Drymariamides A–J, Antiadipogenic Cyclopeptides Incorporating Noncanonical Amino Acids from <i>Drymaria cordata</i>
Zongyi Zhang, Xinhua Gao, Yi Huang, Yao‐Yue Fan, Jian‐Min Yue
Abstract
Herein, we report an extensive phytochemical study on the whole plant of Drymaria cordata, which led to the isolation of ten new orbitides, named drymariamides A–J ( 1 – 10 ). Compounds 2, 3, and 5 incorporate rare residues of noncanonical amino acids of kynurenine (Kyn) or 3a-hydroxypyrroloindoline (HPI). Their structures with absolute configurations were elucidated by a combination of spectroscopic analysis, advanced Marfey’s method, X-ray diffraction, and electronic circular dichroism analysis. Compounds 1 – 10 exhibited antiadipogenic effects in 3T3-L1 adipocytes, and the most potent compound 7 showed an EC 50 value of 1.17 ± 0.19 μM.
Topics & Concepts
PhytochemicalStereochemistryChemistryOrganic chemistryBiochemistryPhytochemical compounds biological activitiesNatural product bioactivities and synthesisTraditional and Medicinal Uses of Annonaceae