Abstract
7a-Hydroxyroyleanone is a bioactive diterpene isolated from leaves of Tetradenia riparia, active against tuberculosis and T. cruzi. In order to use this compound as starting material for the synthesis of compounds with enhanced bioactivity we aimed the dehydration of the 7-alpha-hydroxyl group of royleanone. The reaction performed in acetic acid and hydrochloric acid under reflux gave an unexpected chlorinated naphtoquinone, with aromatization and opening of one of the rings of the starting material, as major product, besides 6,7-dehydroroyleanone and a complex mixture of other products. The reaction products were purified by high-speed countercurrent chromatography with hexane-acetonitrile 1:1. Compounds were tested for their anti-leishmanial activity (L. amazonensis) pointing out a potential leishmanicidal agent which may favor the development of more effective therapies.
Highlights
The benzoquinone 7α-hydroxyroyleanone (1) is a bioactive diterpene from leaves of Tetradenia riparia (Hochstetter) Codd, a member of the family Lamiaceae
The reaction was performed in acetic acid and hydrochloric acid under reflux for 2 h, giving an unexpected chlorinated product (2), with aromatization and opening of one of the rings of the starting material, as major product, besides 6,7-dehydroroyleanone (3), and a complex mixture of other products (Figure 1)
The reaction products were purified by high-speed countercurrent chromatography (HSCCC) (Figure S1, Supplementary Information (SI) section)
Summary
The benzoquinone 7α-hydroxyroyleanone (1) is a bioactive diterpene from leaves of Tetradenia riparia (Hochstetter) Codd, a member of the family Lamiaceae. The reaction product was read at 450 nm after 3 h, and results were expressed in percentage of viable promastigotes compared to untreated control.
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