The four new iridoid glucosides globularicisin (2), globularidin (5), globularimin (9), and globularinin (13), the lignan diglucoside liriodendrin (18), and syringin (20) have been isolated from Globularia alypum L. along with the previously reported glucosides globularin (1) and catalpol (4). Compound 2 is the first report of any cinnamoyl iridoid with a cis‐configuration at the acyl double bond. Compound 5 is another novel iridoid which lacks the characteristic C(3), C(4) double bond in the aglucone part. Compounds 9 and 13 are diastereomeric and contain highly oxygenated aglucone structures. The isolation of liriodendrin, from Globularia alypum is the first demonstration of the occurrence of a lignan in the family Globulariaceae.
The structures have been elucidated by 1H‐ and 13C‐NMR. spectroscopy as well as by chemical transformations. Taxonomical significance of the cooccurrence of iridoid and lignan glycosides as well as the antileukemic potentiality of the latter are also appraised.
OBJECTIVE: Recent research has shown that significant levels of cyclobutane pyrimidine dimers (CPDs) in DNA continue to form in melanocytes for several hours in the dark after exposure to ultraviolet radiation (UVR) ends. We document the utility of a new multifunctional ingredient, 3-(4-hydroxy, 3-methoxybenzyl)-pentane-2,4-dione (INCI acetyl zingerone (AZ)), to protect melanocytes against CPD formation after UVR exposure ends. METHODS: The use of AZ as an intervention to reduce CPD formation after irradiation was assessed in vitro by comparing kinetic profiles of CPD formation for several hours after irradiation in cells that were untreated or treated with AZ immediately after irradiation. Multifunctional performance of AZ as an antioxidant, quencher and scavenger was established using industry-standard in vitro chemical assays, and then, its efficacy in a more biological assay was confirmed by its in vitro ability to reduce intracellular levels of reactive oxygen species (ROS) in keratinocytes exposed to UVA radiation. Molecular photostability was assessed in solution during exposure to solar-simulated UVR and compared with the conventional antioxidant a-tocopherol. RESULTS: Even when added immediately after irradiation, AZ significantly inhibited ongoing formation of CPDs in melanocytes after exposure to UVA. Incubation with AZ before irradiation decreased intracellular levels of UVA-induced ROS formation in keratinocytes. Compared with a-tocopherol, the molecular structure of AZ endows it with significantly better photostability and efficacy to neutralize free radicals (•OH, •OOH), physically quench singlet oxygen ( 1 O 2 ) and scavenge peroxynitrite (ONOO À ). CONCLUSION: These results designate AZ as a new type of multifunctional ingredient with strong potential to extend photoprotection of traditional sunscreens and daily skincare products over the first few hours after sun exposure ends. (ONOO -).CONCLUSION: Ces r esultats montrent que l'AZ, consid er e comme un ingr edient multifonctionnel d'un type nouveau, jouit d'un fort potentiel de prolongation de l'effet photoprotecteur des ecrans solaires traditionnels et des produits de soins de la peau pendant quelques heures apr es la fin de l'exposition au soleil.
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