Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: June 17, 2004
Publication Date: September 1, 2004
Citation: Puckhaber, L.S., Stipanovic, R.D. 2004. Thespesenone and dehydrooxoperezinone-6-methyl ether, new sesquiterpene quinones from Thespesia populnea. Journal of Natural Products. 67(9):1571-1573. Interpretive Summary: Cotton plants produce various types of chemicals when they are attacked by disease causing organisms. These compounds are often toxic to the disease causing organisms, and thus help protect the plant from attack. Compounds related to those produced by cotton plants are also produced by a small tree that grows in Hawaii, Thespesia populnea. We are interested in determining the toxicity of the compounds in the Hawaiian tree to these organisms as compared to those produced in cotton plants. While we were separating the compounds that had previously been found in the tree, we discovered two new chemicals that had not previously been found in nature. In this paper, we report the chemical structures for these new compounds. The discovery of these compounds is the first step in determining the toxicity of these compounds to disease causing organisms.
Technical Abstract: Thespesia populnea is a small tree or large shrub that occurs throughout Polynesia. We now report the isolation of 7-hydroxycadalene (10), thespesenone (1) and dehydrooxoperezinone-6-methyl ether (6) from its red heartwood. Compounds (1) and (6) are reported for the first time in nature. The 13C-NMR spectra of mansonone D (4), mansonone G (3), mansonone M (5), and thespesone (2) are reported for the first time.