Abstract
Two new indole alkaloids, hainanerectamines A (1) and B (2), and one new β-carboline alkaloids, hainanerectamines C (4), along with five known related alkaloids (3, 5–8), have been isolated from the Hainan marine sponge Hyrtios erecta. The structures of new compounds 1, 2 and 4 were determined by detailed analysis of their 1D and 2D NMR spectra and by comparison of their spectroscopic data with those of related model compounds. Compounds 2–4 exhibited moderate inhibitory activity against Aurora A, a member of serine/threonine kinase family involving in the regulation of cell division and a new target in cancer treatment, with IC50 values of 24.5, 13.6, and 18.6 μg/mL, respectively.
Highlights
Marine sponges of the genus Hyrtios (Family Thorectidae, Order Dictyoceratida) have proven to be a rich source of bioactive secondary metabolites, including terpenoids [1,2,3,4,5], macrolides [6,7,8,9,10], and tryptamine-derived alkaloids [11,12,13]
The known alkaloids except for 3 were readily identified as 5-hydroxyindole-3-carbaldehyde (5) [11], 5-hydroxyindole-3-carboxylic acid (6) [25], 5-hydroxy-3-(2-hydroxyethyl)-indole (7) [13], and 5-hydroxytryptophan (8) [25], respectively, by analysis of their NMR data and by comparison with the data reported in the literature
Compounds 1–8 were evaluated for their inhibitory activity against Aurora A, a member of serine/threonine kinase family involving in the regulation of cell division and a new target in cancer treatment [33,34,35]
Summary
Marine sponges of the genus Hyrtios (Family Thorectidae, Order Dictyoceratida) have proven to be a rich source of bioactive secondary metabolites, including terpenoids [1,2,3,4,5], macrolides [6,7,8,9,10], and tryptamine-derived alkaloids [11,12,13]. In our previous paper [14], we reported the isolation of several sesterterpenes including five new ones, hyrtiosins A–E, and two well-known sesterterpenes hyrtiosal [15,16] and scalaradial [17,18,19] from the title sponge. While scalaradial was found for the first time to be a secretory phospholipase A2 inhibitor [23,24] These findings stimulated our interest to search for more structurally unique and biologically active substances from the sponge. Dragendorff positive compounds, of which three are new, named hainanerectamines A–C (1, 2, 4), along with five known related indole alkaloids (3, 5–8) (Chart 1), were isolated. This paper describes the isolation and structure elucidation of these new compounds.
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