Planar Chromatography of Cholic Acid-Derived cis-trans Isomeric bis-Steroidal Tetraoxanes
Apstrakt
Seven pairs of cis-trans isomers of bis-steroidal tetraoxanes have been examined by both normal-phase (NP) and reversed-phase (RP) planar chromatography. Unmodified silica gel was used with ethyl acetate-toluene and ethyl acetate-petroleum ether as mobile phases in typical normal-phase systems. CN-silica with the mobile phases methanol-water and acetone-water and RP-18 silica with water-organic modifier (methanol, acetone, or dioxane) mobile phases were used as reversed-phase systems. For the RP systems a good linear correlation was established between R(M) values and amount ([%] v/v) of organic modifier in the mobile phase (usually r gt 0.99). It was found that under both NP and RP conditions cis isomers were more weakly retained than the corresponding trans isomers. The only exception to this was the chromatographic behavior of C(24) methyl esters. It was established that increasing the polarity of substituents at C(24) and C(24a) led to stronger retention in NP systems, i.e. weake...r retention in RP systems. Highly selective separation was achieved in all the chromatographic systems investigated. Possible separation mechanisms are discussed on the basis of the results obtained.
Ključne reči:
Planar chromatography / cis-trans Isomers / bis-Steroidal tetraoxanes / Separation mechanismsIzvor:
Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography, 2009, 22, 3, 175-181Izdavač:
- Research Inst Medicinal Plants, Budakalasz
Finansiranje / projekti:
- Peroksidni antimalarici i njihove himere sa hinolinima: sinteza i biološka aktivnost (RS-MESTD-MPN2006-2010-142022)
DOI: 10.1556/JPC.22.2009.3.3
ISSN: 0933-4173
WoS: 000267615000003
Scopus: 2-s2.0-67650681846
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Šegan, Sandra B. AU - Opsenica, Dejan M. AU - Šolaja, Bogdan A. AU - Milojković-Opsenica, Dušanka PY - 2009 UR - https://cherry.chem.bg.ac.rs/handle/123456789/995 AB - Seven pairs of cis-trans isomers of bis-steroidal tetraoxanes have been examined by both normal-phase (NP) and reversed-phase (RP) planar chromatography. Unmodified silica gel was used with ethyl acetate-toluene and ethyl acetate-petroleum ether as mobile phases in typical normal-phase systems. CN-silica with the mobile phases methanol-water and acetone-water and RP-18 silica with water-organic modifier (methanol, acetone, or dioxane) mobile phases were used as reversed-phase systems. For the RP systems a good linear correlation was established between R(M) values and amount ([%] v/v) of organic modifier in the mobile phase (usually r gt 0.99). It was found that under both NP and RP conditions cis isomers were more weakly retained than the corresponding trans isomers. The only exception to this was the chromatographic behavior of C(24) methyl esters. It was established that increasing the polarity of substituents at C(24) and C(24a) led to stronger retention in NP systems, i.e. weaker retention in RP systems. Highly selective separation was achieved in all the chromatographic systems investigated. Possible separation mechanisms are discussed on the basis of the results obtained. PB - Research Inst Medicinal Plants, Budakalasz T2 - Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography T1 - Planar Chromatography of Cholic Acid-Derived cis-trans Isomeric bis-Steroidal Tetraoxanes VL - 22 IS - 3 SP - 175 EP - 181 DO - 10.1556/JPC.22.2009.3.3 ER -
@article{ author = "Šegan, Sandra B. and Opsenica, Dejan M. and Šolaja, Bogdan A. and Milojković-Opsenica, Dušanka", year = "2009", abstract = "Seven pairs of cis-trans isomers of bis-steroidal tetraoxanes have been examined by both normal-phase (NP) and reversed-phase (RP) planar chromatography. Unmodified silica gel was used with ethyl acetate-toluene and ethyl acetate-petroleum ether as mobile phases in typical normal-phase systems. CN-silica with the mobile phases methanol-water and acetone-water and RP-18 silica with water-organic modifier (methanol, acetone, or dioxane) mobile phases were used as reversed-phase systems. For the RP systems a good linear correlation was established between R(M) values and amount ([%] v/v) of organic modifier in the mobile phase (usually r gt 0.99). It was found that under both NP and RP conditions cis isomers were more weakly retained than the corresponding trans isomers. The only exception to this was the chromatographic behavior of C(24) methyl esters. It was established that increasing the polarity of substituents at C(24) and C(24a) led to stronger retention in NP systems, i.e. weaker retention in RP systems. Highly selective separation was achieved in all the chromatographic systems investigated. Possible separation mechanisms are discussed on the basis of the results obtained.", publisher = "Research Inst Medicinal Plants, Budakalasz", journal = "Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography", title = "Planar Chromatography of Cholic Acid-Derived cis-trans Isomeric bis-Steroidal Tetraoxanes", volume = "22", number = "3", pages = "175-181", doi = "10.1556/JPC.22.2009.3.3" }
Šegan, S. B., Opsenica, D. M., Šolaja, B. A.,& Milojković-Opsenica, D.. (2009). Planar Chromatography of Cholic Acid-Derived cis-trans Isomeric bis-Steroidal Tetraoxanes. in Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography Research Inst Medicinal Plants, Budakalasz., 22(3), 175-181. https://doi.org/10.1556/JPC.22.2009.3.3
Šegan SB, Opsenica DM, Šolaja BA, Milojković-Opsenica D. Planar Chromatography of Cholic Acid-Derived cis-trans Isomeric bis-Steroidal Tetraoxanes. in Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography. 2009;22(3):175-181. doi:10.1556/JPC.22.2009.3.3 .
Šegan, Sandra B., Opsenica, Dejan M., Šolaja, Bogdan A., Milojković-Opsenica, Dušanka, "Planar Chromatography of Cholic Acid-Derived cis-trans Isomeric bis-Steroidal Tetraoxanes" in Journal of Planar Chromatography: Modern TLC / Thin Layer Chromatography, 22, no. 3 (2009):175-181, https://doi.org/10.1556/JPC.22.2009.3.3 . .