caa a22 4500 463184319 CHVBK 20180406164848.0 cr unu---uuuuu 170326e20070701xx s 000 0 eng 10.1007/s10870-007-9193-x doi (NATIONALLICENCE)springer-10.1007/s10870-007-9193-x 6 S ,8α-Dihydroxy-14,15-Dihydrocarapin (Khayanone) from the Stem Bark of Khaya Senegalensis (Meliaceae): Isolation and its Crystal Structure [Elektronische Daten] [Huaping Zhang, Don VanDerveer, Xi Wang, Feng Chen, Xiao Androulakis, Michael Wargovich] Khayanone was isolated from the stem bark of African mahogany, Khaya senegalensis (Meliaceae), and characterized as 6S,8α-dihydroxy-14,15-dihydrocarapin on the basis of spectral analysis and single crystal X-ray diffraction study. The compound crystallizes in the tetragonal space group P4 1 2 1 2 with unit cell parameters: a=13.2315(19) Å, c=29.118(6) Å, Z=8. The crystal structure has been solved by direct methods and refined to R=0.0375 for 4552 unique reflections. The six-membered rings A and B exist in boat conformations, rings C and D in chair conformations, and the furan ring is planar. The crystal structure is stabilized by O-H···O and C-H···O interactions. This is the first report about 6S configuration of mexicanolide revealed by X-ray diffraction analysis. The configuration of oxygenated C-6 in mexicanolide-group limonoids is discussed. Springer Science+Business Media, LLC, 2007 Crystal structure nationallicence Direct method nationallicence African mahogany nationallicence Khaya senegalensis nationallicence Meliaceae nationallicence Limonoid nationallicence Mexicanolide nationallicence Khayanone nationallicence Configuration nationallicence Zhang Huaping Department of Food Science & Human Nutrition, Clemson University, 29634, Clemson, SC, USA aut VanDerveer Don Department of Chemistry, Clemson University, 29634, Clemson, SC, USA aut Wang Xi Department of Genetics and Biochemistry, Clemson University, 29634, Clemson, SC, USA aut Chen Feng Department of Food Science & Human Nutrition, Clemson University, 29634, Clemson, SC, USA aut Androulakis Xiao Department of Pathology and Microbiology, School of Medicine, University of South Carolina, South Carolina Cancer Center, 29208, Columbia, SC, USA aut Wargovich Michael Department of Pathology and Microbiology, School of Medicine, University of South Carolina, South Carolina Cancer Center, 29208, Columbia, SC, USA aut Journal of Chemical Crystallography Kluwer Academic Publishers-Plenum Publishers; http://www.springer-ny.com 37/7(2007-07-01), 463-467 1074-1542 37:7<463 2007 37 10870 https://doi.org/10.1007/s10870-007-9193-x text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10870-007-9193-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Zhang Huaping Department of Food Science & Human Nutrition, Clemson University, 29634, Clemson, SC, USA aut NATIONALLICENCE 700 1- VanDerveer Don Department of Chemistry, Clemson University, 29634, Clemson, SC, USA aut NATIONALLICENCE 700 1- Wang Xi Department of Genetics and Biochemistry, Clemson University, 29634, Clemson, SC, USA aut NATIONALLICENCE 700 1- Chen Feng Department of Food Science & Human Nutrition, Clemson University, 29634, Clemson, SC, USA aut NATIONALLICENCE 700 1- Androulakis Xiao Department of Pathology and Microbiology, School of Medicine, University of South Carolina, South Carolina Cancer Center, 29208, Columbia, SC, USA aut NATIONALLICENCE 700 1- Wargovich Michael Department of Pathology and Microbiology, School of Medicine, University of South Carolina, South Carolina Cancer Center, 29208, Columbia, SC, USA aut NATIONALLICENCE 773 0- Journal of Chemical Crystallography Kluwer Academic Publishers-Plenum Publishers; http://www.springer-ny.com 37/7(2007-07-01), 463-467 1074-1542 37:7<463 2007 37 10870 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer