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Characterization of in vitro and in vivo metabolites of carnosic acid, a natural antioxidant, by high performance liquid chromatography coupled with tandem mass spectrometry.

Song Y1, Yan H2, Chen J2, Wang Y3, Jiang Y4, Tu P5.Author information 1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, 999078, Macao.2State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.3State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, 999078, Macao.4State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China. Electronic address: yongjiang@bjmu.edu.cn.5State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China. Electronic address: pengfeitu@bjmu.edu.cn.AbstractCarnosic acid (CA) is a widely employed antioxidant and the main active component in rosemary and sage, but its metabolism remains largely unknown. The present study investigated the metabolism of CA in vitro and in vivo for the first time, using high performance liquid chromatography coupled with hybrid triple quadrupole-linear ion trap mass spectrometry (HPLC-Q-trap-MS). A couple of scan modes were adopted in mass spectrometer domain, including Q1 full scan, neutral loss scan-information dependent acquisition-enhanced product ion (NL-IDA-EPI) and precursor ion scan-information dependent acquisition-enhanced product ion (PI-IDA-EPI). In particular, a prediction was carried out on the basis of in vitro metabolism results, and gave birth to a multiple ion monitoring-information dependent acquisition-enhanced product ion (MIM-IDA-EPI) mode aiming to detect the trace metabolites in CA-treated biological samples. A total of ten metabolites (M4-13), along with three degradative products (M1-3), were identified for CA from in vitro metabolism models, including liver microsomes of human and rats (HLMs and RLMs), human intestinal microsomes (HIMs) and two species of Cunninghamella elegans. Twelve (U1-12) and six (F1-6) metabolites were detected from CA-treated urine and feces, respectively. In addition, five metabolites (SM2-6) in vivo were purified and definitely identified using NMR spectroscopy. The results of both in vitro and in vivo metabolism studies indicated poor metabolic stability for CA, and the glucuronidation and oxidation metabolisms extensively occurred for CA in vitro, while oxidation, glucuronidation and methylation were the main metabolic pathways observed in vivo.
Journal of pharmaceutical and biomedical analysis.J Pharm Biomed Anal.2014 Feb 15;89:183-96. doi: 10.1016/j.jpba.2013.11.001. Epub 2013 Nov 15.
Carnosic acid (CA) is a widely employed antioxidant and the main active component in rosemary and sage, but its metabolism remains largely unknown. The present study investigated the metabolism of CA in vitro and in vivo for the first time, using high performance liquid chromatography coupled with h
PMID 24291799

Epimerization-free C-terminal Peptide activation.

Popovic S, Bieräugel H, Detz RJ, Kluwer AM, Koole JA, Streefkerk DE, Hiemstra H, van Maarseveen JH.Author information Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098XH Amsterdam (The Netherlands) http://hims.uva.nl/soc.AbstractSmooth operation: C-terminal peptide activation with full stereointegrity was accomplished using a copper(II)-mediated coupling reaction of carboxylic acids with arylboroxines (see scheme, NCL = native chemical ligation, Boc = tert-butoxycarbonyl). This method allows epimerization-free activation and ligation of peptides with racemization-prone phenylglycine at the C terminus.
Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2013 Dec 9;19(50):16934-7. doi: 10.1002/chem.201303347. Epub 2013 Nov 7.
Smooth operation: C-terminal peptide activation with full stereointegrity was accomplished using a copper(II)-mediated coupling reaction of carboxylic acids with arylboroxines (see scheme, NCL = native chemical ligation, Boc = tert-butoxycarbonyl). This method allows epimerization-free activ
PMID 24307358

Complexes with nitrogen-centered radical ligands: classification, spectroscopic features, reactivity, and catalytic applications.

Olivos Suarez AI, Lyaskovskyy V, Reek JN, van der Vlugt JI, de Bruin B.Author information Homogeneous and Supramolecular Catalysis van't Hoff Institute for Molecular Sciences (HIMS), University of Amsterdam, Science Park 904, 1098 XH Amsterdam (The Netherlands).AbstractThe electronic structure, spectroscopic features, and (catalytic) reactivity of complexes with nitrogen-centered radical ligands are described. Complexes with aminyl ([M(˙NR2)]), nitrene/imidyl ([M(˙NR)]), and nitridyl radical ligands ([M(˙N)]) are detectable and sometimes even isolable species, and despite their radical nature frequently reveal selective reactivity patterns towards a variety of organic substrates. A classification system for complexes with nitrogen-centered radical ligands based on their electronic structure leads to their description as one-electron-reduced Fischer-type systems, one-electron-oxidized Schrock-type systems, or systems with a (nearly) covalent M-N π bond. Experimental data relevant for the assignment of the radical locus (i.e. metal or ligand) are discussed, and the application of complexes with nitrogen-centered radical ligands in the (catalytic) syntheses of nitrogen-containing organic molecules such as aziridines and amines is demonstrated with recent examples. This Review should contribute to a better understanding of the (catalytic) reactivity of nitrogen-centered radical ligands and the role they play in tuning the reactivity of coordination compounds.
Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2013 Nov 25;52(48):12510-29. doi: 10.1002/anie.201301487. Epub 2013 Nov 8.
The electronic structure, spectroscopic features, and (catalytic) reactivity of complexes with nitrogen-centered radical ligands are described. Complexes with aminyl ([M(˙NR2)]), nitrene/imidyl ([M(˙NR)]), and nitridyl radical ligands ([M(˙N)]) are detectable and sometimes even isolable species,
PMID 24214688

Japanese Journal

Regioselective Glucuronidation of Oxyresveratrol, a Natural Hydroxystilbene, by Human Liver and Intestinal Microsomes and Recombinant UGTs

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Drug Metabolism and Pharmacokinetics 29(3), 229-236, 2014
… This study aims to characterize its glucuronidation kinetics in human liver (HLMs) and intestinal (HIMs) microsomes and identify the main UDP-glucuronosyltransferase (UGT) isoforms involved. … Three and four mono-glucuronides of OXY were generated in HIMs and HLMs, respectively, with oxyresveratrol-2-O-β-<span style="font-variant: small-caps;">d</span>-glucuronosyl (G4) as the major metabolite in both organs. …
NAID 130004463381

Identification and Characterization of Human UDP-glucuronosyltransferases Responsible for the In Vitro Glucuronidation of Salvianolic Acid A

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Drug Metabolism and Pharmacokinetics 27(6), 579-585, 2012
… In this study, the kinetics of Sal A glucuronidation by pooled human liver microsomes (HLMs), pooled human intestinal microsomes (HIMs) and 12 recombinant UGT isozymes were investigated. … The glucuronidation of Sal A can be shown both in HLMs and HIMs with Km values of 39.84 ± 3.76 and 54.04 ± 4.36 µM, respectively. …
NAID 130004933514

On the role of spin correlation in the formation, decay, and detection of long-lived, intramolecular charge-transfer states

VERHOEVEN Jan W.
Journal of photochemistry and photobiology. C, Photochemistry reviews 7(1), 40-60, 2006-03-01
NAID 10028159000

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