ABSTRACT
Antifungal bioactivity-guided fractionation of the organic extract of the sponge Polymastia boletiformis, collected from the west coast of Ireland, led to the isolation of two new sulfated steroid-amino acid conjugates (1 and 2). Extensive 1D and 2D NMR analyses in combination with quantum mechanical calculations of the electronic circular dichroism (ECD) spectra, optical rotation, and 13C chemical shifts were used to establish the chemical structures of 1 and 2. Both compounds exhibited moderate antifungal activity against Cladosporium cucumerinum, while compound 2 was also active against Candida albicans. Marine natural products containing steroidal and amino acid constituents are extremely rare in nature.
Subject(s)
Antifungal Agents/isolation & purification , Candida albicans/drug effects , Cholestadienes/isolation & purification , Cladosporium/drug effects , Drug Discovery , Glycine/analogs & derivatives , Porifera/chemistry , Animals , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Atlantic Ocean , Candida albicans/growth & development , Cholestadienes/chemistry , Cholestadienes/pharmacology , Chromatography, High Pressure Liquid , Circular Dichroism , Cladosporium/growth & development , Disk Diffusion Antimicrobial Tests , Glycine/chemistry , Glycine/isolation & purification , Glycine/pharmacology , Ireland , Magnetic Resonance Spectroscopy , Methylation , Molecular Structure , Porifera/growth & development , Quantum Theory , Spectrometry, Mass, Electrospray Ionization , Stereoisomerism , Sulfur Compounds/chemistry , Sulfur Compounds/isolation & purification , Sulfur Compounds/pharmacologyABSTRACT
In continuation of our interest in phytochemical screening of the Egyptian flora for potential drugs, the reinvestigation of the methanolic extract of the roots of Solanum diphyllum, which grows naturally in the south of Egypt and is recorded as new to the Egyptian flora, afforded an interesting, highly cytotoxic compound, named 3-O-(beta-D-glucopyranosyl) etioline [(25S)-22,26-epimino-3beta-(beta-D-glucopyranosyloxy) cholesta-5,22(N)-dien-16alpha-ol]. The chemical structure of this compound was determined by comprehensive NMR studies, including DEPT, COSY, HMQC, and MS. The compound exhibited high cytotoxic effects against the cervical cancer cell line, Hela cells, with an IC50 value of 150 microg/mL.
Subject(s)
Cholestadienes/pharmacology , Solanum/chemistry , Cholestadienes/chemistry , Cholestadienes/isolation & purification , HeLa Cells , Humans , Magnetic Resonance Spectroscopy , Spectrometry, Mass, Electrospray IonizationABSTRACT
OBJECTIVE: To investigate the chemical constituents in the ethyl acerate extract of Lysimachia fortunei. METHOD: The compounds were isolated by silica gel chromatography, and their structures were elucidated by NMR data and references. RESULT: Nine natural constituents were isolated, and their structures were identified as 9, 19-cyclolanost-24-en-3-one (1), 24-ethyl-5alpha-cholesta-7, 22(E)-dien-3-one (2), 1-pentatriacontanol (3), beta-stigmasterol (4), 24-ethyl-5alpha-cholesta-7, 22(E)-dien-3beta-ol (5), palmitic acid (6), isorhamnetin (7), kaempferol (8) and quercetin (9) respectively. CONCLUSION: All compounds mentioned above were isolated from this plant for the first time, and compound 1, 2 and 5 were obtained from the genus for the first time.
Subject(s)
Cholestadienes/isolation & purification , Plants, Medicinal/chemistry , Primulaceae/chemistry , Triterpenes/isolation & purification , Cholestadienes/chemistry , Flavonols/chemistry , Flavonols/isolation & purification , Kaempferols/chemistry , Kaempferols/isolation & purification , Palmitic Acid/chemistry , Palmitic Acid/isolation & purification , Quercetin/analogs & derivatives , Triterpenes/chemistryABSTRACT
A new sterol with a non-conventional side chain has been isolated from the whole plant of Anoectochilus koshunensis, together with four known sterols, a megastigmane glucoside and 2'-deoxyadenosine. The structure of the new sterol was elucidated as 26-methylstigmasta-5,22,25, (27)-trien-3 beta-ol based on chemical and detailed spectroscopic evidence.
Subject(s)
Cholestadienes/chemistry , Plants, Medicinal/chemistry , Carbohydrate Sequence , Cholestadienes/isolation & purification , Chromatography, Gel , Gas Chromatography-Mass Spectrometry , Magnetic Resonance Spectroscopy , Medicine, Chinese Traditional , Molecular Sequence DataABSTRACT
In the course of measuring the concentration of cholesterol in an opacified dog cornea by gas-chromatography, relatively large amounts of an unidentified non-saponifiable lipid were recognized. When the unknown lipid was subjected to gas chromatographic-mass spectral analysis it displayed a major ion at m/z 368 M+. and was identified as cholesta-3,5-diene, cholesterylene, by computer match with mass spectral-registry data. Cholesterylene was then shown to be present in the corneas of normal dogs, cows and humans, accounting for 20-25% of the total steroid-sterol in dog corneas and 5-10% in cow and human. Cholesterylene, which can be considered as an extremely nonpolar dehydration product of cholesterol, has not previously been recognized in animal tissues. Although the source of corneal cholesterylene is unknown, preliminary results suggest non-enzymatic formation from cholesterol.
Subject(s)
Cholestadienes/isolation & purification , Cornea/chemistry , Animals , Cholestadienes/chemistry , Cholestadienes/metabolism , Cholesterol/analysis , Cholesterol/metabolism , Cornea/metabolism , Dogs , Gas Chromatography-Mass Spectrometry , Mevalonic Acid/metabolism , Spectrophotometry, Ultraviolet , Squalene/metabolismABSTRACT
A fraction of 20-isosterols has been isolated from the Baltic Sea bivalve Macoma balthica. The main component of this fraction, (20S)-cholest-5-en-3 beta-ol, has been characterized by 300 MHz nuclear magnetic resonance spectroscopy. 20-Isosterols in M balthica probably originate from sea-bottom sediments, an important component of a diet of the animal studied.
Subject(s)
Cholestenes/isolation & purification , Mollusca/analysis , Acetylation , Animals , Cholestadienes/isolation & purification , Cholesterol/isolation & purification , Chromatography, Gas , Chromatography, High Pressure Liquid , Gas Chromatography-Mass Spectrometry , Magnetic Resonance Spectroscopy , Molecular ConformationABSTRACT
We evaluated the use of a modified phosphotungstic acid/MgCl2 precipitation procedure for the precipitation of apolipoprotein B-containing lipoproteins. Precipitation of these lipoproteins [very-low- and low-density lipoproteins, and lipoprotein (a)] is complete, with negligible coprecipitation of high-density lipoprotein subfractions (HDL1, HDL2, HDL3), even in hypertriglyceridemic sera. In comparison with ultracentrifugation, the precipitation method yields, on the average, values that are 0.17 mmol/L lower for cholesterol values but almost identical for apolipoprotein A-I and phosphatidylcholine. Looking for delta 3,5-cholestadiene formed from cholesterol in the precipitation residue, we used "high-performance" liquid chromatography and "high-performance" thin-layer chromatography and found none.
Subject(s)
Cholesterol/blood , Lipoproteins, HDL/blood , Magnesium , Phosphotungstic Acid , Apolipoproteins/isolation & purification , Apolipoproteins B , Chemical Precipitation , Cholestadienes/isolation & purification , Cholesterol/isolation & purification , Cholesterol, HDL , Evaluation Studies as Topic , Humans , Lipoproteins, HDL/isolation & purification , Magnesium Chloride , Statistics as Topic , Triglycerides/blood , UltracentrifugationABSTRACT
Two steroidal ketones, delta-4-cholesten-3-one and delta-3,-5-cholestadiene-7-one, were isolated and identified for the first time in anhydrous milk fat and in nonfat dry milk. Together with these, two isoprenoid alcohols, phytol and dihydrophytol, were identified in anhydrous milk fat. Their identities were established on the basis of chromatographic and mass spectral data and confirmed by comparison with authentic materials.
Subject(s)
Cholestenes/isolation & purification , Cholestenones/isolation & purification , Diterpenes/isolation & purification , Lipids/analysis , Milk/analysis , Phytol/isolation & purification , Animals , Cattle , Cholestadienes/isolation & purification , Chromatography, Gas , Mass Spectrometry , Phytol/analogs & derivativesABSTRACT
A novel group of antibiotics, comprising microbiologically-active structurally-related factors A25822A, B, D, H, L, M and N, produced by culturing Geotrichum flavo-brunneum NRRL 3862 under submerged aerobic fermentation conditions was isolated by extraction. The individual factors were separated and purified by chromatography and crystallization. The major factor, A25822B, a 15-aza-24-methylene-D-homocholestadiene is a white crystalline compound, C25H45NO. The antibiotics are highly active against fungi and marginally active against bacteria.
Subject(s)
Antifungal Agents/isolation & purification , Cholestadienes/isolation & purification , Mitosporic Fungi/analysis , Aza Compounds/isolation & purification , Chemical Phenomena , Chemistry , Cyclization , Fermentation , Homosteroids/isolation & purification , SolubilityABSTRACT
Although Geotrichum species occur ubiquitously, antibiotic production by members of this genus has not previously been reported. The antibiotic complex designated A25822, consisting of one major and six minor structurally-related components active primarily against Candida and Trichophyton, represents a new family of naturally-occurring compounds. Approximately 90% of the antibiotic activity synthesized remained associated with the fungal cell mass, from which it was recovered by multiple methanolic extractions for quantitation. Antibiotic production was enhanced by tryptophan, iron, zinc, and high levels of dextrin.