Modulation of lipoxygenase activity by bacterial hopanoids.

Tetrahydroxybacteriohopane (1), a bacterial hopanoid, inhibited soybean 15-lipoxygenase with an IC50 of about 10 microM. After per-O-acetylation of 1 no inhibition of the 15-lipoxygenase was observed. Two other bacterial hopanoids, tetrahydroxybacteriohopane glucosamine (2) and tetrahydroxybacteriohopane ether (3), stimulated the activity of soybean 15-lipoxygenase. The activities of two other arachidonic acid-metabolizing enzymes, human 5-lipoxygenase and prostaglandin H synthase, were unaffected by 1.