Stingless Bee Propolis Components from South Sulawesi, Indonesia, Show Xanthine Oxidase Inhibitory Activity

Propolis Components from Stingless Bees Collected on South Sulawesi, Indonesia, and Their Xanthine Oxidase Inhibitory Activity

J. Nat. Prod., Publication Date (Web): February 5, 2019

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Three new compounds, namely, 4-(4′-hydroxy-3′-methoxyphenyl)-3,5,7-trihydroxycoumarin (1) and sulawesins A (2) and B (3), were isolated from the propolis of stingless bees (Tetragonula aff. biroi) collected on South Sulawesi, Indonesia.

In addition, five known compounds, glyasperin A, broussoflavonol F, (2S)-5,7-dihydroxy-4′-methoxy-8-prenylflavanone, (1′S)-2-trans,4-trans-abscisic acid, and (1′S)-2-cis,4-trans-abscisic acid, were identified. The structures of the new compounds were determined by a combination of methods that included mass spectrometry and NMR spectroscopy.

The absolute configuration of sulawesin A (2), a new podophyllotoxin derivative, was determined by X-ray crystallography. The absolute configuration of sulawesin B (3) was also determined by the ECD calculation. 4-(4′-Hydroxy-3′-methoxyphenyl)-3,5,7-trihydroxycoumarin (1) and sulawesin A (2) were examined for xanthine oxidase (XO) inhibitory activity; 1 exhibited XO inhibitory activity, with an IC50 value of 3.9 μM.