Three new 19-membered macrolides, amphidinolides T2 (2), T3 (3), and T4 (4), structurally related
to amphidinolide T1 (1) have been isolated from two strains of marine dinoflagellates of the genus
Amphidinium. The structures of 2−4 were elucidated on the basis of spectroscopic data. The absolute
configurations at C-7, C-8, and C-10 of 1−4 were determined by comparison of NMR data of their
C-1−C-12 segments with those of synthetic model compounds for the tetrahydrofuran portion. The
biosynthetic origins of amphidinolide T1 (1) were investigated on the basis of 13C NMR data of a
13C enriched sample obtained by feeding experiments with [1-13C], [2-13C], and [1,2-13C2] sodium
acetates and 13C-labeled sodium bicarbonate in the cultures of the dinoflagellate. These incorporation
patterns suggested that amphidinolide T1 (1) was generated from four successive polyketide chains,
an isolated C1 unit formed from C-2 of acetates, and three unusual C2 units derived only from C-2
of acetates. Furthermore, it is noted that five oxygenated carbons of C-1, C-7, C-12, C-13, and C-18
were not derived from the C-1 carbonyl, but from the C-2 methyl of acetates.