Wegerski, C.J.; Sonnenschein, R.N.; Cabriales, F.; Valeriote, F.A.; Matainaho, T.; Crews, P. (2006). Stereochemical challenges in characterizing nitrogenous spiro-axane sesquiterpenes from the Indo-Pacific sponges Amorphinopsis and Axinyssa. Tetrahedron. 62(44): 10393-10399.

390076

10.1016/j.tet.2006.08.070 [view]

Wegerski, C.J.; Sonnenschein, R.N.; Cabriales, F.; Valeriote, F.A.; Matainaho, T.; Crews, P.

2006

62(44): 10393-10399

Publication

Available for editors   [request]

An investigation was conducted to identify the structures and bioactive properties of five compounds isolated from the Halichondrida sponges Amorphinopsis foetida and Axinyssa aplysinoides. All compounds possessed the spiro-axane sesquiterpene core and all were substituted at C-2 with nitrogen containing functionality. The stereochemistry of one known compound has been revised to (2R,5R,10S)-2-formamido-6-axene (3). It exhibited mild selective solid tumor and mild antibacterial activity and was found from Axinyssa. A second known substance whose stereochemistry has also been revised, (2R,5R,10S) 2-isothiocyanato-6-axene (4) plus its undescribed diastereomer (5) were isolated from Amorphinopsis. Both sponges were the source of two new N-phenethyl-2-formamido-6-axene diastereomeric compounds 6 and 7. No solid tumor or antibacterial activity was found for 4–7.

Biodiversity, Taxonomic and ecological diversity
Chemistry

Porifera

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