Two New Compounds and Anti-complementary Constituents from Amomum tsao-ko

Abstract

Two new compounds, (2R,3R,4R)–3′,5′-dimethoxy-3,4,7,4′-tetrahydroxy-flavan (1) and 2-(4-hydroxy-3-methoxybenzoyl)-4-methoxy-benzaldehyde (2), together with 35 known phenolic compounds were obtained from the fruits of Amomum tsao-ko. Structures of the new compounds were elucidated on the basis of spectroscopic means, including 2D NMR, and high-resolution MS analysis. The isolated compounds were tested in vitro for their complement-inhibitory properties against the classical pathway (CP) and alternative pathway (AP). The results showed that 14 compounds exhibited anti-complementary activities against the CP and AP with CH₅₀ values of 0.42 - 4.43 mM and AP₅₀ values of 0.53 −1.51 mM. Preliminary mechanism studies showed that 1,7-bis(4-hydroxyphenyl)–4(E)-hepten-3-one (8) blocked C1q, C2, C3, C4, C5 and C9 components of the complement system, and hydroquinone (15) acted on C1q, C2, C3, C5 and C9 components.