113 results on '"Steroids isolation & purification"'
Search Results
52. Steroidal saponins from Smilax medica and their antifungal activity.
- Author
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Sautour M, Miyamoto T, and Lacaille-Dubois MA
- Subjects
- Antifungal Agents chemistry, Antifungal Agents pharmacology, Humans, Mexico, Microbial Sensitivity Tests, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Saponins chemistry, Saponins pharmacology, Steroids chemistry, Steroids pharmacology, Antifungal Agents isolation & purification, Candida drug effects, Plants, Medicinal chemistry, Saponins isolation & purification, Smilax chemistry, Steroids isolation & purification
- Abstract
Three new steroidal saponins (1-3) were isolated from the roots of Smilax medica, together with the known disporoside A (4). The structures of the new compounds were elucidated mainly by extensive spectroscopic analysis (1D and 2D NMR, FABMS, and HRESIMS). Compounds 1, 2, and 4 demonstrated weak antifungal activity against the human pathogenic yeasts Candida albicans, C. glabrata, and C.tropicalis, with MIC values between 12.5 and 50 microg/mL.
- Published
- 2005
- Full Text
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53. Phrygiasterol, a cytotoxic cyclopropane-containing polyhydroxysteroid, and related compounds from the pacific starfish Hippasteria phrygiana.
- Author
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Levina EV, Kalinovsky AI, Andriyashenko PV, Dmitrenok PS, Aminin DL, and Stonik VA
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Calcium antagonists & inhibitors, Drug Screening Assays, Antitumor, Inhibitory Concentration 50, Mice, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Pacific Ocean, Spleen cytology, Spleen drug effects, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured, Antineoplastic Agents isolation & purification, Starfish chemistry, Steroids isolation & purification
- Abstract
The new cyclopropane-containing steroid phrygiasterol (1) and steroid glycoside phrygioside B (2), along with previously known borealoside C (2a) and (20R,24S)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (3), have been isolated from the Pacific starfish Hippasteria phrygiana. On the basis of spectroscopic analyses, using 1D and 2D NMR techniques and some chemical transformations, the structures of 1 and 2 have been established as (20R,24R,25R)-24,26-cyclo-5alpha-cholesta-3beta,6alpha,8,15alpha,16beta,27-hexaol (1) and the sodium salt of (20R,24S)-24-O-(3-O-methyl-4-O-sulfate-beta-d-xylopyranosyl)-5alpha-cholesta-3beta,6alpha,8,15alpha,24-pentaol (2), respectively. Compound 1 inhibited the growth of Ehrlich carcinoma cells with an IC(50) of 50 microg/mL, whereas 2 induced apoptosis of the same cells (EC(50)=70 microg/mL) and inhibited Ca(2+) influx into mouse spleenocytes (EC(50)=20microg/mL).
- Published
- 2005
- Full Text
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54. Steroids from the gorgonian Isis hippuris.
- Author
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Chao CH, Huang LF, Wu SL, Su JH, Huang HC, and Sheu JH
- Subjects
- Animals, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Steroids chemistry, Taiwan, Anthozoa chemistry, Steroids isolation & purification
- Abstract
Six new polyoxygenated steroids, hippuristerones J-L (1-3), hippuristerols E-F (4, 5), and a novel gorgosteroid, 1alpha,3beta,5beta,11alpha-tetrahydroxygorgostan-6-one (6), were isolated from the gorgonian Isis hippuris. The structures of these metabolites were elucidated by extensive spectroscopic analyses and comparison of the NMR data with those of related steroids.
- Published
- 2005
- Full Text
- View/download PDF
55. Diterpenoid, steroid, and triterpenoid agonists of liver X receptors from diversified terrestrial plants and marine sources.
- Author
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Jayasuriya H, Herath KB, Ondeyka JG, Guan Z, Borris RP, Tiwari S, de Jong W, Chavez F, Moss J, Stevenson DW, Beck HT, Slattery M, Zamora N, Schulman M, Ali A, Sharma N, MacNaul K, Hayes N, Menke JG, and Singh SB
- Subjects
- Animals, Annonaceae chemistry, Anthozoa chemistry, Bahamas, Cactaceae chemistry, Campanulaceae chemistry, Cells, Cultured, Costa Rica, Diterpenes chemistry, Diterpenes pharmacology, Guyana, Humans, Inhibitory Concentration 50, Liver X Receptors, Molecular Structure, Olacaceae chemistry, Orphan Nuclear Receptors, Pentacyclic Triterpenes, Peru, Pinaceae chemistry, Polycyclic Aromatic Hydrocarbons chemistry, Polycyclic Aromatic Hydrocarbons pharmacology, Steroids chemistry, Steroids pharmacology, Triterpenes chemistry, Triterpenes pharmacology, United States, Betulinic Acid, DNA-Binding Proteins agonists, Diterpenes isolation & purification, Plants, Medicinal chemistry, Polycyclic Aromatic Hydrocarbons isolation & purification, Receptors, Cytoplasmic and Nuclear agonists, Steroids isolation & purification, Triterpenes isolation & purification
- Abstract
It has been demonstrated that liver X receptors (LXR) play a significant role in cholesterol homeostasis. Agonists of LXR are expected to increase cellular cholesterol efflux, lower LDL, and raise HDL levels. Screening of a natural product library of plant extracts using a LXR-SPA binding assay and bioassay-guided fractionation of a number of plant and marine gorgonian extracts led to the isolation of a number of active compounds. These included acanthoic acid (1) and alcohol (2), viperidone (3), polycarpol (4), rosacea acid (5), a cycloartane derivative (6), a new cycloartane analogue (7), betulinic acid (8), and gorgostane derivatives (9, 10, and 11). Of these compounds, 1, 4, and 11 exhibited potent binding affinity for alpha-receptor with IC(50) values of 0.25, 0.12, and 0.07 microM, respectively. Functionally they also showed strong coactivator association stimulation for LXRalpha receptor with EC50 values of 0.18, 0.03, and 0.05 microM, respectively. They also exhibited 15-, 8-, and 13-fold induction of the alpha-receptor in a transactivation assay in HEK-293 cells, respectively. In general these compounds were selective for the LXR alpha-receptor over the beta-receptor in all assays and were much better stimulators of the alpha-receptor than the endogenous steroid ligands.
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- 2005
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56. Minutosides A and B, antifungal sulfated steroid xylosides from the patagonian starfish Anasterias minuta.
- Author
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Chludil HD and Maier MS
- Subjects
- Animals, Antifungal Agents chemistry, Antifungal Agents pharmacology, Argentina, Glycosides chemistry, Glycosides pharmacology, Microbial Sensitivity Tests, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Steroids chemistry, Steroids pharmacology, Sulfuric Acid Esters chemistry, Sulfuric Acid Esters pharmacology, Antifungal Agents isolation & purification, Aspergillus flavus drug effects, Cladosporium drug effects, Glycosides isolation & purification, Starfish chemistry, Steroids isolation & purification, Sulfuric Acid Esters isolation & purification
- Abstract
Two new sulfated polyhydroxylated steroidal xylosides, minutosides A (1) and B (2), together with the known pycnopodioside B (3), have been isolated from the brine shrimp active fraction of the ethanolic extract of the starfish Anasterias minuta. The structures have been elucidated by extensive 1D and 2D NMR as well as FABMS analysis and chemical methods. Compound 2 is the first example of a polyhydroxylated steroidal xyloside containing an amide function in the aglycon side chain. The three xylosides exhibited antifungal activity against Cladosporium cucumerinum and Aspergillus flavus.
- Published
- 2005
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57. Steroids from the Antarctic octocoral Anthomastus bathyproctus.
- Author
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Mellado GG, Zubía E, Ortega MJ, and López-González PJ
- Subjects
- Animals, Antarctic Regions, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Drug Screening Assays, Antitumor, Humans, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured, Anthozoa chemistry, Antineoplastic Agents isolation & purification, Steroids isolation & purification
- Abstract
Seven new steroids, compounds 1-7, were isolated from the Antarctic octocoral Anthomastus bathyproctus. The structures of the new metabolites have been established by analysis of their spectroscopic data. The in vitro cytotoxicity has been tested against three human tumor cell lines.
- Published
- 2005
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58. Polyoxygenated steroids from the gorgonian Isis hippuris.
- Author
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Chao CH, Huang LF, Yang YL, Su JH, Wang GH, Chiang MY, Wu YC, Dai CF, and Sheu JH
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Crystallography, X-Ray, Drug Screening Assays, Antitumor, Humans, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured, Anthozoa chemistry, Antineoplastic Agents isolation & purification, Steroids isolation & purification
- Abstract
Eleven new hippuristanols (1-4, 7-9, and 11-14), along with eight known metabolites (5, 6, 10, and 15-19), have been isolated from the gorgonian coral Isis hippuris. Single-crystal X-ray diffraction analyses supported the structure elucidation of known steroids 5 and 10. The absolute structures of hippuristanols were established by application of modified Mosher's method on 19. Compounds 14-19 have been found to exhibit significant cytotoxicity against several cancer cell lines.
- Published
- 2005
- Full Text
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59. Steroidal alkaloids from the bulbs of Fritillaria puqiensis.
- Author
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Jiang Y, Li H, Li P, Cai Z, and Ye W
- Subjects
- Alkaloids chemistry, Alkaloids pharmacology, Animals, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Antitussive Agents chemistry, Antitussive Agents pharmacology, China, Crystallography, X-Ray, Humans, Mice, Molecular Conformation, Molecular Structure, Plant Roots chemistry, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured, Alkaloids isolation & purification, Antineoplastic Agents, Phytogenic isolation & purification, Antitussive Agents isolation & purification, Fritillaria chemistry, Plants, Medicinal chemistry, Steroids isolation & purification
- Abstract
Four new steroidal alkaloids, puqienine A (1), puqienine B (2), N-demethylpuqietinone (3), and puqietinonoside (4), along with a known steroidal alkaloid, puqietinone, were isolated from the bulbs of Fritillaria puqiensis. The structures of these compounds were elucidated on the basis of spectroscopic analysis. The compounds exhibited significant antitussive activity on ammonia liquor-induced cough in mice. Furthermore, the compounds were evaluated for activities against A549 human lung carcinoma cell line, BGC-823 human stomach adenocarcinoma cell line, SMMC-7721 human hepatocarcinoma cell line, and HL-60 human promyelocytic leukemia cell line.
- Published
- 2005
- Full Text
- View/download PDF
60. New 3-oxo-chol-4-en-24-oic acids from the marine soft coral Eleutherobia sp.
- Author
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Lievens SC, Hope H, and Molinski TF
- Subjects
- Animals, Cholic Acids chemistry, Cholic Acids pharmacology, Crystallography, X-Ray, Micronesia, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Steroids chemistry, Steroids pharmacology, Anthozoa chemistry, Cholic Acids isolation & purification, Diterpenes chemistry, Steroids isolation & purification
- Abstract
Two novel cholic acid derivatives and three known steroids were isolated from an octocoral Eleutherobiasp. from Pohnpei Micronesia along with the known briareins minabein-1 (6), minabein-4 (7), minabein-6 (8), minabein-8 (9), and minabein-9 (10). X-ray crystallographic analysis of the known compound minabein-4 allowed assignment of its correct relative and absolute stereochemistry. Consequently, a different structure proposed for the same compound (named independently as nui-inoalide-D) is incorrect.
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- 2004
- Full Text
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61. Natural aromatic steroids as potential molecular fossils from the fruiting bodies of the ascomycete Daldinia concentrica.
- Author
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Qin XD and Liu JK
- Subjects
- China, Fossils, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism, Ascomycota chemistry, Steroids chemistry, Steroids isolation & purification
- Abstract
The identification of aromatic steroid hydrocarbons bearing a methyl group at positions 1, 2, 3, 4, or 6 in sediments and petroleum has been puzzling since possible steroidal precursors have not yet been reported in living organisms. Two new aromatic steroids, (17beta,20R,22E,24R)-19-norergosta-1,3,5,7,9,14,22-heptaene (1) and (17beta,20R,22E,24R)-1-methyl-19-norergosta-1,3,5,7,9,14,22-heptaene (2), were isolated from the ascomycete Daldinia concentrica, of which compound 2 bears an unusual methyl group at position 1. We propose that the origin of these compounds is derived from the transformation undergone by their precursor due to microbial action. Compounds 1 and 2 could be the long-sought, biological precursor steroids for organic matter in Earth's subsurface.
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- 2004
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62. Acanthovagasteroids A-D, four new 19-hydroxylated steroids from the South China Sea gorgonian Acanthogorgia vagae Aurivillius.
- Author
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Zhang W, Guo YW, Mollo E, Fontana A, and Cimino G
- Subjects
- Animals, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Oceans and Seas, Steroids chemistry, Anthozoa chemistry, Steroids isolation & purification
- Abstract
Four new steroids, acanthovagasteroids A-D (1-4), along with two known analogues (5, 6), were isolated from the gorgonian Acanthogorgia vagae Aurivillius from the South China Sea. The structures of the new compounds, characterized with 19-hydroxy groups, were identified on the basis of extensive spectral analysis as well as by comparison with literature data. This is the first report of 19-hydroxy steroids from a gorgonian and suggests a possible biosynthetic relationship between 19-nor and 19-hydroxy steroids.
- Published
- 2004
- Full Text
- View/download PDF
63. Cytotoxic steroidal saponins from Polygonatum zanlanscianense.
- Author
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Jin JM, Zhang YJ, Li HZ, and Yang CR
- Subjects
- China, Drug Screening Assays, Antitumor, HeLa Cells, Humans, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Rhizome chemistry, Saponins chemistry, Saponins pharmacology, Steroids chemistry, Steroids pharmacology, Plants, Medicinal chemistry, Polygonatum chemistry, Saponins isolation & purification, Steroids isolation & purification
- Abstract
Four new steroidal saponins, polygonatosides A-D (1-4), were isolated from the rhizomes of Polygonatum zanlanscianense, together with six known spirostanols (5-10) and a known megastigmane glycoside (11). Their structures were elucidated on the basis of spectroscopic analysis and the results of acidic and enzymatic hydrolysis. The cytotoxic activities of 1-11 against HeLa cells are described.
- Published
- 2004
- Full Text
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64. Steroids and sesquiterpenoids from the soft corals Dendronephthya gigantea and Lemnalia cervicorni.
- Author
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Duh CY, El-Gamal AA, Song PY, Wang SK, and Dai CF
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Drug Screening Assays, Antitumor, HT29 Cells, Humans, Leukemia P388, Mice, Mice, Inbred DBA, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Oceans and Seas, Sesquiterpenes chemistry, Sesquiterpenes pharmacology, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured, Anthozoa chemistry, Antineoplastic Agents isolation & purification, Sesquiterpenes isolation & purification, Steroids isolation & purification
- Abstract
One new cytotoxic steroid, dendronesterone A (1), two new steroids, dendronesterones B and C (2 and 3), and a known steroid (4) were isolated from the methylene chloride solubles of the Formosan soft coral Dendronephthya gigantea. Two cytotoxic ylangene-type sesquiterpenoids, lemnalol (5) and the new compound cervicol (6), as well as two ylangene-type sesquiterpenoids, isolemnalol (7) (a new compound) and 4-oxo-alpha-ylangene (8), were isolated from the methylene chloride solubles of the Formosan soft coral Lemnalia cervicorni. Their structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.
- Published
- 2004
- Full Text
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65. Steroidal glycosides from the bulbs of Ornithogalum thyrsoides.
- Author
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Kuroda M, Mimaki Y, Ori K, Sakagami H, and Sashida Y
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Drug Screening Assays, Antitumor, Glycosides chemistry, Glycosides pharmacology, Humans, Japan, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Roots chemistry, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured, Antineoplastic Agents, Phytogenic isolation & purification, Glycosides isolation & purification, Ornithogalum chemistry, Plants, Medicinal chemistry, Steroids isolation & purification
- Abstract
Phytochemical analyses have been carried out on the fresh bulbs of Ornithogalum thyrsoides with particular attention to the steroidal glycoside constituents, resulting in the isolation of four new spirostanol saponins and seven new cholestane glycosides, together with three known steroidal compounds. The structures of the new glycosides were determined on the basis of their spectroscopic data, including 2D NMR spectroscopy, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activities against HL-60 human promyelocytic leukemia cells and HSC-2 human oral squamous cell carcinoma cells.
- Published
- 2004
- Full Text
- View/download PDF
66. Phorbasterones A-D, cytotoxic nor-ring A steroids from the sponge Phorbas amaranthus.
- Author
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Masuno MN, Pawlik JR, and Molinski TF
- Subjects
- Animals, Drug Screening Assays, Antitumor, Florida, HCT116 Cells, Humans, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Oceans and Seas, Steroids chemistry, Steroids pharmacology, Porifera chemistry, Steroids isolation & purification
- Abstract
The sponge Phorbas amaranthus from Florida contains the new ring A-contracted steroids, phorbasterones A-D, and the known anthosterones A and B. The structures of phorbasterones A-D were determined by interpretation of their spectroscopic data. Phorbasterones show moderate cytotoxicity against HCT-116 tumor cells.
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- 2004
- Full Text
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67. Steroidal alkaloid glycosides from tomato (Lycopersicon esculentum).
- Author
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Yahara S, Uda N, Yoshio E, and Yae E
- Subjects
- Alkaloids chemistry, Glycosides chemistry, Japan, Molecular Structure, Stereoisomerism, Steroids chemistry, Alkaloids isolation & purification, Glycosides isolation & purification, Solanum lycopersicum chemistry, Steroids isolation & purification
- Abstract
Three new steroidal alkaloid glycosides, lycoperosides F-H (1-3), were isolated from tomato fruits (Lycopersicon sculentum) along with lycoperosides A-D, esculeoside A, and rutin. The structures of these glycosides were characterized as the 3-O-beta-lycotetraosides of 23(R)-23-acetoxy-27-hydroxy-27-O-beta-d-glucopyranosyltomatidine (1), (23S,24R)-23-acetoxy-24-O-beta-d-glucopyranosylsoladulcidine-24-ol (2), and 22-isopimpifolidine (3), by means of their spectroscopic data. Also obtained was the new natural product lycoperodine-1 (4).
- Published
- 2004
- Full Text
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68. Tyromycic acids B-E, new lanostane triterpenoids from the mushroom Tyromyces fissilis.
- Author
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Quang DN, Hashimoto T, Tanaka M, Takaoka S, and Asakawa Y
- Subjects
- Crystallography, X-Ray, Japan, Molecular Conformation, Molecular Structure, Steroids chemistry, Triterpenes chemistry, Agaricales chemistry, Steroids isolation & purification, Triterpenes isolation & purification
- Abstract
Four new triterpenoids, tyromycic acids B-E (1-4), were isolated from a methanol-soluble extract of the fruit bodies of the Japanese inedible mushroom Tyromyces fissilis. Tyromycic acids B-D possess a lanostane skeleton, while tyromycic acid E is based on a rare 14(13-->12)abeo-lanostane skeleton. Their structures were determined by spectral data analysis and by single-crystal X-ray crystallography.
- Published
- 2004
- Full Text
- View/download PDF
69. A pair of new C-21 steroidal glycoside epimers from the roots of Cynanchum paniculatum.
- Author
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Li SL, Tan H, Shen YM, Kawazoe K, and Hao XJ
- Subjects
- Glycosides chemistry, Glycosides pharmacology, Medicine, Chinese Traditional, Methicillin Resistance, Microbial Sensitivity Tests, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Roots chemistry, Staphylococcus aureus drug effects, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Cynanchum chemistry, Glycosides isolation & purification, Plants, Medicinal chemistry, Steroids isolation & purification
- Abstract
Two new C-21 steroidal glycoside epimers, paniculatumosides A and B (1 and 2), based on a 13,14:14,15-disecopregnane-type skeleton, with neocynapanogenin B (3) and neocynapanogenin C (4) as two new aglycons, were isolated from the roots of Cynanchum paniculatum. Their structures were determined by spectral data interpretation.
- Published
- 2004
- Full Text
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70. New cytotoxic steroidal alkaloids from the Philippine sponge Corticium niger.
- Author
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Ridley CP and Faulkner DJ
- Subjects
- Alkaloids chemistry, Alkaloids pharmacology, Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Cell Line, Tumor, Drug Screening Assays, Antitumor, HCT116 Cells, Humans, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Philippines, Steroids chemistry, Steroids pharmacology, Alkaloids isolation & purification, Antineoplastic Agents isolation & purification, Porifera chemistry, Steroids isolation & purification
- Abstract
Four new steroidal alkaloids, plakinamine I-K (1-3) and dihydroplakinamine K (4), were isolated from the marine sponge Corticium niger. The structures of these compounds were elucidated by interpretation of spectroscopic data. Compounds 1-4 exhibit significant in vitro cytotoxicity.
- Published
- 2003
- Full Text
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71. Mycalosides B-I, eight new spermostatic steroid oligoglycosides from the sponge Mycale laxissima.
- Author
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Antonov AS, Afiyatullov SSh, Kalinovsky AI, Ponomarenko LP, Dmitrenok PS, Aminin DL, Agafonova IG, and Stonik VA
- Subjects
- Animals, Cuba, Glycosides chemistry, Glycosides pharmacology, Male, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Sea Urchins drug effects, Spermatozoa drug effects, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Fertilization drug effects, Glycosides isolation & purification, Porifera chemistry, Steroids isolation & purification
- Abstract
New steroidal oligoglycosides mycalosides B-I (2-9) have been isolated from the polar extract of the Caribbean sponge Mycale laxissima, and their structures have been elucidated by 1D and 2D NMR ((1)H, (13)C, DEPT, COSY-45, COSY-RCT, HSQC, HMBC, and NOESY spectra) and MALDI-TOF mass spectrometry. Mycalosides B (2) and C (3) were shown to be 27- and 28-nor derivatives of the previously known tetraoside mycaloside A (1). Mycaloside D (4) differs from 1 only in the presence of an additional acetyl group in the carbohydrate moiety. Mycaloside E (5) was structurally identified as a 28-nor-4-dehydroxy derivative of 1. Mycalosides F-H (6-8), differing from each other by the structures of their side chains and nonacetylated (7, 8) or acetylated (6) tetrasaccharide carbohydrate moieties, have new 5(6)-unsaturated 3 beta,4 beta,21-trihydroxy-15-keto-steroidal aglycons. Mycaloside I (9) is a tetraoside of a new 7,24(28)-diunsaturated 3beta,15 beta,29-trihydroxystigmastane aglycon. It was established that the total fraction of the mycalosides as well as mycalosides A (1) and G (7) inhibit the fertilization of eggs by sperm of the sea urchin Strongylocentrotus nudus preincubated with these compounds.
- Published
- 2003
- Full Text
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72. Hippuristerones E-I, new polyoxygenated steroids from the gorgonian coral Isis hippuris.
- Author
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Sheu JH, Huang LF, Chen SP, Yang YL, Sung PJ, Wang GH, Su JH, Chao CH, Hu WP, and Wang JJ
- Subjects
- Animals, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Oxygen chemistry, Taiwan, Anthozoa chemistry, Steroids chemistry, Steroids isolation & purification
- Abstract
Five novel (22R,23S,24S)-steroids, hippuristerones E-I (1-5), have been isolated from the gorgonian coral Isis hippuris. The structures of steroids 1-5 were deduced by extensive 1D and 2D NMR studies ((1)H, (13)C, (1)H-(1)H COSY, HMQC, HMBC, and NOESY experiments). The structure of 1 was further supported by molecular mechanics calculations.
- Published
- 2003
- Full Text
- View/download PDF
73. Chantriolides A and B, two new withanolide glucosides from the rhizomes of Tacca chantrieri.
- Author
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Yokosuka A, Mimaki Y, and Sashida Y
- Subjects
- Drugs, Chinese Herbal chemistry, Glucosides chemistry, Hydrolysis, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Rhizome chemistry, Solanaceae chemistry, Stereoisomerism, Steroids chemistry, Dioscoreaceae chemistry, Drugs, Chinese Herbal isolation & purification, Glucosides isolation & purification, Steroids isolation & purification
- Abstract
Two new withanolide glucosides, chantriolides A (1) and B (2), were isolated from the rhizomes of Tacca chantrieri. Their structures were determined on the basis of extensive spectroscopic studies and by acid hydrolysis as (22R)-1alpha,12alpha-diacetoxy-2alpha,3alpha;6alpha,7alpha-diepoxy-27-[(beta-d-glucopyranosyl)oxy]-5alpha-hydroxy-16-oxowith-24-enolide (1) and (22R)-1alpha,12alpha-diacetoxy-2alpha,3alpha;6alpha,7alpha-diepoxy-27-[(beta-d-glucopyranosyl)oxy]-5alpha,16beta-dihydroxywith-24-enolide (2), respectively. It is notable that withanolides, which have been almost exclusively isolated from plants of the family Solanaceae to date, have been found in a species in the family Taccaceae in the present study.
- Published
- 2003
- Full Text
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74. Steroidal saponins from the bark of Dracaena draco and their cytotoxic activities.
- Author
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González AG, Hernández JC, León F, Padrón JI, Estévez F, Quintana J, and Bermejo J
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Apoptosis drug effects, DNA Fragmentation drug effects, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, HL-60 Cells, Humans, Inhibitory Concentration 50, Microscopy, Fluorescence, Nuclear Magnetic Resonance, Biomolecular, Plant Bark chemistry, Saponins chemistry, Saponins pharmacology, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured drug effects, Antineoplastic Agents, Phytogenic isolation & purification, Dracaena chemistry, Plants, Medicinal chemistry, Saponins isolation & purification, Steroids isolation & purification
- Abstract
From the stem bark of Dracaena draco, three new compounds, namely, draconins A-C (1-3), were isolated, along with 17 known compounds. The structures of the new compounds isolated were elucidated on the basis of spectroscopic data interpretation. Several of the isolated compounds showed potent cytotoxic activities measured on the human leukemia cell line HL-60 (IC(50)'s from 2.0 to 9.7 microM at 72 h). The mechanism by which compounds 1 and 2 display their cytostatic properties is through induction of cell death by apoptosis, as evaluated by fluorescence microscopy and DNA fragmentation.
- Published
- 2003
- Full Text
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75. 5alpha-steroidal glycosides from Parepigynum funingense.
- Author
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Hua Y, Liu HY, Ni W, Chen CX, Lu Y, Wang C, and Zheng QT
- Subjects
- China, Crystallography, X-Ray, Glycosides chemistry, Hydrolysis, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Roots chemistry, Stereoisomerism, Steroids chemistry, Apocynaceae chemistry, Glycosides isolation & purification, Steroids isolation & purification
- Abstract
Four new 5alpha-steroidal glycosides with an unusual framework, funingenosides A (1), B (2), C (3), and D (4), were isolated from the roots of Parepigynum funingense. Their structures were elucidated on the basis of 1D and 2D NMR techniques. The structure and relative stereochemistry of compound 1 were demonstrated by X-ray crystallographic analysis.
- Published
- 2003
- Full Text
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76. Bioactive asterosaponins from the starfish Luidia quinaria and Psilaster cassiope. Isolation and structure characterization by two-dimensional NMR spectroscopy.
- Author
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De Marino S, Borbone N, Iorizzi M, Esposito G, McClintock JB, and Zollo F
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Drug Screening Assays, Antitumor, Electron Spin Resonance Spectroscopy, Inhibitory Concentration 50, Japan, Leukemia, Mexico, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Rats, Saponins chemistry, Saponins pharmacology, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured drug effects, Antineoplastic Agents isolation & purification, Saponins isolation & purification, Starfish chemistry, Steroids isolation & purification
- Abstract
An investigation of the polar extracts from two starfish, Luidia quinaria and Psilaster cassiope, led to the isolation of five sulfated "asterosaponins". Two of them, named luidiaquinoside (1) and psilasteroside (2), are new compounds. Luidiaquinoside (1) contains a novel pentasaccharide chain composed of d-glucose, d-quinovose, and d-fucose, with the d-glucose unit being the branching point. Psilasteroside (2) contains a hexasaccharide chain in which an arabinose residue is detectable in the furanose form. Both of these compounds possess a Delta(9(11)),3beta,6alpha-dihydroxysteroidal nucleus with a 20-hydroxy, 23-oxo functionality. The structures of the new asterosaponins were elucidated by a combination of NMR techniques including (1)H-(1)H (COSY, TOCSY, and ROESY) and (1)H-(13)C (HMQC and HMBC) spectroscopy, ESIMS and HRFABMS spectrometry, and GC analyses. The new asterosaponins show marginal in vitro cytotoxicity against RBL-2H3 (rat basophilic leukemia) cell lines.
- Published
- 2003
- Full Text
- View/download PDF
77. Chemical constituents of the ascomycete Daldinia concentrica.
- Author
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Quang DN, Hashimoto T, Tanaka M, Baumgartner M, Stadler M, and Asakawa Y
- Subjects
- Circular Dichroism, Crystallography, X-Ray, Fraxinus chemistry, Germany, Molecular Conformation, Molecular Structure, Polycyclic Aromatic Hydrocarbons chemistry, Pyrones chemistry, Stereoisomerism, Steroids chemistry, Ascomycota chemistry, Polycyclic Aromatic Hydrocarbons isolation & purification, Pyrones isolation & purification, Steroids isolation & purification
- Abstract
Four compounds, daldinone A (1), daldinone B (2), daldiniapyrone (4-methoxy-5-carbomethoxy-6-pentyl-2H-pyran-2-one, 3), and daldinialanone (22R-hydroxylanosta-7,9(11),24-trien-3-one, 4), were isolated from an ethyl acetate extract of fruit bodies of Daldinia concentrica collected in Europe. In addition, 11 known compounds, 4:5:4':5'-tetrahydroxy-1:1'-binaphthyl (5), 3,4,5-trihydroxy-1-tetralone (6), (+)-orthosporin (7), curuilignan D (8), (22E)-cholesta-4,6,8(14),22-tetraen-3-one (9), 3beta,22-dihydroxylanosta-7,9(11),24-triene (10), concentricol (11), concentricol B (12), concentricol C (13), concentricol D (14), and phenochalasin B (15), were obtained. The structures of the new compounds were elucidated by 2D NMR, MS, IR, and UV spectra and by X-ray crystallographic analysis. The absolute configurations of 1 and 4 were determined by CD spectroscopy and the modified Mosher's method, respectively. The chemotaxonomic relevance of the compounds obtained in this investigation is discussed.
- Published
- 2002
- Full Text
- View/download PDF
78. Steroidal glycosides from the leaves of Cestrum nocturnum.
- Author
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Mimaki Y, Watanabe K, Sakagami H, and Sashida Y
- Subjects
- Acetylation, Antineoplastic Agents, Phytogenic chemistry, Antineoplastic Agents, Phytogenic pharmacology, Carcinoma, Squamous Cell, Catalysis, Doxorubicin pharmacology, Drug Screening Assays, Antitumor, Glycosides chemistry, Glycosides pharmacology, Humans, Hydrolysis, Japan, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Plant Leaves chemistry, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured drug effects, Antineoplastic Agents, Phytogenic isolation & purification, Cestrum chemistry, Glycosides isolation & purification, Plants, Medicinal chemistry, Steroids isolation & purification
- Abstract
Further phytochemical analysis aimed at the steroidal glycoside constituents of the leaves of Cestrum nocturnum has resulted in the isolation of eight new steroidal glycosides (1-8), which were classified into a spirostanol saponin (1), a furostanol saponin (2), a pseudo-furostanol saponin (3), two pregnane glycosides (4, 5), two cholestane glycosides (6, 7), and pregnane-carboxylic acid gamma-lactone glycoside (8), and of two known spirostanol glycosides (9, 10). The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.
- Published
- 2002
- Full Text
- View/download PDF
79. New steroidal glycosides from the fruits of Solanum anguivi.
- Author
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Honbu T, Ikeda T, Zhu XH, Yoshihara O, Okawa M, Nafady AM, and Nohara T
- Subjects
- Chromatography, High Pressure Liquid, Fruit chemistry, Glycosides chemistry, Japan, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Seeds chemistry, Spectrometry, Mass, Fast Atom Bombardment, Stereoisomerism, Steroids chemistry, Glycosides isolation & purification, Plants, Medicinal chemistry, Solanum chemistry, Steroids isolation & purification
- Abstract
Four new steroidal saponins, anguiviosides III (1), XI (2), XV (3), and XVI (4), were isolated and characterized from the fruits of Solanum anguivi. Their structures were elucidated on the basis of spectroscopic analysis. The occurrence of the cholestane glycosides 3 and 4 is considered from a biogenetic point of view.
- Published
- 2002
- Full Text
- View/download PDF
80. New cytotoxic constituents from the Formosan soft corals Clavularia viridis and Clavularia violacea.
- Author
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Duh CY, El-Gamal AA, Chu CJ, Wang SK, and Dai CF
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Colonic Neoplasms, Drug Screening Assays, Antitumor, Humans, Leukemia P388, Lung Neoplasms, Methylene Chloride, Mice, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Prostaglandins chemistry, Prostaglandins pharmacology, Steroids chemistry, Steroids pharmacology, Taiwan, Tumor Cells, Cultured drug effects, Anthozoa chemistry, Antineoplastic Agents isolation & purification, Prostaglandins isolation & purification, Steroids isolation & purification
- Abstract
Three new cytotoxic prostanoids, claviridenone E-G (1-3), and three new cytotoxic steroids, stoloniferone E-G (4-6), were isolated from the methylene chloride solubles of the Formosan soft coral Clavulariaviridis. A cytotoxic cembranoid, claviolide (7), was isolated from the methylene chloride solubles of the Formosan soft coral Clavularia violacea. The structures were elucidated by 1D and 2D NMR spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.
- Published
- 2002
- Full Text
- View/download PDF
81. Nanjiols A-C, new steroids from the Chinese soft coral Nephthea bayeri.
- Author
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Shao ZY, Zhu DY, and Guo YW
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Carcinoma, Hepatocellular, China, Drug Screening Assays, Antitumor, Electron Spin Resonance Spectroscopy, HL-60 Cells drug effects, Humans, Inhibitory Concentration 50, Leukemia, Myeloid, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Spectroscopy, Fourier Transform Infrared, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured drug effects, Anthozoa chemistry, Antineoplastic Agents isolation & purification, Steroids isolation & purification
- Abstract
Three new polyoxygenated steroids, nanjiol A (1), B (2), and C (3), were isolated from an East China Sea soft coral Nephthea bayeri, and their structures were characterized by spectroscopic methods and comparison with known compounds. The new molecules were structurally related to (20S)-cholesta-1,4-diene-18,20-diol-3-one (4), a typical metabolite from the black coral Antipathes subpinnata.
- Published
- 2002
- Full Text
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82. Screening of ubiquitous plant constituents for COX-2 inhibition with a scintillation proximity based assay.
- Author
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Huss U, Ringbom T, Perera P, Bohlin L, and Vasänge M
- Subjects
- Acrolein pharmacology, Alkaloids chemistry, Alkaloids isolation & purification, Alkaloids pharmacology, Animals, Anthraquinones chemistry, Anthraquinones isolation & purification, Anthraquinones pharmacology, Aspirin pharmacology, Biological Assay, Catalysis, Cinnamomum zeylanicum chemistry, Cyclooxygenase 2, Cyclooxygenase 2 Inhibitors, Dinoprostone biosynthesis, Dose-Response Relationship, Drug, Eugenol pharmacology, Flavonoids chemistry, Flavonoids isolation & purification, Flavonoids pharmacology, Indomethacin pharmacology, Inhibitory Concentration 50, Kinetics, Lactones pharmacology, Models, Molecular, Nitrobenzenes pharmacology, Oleanolic Acid pharmacology, Pyrogallol pharmacology, Steroids chemistry, Steroids isolation & purification, Steroids pharmacology, Sulfonamides pharmacology, Sulfones, Syzygium chemistry, Terpenes chemistry, Terpenes isolation & purification, Terpenes pharmacology, Triterpenes pharmacology, Ursolic Acid, Acrolein analogs & derivatives, Cyclooxygenase Inhibitors pharmacology, Isoenzymes metabolism, Plants, Medicinal chemistry, Prostaglandin-Endoperoxide Synthases metabolism
- Abstract
A rapid semi-homogeneous cyclooxygenase-2 (COX-2) enzymatic assay using scintillation proximity assay (SPA) technology was developed, and 49 ubiquitous plant secondary metabolites were screened for inhibition of COX-2-catalyzed prostaglandin E(2) (PGE(2)) biosynthesis. Assay conditions were optimized with respect to reaction time, amount of antibody, radiolabeled PGE(2), and SPA beads, and the kinetic parameter, K(m), was estimated. The assay was validated with two natural triterpenoids, ursolic and oleanolic acid, known to inhibit COX-2, as well as with four synthetic COX inhibitors, NS-398, rofecoxib, indomethacin, and aspirin. Plant metabolites of different biosynthetic origin representing several substance classes, including alkaloids, anthraquinones, flavonoids, phenylpropanes, steroids, and terpenes, were screened for inhibition of COX-2-catalyzed PGE(2) production. Of these 49 plant metabolites, eugenol, pyrogallol, and cinnamaldehyde (with IC(50) values of 129, 144, and 245 microM, respectively) were found to inhibit COX-2. This study showed that a COX-2-catalyzed PGE(2) assay using SPA is suitable for screening natural compounds with respect to COX-2 inhibition.
- Published
- 2002
- Full Text
- View/download PDF
83. New saponins from the starfish Certonardoa semiregularis.
- Author
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Wang W, Li F, Alam N, Liu Y, Hong J, Lee CK, Im KS, and Jung JH
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Antiviral Agents chemistry, Antiviral Agents pharmacology, Artemia, HeLa Cells drug effects, Humans, Korea, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Saponins chemistry, Saponins pharmacology, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Antineoplastic Agents isolation & purification, Antiviral Agents isolation & purification, Saponins isolation & purification, Starfish chemistry, Steroids isolation & purification
- Abstract
Ten new saponins designated as certonardosides A-J (1-5, 7-11) and the known halityloside D (6) were isolated from the brine shrimp active fraction of the MeOH extract of the starfish Certonardoa semiregularis. The structures were determined on the basis of spectral analysis and chemical manipulation. The compounds were evaluated for antiviral activity against HIV, HSV, CoxB, EMCV, and VSV and displayed insignificant activity within the range of noncytotoxic concentrations.
- Published
- 2002
- Full Text
- View/download PDF
84. Steroidal and pregnane glycosides from the rhizomes of Tacca chantrieri.
- Author
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Yokosuka A, Mimaki Y, and Sashida Y
- Subjects
- Acetylation, Hydrolysis, Medicine, Chinese Traditional, Methanol, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Saponins chemistry, Stereoisomerism, Steroids chemistry, Plants, Medicinal chemistry, Rhizome chemistry, Saponins isolation & purification, Steroids isolation & purification
- Abstract
The rhizomes of Tacca chantrieri have been analyzed as part of a systematic study on saponin constituents of medicinal plants. This has resulted in the isolation of three new bisdesmosidic furostanol saponins (1-3), two new bisdesmosidic pseudofurostanol saponins (4, 5), and two new pregnane glycosides (6, 7). Their structures were determined on the basis of extensive spectroscopic studies and a few chemical transformations.
- Published
- 2002
- Full Text
- View/download PDF
85. Minor steroidal alkaloids from the marine sponge Corticium sp.
- Author
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Borbone N, De Marino S, Iorizzi M, Zollo F, Debitus C, Esposito G, and Iuvone T
- Subjects
- Alkaloids chemistry, Alkaloids pharmacology, Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Cells, Cultured drug effects, Chromatography, High Pressure Liquid, Dose-Response Relationship, Drug, Glioma, Inhibitory Concentration 50, Macrophages drug effects, Mice, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Rats, Steroids chemistry, Steroids pharmacology, Vanuatu, Alkaloids isolation & purification, Antineoplastic Agents isolation & purification, Porifera chemistry, Steroids isolation & purification
- Abstract
Four new steroidal alkaloids, plakinamine G (1), plakinamine H (2), 4alpha-hydroxydemethylplakinamine B (3), and tetrahydroplakinamine A (4), along with three known compounds, were isolated from the marine sponge Corticium sp. The structures of these metabolites were elucidated largely by 1D and 2D NMR methods and accurate mass measurements (HR-EIMS). Compounds 1, 2, and 4 show significant in vitro cytotoxicity.
- Published
- 2002
- Full Text
- View/download PDF
86. Induction of quinone reductase by withanolides.
- Author
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Misico RI, Song LL, Veleiro AS, Cirigliano AM, Tettamanzi MC, Burton G, Bonetto GM, Nicotra VE, Silva GL, Gil RR, Oberti JC, Kinghorn AD, and Pezzuto JM
- Subjects
- Animals, Breast enzymology, Colon enzymology, Enzyme Induction drug effects, Inhibitory Concentration 50, Liver enzymology, Lung enzymology, Mice, Mice, Inbred BALB C, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism, Steroids isolation & purification, Steroids pharmacology, Stomach enzymology, Tumor Cells, Cultured drug effects, Brassicaceae chemistry, Carcinoma, Hepatocellular enzymology, Plants, Medicinal chemistry, Quinone Reductases biosynthesis, Solanaceae chemistry, Steroids chemistry, Stilbenes pharmacology
- Abstract
Thirty-seven naturally occurring withanolides (1-37), previously isolated in our laboratories, were evaluated for their potential to induce quinone reductase with cultured murine hepatoma cells (Hepa 1c1c7). Spiranoid (29, 32) and 18-functionalized withanolides (2-5, 7-9, 24) were found to be potent inducers of the enzyme, while 5alpha-substituted derivatives exhibited weak activity. Preliminary studies were performed with compound 29 to evaluate enzyme-inducing capacity in multiple organ sites of BALB/c mice. Significant induction was observed in liver and colon, but not in lung, stomach, or mammary gland.
- Published
- 2002
- Full Text
- View/download PDF
87. Clathriol, a novel polyoxygenated 14beta steroid isolated from the New Zealand marine sponge Clathria lissosclera.
- Author
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Keyzers RA, Northcote PT, and Webb V
- Subjects
- Animals, Anti-Inflammatory Agents chemistry, Anti-Inflammatory Agents pharmacology, Chromatography, Thin Layer, Histamine Release drug effects, Mast Cells drug effects, New Zealand, Nuclear Magnetic Resonance, Biomolecular, Rats, Steroids chemistry, Steroids pharmacology, Anti-Inflammatory Agents isolation & purification, Porifera chemistry, Steroids isolation & purification
- Abstract
Clathriol (1), a highly oxygenated steroid with the unusual 14beta configuration, was isolated from the New Zealand marine sponge Clathria lissosclera. The structure was elucidated from a combination of NMR and mass spectroscopy. Clathriol showed in vitro antiinflammatory activity against human neutrophyl and rat mast cells.
- Published
- 2002
- Full Text
- View/download PDF
88. New steroidal alkaloids from an undescribed sponge of the genus Corticium.
- Author
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Lee HS, Seo Y, Rho JR, Shin J, and Paul VJ
- Subjects
- Alkaloids chemistry, Alkaloids pharmacology, Animals, Anti-Bacterial Agents, Anti-Infective Agents chemistry, Anti-Infective Agents pharmacology, Antifungal Agents chemistry, Antifungal Agents pharmacology, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Candida albicans drug effects, Chromatography, High Pressure Liquid, DNA drug effects, DNA, Bacterial drug effects, Drug Screening Assays, Antitumor, Electrophoresis, Escherichia coli genetics, Guam, Humans, Leukemia, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, RNA, Ribosomal, 16S drug effects, Spectrophotometry, Infrared, Spectrophotometry, Ultraviolet, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured drug effects, Alkaloids isolation & purification, Anti-Infective Agents isolation & purification, Antifungal Agents isolation & purification, Antineoplastic Agents isolation & purification, Porifera chemistry, Steroids isolation & purification
- Abstract
Two new steroidal alkaloids, along with a previously reported one of the plakinamine class, were isolated from the sponge Corticium sp. collected from Guam. The structures of the new compounds were determined by combined spectroscopic methods. These compounds exhibited moderate cytotoxicity and antifungal activity as well as DNA- and RNA-cleaving activities.
- Published
- 2001
- Full Text
- View/download PDF
89. New steroid glycosides from the starfish Asterias rathbuni.
- Author
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Ivanchina NV, Kicha AA, Kalinovsky AI, Dmitrenok PS, Prokofreva NG, and Stonik VA
- Subjects
- Animals, Chromatography, High Pressure Liquid, Dose-Response Relationship, Drug, Female, Glycosides chemistry, Glycosides pharmacology, Magnetic Resonance Spectroscopy, Molecular Structure, Ovum cytology, Ovum drug effects, Ovum metabolism, Sea Urchins, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization, Steroids chemistry, Steroids pharmacology, Structure-Activity Relationship, Cell Division drug effects, Glycosides isolation & purification, Marine Toxins pharmacology, Starfish chemistry, Steroids isolation & purification
- Abstract
Two novel steroidal 24-O-xylosides, designated as rathbuniosides R(1) (1) and R(2) (2), and the known amurensoside A (3) and 3-O-sulfomarthasterone (4) have been isolated from the starfish Asterias rathbuni. The structures of all the compounds were determined from their spectroscopic data, including one- and two-dimensional NMR methods. The compounds 1 and 4 inhibit the cell division of fertilized sea urchin eggs at doses of 7.0 x 10(-5) and 2.9 x 10(-5) M, respectively.
- Published
- 2001
- Full Text
- View/download PDF
90. Two new 26,27-cyclosterols from the marine sponge Strongylophora corticata.
- Author
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Umeyama A, Ito S, Yoshigaki A, and Arihara S
- Subjects
- Animals, Chloroform, Solvents, Cholestanols isolation & purification, Cholestenones isolation & purification, Porifera chemistry, Steroids isolation & purification
- Abstract
Two novel steroids with a cyclopropane ring at C-25 and C-26, 7-oxopetrosterol (1) and 7alpha-hydroxypetrosterol (2), along with two known compounds, petrosterol (3) and 23,24-dihydrocalysterol (4), have been isolated from the Japanese marine sponge Strongylophora corticata. The structures of 1 and 2 were determined as 26, 27-cyclo-24,27-dimethyl-3beta-hydroxycholest-5-en-7-one and 26, 27-cyclo-24,27-dimethylcholest-5-en-3beta,7alpha-diol on the basis of spectroscopic investigations.
- Published
- 2000
- Full Text
- View/download PDF
91. Steroidal glycosides from the aerial parts of Polianthes tuberosa.
- Author
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Mimaki Y, Yokosuka A, and Sashida Y
- Subjects
- Antineoplastic Agents, Phytogenic chemistry, Carbohydrate Sequence, Chromatography, High Pressure Liquid, Drug Screening Assays, Antitumor, Glycosides chemistry, Glycosides pharmacology, Humans, Hydrolysis, Magnetic Resonance Spectroscopy, Molecular Sequence Data, Spectrophotometry, Infrared, Spectrophotometry, Ultraviolet, Steroids chemistry, Steroids pharmacology, Tumor Cells, Cultured, Antineoplastic Agents, Phytogenic isolation & purification, Glycosides isolation & purification, Plants, Medicinal chemistry, Steroids isolation & purification
- Abstract
A chemical investigation of the aerial parts of Polianthes tuberosa resulted in the isolation of a new bisdesmosidic cholestane glycoside (1) and three new spirostanol saponins (2-4), along with a known cholestane glycoside. The structures of new glycosides were determined by spectroscopic analysis, including 2D NMR spectroscopic data, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity on HL-60 human promyelocytic leukemia cells.
- Published
- 2000
- Full Text
- View/download PDF
92. New 24-isopropylcholesterol and 24-isopropenylcholesterol sulfate from the marine sponge Epipolasis species.
- Author
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Umeyama A, Adachi K, Ito S, and Arihara S
- Subjects
- Animals, Cholesterol chemistry, Cholesterol isolation & purification, Chromatography, Gel, Gas Chromatography-Mass Spectrometry, Japan, Magnetic Resonance Spectroscopy, Optical Rotation, Spectrophotometry, Infrared, Spectrophotometry, Ultraviolet, Steroids chemistry, Steroids isolation & purification, Cholesterol analogs & derivatives, Porifera chemistry
- Abstract
Two novel steroids, polasterol A (1) and polasterol B sulfate (2), along with two known compounds, 22(E),24-isopropylcholesta-5, 22-dien-3 beta-ol (3) and halistanol sulfate (4), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1 and 2 were determined as 3 beta-hydroxy-24-isopropylcholesta-5, 22(E)-dien-7-one and 24xi-isopropenylcholesta-22(Z), 28(29)-diene-2 beta,3 alpha,6 alpha-triyl trisodium sulfate on the basis of spectroscopic investigations and a chemical conversion.
- Published
- 2000
- Full Text
- View/download PDF
93. Hemolytic polar steroidal constituents of the starfish Aphelasterias japonica.
- Author
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Ivanchina NV, Kicha AA, Kalinovsky AI, Dmitrenok PS, Stonik VA, Riguera R, and Jiménez C
- Subjects
- Animals, Biological Assay, Chromatography, Gel, Chromatography, High Pressure Liquid, Chromatography, Ion Exchange, Chromatography, Thin Layer, Erythrocytes chemistry, Magnetic Resonance Spectroscopy, Mice, Optical Rotation, Russia, Sodium analysis, Spectrometry, Mass, Fast Atom Bombardment, Spectrophotometry, Atomic, Spectrophotometry, Infrared, Steroids chemistry, Steroids pharmacology, Starfish chemistry, Steroids isolation & purification
- Abstract
A reinvestigation of the polar steroid fraction from the starfish Aphelasterias japonica, collected near the Russian shore of the Sea of Japan, has afforded two new compounds, the disulfated quinovoside aphelasteroside C (1) and the monosulfated polyhydroxysteroid aphelaketotriol (2). Compounds 1 and 2 contain a unique 23-oxo-24-hydroxylated side chain that is unprecedented in marine steroids. The known compounds cheliferoside L1 (3), 3-O-sulfoasterone (4), forbeside E3 (5), and 3-O-sulfothornasterol A (6) were also isolated from this source. Compounds 1-3, 5, and 6 showed hemolytic activity to mouse erythrocytes.
- Published
- 2000
- Full Text
- View/download PDF
94. Novel epoxy steroids from the indian ocean soft coral Sarcophyton crassocaule.
- Author
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Anjaneyulu AS, Krishna Murthy MV, and Gowri PM
- Subjects
- Animals, Molecular Structure, Spectrum Analysis, Steroids chemistry, Cnidaria chemistry, Steroids isolation & purification
- Abstract
A detailed further examination of the Indian Ocean soft coral Sarcophyton crassocaule resulted in the isolation of altogether 17 compounds of which two (1 and 2) are novel 17beta,20beta-epoxy steroids and one is a new dihydroxygorgost-5-en (3). The other compounds include the four hippurin steroids (4-7) reported earlier, and some known derivatives such as methyl arachidonate, batyl alcohol, a mixture of monohydroxy sterols, 3beta-hydroxypregn-5-en-20-one, two prostaglandin derivatives (PGB(2) acid and its methyl ester), and 9-oxo-9, 11-secogorgost-5-ene-3beta,11-diol (8). The structure of new dihydroxygorgostene derivative was established as gorgost-5-ene-3beta,11alpha-diol (3), while the structures of the novel epoxy steroids were established as 17beta,20beta-epoxy-23, 24-dimethylcholest-5-ene-3beta,22-diol (2) and its 3beta, 22-diacetate (1), respectively.
- Published
- 2000
- Full Text
- View/download PDF
95. Bioactive steroids from the whole herb of Euphorbia chamaesyce.
- Author
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Tanaka R, Kasubuchi K, Kita S, Tokuda H, Nishino H, and Matsunaga S
- Subjects
- Antigens, Viral drug effects, Drug Screening Assays, Antitumor, Magnetic Resonance Spectroscopy, Molecular Structure, Spectrum Analysis, Steroids chemistry, Steroids pharmacology, Euphorbiaceae chemistry, Steroids isolation & purification
- Abstract
Three new ergostane-type steroids, 3beta-hydroxy-4alpha, 14alpha-dimethyl-5alpha-ergosta-8,24(28)-dien-11 -one (1); 3beta, 11alpha-dihydroxy-4alpha,14alpha-dimethyl-5alpha -ergosta-8, 24(28)-dien-7-one (2); and 3beta,7alpha-dihydroxy-4alpha, 14alpha-dimethyl-5alpha-ergosta-8,24(28)-dien-11 -one (3), were isolated, together with two known triterpenoids, wrightial and lup-20(30)-ene-3beta,29-diol from the whole herb of Euphorbia chamaesyce. Compound 3 showed a potent inhibitory effect on Epstein-Barr virus early antigen activation induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate (TPA).
- Published
- 2000
- Full Text
- View/download PDF
96. Steroids from the roots of Nerium oleander.
- Author
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Huq MM, Jabbar A, Rashid MA, Hasan CM, Ito C, and Furukawa H
- Subjects
- Carbohydrate Sequence, Magnetic Resonance Spectroscopy, Molecular Sequence Data, Plant Roots chemistry, Spectrophotometry, Infrared, Spectrophotometry, Ultraviolet, Steroids isolation & purification, Plants, Medicinal chemistry, Steroids chemistry
- Abstract
Two new cardenolides, 3beta-hydroxy-5alpha-carda-14(15), 20(22)-dienolide (beta-anhydroepidigitoxigenin) (1) and 3beta-O-(D-digitalosyl)-21-hydroxy-5beta-carda-8,14,16 , 20(22)-tetraenolide (neriumogenin-A-3beta-D-digitaloside) (2), and two known compounds, proceragenin and neridienone A (3), have been isolated from the roots of Nerium oleander. The structures of 1 and 2 were elucidated on the basis of spectral data interpretation.
- Published
- 1999
- Full Text
- View/download PDF
97. Cytotoxic and leishmanicidal aminoglycosteroids and aminosteroids from Holarrhena curtisii.
- Author
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Kam TS, Sim KM, Koyano T, Toyoshima M, Hayashi M, and Komiyama K
- Subjects
- Alkaloids isolation & purification, Animals, Antineoplastic Agents, Phytogenic isolation & purification, Antiprotozoal Agents isolation & purification, Drug Screening Assays, Antitumor, HL-60 Cells, Humans, Leukemia P388 drug therapy, Magnetic Resonance Spectroscopy, Mice, Steroids isolation & purification, Alkaloids pharmacology, Antineoplastic Agents, Phytogenic pharmacology, Antiprotozoal Agents pharmacology, Leishmania donovani drug effects, Plants, Medicinal chemistry, Steroids pharmacology
- Abstract
The EtOH extract of the leaves of Holarrhena curtisii yielded five new steroidal alkaloids: 17-epi-holacurtine (3), 17-epi-N-demethylholacurtine (4), holacurtinol (5), 3alpha-amino-14beta-hydroxypregnan-20-one (7), and 15alpha-hydroxyholamine (8), in addition to the known compounds, holacurtine (1), N-demethylholacurtine (2), and holamine (6). All eight compounds showed significant cytotoxic and leishmanicidal activities.
- Published
- 1998
- Full Text
- View/download PDF
98. Acanthosterol sulfates A-J: ten new antifungal steroidal sulfates from a marine sponge Acanthodendrilla sp.
- Author
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Tsukamoto S, Matsunaga S, Fusetani N, and van Soest RW
- Subjects
- Animals, Antifungal Agents isolation & purification, Magnetic Resonance Spectroscopy, Microbial Sensitivity Tests, Saccharomyces cerevisiae drug effects, Spectrometry, Mass, Fast Atom Bombardment, Steroids isolation & purification, Sulfuric Acid Esters isolation & purification, Antifungal Agents pharmacology, Porifera chemistry, Steroids pharmacology, Sulfuric Acid Esters pharmacology
- Abstract
Ten new steroidal sulfates, acanthosterol sulfates A-J (1-10), have been isolated from a marine sponge, Acanthodendrilla sp., collected in western Japan. Acanthosterol sulfates I and J (9 and 10) showed antifungal activity against the yeast Saccharomyces cerevisiae A364A and its mutants at 0.1 mg/disk.
- Published
- 1998
- Full Text
- View/download PDF
99. A new steroidal glycoside from a Caribbean gorgonian, Eunicea sp.1.
- Author
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Cóbar OM, Rodríguez AD, and Padilla OL
- Subjects
- Animals, Carbohydrate Sequence, Gas Chromatography-Mass Spectrometry, Glycosides chemistry, Glycosides isolation & purification, Hydrolysis, Molecular Sequence Data, Spectrophotometry, Ultraviolet, Steroids chemistry, Cnidaria chemistry, Steroids isolation & purification
- Abstract
A new saponin possessing a pregnene-derived aglycon (1) has been isolated from the Caribbean gorgonian octocoral Eunicea sp. The structure of the new compound was assigned on the basis of chemical and spectral studies.
- Published
- 1997
- Full Text
- View/download PDF
100. Isolation, structure elucidation, and biological activity of the steroid oligoglycosides and polyhydroxysteroids from the Antarctic starfish Acodontaster conspicuus.
- Author
-
De Marino S, Iorizzi M, Zollo F, Minale L, Amsler CD, Baker BJ, and McClintock JB
- Subjects
- Animals, Anti-Bacterial Agents chemistry, Bacteria drug effects, Magnetic Resonance Spectroscopy, Microbial Sensitivity Tests, Spectrometry, Mass, Fast Atom Bombardment, Steroids chemistry, Anti-Bacterial Agents isolation & purification, Anti-Bacterial Agents pharmacology, Starfish metabolism, Steroids isolation & purification, Steroids pharmacology
- Abstract
A total of 19 steroids, of which 13 steroidal oligoglycosides (nine new and four known) and six polyhydroxylated steroids (four new and two known), has been isolated from the Antarctic starfish Acodontaster conspicuus. The mixture is dominated by glycosides composed of steroidal aglycons having the hydroxyl groups typically disposed on one side of the tetracyclic nucleus, i.e., 3 beta,4 beta,6 alpha,8,15 beta-, with some having a sulfate at C-6, and differing in the side chains and/or in the disaccharide moieties that are usually attached at C-26, with some at C-28 and C-29. Those compounds are accompanied by minute amounts of glycosides with a delta 8(14)-double bond in the steroid, which is a structural feature not previously found among polyhydroxysteroids derived from starfish. Small amounts of six related unglycosidated polyhydroxysteroids and three higher-molecular-weight asterosaponins complete the composition of the mixture. The structures of the new compounds were determined by interpretation of their spectral data and by comparison with spectral data of known compounds. Eighteen of these compounds were evaluated for their ability to inhibit growth in Antarctic marine bacteria isolated from either the water column or the surfaces of benthic marine invertebrates. Of these compounds, 50% were active against at least one Antarctic marine bacterium. This suggests that these compounds may play an important role in deterring microbial fouling.
- Published
- 1997
- Full Text
- View/download PDF
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