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 | |
| State | Published - Jul 2007 |
| Externally published | Yes |
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Keywords
- African mahogany
- Configuration
- Crystal structure
- Direct method
- Khaya senegalensis
- Khayanone
- Limonoid
- Meliaceae
- Mexicanolide
ASJC Scopus subject areas
- Spectroscopy
- Condensed Matter Physics
- Structural Biology
Cite this
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, 07.2007, p. 463-467.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 6S,8α-dihydroxy-14,15-dihydrocarapin (Khayanone) from the stem bark of Khaya senegalensis (Meliaceae)
T2 - Isolation and its crystal structure
AU - Zhang, Huaping
AU - Vanderveer, Don
AU - Wang, Xi
AU - Chen, Feng
AU - Androulakis, Xiao M.
AU - Wargovich, Michael J
PY - 2007/7
Y1 - 2007/7
N2 - 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.
AB - 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.
KW - African mahogany
KW - Configuration
KW - Crystal structure
KW - Direct method
KW - Khaya senegalensis
KW - Khayanone
KW - Limonoid
KW - Meliaceae
KW - Mexicanolide
UR - http://www.scopus.com/inward/record.url?scp=34347247290&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34347247290&partnerID=8YFLogxK
U2 - 10.1007/s10870-007-9193-x
DO - 10.1007/s10870-007-9193-x
M3 - Article
VL - 37
SP - 463
EP - 467
JO - Journal of Crystallographic and Spectroscopic Research
JF - Journal of Crystallographic and Spectroscopic Research
SN - 0277-8068
IS - 7
ER -