A novel sulphated steroid with a 7-membered 5-oxalactone B-ring from an Antarctic starfish of the family Asteriidae
| Autor: | Simona De Marino, Elio Palagiano, Maria Iorizzi, Franco Zollo, Luigi Minale |
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| Přispěvatelé: | DE MARINO, Simona, E., Palagiano, Zollo, Franco, L., Minale, M., Iorizzi |
| Rok vydání: | 1997 |
| Předmět: |
Sulphated polyhydroxylated steroid
Chromatography biology Chemistry Stereochemistry medicine.medical_treatment Organic Chemistry Starfish biology.organism_classification Biochemistry High-performance liquid chromatography Steroid Solvent chemistry.chemical_compound Sulfation Sephadex Drug Discovery Asterasterols medicine Acetone Asteriidae |
| Zdroj: | Tetrahedron. 53:8625-8628 |
| ISSN: | 0040-4020 |
| Popis: | Three novel sulphated polyhydroxylated steroids, named asterasterols A-C (1-3), have been isolated from an Antarctic starfish of the family Asteriidae and their structures elucidated by spectroscopic studies. Steroid 1 has the seven-membered 5-oxalactone B-ring; 2 and 3 are the corresponding 6-oxo steroids. © 1997 Published by Elsevier Science Ltd. In connection with our systematic investigation of steroid constituents from echinoderms, we examined some Antarctic starfish species, t'2 These studies have led to the isolation of a series of sulfated polyhydroxysteroids and steroidal glycosides structurally very close, some identical, with those found in species collected in warm environments. 3 During the investigation of the polar extracts of an Antarctic starfish of the family Asteriidae, which is the subject of this report, we have isolated a structurally novel steroid exhibiting 7-membered 5- oxalactone B-ring, along with the corresponding 6-oxo steroids. The starfish, Asteriidae family, was collected in Tethis Bay during the Italian-Antarctic expedition in January 1990 at a depth of 50-100 mt. The starfish (500 g fresh) was extracted with water and then with acetone; from the aqueous extract the sulphated steroids and steroidal glycosides were recovered by passing it through a column of Amberlite, washing out salts with distilled water, and eluting the absorbed material with methanol. The acetone extracts were solvent partitioned between water and n-butanol. The combined methanol eluate and n-butanol soluble material, were separated by sequential application of gel permeation on Sephadex LH- 60, DCCC and HPLC, to give the sulphated steroids 1-3, in small amounts, ranging from 7.2 mg of 1 (major) to 3.4 mg of 3 (minor). |
| Databáze: | OpenAIRE |
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