lower toxic and strongly active compounds, the structure of sesquiterpene lactones from Elephantopus scaber was modified. Deoxyelephantopin and scabertopin were isolated from the whole plant of Elephantopus scaber and hydrogenated and epoxidated. Five sesquiterpenoide derivatives were prepared and their structures were identified by IR, NMR and MS spectra analysis. Four sesquiterpenoides are new compounds. Part of the compounds show definite antitumor activity.
Subject(s)
Humans , Antineoplastic Agents, Phytogenic , Chemistry , Pharmacology , Asteraceae , Chemistry , HeLa Cells , Hydrogenation , Lactones , Chemistry , Pharmacology , Molecular Structure , Plants, Medicinal , Chemistry , Sesquiterpenes , Chemistry , Pharmacology , Terpenes , Chemistry , PharmacologyABSTRACT
<p><b>AIM</b>In order to compare the calcium antagonist activity between the derivatives of (+)-praeruptorin A with C-3' and C-4' cis-configuration and trans-configuration, and to look for new active compounds, some derivatives with C-3', C-4' trans-configuration of (+)-praeruptorin A were semi-synthsized.</p><p><b>METHODS</b>(+)-Praeruptorin A was isolated from the root of Peucedanum praeruptorum. Basic hydrolysis of (+)-praeruptorin A was carried out. From the alkaline hydrolysis product (2), eight new products (5-12) with C-3', C-4' trans-configuration were semi-synthsized whose C-3' was linked to angeloyloxy and C-4' was linked to various acyloxy, using respective acids as acylating agents, DCC as a dehydrant, DMAP as catalyst. From the alkaline hydrolysis product (4), five new products (13-17) with C-3', C-4' trans-configuration were obtained whose C-3', C-4' is linked to various same acyloxys, using respective acids as acylating agents, DCC as dehydrant, DMAP as catalyst. Also from the alkaline hydrolysis product (4), using respective acyl chlorides as acylating agents, anhydrous dichloromethane containing minor pyridine as a solvent, the improved Schotten-Baumann reactions were carried out, two new products (18, 20) with C-3', C-4' trans-configuration were obtained whose only C-3' linked to acyloxy and two other new products (19, 21) with C-3', C-4' trans-configuration were obtained whose C-3' and C-4' linked two acyloxys. The structures of all the products were elucidated by spectral analyses including IR, 1HNMR and EIMS. The calcium antagonist activity of all of the products were tested by inhibition of the systole of rat artery ring.</p><p><b>RESULTS</b>Seventeen compounds with C-3', C-4' trans-configuration were semi-synthesized from (+)-praeruptorin A for the first time and their calcium antagonist activity were evaluated.</p><p><b>CONCLUSION</b>All of the derivatives were new compounds. Bioactivity assay indicated that some new compounds with C-3', C-4' trans-configuration showed obvious calcium antagonist activity, but they are not as strong as (+)-praeruptorin A. The activity of some products was shown to be similar to that of the derivatives with C-3', C-4' cis-configuration for the first time.</p>
Subject(s)
Animals , Rats , Aorta, Thoracic , Calcium Channel Blockers , Pharmacology , Coumarins , Chemistry , Pharmacology , Drugs, Chinese Herbal , Chemistry , Pharmacology , Molecular Structure , Muscle Contraction , Muscle, Smooth, Vascular , StereoisomerismABSTRACT
<p><b>OBJECTIVE</b>To isolate and elucidate the chemical constituents of the whole plant of Vernonia patula, and to provide samples for biological activity screening.</p><p><b>METHOD</b>The chromatography on silica gel was used and the structures were determined by IR, NMR and MS spectra analysis and physicochemical property comparion.</p><p><b>RESULT</b>Four triterpenoids were isolated and identified as bauerenyl acetate(I), friedelin(II), epifriedelanol(III), 20(30)-taraxastene-3 beta, 21 alpha-diol(IV).</p><p><b>CONCLUSION</b>Compounds I and IV were isolated from genus Vernonia for the first time and compounds II and III were isolated from the whole plant of V. patula for the first time. The four compounds show no inhibitory effect on the growing of PC-12 cells.</p>
Subject(s)
Animals , Rats , Cell Division , Drugs, Chinese Herbal , Pharmacology , Oleanolic Acid , Chemistry , Pharmacology , PC12 Cells , Plants, Medicinal , Chemistry , Triterpenes , Chemistry , Pharmacology , Vernonia , ChemistryABSTRACT
<p><b>AIM</b>To study the chemical constituents of the stems of Opuntia vulgaris Mill(Cactaceae).</p><p><b>METHODS</b>The compounds of Opuntia vulgaris were isolated by chromatography of Amberlite Dowex 50 and silica gel, and identified by means of UV, IR, MS, 1D and 2D NMR.</p><p><b>RESULTS</b>Three compounds were isolated and identified as: opuntin B(I), 4-hydroxyproline(II) and tyrosine(III).</p><p><b>CONCLUSION</b>Compound I is a new alkaloid.</p>
Subject(s)
Hydroxyproline , Chemistry , Maleimides , Chemistry , Molecular Conformation , Molecular Structure , Opuntia , Chemistry , Phenols , Chemistry , Plants, Medicinal , Chemistry , Tyrosine , ChemistryABSTRACT
<p><b>AIM</b>In order to look for new active compounds, the structure of (+)-praeruptorin A is modified.</p><p><b>METHODS</b>(+)-Praeruptorin A was isolated from the root of Peucedanum praeruptorum, basic hydrolysis of (+)-praeruptorin A and acyled reactions of hydrolysis product of (+)-praeruptorin A were carried out.</p><p><b>RESULTS</b>Eighteen compounds were semi-synthesized from (+)-praeruptorin A.</p><p><b>CONCLUSION</b>Fourteen compounds (5-18) among them are new compounds. Preliminary bioactivity assay indicated that the new compounds show calcium antagonist activity, but they are not as strong as (+)-praeruptorin A.</p>