Novel and unusual triterpene from Black Cohosh. Determination of structure of 9,10-seco-9,19-cyclolanostane xyloside (cimipodocarpaside) by NMR, IR and Raman spectroscopy and DFT calculations

Jamróz, Marta K.; Jamróz, Michał H.; Dobrowolski, Jan Cz.; Gliński, Jan A.; Davey, Matthew H.; Wawer, Iwona

doi:10.1016/j.saa.2010.09.005

Cited by 39 publications

(13 citation statements)

References 15 publications

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“…We had previously reported this reactionf or the first time although only one product was obtained. [18] In the presentw ork, we obtained six new products (23)(24)(25)(26)(27)(28) with the 9,10-seco-cycloartane skeleton. 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.…”

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

confidence: 92%

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

confidence: 92%

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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“…In all the tables demonstrated here, the scaled value of ν is presented. More details about the PED analysis and VEDA program can be found elsewhere . The geometry optimizations and vibrational wavenumbers were calculated by means of the Gaussian ’09 software package…”

Section: Methodsmentioning

confidence: 99%

Adsorption of 1,2,4‐triazole on a silver electrode: surface‐enhanced Raman spectroscopy and density functional theory studies

Wrzosek

Cukras

Bukowska

2012

J Raman Spectroscopy

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The pH‐dependent surface‐enhanced Raman scattering (SERS) of 1,2,4‐triazole adsorbed on silver electrode and normal Raman (NR) spectra of this compound in the aqueous solutions were investigated. The observed bands in the NR and SERS spectra were assigned with the help of density functional theory calculations for model molecules in the neutral, anionic, and cationic forms and their complexes with silver. The Raman wavenumbers and intensities were computed at the optimized molecular geometry. Vibrational assignments of the SERS and NR spectra are provided by calculated potential energy distributions. The combination of experimental SERS results and density functional theory calculations provide an insight into the molecular structure of adlayers formed by 1,2,4‐triazole on a silver surface at varying pH values and enable the determination of molecular orientation with respect to the surface. Copyright © 2012 John Wiley & Sons, Ltd.

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“…Furthermore, the 1 H NMR spectrum gave a pair of diagnostic methylene protons at δ H 2.90 (br d, J = 14.4 Hz) and 2.70 (br d, J = 14.4 Hz). The above information indicated that compound 3 might possess a 9,10-seco-cycloartane triterpenoid skeleton [17][18][19][20][21]. This was confirmed as follows: The 1 H-1 H COSY spectrum provided five spin systems as shown in l " Fig.…”

Section: Resultsmentioning

confidence: 55%

“…Rotundusolide C (9) was a 9,10seco-cycloartane triterpenoid. A literature search showed that, so far, there have been only eleven such triterpenoid types discovered from a natural source [17][18][19][20][21]. A literature search showed that secomacrogenin B (9b), an analogue of rotundusolide C (9), shared the same coupling pattern for H-3 (dd, J = 9.6, 6.0 Hz) as that of rotundusolide C (9) [19].…”

Section: Resultsmentioning

confidence: 99%

Structurally Diverse Terpenoids from the Rhizomes ofCyperus rotundusL.

Yang¹,

Shi²

2011

Planta Med

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An extract of the rhizomes of Cyperus rotundus L. afforded two new sesquiterpenoids (2 and 3) with rearranged secoeudesmane and germacrane skeletons, and a new 9,10-seco-cycloartane triterpenoid (9), as well as seven previously reported terpenoids, including a monoterpenoid (1), five sesquiterpenoids (4-8) with guaiane, patchoulane, and eudesmane skeletons, and a 3,4- seco-dammarane nortriterpenoid (10). The structures of 1-10 were elucidated by extensive spectroscopic methods and comparison with the literature data. The structures of 2 and 6 were confirmed by single-crystal X-ray diffraction analysis. The carbon skeleton of 2 is the third example reported thus far of such a skeleton and the 9,10-seco-cycloartane framework of 9 has rarely been found from a natural source. Compound 7 was a new natural product and compounds 1-5 and 7-10 were discovered from the genus Cyperus for the first time. This study may provide some useful information for the chemotaxonomy for the plant Cyperus rotundus.

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Novel and unusual triterpene from Black Cohosh. Determination of structure of 9,10-seco-9,19-cyclolanostane xyloside (cimipodocarpaside) by NMR, IR and Raman spectroscopy and DFT calculations

Cited by 39 publications

References 15 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

Adsorption of 1,2,4‐triazole on a silver electrode: surface‐enhanced Raman spectroscopy and density functional theory studies

Structurally Diverse Terpenoids from the Rhizomes ofCyperus rotundusL.

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