scholarly journals New Steroidal Saponins from Rhizomes of Costus spiralis

2004 ◽  
Vol 59 (1-2) ◽  
pp. 81-85 ◽  
Author(s):  
Bernadete P. da Silva ◽  
José P. Parente
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Spectroscopic Techniques ◽  
Steroidal Saponins ◽  
Anti Inflammatory ◽  
C Nmr

Two new steroidal saponins were isolated from the rhizomes of Costus spiralis Rosc. Their structures were established as (3β,25R)-26-(β-ᴅ-glucopyranosyloxy)-22-hydroxyfurost-5- en-3-ylO-d-apio-β-ᴅ-furanosyl-(1→2)-O-[α-ʟ-rhamnopyranosyl-(1→4)]-β-ᴅ-glucopyranoside (1) and (3β,25R)-26-(β-ᴅ-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-ᴅ-apio-β-ᴅ-furanosyl-( 154)-O-[α-ʟ-rhamnopyranosyl-(1→2)]-β-ᴅ-glucopyranoside (2). Their structural identifications were performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponins were evaluated for anti-inflammatory activity.

A New Bioactive Steroidal Saponin from Agave attenuata

2002 ◽  
Vol 57 (5-6) ◽  
pp. 423-428 ◽  
Author(s):  
Bernadete P. da Silva ◽  
Allyne C. de Sousa ◽  
Graziela M. Silva ◽  
Tatiana P. Mendes ◽  
José P. Parente
Keyword(s):  
Nmr Spectra ◽  
Capillary Permeability ◽  
Structural Identification ◽  
2D Nmr ◽  
Inflammatory Activity ◽  
Steroidal Saponin ◽  
Spectroscopic Techniques ◽  
Anti Inflammatory ◽  
Permeability Assay ◽  
C Nmr

A new steroidal saponin was isolated from the leaves of Agave attenuata Salm-Dyck. Its structure was established as (3β,5β,22α,25S)-26-(β-ᴅ-glucopyranosyloxy)-22-methoxyfurostan- 3-yl O-β-ᴅ-glucopyranosyl-(1→2)-β-ᴅ-glucopyranosyl-(1→2)-O-[β-ᴅ-glucopyranosyl- (1→3)]-β-ᴅ-glucopyranosyl-(1→4)-β-ᴅ-galactopyranoside. The structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR and COLOC) and chemical conversions. The haemolytic potential of the steroidal saponin was evaluated and the anti-inflammatory activity was performed using the capillary permeability assay.

Three New Steroidal Saponins from Smilax officinalis

2008 ◽  
Vol 63 (1) ◽  
pp. 95-100 ◽  
Author(s):  
Bernadete P. da Silva ◽  
José P. Parente
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Steroidal Saponins ◽  
C Nmr

Three new steroidal saponins were isolated from the roots of Smilax officinalis Kunth. Their structures were established as (3β,5β,22α,25S)-26-(β-D-glucopyranosyloxy)-22-hydroxyfurostan- 3-yl O-α-L-arabinopyranosyl-(1→6)-O-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside, (3β,5α,22α,25S)-26-(β-D-glucopyranosyloxy)-22-hydroxyfurostan-3-yl O-α-L-arabinopyranosyl-( 1→6)-O-[β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside and (3β,5α,6β,22α,25S)-26-(β- D-glucopyranosyloxy)-6,22-dihydroxyfurostan-3-yl O-α-L-arabinopyranosyl-(1→6)-O-[β-D-glucopyranosyl-( 1→4)]-β-D-glucopyranoside. Their structure elucidations were performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HSQC, HMBC and HMQC) and chemical conversions.

scholarly journals A New Bioactive Steroidal Saponin from Leaves of Furcraea gigantea

2006 ◽  
Vol 61 (9) ◽  
pp. 1153-1157 ◽  
Author(s):  
Bernadete P. da Silva ◽  
José P. Parente
Keyword(s):  
Nmr Spectra ◽  
Capillary Permeability ◽  
Structural Identification ◽  
2D Nmr ◽  
In Vitro Assays ◽  
Steroidal Saponin ◽  
Spectroscopic Techniques ◽  
C Nmr

Abstract A new bidesmosidic furostanol saponin was isolated from leaves of Furcraea gigantea Vent. Its structure was established as 3-[(O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β -D-glucopyranosyl-( 1→3)-O-[O-β -D-glucopyranosyl-(1→3)-β -D-glucopyranosyl-(1→2)-O-β -D-glucopyranosyl- (1→4)-β -D-galactopyranosyl)oxy]-(3β ,5α,15α,22α,25R)-26-(β -D-glucopyranosyloxy)-15,22-dihydroxy- furost-12-one. Its structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponin showed no haemolytic effects in the in vitro assays and demonstrated inhibition of the capillary permeability activity.

E-Homolupane Derivatives Substituted in Position 17 and 22a. 1H NMR, 13C NMR and IR Spectra

1995 ◽  
Vol 60 (4) ◽  
pp. 619-635 ◽  
Author(s):  
Václav Křeček ◽  
Stanislav Hilgard ◽  
Miloš Buděšínský ◽  
Alois Vystrčil
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Coupling Constants ◽  
Side Chain ◽  
Oxidation Reactions ◽  
H Nmr ◽  
Complete Assignment ◽  
Nmr Techniques ◽  
Intramolecular Association ◽  
C Nmr

A series of derivatives with various oxygen functionalities in positions 17,22a or 19,20 was prepared from diene I and olefin XVI by addition and oxidation reactions. The structure of the obtained compounds was confirmed by 1H NMR, 13C NMR and IR spectroscopy. The kind of intramolecular association of the 17α-hydroxy group was studied in connection with modification of the side chain and substitution in position 22a. Complete assignment of the hydrogen signals and most of the coupling constants was accomplished using a combination of 1D and 2D NMR techniques. The 1H and 13C NMR spectra are discussed.

scholarly journals Competitive Diels–Alder and ene addition of N-arylmaleimides to 7-dehydrocholesteryl acetate

1992 ◽  
Vol 70 (11) ◽  
pp. 2730-2744 ◽  
Author(s):  
William J. Leigh ◽  
Donald W. Hughes ◽  
D. Scott Mitchell
Keyword(s):  
Molecular Mechanics ◽  
Nmr Spectra ◽  
Benzene Solution ◽  
Diels Alder ◽  
Spectroscopic Techniques ◽  
Two Dimensional ◽  
A Minor ◽  
C Nmr ◽  
Alder Adduct ◽  
Ene Addition

Thermolysis of N-phenyl, N-para-biphenyl, and N-para, para′-terphenylmaleimide with 7-dehydrocholesteryl acetate in benzene solution at 200 °C yields mixtures of four cycloadducts in relative yields that are essentially independent of the maleimide substituent. The three major products are those of ene addition to C7 of the steroid with abstraction of the proton at C9 or C14. The α-endo-Diels-Alder adduct is formed as a minor product. The structures of the adducts have been elucidated on the basis of one- and two-dimensional 1H and 13C NMR spectroscopic techniques, including homonuclear 1H decoupling, NOE, 1H–1H COSY, heteronuclear 1H–13C shift correlation, and TOCSY 2-D experiments, and the results of molecular mechanics (MMX) calculations. The combination of these techniques has made it possible to almost completely assign the 1H and 13C NMR spectra for two of the ene adducts and the Diels–Alder adduct from reaction of 7-dehydrocholesteryl acetate with N-phenyl maleimide.

scholarly journals Two New Glycosides from Conyza bonariensis

2010 ◽  
Vol 5 (7) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Aqib Zahoor ◽  
Imran Nafees Siddiqui ◽  
Afsar Khan ◽  
Viqar Uddin Ahmad ◽  
Amir Ahmed ◽  
...  
Keyword(s):  
2D Nmr ◽  
Mass Spectrometric ◽  
Spectroscopic Techniques ◽  
H Nmr ◽  
Alkyl Glycoside ◽  
Conyza Bonariensis ◽  
C Nmr

Studies on Conyza bonariensis (L.) Cronq. led to the isolation of two new glycosides trivially named as erigeside E and F (1–2), along with two new source compounds; benzyl-β-D-glucopyranoside (3) and 2-phenylethyl-β-D-glucopyranoside (4). Compounds 1, 3, and 4 are aromatic glycosides, while compound 2 is an alkyl glycoside. Their structures were elucidated through mass spectrometric, and 1D- and 2D-NMR spectroscopic techniques, including 1H NMR, 13C NMR, HMQC, HSQC and HMBC.

scholarly journals Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

2018 ◽  
Vol 14 ◽  
pp. 3011-3017
Author(s):  
Akın Sağırlı ◽  
Yaşar Dürüst
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Synthetic Route ◽  
X Ray ◽  
H Nmr ◽  
2D Nmr Spectra ◽  
Tof Ms ◽  
C Nmr

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen which could not be detected or isolated. In addition, the plausible mechanisms were proposed for both transformations. The structures of the title compounds were identified by means of IR, 1H NMR, 13C NMR, 2D NMR spectra, TOF–MS and X-ray measurements.

scholarly journals Isolation and Quantification of Pinitol, a Bioactive Cyclitol, in Retama spp

2016 ◽  
Vol 11 (3) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Nuria H. González-Mauraza ◽  
Antonio J. León-González ◽  
José L. Espartero ◽  
Juan B. Gallego-Fernández ◽  
Marina Sánchez-Hidalgo ◽  
...  
Keyword(s):  
Mediterranean Region ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Aqueous Extracts ◽  
Aerial Parts ◽  
The Mediterranean ◽  
Anti Inflammatory ◽  
Identification And Quantification

The genus Retama (Fabaceae) is widely distributed in the Mediterranean region. In the present study, pinitol (3- O-methyl- chiro-inositol), an anti-inflammatory and antidiabetic molecule, was isolated from aerial parts of R. monosperma, and its structure established on the basis of spectroscopic techniques (1D/2D NMR) and MS. Identification and quantification of pinitol in R. raetam and R. sphaerocarpa were also performed. R. monosperma had the highest concentration of pinitol (2.3%). The presence of pinitol in aqueous extracts of Retama spp. may explain the adaptation of these plants to drought and salinity. Furthermore, pinitol could be considered as a mediator in the anti-inflammatory and hypoglycemic activities of Retama spp., which are traditionally used to treat diabetes.

Polystachyasaponin with Adjuvant Activity from Entada polystachya

2010 ◽  
Vol 65 (5) ◽  
pp. 628-634 ◽  
Author(s):  
Bernadete P. da Silva ◽  
José P. Parente
Keyword(s):  
2D Nmr ◽  
In Vitro Assays ◽  
Triterpenoid Saponin ◽  
Spectroscopic Techniques ◽  
Adjuvant Activity ◽  
In Vivo Assays ◽  
Cellular Immune ◽  
C Nmr

A new complex triterpenoid saponin, polystachyasaponin, was isolated from leaves of Entada polystachya (L.) DC. (Leguminosae) by using chromatographic methods. Its structure was established as 15,16-dihydroxy-3-[[O-β -D-xylopyranosyl-(1→2)-O-α-L-arabinopyranosyl-(1→6)-2- (acetylamino)-2-deoxy-β -D-glucopyranosyl]oxy]-(3β ,15α,16α)-olean-12-en-28-oic acid O-D-apio- β -D-furanosyl-(1→3)-O-β -D-xylopyranosyl-(1→2)-O-[β -D-glucopyranosyl-(1→4)]-6-O-[(2E,6R)- 6-hydroxy-2,6-dimethyl-1-oxo-2,7-octadienyl]-β -D-glucopyranosyl ester. Structural elucidation was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques and chemical conversions. The hemolytic activity of the saponin was evaluated using in vitro assays, and its adjuvant potential on the cellular immune response against ovalbumin antigen was investigated using in vivo assays.

Biological Activity of a Phloroglucinol Glucoside Derivative from Conyza aegyptiaca

2009 ◽  
Vol 64 (7-8) ◽  
pp. 513-517 ◽  
Author(s):  
Ahmed A. Mahmoud ◽  
Shar S. Al-Shihry ◽  
Mohamed-Elamir F. Hegazy
Keyword(s):  
2D Nmr ◽  
Raw 264.7 ◽  
Spectroscopic Techniques ◽  
Hep G2 ◽  
Dpph Assay ◽  
Cytotoxic Effects ◽  
Aerial Parts ◽  
Different Types ◽  
Hct 116 ◽  
C Nmr

The phloroglucinol glucoside derivative [2,4-dihydroxy-6-(β-D-glucopyranosyloxy)phenyl]- butan-1-one (1), roseoside (2), and kaempferol-3-O-β-D-glucopyranoside (3) were isolated from the aerial parts of Conyza aegyptiaca (L.). To the best of our knowledge, this is the first isolation of compounds 1 - 3 from C. aegyptiaca. Their structures were determined by spectroscopic techniques including, IR, HR-EIMS, and extensive 500 MHz 1D- and 2D-NMR analyses (1H, 13C NMR, DEPT, 1H-1H COSY, HMQC and HMBC experiments). The antioxidant activity of 1, using the DPPH assay, was investigated; in addition, 1 was investigated against different types of cell lines, including Hep-G2, HCT-116, and RAW 264.7 for its cytotoxic effects. Also, this is the first report on the activity of 1.

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