Antiviral naphthoquinone compounds, compositions and uses thereof

A method of isolating an antiretroviral naphthoquinone or antiretroviral derivative thereof from a plant of the genus Conospermum, which method comprises the steps of:

• (a) extracting dried plant material with an organic solvent to obtain a crude extract, and
• (b) isolating an active antiretroviral naphthoquinone from said crude extract by:
• (i) solvent-solvent partitioning said crude extract to obtain an antiretroviral active fraction,
• (ii) subjecting said active fraction to centrifugal countercurrent chromatography to obtain an enriched antiretroviral active fraction,
• (iii) subjecting said enriched active fraction to low pressure column chromatography and/or gel permeation chromatography to obtain a crude, semipure antiretroviral active compound, and
• (iv) subjecting said semipure active compound to HPLC to obtain an antiretroviral active naphthoquinone in substantially pure form.

A method of synthesizing a trimeric naphthoquinone selected from the group consisting of ##STR10## wherein R.sub.1 -R.sub.12 are the same or different, and each may be H, a C.sub.1 -C.sub.10 straight-chain or branched-chain saturated or unsaturated alkyl, an aryl, OCH.sub.3, or OH;

• and a derivative thereof;
• which method comprises the steps of:
• (a) acid- or base-catalyzed coupling an appropriately substituted or unsubstituted 2,3-deoxy-1,4-naphthoquinone compound with two other subunits, each of which may be the same or different and each of which may be an appropriately substituted or unsubstituted 3-hydroxy-1,4-naphthoquinone compound or 2-hydroxy-1,4-naphthoquinone compound, to yield a corresponding trimeric naphthoquinone compound, and
• (b) purifying, to a substantially pure form, said trimeric naphthoquinone.

A method of synthesizing a trimeric naphthoquinone selected from the group consisting of:

• ##STR11## wherein each of R.sub.1 -R.sub.4 are the same or different and each may be H, a C.sub.1 -C.sub.10 straight-chain or branched-chain saturated or unsaturated alkyl, an aryl, OCH.sub.3, or OH;
• and R.sub.5 -R.sub.12 are the same or different, and each may be a C.sub.1 -C.sub.10 straight-chain or branched-chain unsaturated alkyl, a C.sub.1 -C.sub.10 branched-chain alkyl, an aryl, OCH.sub.3, or OH;
• and a derivative thereof;
• which method comprises the steps of:
• (a) acid- or base-catalyzed coupling an appropriately substituted or unsubstituted 2,3-deoxy-1,4-naphthoquinone compound with two other subunits, each of which may be the same or different and each of which may be an appropriately substituted or unsubstituted 3-hydroxy-1,4naphthoquinone compound or 2-hydroxy-1,4-naphthoquinone compound, to yield a corresponding trimeric naphthoquinone compound, and
• (b) purifying, to a substantially pure form, said trimeric naphthoquinone.