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Jamroz M.K.,Medical University of Warsaw | Jamroz M.H.,Industrial Chemistry Research Institute | Dobrowolski J.C.,Industrial Chemistry Research Institute | Dobrowolski J.C.,Polish National Medicines Institute | And 3 more authors.
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy | Year: 2011

A new triterpene xyloside, designated cimipodocarpaside was isolated from a Black Cohosh (Actea racemosa L.) extract and its structure was elucidated by means of 1H, 13C NMR, IR and Raman spectroscopy supported by B3LYP/6-31G** calculations. The vibrational spectra were interpreted using the PED analysis of 273 fundamentals. Its structure comprises four condensed rings A-D which are 6, 7, 6, and 5-membered, respectively. An oxiirane ring is located in the side chain and a xylose moiety is attached to the A-ring. Comparison of the experimental 13C NMR data with the theoretical chemical shifts of 24S- and 24R-cimipodocarpaside isomers revealed that the isolated compound has the 24S-configuration. Combined spectroscopic and computational studies enabled the determination of the structure of cimipodocarpaside as (24S)-3β-hydroxy-24,25-oxiirane-16,23-dione-9,10-seco- 9,19-cyclolanost-7(8),9(11),10(19)-trien-3-O-β-d-xylopyranoside. Triterpenes with 7-membered ring were thus far isolated from only Actea podocarpa DC. plants. This is the first report on the isolation of such a compound from Black Cohosh. © 2010 Elsevier B.V. All rights reserved.


Jamroz M.K.,Medical University of Warsaw | Jamroz M.H.,Industrial Chemistry Research Institute | Dobrowolski J.Cz.,Industrial Chemistry Research Institute | Dobrowolski J.Cz.,Polish National Medicines Institute | And 2 more authors.
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy | Year: 2012

One new and six known triterpene xylosides were isolated from Cimicifuga racemosa (black cohosh, Actaea racemosa). The structure of a new compound, designated as isocimipodocarpaside (1), was established to be (24S)-3β-hydroxy-24,25-oxiirane-16,23-dione-9,10-seco-9, 19-cyclolanost-1(10),7(8),9(11)-trien 3-O-β-d-xylopyranoside, by means of 1H and 13C NMR, IR and Raman spectroscopies and Mass Spectrometry. The six known compounds are: 23-epi-26-deoxycimicifugoside (2), 23-epi-26-deoxyactein (3), 25-anhydrocimigenol xyloside (4), 23-O-acetylshengmanol xyloside (5), 25-O-acetylcimigenol xyloside (6) and 3′-O-acetylcimicifugoside H-1 (7). On the basis of NMR data supported by DFT calculations of NMR shielding constants of (2), its structure, previously described as 26-deoxycimicifugoside was corrected and determined as 23-epi-26-deoxycimicifugoside. The 13C CPMAS NMR spectra of the studied compounds (1)-(7) provided data on their solid-state interactions. The IR and Raman spectra in the C=O, C=C, and C-H stretching vibration regions clearly discriminate different triterpenes found in C. racemosa. © 2012 Elsevier B.V. All rights reserved.


PubMed | Kyolab Laboratories, Federal University of Rio de Janeiro, Jawaharlal Nehru Centre for Advanced Scientific Research, Lex Company Research Laboratories and 2 more.
Type: | Journal: Virology | Year: 2014

The ability of HIV to establish long-lived latent infection is mainly due to transcriptional silencing of viral genome in resting memory T lymphocytes. Here, we show that new semi-synthetic ingenol esters reactivate latent HIV reservoirs. Amongst the tested compounds, 3-caproyl-ingenol (ING B) was more potent in reactivating latent HIV than known activators such as SAHA, ingenol 3,20-dibenzoate, TNF-, PMA and HMBA. ING B activated PKC isoforms followed by NF-B nuclear translocation. As virus reactivation is dependent on intact NF-B binding sites in the LTR promoter region ING B, we have shown that. ING B was able to reactivate virus transcription in primary HIV-infected resting cells up to 12 fold and up to 25 fold in combination with SAHA. Additionally, ING B promoted up-regulation of P-TEFb subunits CDK9/Cyclin T1. The role of ING B on promoting both transcription initiation and elongation makes this compound a strong candidate for an anti-HIV latency drug combined with suppressive HAART.


Wang Y.,Rutgers University | Singh A.P.,Rutgers University | Hurst W.J.,The Hershey Company | Glinski J.A.,Planta Analytica LLC. | And 2 more authors.
Journal of Agricultural and Food Chemistry | Year: 2016

Proanthocyanidins (PACs) are naturally occurring flavonoids possessing health beneficial bioactivities. Their quantification often utilizes the 4-dimethylaminocinnamaldehyde (DMAC) spectrophotometric assay with the assumption that molar absorption coefficients (MACs) are similar across the various PAC species. To assess the validity of this assumption, individual PAC monomers and oligomers were examined for their absorbance response with DMAC. Our results have shown that PAC dimers and trimers with interflavan linkage variations exhibited differential absorbance response. Absence of A-type linkage between the terminal and second units in PAC molecule not only impacts absorbance intensity at 640 nm but also elicits a prominent secondary 440 nm absorbance peak. Cranberry (A-type) and cocoa (B-type) oligomeric PACs exhibited differential absorbance (MACs) relationship with degree-of-polymerization. Thus, PAC structural variations have considerable impact on the resulting MAC. The use of DMAC assay in PAC quantification, especially in comparing across specific oligomers and compositions, should not assume MACs are similar. © 2016 American Chemical Society.


PubMed | University of Pennsylvania, Planta Analytica LLC., The Hershey Company and Rutgers University
Type: Journal Article | Journal: Journal of agricultural and food chemistry | Year: 2016

Proanthocyanidins (PACs) are naturally occurring flavonoids possessing health beneficial bioactivities. Their quantification often utilizes the 4-dimethylaminocinnamaldehyde (DMAC) spectrophotometric assay with the assumption that molar absorption coefficients (MACs) are similar across the various PAC species. To assess the validity of this assumption, individual PAC monomers and oligomers were examined for their absorbance response with DMAC. Our results have shown that PAC dimers and trimers with interflavan linkage variations exhibited differential absorbance response. Absence of A-type linkage between the terminal and second units in PAC molecule not only impacts absorbance intensity at 640 nm but also elicits a prominent secondary 440 nm absorbance peak. Cranberry (A-type) and cocoa (B-type) oligomeric PACs exhibited differential absorbance (MACs) relationship with degree-of-polymerization. Thus, PAC structural variations have considerable impact on the resulting MAC. The use of DMAC assay in PAC quantification, especially in comparing across specific oligomers and compositions, should not assume MACs are similar.


Glensk M.,Wroclaw Medical University | Glinski J.A.,Planta Analytica LLC | Jamroz M.,Medical University of Warsaw | Stefanowicz P.,Wrocław University | Kazmierski S.,Polish Academy of Sciences
Records of Natural Products | Year: 2016

Alchornea castaneifolia is a tree growing commonly in several South American countries. It is best known under its Peruvian name Iporuru. The leaves are being used as a folk remedy against numerous symptoms associated with pain and inflammation. It has a reputation for being a tonic and booster of male libido. In this study, using a combination of chromatographic techniques, we isolated phenolic constituents present in leaves, and elucidated their structures using MS and NMR techniques. The isolated and characterized compounds were myricetin glucoside, myricetin galactoside, proanthocyanidin A1 and A2, epicatechin, gallic acid, shikimic acid, putranjivain A, elaeocarpusin and never before isolated methyl ester of repandusinic acid A. © 2015 ACG Publications. All rights reserved.


Keller M.,Washington State University | Shrestha P.M.,Washington State University | Shrestha P.M.,Planta Analytica LLC
Planta | Year: 2014

Phloem unloading is thought to switch from a symplastic route to an apoplastic route at the beginning of ripening in grape berries and some other fleshy fruits. However, it is unclear whether different solutes accumulate in both the mesocarp vacuoles and the apoplast. We modified a method developed for tomato fruit to extract apoplastic sap from grape berries and measured the changes in apoplastic and vacuolar pH, soluble sugars, organic acids, and potassium in ripening berries of Vitis vinifera ‘Merlot’ and V. labruscana ‘Concord’. Solute accumulation varied by genotype, compartment, and chemical species. The apoplast pH was substantially higher than the vacuolar pH, especially in Merlot (approximately two units). However, the vacuole–apoplast proton gradient declined during ripening and in Merlot, but not in Concord, collapsed entirely at maturity. Hexoses accumulated in both the vacuoles and apoplast but at different rates. Organic acids, especially malate, declined much more in the vacuoles than in the apoplast. Potassium accumulated in the vacuoles and apoplast of Merlot. In Concord, by contrast, potassium increased in the vacuoles but decreased in the apoplast. These results suggest that solutes in the fruit apoplast are tightly regulated and under developmental control. © Springer-Verlag Berlin Heidelberg 2013.


Keller M.,Washington State University | Zhang Y.,Washington State University | Shrestha P.M.,Washington State University | Shrestha P.M.,Planta Analytica LLC | And 2 more authors.
Plant, Cell and Environment | Year: 2015

We tested the common assumption that fleshy fruits become dependent on phloem water supply because xylem inflow declines at the onset of ripening. Using two distinct grape genotypes exposed to drought stress, we found that a sink-driven rise in phloem inflow at the beginning of ripening was sufficient to reverse drought-induced berry shrinkage. Rewatering accelerated berry growth and sugar accumulation concurrently with leaf photosynthetic recovery. Interrupting phloem flow through the peduncle prevented the increase in berry growth after rewatering, but interrupting xylem flow did not. Nevertheless, xylem flow in ripening berries, but not berry size, remained responsive to root or shoot pressurization. A mass balance analysis on ripening berries sampled in the field suggested that phloem water inflow may exceed growth and transpiration water demands. Collecting apoplastic sap from ripening berries showed that osmotic pressure increased at distinct rates in berry vacuoles and apoplast. Our results indicate that the decrease in xylem inflow at the onset of ripening may be a consequence of the sink-driven increase in phloem inflow. We propose a conceptual model in which surplus phloem water bypasses the fruit cells and partly evaporates from the berry surface and partly moves apoplastically to the xylem for outflow. © 2014 John Wiley & Sons Ltd.


Glensk M.,Wroclaw Medical University | Glinski J.A.,Planta Analytica LLC | Wlodarczyk M.,Wroclaw Medical University | Stefanowicz P.,Wrocław University
Chemistry and Biodiversity | Year: 2014

Elderberries are used in the preparation of pie, jelly, punch, wine, or liqueur, as well as in many herbal remedies and food supplements. Elderberry products may provide diaphoretic, diuretic, antioxidant, and immunostimulant activities that offer protection against cold and flu. Herein, we report for the first time the qualitative and quantitative evaluation of two isomeric triterpenoids isolated from Sambuci fructus. The analysis revealed that ursolic acid and oleanolic acid are present in Sambuci fructus. The average concentration of ursolic acid was ca. three times higher than the concentration of oleanolic acid. The triterpenoids were detected and quantified using chromatographic methods such as TLC and HPLC. Spectroscopic techniques, including HR-MS and 2D-NMR, allowed unequivocal structure determination. © 2014 Verlag Helvetica Chimica Acta AG.


Berhow M.A.,National United University | Polat U.,Uludag University | Glinski J.A.,Planta Analytica LLC | Glensk M.,Planta Analytica LLC | And 6 more authors.
Industrial Crops and Products | Year: 2013

Gold-of-pleasure or false flax (Camelina sativa L. Crantz) is being developed as an alternative oil crop for biodiesel and for food use. The seed meal, which contains three relatively unique glucosinolates, is being evaluated for approval for use as an ingredient in animal feeds and for other uses. The objective of this research was to develop reproducible methods for the isolation of large quantities of pure camelina glucosinolates (glucoarabin, glucocamelinin, and 11-(methylsulfinyl)-undecylglucosinolate) and develop efficient methods for quantifying these compounds. The separation and purification of the camelina glucosinolates were achieved using a combination of reverse phase chromatography, counter-current chromatography and ion exchange chromatography. An efficient reverse phase HPLC separation method was used to quantitate the glucosinolate content in camelina seed and plant extracts. The quantitation methodology was used to measure glucosinolate levels in seeds from 30 cultivars grown in a U.S. field trial and measure glucosinolates levels in sprouted camelina seeds. © 2012 .

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