Abstract

Phytochemical investigation of the ethanol extract of underground parts of Iris tenuifolia Pall. afforded five new compounds; an unusual macrolide termed moniristenulide (1), 5-methoxy-6,7-methylenedioxy-4-O-2′-cycloflavan (2), 5,7,2′,3′-tetrahydroxyflavanone (3), 5-hydroxy-6,7-dimethoxyisoflavone-2′-O-β-d-glucopyranoside (9), 5,2′,3′-dihydroxy-6,7-dimethoxyisoflavone (10), along with seven known compounds (4–8, 11–12). The structures of all purified compounds were established by analysis of 1D and 2D NMR spectroscopy and HR-ESI-MS. The antimicrobial activity of the compounds 1–3, 5, 9, and 10 was investigated using the agar diffusion method against fungi, Gram-positive and Gram-negative bacteria. In consequence, new compound 3 was found to possess the highest antibacterial activity against Enterococcus faecalis VRE and Mycobacterium vaccae. Cell proliferation and cytotoxicity tests were also applied on all isolated compounds and plant crude extract in vitro with the result of potent inhibitory effect against leukemia cells. In particular, the newly discovered isoflavone 10 was active against both of the leukemia cells K-562 and THP-1 while 4–6 of the flavanone type compounds were active against only THP-1.

Highlights

  • Iris is a genus of the family Iridaceae that consists of about 360 species of perennial herbs and sub shrubs

  • All tested compounds possessed weak to moderate activity against vancomycin resistant (VRE) Enterococcus faecalis

  • Ultraviolet-visible (UV-Vis) data were extracted from diode array detector (DAD) data obtained during high performance liquid chromatography-electrospray ionization-high resolution mass spectrometry (HPLC-ESI-HRMS) experiments

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Summary

Introduction

Iris is a genus of the family Iridaceae that consists of about 360 species of perennial herbs and sub shrubs. Iris tenuifolia Pall., a characteristic plant of desert grasslands of Mongolia, is distributed in Mongol-Altai, Molecules 2021, 26, 6705 betic and molluscicidal activities [1,4,5,6,7]. Iris tenuifolia Pall., a characteristic plant of desert grasslands of Mongolia, is distribuEtaesdteirnnMMoonnggooll-iAa,ltEaai,sEtearsnteGrnobMi aonndgoGlioab, iE-AaslttearinpGroovbini caend[8G,9o].bTi-hAeltraoioptsroavnidncrehi[z8o,9m].eTshoef rIo. otetnsuainfodliarhairzeomallescoomf Im. toennulyifoulisaedaraesaall tcroamdimtioonnalyl MusoendgaosliaantramdeitdioicnianleMfoorntgreoalitamnemntedo-f ikciidnneefyordtirseoartdmere.nAt orfooktiddneecyocdtiiosonrodferth. Connectivity of sugar moiety with chromane ring was deduced through HMBC correlation from the anomeric proton H-1” (δH 5.09) to C-7 (δC 164.1) of aglycon. HMBC correlations from olefinic protons H-2 and H-3 to a carbonyl carbon at δC 164.8 (C-1 ) allowed for establishing 6-hydroxy-2-hexenoic acid residue. A macrolide structure was established via ester linkage between sugar residue and carbonyl carbon of hexenoic acid by strong heteronuclear long-range correlation from H-6” to C-1. H-2” H-1”, 2”-OH H-4”, 3”-OH H-5”, 4”-OH H-4”, H-6”a, H-6”b H-5”, H-6”b H-5”, H-6”a

H-6 H-2” H-3” H-4”
Antimicrobial Activity
Antiproliferative and Cytotoxic Activities
General Experimental Procedures
Plant Material
Extraction and Isolation
Antimicrobial Activity Assay
Antiproliferation and Cytotoxicity Assays
Findings
Conclusions
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