Achyrophenols A–F: Polycyclic Polyphenol Lactone Skeletons and a Nor-Ursane-Type Triterpenoid from Achyrocline Satureioides

Abstract

Two novel derivatives of 2-methyl-1-(2,3,4,6-tetra­hydroxy­phenyl)­propan-1-one and (S)-2-methyl-1-(2,3,4,6-tetra­hydroxy­phenyl)­butan-1-one (1 and 2), four novel six-membered lactone phenols (3–6), and a nor-ursane type triterpenoid (7) named Achroacid, were isolated from the aerial part of Achyrocline satureioides. The absolute configurations of 1–7 are presented by spectroscopic data and X-ray crystallographic analysis. A DP4plus evaluation was applied to determine the final stereochemistry for 1 and 2. The biosynthesis pathway of 1 and 2 was proposed. 1 has potential on anti-Gram-negative bacteria. Both 1 and 2 exhibited a significant impact on anti-H1299 cells. Compounds 3–7 showed moderate cancer cell lethality and significant anti-inflammatory activities.