One new and six known triterpene xylosides from Cimicifuga racemosa: FT-IR, Raman and NMR studies and DFT calculations

Jamróz, Marta K.; Jamróz, Michał H.; Dobrowolski, Jan Cz.; Gliński, Jan A.; Gleńsk, Michał

doi:10.1016/j.saa.2012.02.064

Cited by 19 publications

(9 citation statements)

References 13 publications

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“…Compound 25 had the molecular formula of C 30 TheH R-ESI-MS data established the molecular formula of compound 26 as C 30 …”

Section: Ring Expansion Products 23-28mentioning

confidence: 97%

“…Them olecular formula of compound 24 was established as C 30 Figure 3). Basedo nt he above findings,t he structure of compound 24 was identifieda s( 20R,24S)-6a,16b,25-trihydroxy-3b,10b;20,24-diepoxy-9,10-secocycloartan-9(11)-ene.…”

Section: Ring Expansion Products 23-28mentioning

confidence: 99%

“…[18] Them olecular formulao fc ompound 4 was established as C 30 (Figure 4). Accordingly, the resonances for C-9( d C =35.1) and C-12 (d C = 52.9) were shifted downfield by 13.9 and 19.7 ppm, respectively,w hen compared to those of 2.…”

Section: C-3 or C-11 Oxidation Products 2-4mentioning

confidence: 99%

“…Compound 14 had the molecular formula of C 30 Figure S2). Therefore,c ompound 22 was identified as (20R,24S,2'R)-3b,6a,16b,25-tetrahydroxy-19-(2'-hydroxyl)-propionyloxy-ranunculan-9(10)-ene.…”

Section: C-3 or C-6 Acetylation Products 9-12mentioning

confidence: 99%

“…To the best of our knowledge, only twelvec ompounds with the C 6 -C 7 -C 6 -C 5 triterpene skeleton have been isolated from natural sources,s of ar. [25][26][27][28][29][30] Although the chemical semi-synthesis of compoundsw ith aC 6 -C 7 -C 6 -C 5 core has been reported, only biocatalysis couldr ealize this reactionu nder mild conditions. [31][32][33] More interestingly,t he biocatalysis of CA by S. racemosum could form 3,10-epoxy (23-26)o r6 ,19-epoxy (27)s tructures, which are reported for the first timef or 9,10-seco-cycloartanes.…”

Section: C-3 or C-6 Acetylation Products 9-12mentioning

confidence: 99%

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Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Feng

Qiao

et al. 2015

Adv Synth Catal

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Cycloastragenol is ac ycloartane-type triterpenoid with significant telomerase-activating activities.Inthis paper, the biocatalysisofc ycloastragenol by two strains of filamentous fungi, namely Syncephalastrum racemosum AS 3.264 and Alternaria alternata AS 3.4578, was investigated. Scaled-up biotransformation reactions yielded 27 metabolites. Their structures were established on the basis of extensiveN MR and HR-ESI-MS data analyses,a nd 18 of them are new compounds.T he twof ungal strains exhibited distinct biocatalytic features. S. racemosum could catalyzer ing expansion ande poxidation reactions to form 3b,10b-epoxy-o r6 a ,19a-epoxy-9,10-seco-cycloartane structures,w hereas A. alternata preferredt oc atalyzea cetylation reactions,e specially at 3-OH, 6-OH and1 9-OH. These regio-ands tereoselective reactions are difficult to achieve by chemical means,b ut could be realized under mild conditions by biocatalysis.F urthermore,w ef ound that some acetylated derivatives at 50 mMc ould significantly extend the lifespan of Caenorhabditise legans from 16.93 AE 0.70 do ft he control group to 20.01 AE 0.75 d (P < 0.01), versus 18.54 AE 0.67 df or cycloastragenol. These biotransformed derivatives of cycloastragenol could be potential anti-aginga gents.

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“…Compound 25 had the molecular formula of C 30 TheH R-ESI-MS data established the molecular formula of compound 26 as C 30 …”

Section: Ring Expansion Products 23-28mentioning

confidence: 97%

Section: Ring Expansion Products 23-28mentioning

confidence: 99%

Section: C-3 or C-11 Oxidation Products 2-4mentioning

confidence: 99%

Section: C-3 or C-6 Acetylation Products 9-12mentioning

confidence: 99%

Section: C-3 or C-6 Acetylation Products 9-12mentioning

confidence: 99%

See 3 more Smart Citations

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Feng

Qiao

et al. 2015

Adv Synth Catal

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Systematically identifying the anti‐inflammatory constituents of Cimicifuga dahurica by UPLC–Q/TOF–MS combined with network pharmacology analysis

Pang

Liu

et al. 2021

Biomedical Chromatography

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Cimicifuga dahurica (Turcz.) Maxim, which is also regarded as the main origin of "Shengma" in the Chinese Pharmacopoeia, has been used as a cooling and detoxification agent for thousands of years. Our previous phytochemical investigations of C. dahurica extracts (CDEs) led to the isolation of a series of 9,19-cycloalkane triterpenoids and phenolic acids showing a potential anti-inflammatory activity. However, the chemical profiling of CDEs and the material basis of its anti-inflammatory effect in vivo has not been clarified. In the present study, the CDE chemical profile and prototype components in rat plasma were identified via ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. As a result, a total of 106 components were identified or tentatively characterized in CDEs, including 54 triterpenoids, 35 phenolic acids, eight amides and nine other type constituents (39 compounds were confirmed with the reference standards). In addition, 20 prototype components (15 triterpenoids and five phenolic acids) were identified in rat plasma, which potentially related to the anti-inflammatory effects of CDEs.Moreover, the anti-inflammatory activities of the main prototype components were further evaluated by their inhibitory effects on the production of NO, as well as the expressions of iNOS and COX-2 in lipopolysaccharide-stimulated RAW264.7 cells, which indicated that 9,19-cycloalkane triterpenoids may play an anti-inflammatory role by down-regulating the expression of iNOS.

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pH‐sensing nanostar probe using surface‐enhanced Raman scattering (SERS): theoretical and experimental studies

Yang

Yuan

Fales

et al. 2013

J Raman Spectroscopy

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Local pH environment has been considered to be a potential biomarker for tumor diagnosis because solid tumors contain highly acidic environments. A pH‐sensing nanoprobe based on surface‐enhanced Raman scattering (SERS) using nanostars under near‐infrared excitation has been developed for potential biomedical applications. To theoretically investigate the effect of protonation state on SERS spectra of p‐mercaptobenzoic acid (pMBA), we used the density functional theory (DFT) with the B3LYP functional to calculate Raman vibrational spectra of pMBA‐Au/Ag complex in both protonated and deprotonated states. Vibrational spectral bands were assigned with DFT calculation and used to investigate SERS spectral changes observed from experiment when varying pH value between five and nine. The SERS peak position of pMBA at ~1580 cm−1 was identified to be a novel pH‐sensing index, which has small but noticeable downshift with pH increase. This phenomenon is confirmed and well‐explained with theoretical simulation. The study demonstrates that SERS is a sensitive tool to monitor minor structural changes due to local pH environment, and DFT calculations can be used to investigate Raman spectra changes associated with minor differences in molecular structure. Copyright © 2013 John Wiley & Sons, Ltd.

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One new and six known triterpene xylosides from Cimicifuga racemosa: FT-IR, Raman and NMR studies and DFT calculations

Cited by 19 publications

References 13 publications

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Biocatalysis of Cycloastragenol by Syncephalastrum racemosum and Alternaria alternata to Discover Anti‐Aging Derivatives

Systematically identifying the anti‐inflammatory constituents of Cimicifuga dahurica by UPLC–Q/TOF–MS combined with network pharmacology analysis

pH‐sensing nanostar probe using surface‐enhanced Raman scattering (SERS): theoretical and experimental studies

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