6S,8α-dihydroxy-14,15-dihydrocarapin (Khayanone) from the stem bark of Khaya senegalensis (Meliaceae): Isolation and its crystal structure

Huaping Zhang; Don Vanderveer; Xi Wang; Feng Chen; Xiao M. Androulakis; Michael J. Wargovich

doi:10.1007/s10870-007-9193-x

6S,8α-dihydroxy-14,15-dihydrocarapin (Khayanone) from the stem bark of Khaya senegalensis (Meliaceae): Isolation and its crystal structure

Huaping Zhang, Don Vanderveer, Xi Wang, Feng Chen, Xiao M. Androulakis, Michael J. Wargovich

Molecular Medicine

Research output: Contribution to journal › Article

4 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	463-467
Number of pages	5
Journal	Journal of Chemical Crystallography
Volume	37
Issue number	7
DOIs	https://doi.org/10.1007/s10870-007-9193-x
State	Published - Jul 1 2007

Keywords

African mahogany
Configuration
Crystal structure
Direct method
Khaya senegalensis
Khayanone
Limonoid
Meliaceae
Mexicanolide

ASJC Scopus subject areas

Chemistry(all)
Condensed Matter Physics

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Zhang, H., Vanderveer, D., Wang, X., Chen, F., Androulakis, X. M., & Wargovich, M. J. (2007). 6S,8α-dihydroxy-14,15-dihydrocarapin (Khayanone) from the stem bark of Khaya senegalensis (Meliaceae): Isolation and its crystal structure. Journal of Chemical Crystallography, 37(7), 463-467. https://doi.org/10.1007/s10870-007-9193-x

6S,8α-dihydroxy-14,15-dihydrocarapin (Khayanone) from the stem bark of Khaya senegalensis (Meliaceae) : Isolation and its crystal structure. / Zhang, Huaping; Vanderveer, Don; Wang, Xi; Chen, Feng; Androulakis, Xiao M.; Wargovich, Michael J.

In: Journal of Chemical Crystallography, Vol. 37, No. 7, 01.07.2007, p. 463-467.

Research output: Contribution to journal › Article

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abstract = "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) {\AA}, c = 29.118(6) {\AA}, 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.",

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