ABSTRACT
The phytochemical investigations of the tuber roots of Asparagus flagellaris led to the isolation of a new alkaloid, schweinfurthiamide (1) and eight known compounds. The structures of the isolated compounds were elucidated using spectroscopic techniques 1D and 2D NMR (1H, 13C, COSY, HMBC, HMQC, HSQC-TOCSY). The absolute configuration of 1 was unambiguously determined using DP4+ calculations. Compound 1 showed significant cytotoxicity against MCF-7 (breast cancer), NCI-H460 (lung cancer), and Hela (cervical cancer) cancer cell lines with IC50 values of 1.18 ± 0.02 µM, 2.25 ± 0.19 µM, and 4.23 ± 0.26 µM, respectively and no toxicity against normal human fibroblast (BJ).
ABSTRACT
Six new triterpenoid saponins, named senegalosides A-F (1-6) were isolated from the seedpods and roots of Acacia senegal (Mimosaceae). Their structures were elucidated using 1D and 2D-NMR spectroscopic analysis and mass spectrometry. Compound 1 possesses an unusual sapogenin, 3ß-hydroxy-21-oxo-olean-12-en-28-oic acid (machaeric acid), and was reported here in its natural form for the first time within the genus Acacia. Senegaloside A is the first example of a machaeric-type triterpenoid glycoside in the plant kingdom. The cytotoxic effect of isolated saponins was evaluated on the H4IIE rat hepatoma cell line. As a result, compounds 1, 3-6 were not significantly cytotoxic to H4IIE cells even at 200 µM. Compound 2 was suppressed cell viability at 50-200 µM.
Subject(s)
Acacia/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Saponins/pharmacology , Triterpenes/pharmacology , Animals , Antineoplastic Agents, Phytogenic/isolation & purification , Cameroon , Cell Line, Tumor , Cell Survival , Drug Screening Assays, Antitumor , Molecular Structure , Phytochemicals/isolation & purification , Phytochemicals/pharmacology , Plant Roots/chemistry , Rats , Saponins/isolation & purification , Triterpenes/isolation & purificationABSTRACT
Three new fusarielins, 3-epi-fusarielin H (1), 3-O-methyl-fusarielin H (2), and 3-O-methyl-epi-fusarielin H (3), were isolated from the fungus Fusarium sp. together with the known analogues, fusarielins F (4) and G (5). The structures of these compounds were elucidated by analysis of their ESI-HRTOFMS, 1D and 2D NMR spectroscopic data. The new compounds exhibited weak antibacterial effect against Staphylococcus aureus.
Subject(s)
Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Fusarium/chemistry , Naphthalenes/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Epoxy Compounds/chemistry , Epoxy Compounds/pharmacology , Fermentation , Humans , Magnetic Resonance Spectroscopy , Naphthalenes/pharmacologyABSTRACT
Two new triterpene saponins, albidosides H (1) and I (2), along with the three known saponins were isolated from the barks of Acacia albida. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR studies and mass spectrometry. Albidosides H (1) and I (2) were assayed for their cytotoxicity against HeLa and HL60 cells using MTT method.
Subject(s)
Acacia/chemistry , Saponins/chemistry , Triterpenes/chemistry , Drug Screening Assays, Antitumor/methods , HL-60 Cells , HeLa Cells , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , Oleanolic Acid/analogs & derivatives , Plant Bark/chemistry , Saponins/pharmacology , Triterpenes/pharmacologyABSTRACT
Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1-4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D- and 2D-NMR data and HR-ESI-MS analyses. At concentrations of 100 µM of each compounds, none of the tested compounds caused a significant growth reduction against HL60 cells.
Subject(s)
Acacia/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Plant Roots/chemistry , Saponins/chemistry , Triterpenes/chemistry , Triterpenes/pharmacology , Cell Proliferation/drug effects , HL-60 Cells , HumansABSTRACT
A new eremophilane sesquiterpene, 13,13-dimethoxyintegric acid (1), together with known compound integric acid (2) have been isolated from a fungus, Xylaria sp. V-27, obtained from a dead branch. The structure of 1 was established by means of spectroscopic analyses. 1 and 2 promoted growth restoring activity against the mutant yeast strain (Saccharomyces cerevisiae (zds1Δ erg3Δ pdr1Δ pdr3Δ)) and inhibited degranulation of rat basophilic leukemia RBL-2H3 cells stimulated by immnunoglobulin G + 2,4-dinitrophenylated-bovine serum albumin (IgE+DNP-BSA), thapsigargin and A23187.
Subject(s)
Carboxylic Acids/pharmacology , Cell Degranulation/drug effects , Naphthalenes/pharmacology , Saccharomyces cerevisiae/growth & development , Sesquiterpenes/pharmacology , Animals , Carboxylic Acids/isolation & purification , Cell Line, Tumor , Naphthalenes/isolation & purification , Polycyclic Sesquiterpenes , Rats , Saccharomyces cerevisiae/genetics , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Xylariales/metabolismABSTRACT
Seven previously undescribed bidesmosidic triterpenoid saponins named albidosides A - G, were isolated from a methanol extract of the roots of Acacia albida. Their structures were elucidated using 1D and 2D NMR spectroscopy and mass spectrometry and determined to be bidesmosides of oleanolic acid and of 16α-hydroxyoleanolic acid. Albidosides B - G were assayed for their cytotoxicity against HeLa and HL60 cells using MTT method and microscopic observation.
Subject(s)
Acacia/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Oleanolic Acid/analogs & derivatives , Saponins/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Cameroon , Drug Screening Assays, Antitumor , HL-60 Cells , HeLa Cells , Humans , Inhibitory Concentration 50 , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oleanolic Acid/chemistry , Oleanolic Acid/isolation & purification , Oleanolic Acid/pharmacology , Plant Roots/chemistry , Saponins/chemistryABSTRACT
A new compound, (3aS,6aR)-4,5-dimethyl-3,3a,6,6a-tetrahydro-2H-cyclopenta [b]furan-2-one (2), along with two known metabolites, myrotheciumone A (1) and 4-oxo-4H-pyron-3-acetic acid (3) was isolated from the ethyl acetate extract of fermentation broth of Xylaria curta 92092022. The structures of these compounds were elucidated on the basis of spectroscopic methods (UV, IR, HRESITOFMS, 1D NMR, and 2D NMR). Compounds 1 and 2 showed moderate antibacterial and phytotoxic activities.
Subject(s)
Anti-Bacterial Agents/pharmacology , Lactones/chemistry , Xylariales/chemistry , Acetates/chemistry , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Cyclopentanes/chemistry , Drug Evaluation, Preclinical , Endophytes/chemistry , Fermentation , Furans/chemistry , Lactones/isolation & purification , Lactones/pharmacology , Lactuca/drug effects , Magnetic Resonance Spectroscopy , Molecular Structure , Pyrones/chemistry , Spectrophotometry, Ultraviolet , Toxicity TestsABSTRACT
Phytochemical investigation of the roots of Albizia chevalieri led to the isolation of two new 5-deoxyflavan-3,4-diol glucosides from roots of A. chevalieri, Chevalieriflavanosides A and B. Their structures were established by 2D NMR techniques, UV, IR, CD, and mass spectrometry. Cytotoxicity of the two compounds was evaluated against acute promyelocytic leukemia HL60 cells. The antibacterial activities of 1 and 2 also were evaluated against Pseudomonas aeruginosa and Staphylococcus aureus using the agar diffusion test. Copyright © 2016 John Wiley & Sons, Ltd.