Lacinilene C methyl ether

Small airway constriction and recruitment of leukocytes on pulmonary surfaces are prominent, documented responses to the inhalation of cotton dust. Currently, one or both of these effects are generally ascribed to endotoxin (8-10), to antigen-antibody reactions (11), to lacinilene C-7 methyl ether (1, 13), to a low molecular weight ( 1000 daltons), neutral, highly water soluble substance that is stable in boiling water and found in cotton bracts (14), to chemotaxins present in cotton mill dust extracts (15, 16) or to histamine releasing substances (17). 

Intermediate for the 58 total synthesis of lacinilene C-7 methyl ether... 

Hernandezine (=Thalicsimine Thaliximine) (bisbenzylisoquinoline) Lacinilene C 7-methyl ether (sesquiterpene)... 

Aflatoxin Bj is the most potent carcinogenic known substance occurring naturally. Interestingly enough 3-methyl-2-butanol is one of the main characteristic odors of living colonies of A. flavus. As an illustration of the complexity of these interactions it may be mentioned that treating cotton leaves with cell-free extracts of A. flavus induces five phytoalexins (lacinilene C, lacinilene C 7-methyl ether, scopoletin, 2-hydroxy-7-methoxycadalene, and 2,7-dihydroxycadalene) in the leaves (135). 

Scheme 7. Five phytoalexins, lacinilene C [1], lacinilene C 7-methyl ether [2], scopoletin [3], 2-hydroxy-7-methoxycadalene [4], and 2,7 dihydroxycadalene [5]) induced by A. flavus in cotton leaves. The antibiotic cortalcerone [6] is induced in the fungus Corticium caeruleum by various stimuli.

Fig. 2. Structures and biochemical relationships of 2,7-dihydroxycadalene, 2-hydroxy-7-methoxycadalene, lacinilene C, and lacinilene C methyl ether.

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