Cytotoxic annonaceous acetogenins from annona muricata

Annonaceous acetogenins substantially pure compounds having the structures a-g.

• a. muricin A having formula as:
• 2
• wherein the muricin a having an α,β-unsaturated γ-lactone with a hydroxyl group at C-4 position, a mono-THF ring placed between C-15 and C-18 with one flanking hydroxyl in a threo conformation, two methylene groups of the mono-thf ring corresponding to trans conformation, two hydroxyl groups at C-26 and C-27 as vicinal diol assigned as threo based, and the stereochemistry at C-34 on the γ-lactone fragment performed in (s)-configuration:
• b. muricin B having formula as:
• 3
• wherein the muricin B having an α, β-unsaturated 65 -lactone with a hydroxyl group at C-4 position, a mono-THF ring placed between C-15 and C-18 with one flanking hydroxyl in a trans/threo conformation, two methylene groups of the mono-THF ring corresponding to trans conformation, two hydroxyl groups at C-26 and C-27 as vicinal diol assigned as threo based, and the stereochemistry at C-34 on the γ-lactone fragment performed in (S)-configuration.
• c. muricin C having formula:
• 4
• wherein the muricin C having an α,β-unsaturated γ-lactone with a hydroxyl group at C-4 position, a mono-THF ring placed between C-17 and C-20 with one flanking hydroxyl in trans/threo or threo/trans conformation, two hydroxyl groups at C-24 and C-25 as vicinal diol assigned as threo based, and the stereochemistry at C-34 on the γ-lactone fragment performed in (S)-configuration.
• d. muricin D having formula:
• 5
• wherein the muricin D having an α,β-unsaturated γ-lactone with a hydroxyl group at C-4 position, a mono-THF ring placed between C-15 and C-18 with one flanking hydroxyl in threo/trans conformation, two hydroxyl groups at C-22 and C-23 as vicinal diol assigned as threo based.
• e. muricin E having formula:
• 6
• wherein the muricin E having an α,β-unsaturated γ-lactone with a hydroxyl group at C-4 position, a mono-THF ring placed between C-12 and C-15 with one flanking hydroxyl in threo/trans conformation, two hydroxyl groups at C-22 and C-23 as vicinal diol assigned as threo based.
• f. muricin F having formula:
• 7
• wherein the muricin F having an α,β-unsaturated γ-lactone with a hydroxyl group at C-4 position, a mono-THF ring placed between C-17 and C-20 with one flanking hydroxyl in threo/trans conformation, two hydroxyl groups at C-27 and C-28 as vicinal diol assigned as threo based, and a double bond determined at C-24/C-25.
• g. muricin G having formula:
• 8
• wherein the muricin G having an α,β-unsaturated γ-lactone with a hydroxyl group at C-4 position, a mono-THF ring placed between C-16 and C-19 with one flanking hydroxyl in threo/trans/threo conformation, one hydroxyl groups formed at C-10, a double bond determined at C-23/C-24, and the stereochemistry at C-34 on the γ-lactone fragment performed in (S)-configuration.