Kinmoonosides A−C, Three New Cytotoxic Saponins from the Fruits of Acacia concinna, a Medicinal Plant Collected in Myanmar

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Abstract
Three genuine saponins, named kinmoonosides A−C (1−3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A−C were elucidated on the basis of spectral analysis as 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6R,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinovopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (1); 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-{(6S,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2‘E)-6‘-hydroxyl-2‘-hydroxymethyl-6‘-methyl-2‘,7‘-octadienoyl-β-d-quinobopyranosyl]-2,7-octadienoyl}acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (2); and 3-O-{α-l-arabinopyranosyl(1→6)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl}-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]acacic acid 28-O-α-l-arabinofuranosyl(1→4)-[β-d-glucopyranosyl(1→3)]-α-l-rhamnopyranosyl(1→2)-β-d-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl]-d-quinovopyranose. Compounds 1−3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.