ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The tropical green seaweed Caulerpa taxifolia (VAHL) C. AGARDH (Caulerpales) which is invading the Mediterranean is shown to contain trace amounts of two further novel terpenes, 7,7-C-didehydro-6-hydroxy-6,7-dihydrocaulerpenyne (= (4S, 6S,1E)-3-[(Z)-acetoxymethylidene]-6-hydroxy-11-methyl-7-methylidenedodeca-1,10-dien-8-yne-1,4-diyl diacetate; 3a) and taxifolione (= 6-methylhept-5-en-3-yn-2-one; 4). The former is the most active of the toxins so far isolated from this seaweed, both as an in vitro inhibitor of the growth of marine bacteria and as a cytotoxic agent toward marine ciliate protists. This suggests a central ecotoxicological role for triacetate 3a as an adjuvant factor in the invasion of the Mediterranean by this seaweed. Moreover, the almost equally toxic 10,11 -epoxycaulerpenyne (2) which is scarcely available from Nature for bioassays can now be obtained by peroxy-acid epoxidation of caulerpenyne (1), along with the 6,7-epoxycaulerpenynes 6b and 6a. The latter are very labile, 6a giving triacetate 3a, suggesting epoxides to be late biogenetic intermediates in C. taxifolia.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19930760209
