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

Research output: Contribution to journal › Article › peer-review

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 2007
Externally published	Yes

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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10.1007/s10870-007-9193-x

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

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.",

keywords = "African mahogany, Configuration, Crystal structure, Direct method, Khaya senegalensis, Khayanone, Limonoid, Meliaceae, Mexicanolide",

author = "Huaping Zhang and Don Vanderveer and Xi Wang and Feng Chen and Androulakis, {Xiao M.} and Wargovich, {Michael J.}",

note = "Funding Information: Acknowledgement The authors are grateful to the financial support from South Carolina Nutrition Research Consortium and a grant from National Institutes of Health, R21CA107138.",

year = "2007",

month = jul,

doi = "10.1007/s10870-007-9193-x",

language = "English (US)",

volume = "37",

pages = "463--467",

journal = "Journal of Crystallographic and Spectroscopic Research",

issn = "0277-8068",

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number = "7",

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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.

N1 - Funding Information: Acknowledgement The authors are grateful to the financial support from South Carolina Nutrition Research Consortium and a grant from National Institutes of Health, R21CA107138.

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

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JO - Journal of Crystallographic and Spectroscopic Research

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SN - 0277-8068

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ER -

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

Abstract

Keywords

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