Onnamide F:  A New Nematocide from a Southern Australian Marine Sponge, Trachycladus laevispirulifer

Abstract

A southern Australian marine sponge, Trachycladus laevispirulifer, has yielded a potent new nematocide with antifungal activity which has been identified as onnamide F (1). The structure for 1 was assigned by detailed spectroscopic analysis and chemical conversion to the methyl ester 2. Onnamide F contains a common structural motif previously described in a number of natural products exhibiting interesting pharmacological activities, including the insect chemical defense agent pederin (3), and the sponge metabolites the onnamides, mycalamides, and theopederins.

Biosynthesis of polyketides by trans-AT polyketide synthases

“…100,[173][174][175][176][177][178] Structurally, they are remarkably similar to pederin 26, discussed above, and many compounds exhibit similarly potent cytotoxicities. However, unlike 26 they do not appear to exert any dermatotoxic effects.…”

The Influence of Brazilian Biodiversity on Searching for Human Use Pharmaceuticals

“…However, to bring the full story to its climax, one has to return to the marine environment, as in the years from 1988 to early 2000, a significant number of sponge extracts produced molecules such as the onnamides, with onnamide F being an example (15), 30 and theopederins such as K and L (16,17). 31 Then, in 2002, Kellner 32 identified the endosymbiont as a very close relative to Pseudomonas aeruginosa and showed that interspecific transmission of the endosymbionts was related to the different genetic makeup of individual isolates.…”

Cytotoxic Polyketides from the Marine Sponge Discodermia calyx

“…A signal at δ C 158.0 was assigned as a guanidine carbon of arginine, and this analysis confirmed close relationship with the bioactive metabolites known as theopederins, [12][13][14] mycalamides, [15][16][17][18] and onnamides. [19][20][21][22] (Fig. 2).…”

“…14 (subclass Tetractinomorpha, order Lithistida, family Theonellidae), and Trachycladus laevispiralifer (subclass Tetractinomorpha, order Axinellida, family Spirastrellidae). 22 Reports on isolation of pederin class of compounds from taxonomically distant organisms indicate the possible microbial origin of the compounds.…”