The absolute configuration of (-)-3-hydroxy-alpha-calacorene.
3-Hydroxy-alpha-calacorene was identified in extracts from cold-shocked seedlings of cotton (Gossypium hirsutum L.) and kenaf (Hibiscus cannabinus L.), both of which are members of the Malvaceae family. (-)-3-Hydroxy-alpha-calacorene was isolated from Heterotheca inuloides Cass. (Asteraceae). HPLC on a chiral stationary phase column showed that the 3-hydroxy-alpha- calacorene from cotton and kenaf had the same relative configuration, while that from H. inuloides was of the opposite configuration. X-ray crystallographic analysis established the absolute configuration of the compound in H. inuloides as (8R)-(-)-3-hydroxy-alpha-calacorene.
Stipanovic
Robert D
RD
Southern Plains Agricultural Research Center, Agricultural Research Service, US Department of Agriculture, 2765 F&B Road, College Station, TX 77845, USA. rdstip@cpru.usda.gov
Puckhaber
Lorraine S
LS
Reibenspies
Joseph H
JH
Williams
Howard J
HJ
D019659:Asteraceae / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003368:Gossypium / Q000737:chemistry; D031584:Hibiscus / Q000737:chemistry; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification
C514265:3-hydroxy-alpha-calacorene; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes