Revision of the absolute configurations of bethosides B and C and their aglycone

Journal of Organic Chemistry

Volumn 76, Issue 17, 2011, Pages 7275-7280

  Challinor, Victoria L ^a   Hayes, Patricia Y ^a   Bernhardt, Paul V ^a   Kitching, William ^a   Lehmann, Reginald P ^b   De Voss, James J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

^b Integria Healthcare   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ABSOLUTE STEREOCHEMISTRY; AGLYCONES; SPECTRAL CHARACTERIZATION; STEROIDAL SAPONINS; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

SPECTRUM ANALYZERS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

METABOLITES;

3BETA,11ALPHA,16BETA,22,26 PENTAACETOXYCHOLEST 5 ENE; 3BETA,11ALPHA,22,26 TETRAACETOXY 16BETA HYDROXYCHOLEST 5 ENE; 3BETA,16BETA,22,26 TETRAACETOXYCHOLEST 5 ENE; 3BETA,16BETA,22,26 TETRAHYDROXYCHOLEST 5 ENE; 3BETA,16BETA,26 TRIACETOXY 22 HYDROXYCHOLEST 5 ENE; AGLYCONE; BETHOSIDE B; BETHOSIDE C; SAPONIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; HETERONUCLEAR MULTIPLE BOND CORRELATION; PHYTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ALCOHOLS; CRYSTALLOGRAPHY, X-RAY; GLYCOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHYTOSTEROLS; SAPONINS; STEREOISOMERISM;

EID: 80052148181     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2012797     Document Type: Article

References (15)

1. Sparg, S. G.; Light, M. E.; van Staden, J. J. Ethnopharmacol. 2004, 94, 219-243
2. Challinor, V. L.; Stuthe, J. M. U.; Bernhardt, P. V.; Lehmann, R. P.; Kitching, W.; De Voss, J. J. J. Nat. Prod. 2011, 74, 1557-1560
3. Yahara, S.; Ohtsuka, M.; Nakano, K.; Nohara, T. Chem. Pharm. Bull. 1989, 37, 1802-1804
4. Zhu, X. H.; Tsumagari, H.; Honbu, T.; Ikeda, T.; Ono, M.; Nohara, T. Tetrahedron Lett. 2001, 42, 8043-8046
5. Sang, S. M.; Mao, S. L.; Lao, A. N.; Chen, Z. L.; Ho, C. T. Food Chem. 2003, 83, 499-506
6. Hayes, P. Y.; Lehmann, R.; Penman, K.; Kitching, W.; De Voss, J. J. Phytochemistry 2009, 70, 105-113
7. Hooft, R. W. W.; Straver, L. H.; Spek, A. L. J. Appl. Crystallogr. 2008, 41, 96-103
8. Fernandez-Herrera, M. A.; Sandoval-Ramirez, J.; Meza-Reyes, S.; Montiel-Smith, S. J. Mex. Chem. Soc. 2009, 53, 126-130
9. Fernandez-Herrera, M. A.; Lopez-Munoz, H.; Hernandez-Vazquez, J. M. V.; Lopez-Davila, M.; Escobar-Sanchez, M. L.; Sanchez-Sanchez, L.; Pinto, B. M.; Sandoval-Ramirez, J. Bioorg. Med. Chem. 2010, 18, 2474-2484
10. Noda, N.; Kogetsu, H.; Kawasaki, T.; Miyahara, K. Phytochemistry 1990, 29, 3565-3569
11. Kotowicz, C.; Hernandez, L. R.; Cerda-Garcia-Rojas, C. M.; Villecco, M. B.; Catalan, C. A. N.; Joseph-Nathan, P. J. Nat. Prod. 2001, 64, 1326-1331
12. Wang, H.; Guo, Y.; Guan, Y.; Zhou, L.; Lei, P. Steroids 2011, 76, 18-27
13. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, A64, 112-122
14. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565
15. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838