77-95-2Relevant articles and documents
Eucommicin A, a β-truxinate lignan from Eucommia ulmoides, is a selective inhibitor of cancer stem cells
Fujiwara, Ayaka,Nishi, Mayuko,Yoshida, Shigeo,Hasegawa, Morifumi,Yasuma, Chieko,Ryo, Akihide,Suzuki, Yoshihito
, p. 139 - 145 (2016)
Cancer stem cells (CSCs) constitute a small population of undifferentiated cells within a tumor that have the ability to self-renew and drive tumor formation, thus behaving as cancer-initiating cancer cells. Therapeutic interventions that eliminate CSCs are necessary to completely cure patients, since CSCs are a crucial source of tumor recurrence and metastasis. An induced CSC-like (iCSCL) model was recently established using induced pluripotent stem cells (iPSCs). In this study, a natural product - eucommicin A - was identified from Eucommia ulmoides leaves by screening for anti-CSC activity using the iCSCL model. Its structure was elucidated by spectroscopic methods as a quinic acid diester of 3,4,3′,4′-tetrahydroxy-β-truxinic acid. Eucommicin A exhibited selective anti-CSC activity and inhibited tumor sphere formation by iCSCL cells. The results of this study suggest that eucommicin A could serve as a lead compound in the development of drugs to abrogate the stemness and self-renewal ability of CSCs.
SEVEN QUINIC ACID GALLATES FROM QUERCUS STENOPHYLLA
Nishimura, Hiroaki,Nonaka, Gen-Ichiro,Nishioka, Itsuo
, p. 2621 - 2624 (1984)
A chemical investigation of the bark of Quercus stenophylla has led to the isolation and characterization of all of the possible structural isomers of quinic acid gallates; 3-O-, 4-O-, 5-O-, 3,4-di-O-, 3,5-di-O-, 4,5-di-O- and 3,4,5-tri-O-galloylquinic acids.Evidence for the structures of these compounds was obtained from analysis of the 1H and 13C NMR spectra, and hydrolytic studies.Key Word Index - Quercus stenophylla; Fagaceae; quinic acid gallates; gallotannins; tannase.
Senecio scandens derivative and application thereof in drugs
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Paragraph 0019; 0032; 0037, (2018/08/04)
The invention discloses a senecio scandens derivative and application thereof in drugs. The enecio scandens derivative is the derivative of the effective component chlorogenic acid of senecio scandens. The derivative of the chlorogenic acid is a compound as shown in chemical generation formula I, II, III or IV or one or the combination of the stereisomer, geometrical isomer, tautomer, solvate, polymorphic substance, metabolite, ester, pharmaceutically acceptable salt, prodrug, pharmaceutically acceptable prodrug salt, pharmaceutically acceptable carrier, excipient, diluent, adjuvant and intermedium of the compound. The senecio scandens derivative is used for preparing antiviral drugs. The senecio scandens derivative is good in solubility, high in purity, good in antipyretic performance andespecially suitable for being used as the effective component to prepare antipyretic, anti-inflammation and antibacterial drugs.
Analysis of protein-phenolic compound modifications using electrochemistry coupled to mass spectrometry
Kallinich, Constanze,Schefer, Simone,Rohn, Sascha
, (2018/02/07)
In the last decade, electrochemical oxidation coupled with mass spectrometry has been successfully used for the analysis of metabolic studies. The application focused in this study was to investigate the redox potential of different phenolic compounds such as the very prominent chlorogenic acid. Further, EC/ESI-MS was used as preparation technique for analyzing adduct formation between electrochemically oxidized phenolic compounds and food proteins, e.g., alpha-lactalbumin or peptides derived from a tryptic digestion. In the first step of this approach, two reactant solutions are combined and mixed: one contains the solution of the digested protein, and the other contains the phenolic compound of interest, which was, prior to the mixing process, electrochemically transformed to several oxidation products using a boron-doped diamond working electrode. As a result, a Michael-type addition led to covalent binding of the activated phenolic compounds to reactive protein/peptide side chains. In a follow-up approach, the reaction mix was further separated chromatographically and finally detected using ESI-HRMS. Compound-specific, electrochemical oxidation of phenolic acids was performed successfully, and various oxidation and reaction products with proteins/peptides were observed. Further optimization of the reaction (conditions) is required, as well as structural elucidation concerning the final adducts, which can be phenolic compound oligomers, but even more interestingly, quite complex mixtures of proteins and oxidation products.
Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid
Deshpande, Sagar,Matei, Marius Febi,Jaiswal, Rakesh,Bassil, Bassem S.,Kortz, Ulrich,Kuhnert, Nikolai
, p. 7298 - 7306 (2016/10/07)
(-)-Quinic acid possess eight possible stereoisomers, which occur both naturally and as products of thermal food processing. In this contribution, we have selectively synthesized four isomers, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid, and scyllo-quinic acid, to develop a tandem LC-MS method identifying all stereoisomeric quinic acids. Four derivatives have been unambiguously characterized by single-crystal X-ray crystallography. The missing diastereomers of quinic acid were obtained by nonselective isomerization of (-)-quinic acid using acetic acid/concentrated H2SO4 allowing chromatographic separation and assignment of all diastereomers of quinic acid. We report for the first time that a full set of stereoisomers are reliably distinguishable on the basis of their tandem mass spectrometric fragment spectra as well as their elution order. A rationale for characteristic fragmentation mechanisms is proposed. In this study, we also observed that muco-quinic acid, scyllo-quinic acid, and epi-quinic acid are present in hydrolyzed Guatemalan roasted coffee sample as possible products of roasting.
A novel stereoselective synthesis of (-)-quinic acid starting from the naturally abundant (-)-shikimic acid
Zhang, Wei,Zhu, Xing-Liang,Ding, Wei,Shi, Xiao-Xin
, p. 1375 - 1381 (2015/11/25)
A new stereoselective synthesis of (-)-quinic acid from the naturally abundant (-)-shikimic acid is described. Ethyl shikimate 2 was first prepared in 97% yield via esterification of (-)-shikimic acid according to a previous report. Ester 2 was then transformed into an epimeric mixture of 3,4-O-benzylidene shikimate 3, which was directly converted into compound 4 in 90% yield (over 2 steps from ester 2) via an NBS-mediated acetal ring-opening reaction. Acetylization of the hydroxyl group at the C-5 position of compound 4 gave compound 5 in 98% yield. Compound 5 was transformed into compound 6 in 91% yield via a highly stereoselective Ru-catalyzed dihydroxylation. Subsequently, compound 6 was converted into epoxide 7 in 82% yield via an intramolecular SN2 type substitution. A regioselective epoxide-opening of compound 7 by PPh3-I2 complex furnished an iodo compound 8 in 79% yield. Removal of the iodine atom in compound 8 by Pd/C-catalyzed hydrogenation produced compound 9 in 92% yield. Methanolysis of compound 9 gave methyl quinate 10 in 92% yield. Finally, hydrolysis of compound 10 afforded the targeted compound (-)-quinic acid 1 in 90% yield. The title compound (-)-quinic acid 1 was stereoselectively synthesized through 10 steps starting from (-)-shikimic acid in 38% overall yield.
An easy 'Filter-and-Separate' method for enantioselective separation and chiral sensing of substrates using a biomimetic homochiral polymer
Senthilkumar,Asha
supporting information, p. 8931 - 8934 (2015/05/27)
We present a polyfluorene appended with protected l-glutamic acid that exhibited a reversible α-helix/β-sheet-like conformation and helical porous fibrous morphology mimicking the super-structure of proteins. The new homochiral polymer probe enabled efficient heterogeneous enantioselective separation and chiral sensing of a wide variety of substrates from their aqueous racemic mixture using an easy 'Filter-and-Separate' method.
1,5-DI-O-Isoferuloylquinic acid and other phenolic compounds from pollen of calendula officinalis
Olennikov,Kashchenko
, p. 589 - 593 (2015/02/02)
A new phenylpropanoid that was identified as 1,5-di-O-isoferuloylquinic acid (1) and 17 known compounds including 1,5-di-O-feruloylquinic acid (2), which was obtained for the first time from a plant and was synthesized previously, were isolated from pollen of Calendula officinalis. Compounds 1 and 2 were the dominant phenolic compounds from pollen of C. officinalis. It was found that 1 possessed pronounced inhibitory activity against tyrosinase (IC50 11.26μg/mL).
Prenylated coumarins: Natural phosphodiesterase-4 inhibitors from toddalia asiatica
Lin, Ting-Ting,Huang, Yi-You,Tang, Gui-Hua,Cheng, Zhong-Bin,Liu, Xin,Luo, Hai-Bin,Yin, Sheng
, p. 955 - 962 (2014/05/20)
Bioassay-guided fractionation of the ethanolic extract of the roots of Toddalia asiatica led to the isolation of seven new prenylated coumarins (1-7) and 14 known analogues (8-21). The structures of 1-7 were elucidated by spectroscopic analysis, and their absolute configurations were determined by combined chemical methods and chiral separation analysis. Compounds 1-5, named toddalin A, 3t′-O-demethyltoddalin A, and toddalins B-D, represent an unusual group of phenylpropenoic acid-coupled prenylated coumarins. Compounds 1-21 and four modified analogues, 10a, 11a, 13a, and 17a, were screened by using tritium-labeled adenosine 3,5-cyclic monophosphate ([3H]-cAMP) as substrate for their inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 3, 8, 10, 10a, 11, 11a, 12, 13, 17, and 21 exhibited inhibition with IC50 values less than 10 μM. Toddacoumalone (8), the most active compound (IC50 = 0.14 μM), was more active than the positive control, rolipram (IC50 = 0.59 μM). In addition, the structure-activity relationship and possible inhibitory mechanism of the active compounds are also discussed.
Acylated sucroses and acylated quinic acids analogs from the flower buds of Prunus mume and their inhibitory effect on melanogenesis
Nakamura, Seikou,Fujimoto, Katsuyoshi,Matsumoto, Takahiro,Nakashima, Souichi,Ohta, Tomoe,Ogawa, Keiko,Matsuda, Hisashi,Yoshikawa, Masayuki
, p. 128 - 136 (2013/10/21)
The methanolic extract from the flower buds of Prunus mume, cultivated in Zhejiang Province, China, showed an inhibitory effect on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells. From the methanolic extract, five acylated sucroses, mumeoses A-E, and three acylated quinic acid analogs, 5- O-(E)-p-coumaroylquinic acid ethyl ester, and mumeic acid-A and its methyl ester, were isolated together with 13 known compounds. The chemical structures of the compounds were elucidated on the basis of chemical and physicochemical evidence. Inhibitory effects of the isolated compounds on melanogenesis in theophylline-stimulated B16 melanoma 4A5 cells were also investigated. Acylated quinic acid analogs substantially inhibited melanogenesis. In particular, 5-O-(E)-feruloylquinic acid methyl ester exhibited a potent inhibitory effect [inhibition (%): 21.5 ± 1.0 (P 97% at 10 μM]. It is concluded that acylated quinic acid analogs are promising therapeutic agents for the treatment of skin disorders.
