ARS | Publication request: ABSOLUTE CONFIGURATION OF (-)-3-HYDROXY-ALPHA-CALACORENE

Submitted to: Phytochemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: November 3, 2006
Publication Date: November 15, 2006
Citation: Stipanovic, R.D., Puckhaber, L.S., Reibenspies, J.H., Williams, H.J. 2006. Absolute configuration of (-)-3-hydroxy-alpha-calacorene. Phytochemistry. 67:1304-1308.

Interpretive Summary: Lacinilene C is a compound that occurs naturally in the cotton plant. It helps protect the plant from disease. It is not known how it is synthesized in the plant. If this were known, it might be possible to alter the genetic character of the plant such that new compounds were produced that would make the plant more resistant to pathogens. We have shown that cotton and other plants related to cotton have a common intermediate that leads to lacinilene C. Some of these plants are more resistant to pathogens than cotton, and the compounds they produce are more toxic to plant pathogens. Thus, it might be possible to genetically alter cotton such that it would produce the more toxic compounds. If this were accomplished, losses to cotton diseases would be reduced.

Technical Abstract: 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. HPLC on a column with a chiral stationary phase 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.