scholarly journals Flavonoid, Phenylethanoid and Iridoid Glycosides from Globularia aphyllanthes

2009 ◽  
Vol 64 (2) ◽  
pp. 252-256 ◽  
Author(s):  
Hasan Kırmızıbekmez ◽  
Carla Bassarello ◽  
Sonia Piacente ◽  
Galip Akaydın ◽  
İhsan Çalış
Keyword(s):  
Spectroscopic Analysis ◽  
Iridoid Glycosides ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Phenylethanoid Glycosides ◽  
Meoh Extract ◽  
Flavone Glycoside ◽  
Aerial Parts

A new flavone glycoside, 6-hydroxyluteolin 7-O-[6m-benzoyl-β -D-glucopyranosyl-(1 → 2)]-β - D-glucopyranoside (aphyllanthoside, 1) was isolated from the MeOH extract of the aerial parts of Globularia aphyllanthes. Besides this new compound, two flavonoid glycosides (6-hydroxyluteolin 7-O-[6m-(E)-caffeoyl-β -D-glucopyranosyl-(1 → 2)]-β -D-glucopyranoside and isoquercitrin), three phenylethanoid glycosides (verbascoside, rossicaside A, and trichosanthoside A), and 11 iridoid glycosides (aucubin, catalpol, 10-O-benzoylcatalpol, globularin, asperuloside, besperuloside, asperulosidic acid, daphylloside, scandoside, alpinoside and baldaccioside) were also obtained and characterized. Identification of the isolated compounds was carried out by spectroscopic analysis including 1D and 2D NMR experiments as well as HRMS

scholarly journals Flavonoid Constituents of Pistacia integerrima

2012 ◽  
Vol 7 (8) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Zia Ullah ◽  
Rashad Mehmood ◽  
Muhammad Imran ◽  
Abdul Malik ◽  
Rehana A. Afzal
Keyword(s):  
Spectroscopic Analysis ◽  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Acidic Hydrolysis ◽  
Aerial Parts ◽  
First Time

Pistacides A and B (1–2), two new flavonoid glycosides, have been isolated from the methanolic extract of the aerial parts of Pistacia integerrima, along with 2′-hydroxyisoorientin (3), echioidinin 2′- O-β-D-(6″- O-acetyl) glucopyranoside (4), chrysoeriol (5), and diandraflavone A (6), reported for the first time from this species. Their structures were elucidated by spectroscopic analysis including 2D NMR, FAB-MS, and acidic hydrolysis.

scholarly journals Phenolic Constituents of Knautia arvensis Aerial Parts

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Jaroslaw Moldoch ◽  
Barbara Szajwaj ◽  
Milena Masullo ◽  
Lukasz Pecio ◽  
Wieslaw Oleszek ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Flavone Glycoside ◽  
Aerial Parts ◽  
Dicaffeoylquinic Acid ◽  
Phenolic Constituents ◽  
First Time

A new C-6 flavone glycoside (6), together with seven known compounds, cryptochlorogenic acid (1), chlorogenic acid (2), 2- O- trans-caffeoylhydrocitric acid (3), isovitexin 7-β-D-glucopyranoside (4), 7,4′-dihydroxy-5-methoxyflavone-6- C-β-D-glucopyranoside (5), 3,5- O-dicaffeoylquinic acid (7) and 4,5- O-dicaffeoylquinic acid (8), were isolated from the aerial parts of Knautia arvensis. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis. Compounds 1, 3-5 and 8 are reported for the first time in Knautia arvensis.

Flavon- and Flavonolglycosides from Achillea pannonica Scheele

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Techniques ◽  
Chemotaxonomic Study ◽  
First Time ◽  
C Nmr

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly

Iridoid Glucosides from Turkish Phlomis tuberosa

2005 ◽  
Vol 60 (12) ◽  
pp. 1295-1298 ◽  
Author(s):  
Ihsan Calis ◽  
Hasan Kirmizibekmez ◽  
Tayfun Ersoz ◽  
Ali A. Dönmez ◽  
Charlotte H. Gotfredsen ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Spectroscopic Data ◽  
Phenylethanoid Glycosides ◽  
Iridoid Glucoside ◽  
Flavone Glycoside ◽  
Aerial Parts ◽  
Iridoid Glucosides ◽  
Dehydrodiconiferyl Alcohol

From the aerial parts of Phlomis tuberosa a new iridoid glucoside, chlorotuberoside was isolated together with five known iridoid glucosides, lamalbide, shanzhiside methyl ester, 7-epi-phlomiol (= phloyoside I), sesamoside and 5-deoxysesamoside. Two known phenylethanoid glycosides, forsythoside B, and decaffeoylacteoside, three known neolignan glycosides, dehydrodiconiferyl alcohol 9’-O-β -D-glucopyranoside, dihydrodehydrodiconiferyl alcohol 9-O-β -D-glucopyranoside and dihydrodehydrodiconiferyl alcohol 9’-O-β -D-glucopyranoside, one flavone glycoside, luteolin 7-O-β - D-glucopyranoside, as well as β -sitosterol 3-O-β -D-glucopyranoside and 1-methyl-O-β -D-glucopyranoside were also obtained and characterized. The structures of the isolates were elucidated on the basis of spectroscopic data. The three known phenylethanoid glycosides, verbascoside, leucosceptoside A and martynoside were identified by TLC comparison with authentic compounds.

scholarly journals Secondary Metabolites from Eremostachys Laciniata

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
İhsan Çalış ◽  
Ayşegül Güvenç ◽  
Metin Armağan ◽  
Mehmet Koyuncu ◽  
Charlotte H. Gotfredsen ◽  
...  
Keyword(s):  
Methyl Ester ◽  
2D Nmr ◽  
Phenylethanoid Glycosides ◽  
Iridoid Glucoside ◽  
Aerial Parts ◽  
Iridoid Glucosides ◽  
Close Relationship ◽  
Flavone Derivatives ◽  
Optical Rotations ◽  
Relationship Of

From the aerial parts of Eremostachys laciniata (Lamiaceae), a new acidic iridoid glucoside, 5-desoxysesamosidic acid (1) was isolated in addition to thirteen known iridoid glucosides, 5-desoxysesamoside (2), sesamoside (3), 6β-hydroxy-7- epi-loganin (4), chlorotuberoside (5), 5-deoxypulchelloside I (6), lamalbide (7), lamalbidic acid (8), phloyosides I (7- epi-phlomiol) (9), and II (10), phlomiol (11), shanzhiside (12), shanzhiside methyl ester (13), and barlerin (8- O-acetylshanzhiside methyl ester) (14), four phenylethanoid glycosides, verbascoside (15), leucosceptoside A (16), martynoside (17), and forsythoside B (18), and five flavone derivatives, luteolin (19), luteolin 7- O-β-D-glucopyranoside (20), luteolin 7- O-(6″- O-β-D-apiofuranosyl)-β-D-glucopyranoside (21), apigenin 7- O-β-D-glucopyranoside (22), and apigenin 7- O-(6″- O-p-coumaroyl)-β-D-glucopyranoside (23). The structures of the metabolites were elucidated from spectroscopic (UV, IR, 1D- and 2D-NMR) and ESI-MS evidence, as well as from their specific optical rotations. The presence of these metabolites of three different classes strongly supports the close relationship of the genera Eremostachys and Phlomis.

scholarly journals Chemical and Biological Investigation of Some Secondary Metabolites in Atriplex Halimus Growing in Egypt

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701 ◽  
Author(s):  
Amal Kabbash ◽  
Nagwa Shoeib
Keyword(s):  
Multidrug Resistance ◽  
Soluble Fraction ◽  
Radical Scavenging ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Dpph Radical ◽  
Biological Investigation ◽  
Atriplex Halimus ◽  
Aerial Parts ◽  
Dpph Radical Scavenging

The n-BuOH-soluble fraction of the MeOH-CH2Cl2 (1:1) extract of the aerial parts of Egyptian Atriplex halimus L. yielded two new flavonol glycosides, designated as atriplexoside A (1) [3′- O-methylquercetin-4′- O-β-apiofuranoside-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside)] and atriplexoside B (2) [3′- O-methylquercetin-4′- O-(5″″- O-β-xylopyranosyl-β-apiofuranoside)-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside)], together with six known compounds: two phenolic glucosides (3, 4), one ecdysteroid (5), one megastigmane (6) and two methoxylated flavonoid glycosides (7, 8). The structures of the compounds were elucidated by detailed spectroscopic analysis, including HR-ESI-MS and 2D-NMR spectroscopic data. DPPH radical scavenging, antileishmanial and anti-multidrug resistance activities were investigated using the n-BuOH-soluble fraction as well as the isolated compounds. Compound 8 (5- O-methylquercetin-3- O-(6″- O-α-rhamnopyranosyl-β-glucopyranoside) presented marked DPPH radical scavenging, weak antileishmanial and anti-multidrug resistance activity while the other tested compounds showed weaker activities.

scholarly journals Antioxidant Effects of Secondary Metabolites from Geranium psilostemon

2010 ◽  
Vol 5 (6) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Didem Şöhretoğrlu ◽  
Suna Atasayar Sabuncuoğrlu ◽  
M. Koray Sakar ◽  
Hilal Özgüneş ◽  
Olov Sterner
Keyword(s):  
Lipid Peroxidation ◽  
2D Nmr ◽  
Antioxidant Enzyme Activities ◽  
Meoh Extract ◽  
Etoac Extract ◽  
Human Red Blood Cells ◽  
Aerial Parts ◽  
Endogenous Antioxidant ◽  
Lipid Peroxidation Inhibition ◽  
Antioxidant Effects

An investigation was made of the effects on endogenous antioxidant enzyme activities and H2O2-induced lipid peroxidation inhibition in human red blood cells of the crude MeOH extract and its EtOAc, n-BuOH, and H2O sub-extracts obtained from aerial parts of Geranium psilostemon Ledeb., as well as compounds isolated from the most active EtOAc extract. Gallic acid (1), methyl gallate (2), pusilagin (3), 1,3,6-tri- O-galloyl-β-glucopyranoside (4), 1,2,3,4,6-penta- O-galloyl-β-glucopyranoside (5), kaempferol (6), quercetin (7), kaempferol 7- O-α-rhamnopyranoside (8), and quercetin 7- O-α-rhamnopyranoside (9) were isolated from the aerial parts of the title plant, and their structures identified from spectroscopic (UV, 1D- and 2D- NMR) and spectrometric (TOF-MS) data. All extracts and isolated compounds inhibited H2O2-induced lipid peroxidation and also enhanced the activity of superoxide dismutase (SOD) and catalase (CAT).

scholarly journals New Coumarin-Hemiterpene Ether Glucosides and a Structurally Related Phenylpropanoic Acid Derivative from Artemisia Armeniaca

2010 ◽  
Vol 5 (10) ◽  
pp. 1934578X1000501 ◽  
Author(s):  
Mahdi Mojarrab ◽  
Abbas Delazar ◽  
Matthias Hamburger ◽  
Olivier Potterat
Keyword(s):  
Acid Hydrolysis ◽  
Acid Derivative ◽  
Spectroscopic Analysis ◽  
Methanolic Extract ◽  
2D Nmr ◽  
Aerial Parts

Two new coumarin-hemiterpene ether glucosides, 4’- O-(β-D-glucopyranosyl) desoxylacarol (1), and 5- O-(β-D-glucopyranosyl) lacarol (2), were isolated from the methanolic extract of the aerial parts of Artemisia armeniaca Lam. Their structures were established by means of spectroscopic analysis including 1H- and 2D-NMR, HRESIMS, and acid hydrolysis. In addition, a structurally related phenylpropanoic acid derivative (3) was obtained in small amounts, and its structure tentatively assigned as 3-(4-hydroxy–3-methylbutoxy)-4-methoxy melilotic acid.

scholarly journals Saikosaponins from Bupleurum chinense and Inhibition of HBV DNA Replication Activity

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Feng Yin ◽  
Ruixiang Pan ◽  
Rongmin Chen ◽  
Lihong Hu
Keyword(s):  
Dna Replication ◽  
2D Nmr ◽  
Hbv Dna ◽  
Chemical Degradation ◽  
Meoh Extract ◽  
Aerial Parts ◽  
Spectral Interpretation ◽  
Replication Activity ◽  
Saikosaponin A

One new saikosaponin, 3β,16α,23,28,30-pentahydroxyoleana-11,13(18)-diene 3- O-β-D-fucopyranoside (1), along with eight known compounds, saikosaponin a, b1, b2, b3, d, g, k, and l were isolated from the MeOH extract of the aerial parts of Bupleurum chinense DC. Their structures were elucidated by 1D and 2D NMR spectral interpretation, as well as by chemical degradation. Saikosaponin d exhibited significant bioactivity in inhibiting HBV DNA replication.

scholarly journals New Acylated Triterpene Glycosides from the Roots of Polygala tenuifolia

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900
Author(s):  
Minpei Kuroda ◽  
Takaaki Shizume ◽  
Yoshihiro Mimaki
Keyword(s):  
Alkaline Hydrolysis ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Triterpene Glycosides ◽  
Meoh Extract ◽  
Dioic Acid ◽  
Polygala Tenuifolia ◽  
New Compounds

Two new and five known acylated triterpene glycosides were isolated from the MeOH extract of the roots of Polygala tenuifolia. Based on extensive spectroscopic analysis, including 2D NMR experiments, and the results of alkaline hydrolysis, the structures of the new compounds were assigned as 3β-[(β-D-glucopyranosyl)oxy]–2β,27-dihydroxyolean-12-ene-23,28-dioic acid 28- O-β-D-apiofuranosyl-(1→3)-[β-D-galactopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-3- O-( E)-3,4,5-trimethoxycinnamoyl-β-D-fucopyranosyl ester (1) and 3β-[(β-D-glucopyranosyl)oxy]–2β,27-dihydroxyolean-12-ene-23,28-dioic acid 28- O-β-D-apiofuranosyl-(1→3)-[β-D-galactopyranosyl-(1→4)-β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-4- O-( E)-3,4-dimethoxycinnamoyl-β-D-fucopyranosyl ester (2).

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