3-Hydroxyirisquinone

Metabolomic Responses of Lettuce (Lactuca sativa) to Allelopathic Benzoquinones from Iris sanguinea Seeds.[Pubmed:36961423]

J Agric Food Chem. 2023 Apr 5;71(13):5143-5153.

Weed management is important in modern crop protection. Chemical weed control using synthetic herbicides, however, suffers from resistance and ecotoxicity. Metabolomic investigation of allelopathy (or allelochemicals) may provide novel alternatives to synthetic herbicides. This study aimed to investigate the detailed metabolomic responses of plants to allelochemicals in Iris seed extracts. The seed extracts of Iris sanguinea showed the strongest growth inhibitory activity against alfalfa, barnyard grass, lettuce, and mustard. 3-Hydroxyirisquinone (3-[10(Z)-heptadecenyl]-2-hydroxy-5-methoxy-1,4-benzoquinone) was isolated as a major allelochemical from I. sanguinea seeds through bioassay-guided fractionation. The compound inhibited the growth of shoots and roots by browning root tips. Discriminant analysis identified 33 differentially regulated lettuce metabolites after treatment with 3-Hydroxyirisquinone (3HIQ). Metabolic pathway analysis revealed that several metabolic pathways, including aromatic amino acid biosynthesis and respiratory pathways, were affected by the compounds. Differential responses of membrane lipids (accumulation of unsaturated fatty acids) and extensive formation of reactive oxygen species were observed in root tissues following treatment with 3HIQ. Overall, alkylbenzoquinone from I. sanguinea induced extensive metabolic modulation, oxidative stress, and growth inhibition. The metabolomic responses to allelochemicals may provide fundamental information for the development of allelochemical-based herbicides.

A new belamcandaquinone from the seeds of Iris bungei Maxim.[Pubmed:21820495]

Fitoterapia. 2011 Oct;82(7):1137-9.

A novel dimeric 1,4-benzoquinone and resorcinol derivative, Belamcandaquinone N (1), and two known compounds, 3-Hydroxyirisquinone (2) and 5-[(Z)-10-heptadecenyl] resorcinol (3), were isolated from the seeds of Iris bungei Maxim. Their structures were elucidated by spectroscopic methods and comparing with literature data of known compounds. These compounds showed remarkable cytotoxic activity against RM-1 cell lines.

Antioxidant and anticholinesterase constituents from the petroleum ether and chloroform extracts of Iris suaveolens.[Pubmed:20830698]

Phytother Res. 2011 Apr;25(4):522-9.

The aim of this study was to investigate the phytochemical, antioxidant and anticholinesterase activities of Iris suaveolens. After determining total phenolic and flavonoid contents of the petroleum ether, chloroform and methanol extracts prepared from the rhizomes, the antioxidant capacity of the extracts was established using beta-carotene-linoleic acid and CUPRAC methods. The chloroform extract which was rich in phenolic content exhibited the highest inhibition of lipid peroxidation in the beta-carotene-linoleic acid system, and the best cupric reducing antioxidant capacity among the tested extracts. The petroleum ether extract indicated moderate anticholinesterase activity while the chloroform extract revealed significant butyrylcholinesterase inhibitory activity (75.03 +/- 1.29%). Spectroscopic methods were used for the structural elucidation of the compounds (1-13) isolated from the petroleum ether and chloroform extracts. Coniferaldehyde (6), having the highest antioxidant activity in the beta-carotene-linoleic acid assay at 25 and 50 microg/mL, demonstrated also the best effect in the CUPRAC method among the tested compounds (1-12). 3-Hydroxyirisquinone (10) showed the best anticholinesterase activity among the tested compounds (1-4, 6-12), and coniferaldehyde exhibited almost the same butyrylcholinesterase inhibitory activity (82.60 +/- 2.33%) as galantamine (86.26 +/- 0.66%).

Two new quinones from Iris bungei.[Pubmed:10823714]

Chem Pharm Bull (Tokyo). 2000 May;48(5):738-9.

Two new benzoquinone derivatives, bungeiquinone (1) and dihydrobungeiquinone (2), and two known derivatives, 3-Hydroxyirisquinone (3) and 3-hydroxydihydroirisquinone (4), were isolated from the roots of Iris bungei. The structures of the new compounds were established on the basis of spectroscopic methods.