scholarly journals Iridoid and Phenylethanoid Glycosides from Phlomis tuberosa L.

2001 ◽  
Vol 56 (9-10) ◽  
pp. 695-698 ◽  
Author(s):  
Tayfun Ersöz ◽  
Stefanka Ivancheva ◽  
Pinar Akbay ◽  
Otto Sticher ◽  
İhsan Çalış
Keyword(s):  
Methyl Ester ◽  
Phenylethanoid Glycosides ◽  
Iridoid Glucoside ◽  
Spectroscopic Evidence ◽  
Aerial Parts ◽  
Iridoid Glucosides

AbstractA new iridoid glucoside, 8-O-acetylshanzhiside (1), was isolated from the aerial parts of Phlomis tuberosa, together with two known iridoid glucosides, shanzhiside methyl ester and lamalbide. The known phenylethanoid glycosides acteoside and forsythoside B were also obtained and characterized. The structure of 1 was determined by means of 1D - and 2DNMR spectroscopic evidence.

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.

Physocalycoside, a New Phenylethanoid Glycoside from Phlomis physocalyx Hub.-Mor.

2003 ◽  
Vol 58 (7-8) ◽  
pp. 471-476 ◽  
Author(s):  
Tayfun Ersöz ◽  
Kalina Iv. Alipieva ◽  
Funda Nuray Yalçın ◽  
Pınar Akbay ◽  
Nedjalka Handjieva ◽  
...  
Keyword(s):  
Radical Scavenging ◽  
Dpph Radical ◽  
Phenylethanoid Glycosides ◽  
Iridoid Glucoside ◽  
Spectroscopic Evidence ◽  
Phenylethanoid Glycoside ◽  
Aerial Parts ◽  
Radical Scavenging Properties

Abstract A new phenylethanoid tetraglycoside, physocalycoside (2), was isolated from the aerial parts of Phlomis physocalyx. Its structure was identified as 3-hydroxy-4-methoxy-β-phenyl-ethoxy-O-[α-ʟ-rhamnopyranosyl-(1→2)-α-ʟ-rhamnopyranosyl-(1→3)]-4-O-feruloyl-[β-ᴅ- glucopyranosyl-(1→6)]-|β-ᴅ-glucopyranoside, on the basis of spectroscopic evidence. In addition, one known iridoid glucoside, lamiide (1) and five known phenylethanoid glycosides, wiedemannioside C (3), verbascoside (= acteoside) (4). leucosceptoside A (5), martynoside (6), and forsythoside B (7) were also characterized. Compounds 2-7 demonstrated radical scavenging properties towards the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical.

The Minor Iridoid Glucosides of Barleria lupulina: Isolation, Crystal Structure and Plant Growth-Inhibiting Properties of 6-O-Acetylshanzhiside Methyl Ester

1987 ◽  
Vol 40 (5) ◽  
pp. 785 ◽  
Author(s):  
LT Byrne ◽  
JM Sasse ◽  
BW Skelton ◽  
A Suksamrarn ◽  
AH White
Keyword(s):  
Crystal Structure ◽  
Methyl Ester ◽  
Plant Growth ◽  
Structure Determination ◽  
Chemical Methods ◽  
X Ray ◽  
Aerial Parts ◽  
Iridoid Glucosides ◽  
Wheat Embryos ◽  
Growth Inhibiting

The minor iridoid glucosides present in the aerial parts of Barleria lupulina Lindl. ( Acanthaceae ) have been identified as ipolamiidoside (7) and the new compound 6-O-acetylshanzhiside methyl ester (3). The structure of (3) was determined by spectroscopic and chemical methods, and was confirmed by a single-crystal X-ray structure determination. Crystals of (3) are orthorhombic P212121, a 43.75(1), b 8.151(3), c 5.695(2) �, Z 4. The crystal structure was determined at 295 K from diffractometer data [I528 reflections with I > 3σ(I)] and refined to a residual of 0.043. Shanzhiside methyl ester (1) and its 6-Oacetyl (3), 8-Oacetyl (2) and 6,8-O,O-diacetyl (4) derivatives, all of which occur in Barleria lupulina, have been found to inhibit the growth of wheat embryos.

scholarly journals Iridoids from Globularia dumulosa

2003 ◽  
Vol 58 (3-4) ◽  
pp. 181-186 ◽  
Author(s):  
Hasan Kirmizibekmez ◽  
Pinar Akbay ◽  
Otto Sticher ◽  
İhsan Çalış
Keyword(s):  
Structure Elucidation ◽  
2D Nmr ◽  
Phenylethanoid Glycosides ◽  
Aerial Parts ◽  
Iridoid Glucosides ◽  
Nmr Methods

Two new iridoids, 10-O-benzoylglobularigenin (1) and dumuloside (2) were isolated from the aerial parts of Globularia dumulosa together with seven known iridoid glucosides, davisioside (3), aucubin (4), melampyroside (5), catalpol (6), 10-O-benzoylcatalpol (7), alpinoside (8) and deacetylalpinoside (9). Three phenylethanoid glycosides, verbascoside, decaffeoylverbascoside, leucosceptoside A and three flavone glucosides, pectolinarigenin 7-O-β-ᴅ-glucopyranoside, nepetin 7-O-β-ᴅ-glucopyranoside, demethoxycentaureidin 7-O-β-ᴅ-glucopyranoside were also isolated and characterized. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, HR-MALDIMS, 1D- and 2D NMR) methods.

Iridoid Glucosides from Phlomis tuberosa L. and Phlomis herba-ventis L.

2000 ◽  
Vol 55 (3-4) ◽  
pp. 137-140 ◽  
Author(s):  
Kalina Iv. Alipieva ◽  
Soren R. Jensen ◽  
Henrik Franzyk ◽  
Nedjalka V. Handjieva ◽  
Ljuba N. Evstatieva
Keyword(s):  
Methyl Ester ◽  
Iridoid Glucoside ◽  
Iridoid Glucosides ◽  
High Concentrations

Abstract A new iridoid glucoside, 5-desoxysesamoside, was isolated from Phlomis tuberosa L. (Lamiaceae) together with three known iridoid glucosides sesamoside, shanziside methyl ester and lamalbid. Lamiide was found in P. herba-ventis ssp. pungens in high concentrations.

scholarly journals Two New Iridoid Glucosides from Verbascum salviifolium Boiss.

2005 ◽  
Vol 60 (1) ◽  
pp. 113-117 ◽  
Author(s):  
Zeliha S Akdemir ◽  
I. Irem Tatli ◽  
Erdal Bedir ◽  
Ikhlas A. Khan
Keyword(s):  
Iridoid Glycosides ◽  
Spectroscopic Evidence ◽  
Aerial Parts ◽  
Iridoid Glucosides ◽  
New Compounds

From the aerial parts of the plant Verbascum salviifolium, two new iridoid glucosides, 6-O- β-D-glucopyranosylcatalpol (1) and 6-O-(6″-O-trans-p-hydroxycinnamoyl)- β -D-glucopyranosylaucubin (2) along with five known iridoid glycosides, 6-O- β -D-glucopyranosylaucubin (3), 6-O-α-L-rhamnopyranosylcatalpol (4), verbaspinoside [= 6-O-(2″-O-trans-cinnamoyl)-α-L-rhamnopyranosylcatalpol] (5), pulverulentoside I [= 6-O-(2″-O-trans-p-methoxycinnamoyl-3″ -O-acetyl)-α-L-rhamnopyranosylcatalpol] (6), and buddlejoside A8 [= 6-O-(4″-O-trans-3,4-dimethoxycinnamoyl)- α-L-rhamnopyranosylcatalpol] (7) were isolated. The structures of the new compounds were established on the basis of spectroscopic evidence.

Iridoid and Phenylethanoid Glycosides from Phlomis nissolii and P. capitata

2004 ◽  
Vol 59 (5) ◽  
pp. 609-613 ◽  
Author(s):  
Hasan Kırmızıbekmez ◽  
Sonia Piacente ◽  
Cosimo Pizza ◽  
Ali A. Dönmez ◽  
İhsan Çaliș
Keyword(s):  
Chlorogenic Acid ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Phenylethanoid Glycosides ◽  
Iridoid Glucoside ◽  
Ester Derivative ◽  
Iridoid Glucosides ◽  
Lignan Glycoside

Abstract A new iridoid glucoside, lamiidic acid was isolated from Phlomis nissolii, along with one known iridoid glucoside, lamiide and 13 phenylethanoid glycosides, verbascoside, isoverbascoside, leucosceptosides A and B, martynoside, arenarioside, forsythoside B, alyssonoside, lamiophlomiside A, samioside, integrifoliosides A and B, and hattushoside. A new iridoid glucoside, ipolamiidic acid was isolated from Phlomis capitata together with two known iridoid glucosides, lamiide and ipolamiide. The known phenylethanoid glycosides, isoverbascoside, forsythoside B, alyssonoside and hattushoside, a known lignan glycoside, liriodendrin, three flavonoid glycosides, luteolin 7-O- (6”-O-α-L-rhamnopyranosyl)-β -D-glucopyranoside, luteolin 7-O-(6”-O-β -D-apiofuranosyl)-β -Dglucopyranoside and chrysoeriol 7-O-β -D-glucopyranoside, an acyclic monoterpene, betulalbuside A, and a quinic ester derivative, chlorogenic acid were also obtained and characterized. The structures of the isolated compounds were elucidated by means of spectroscopic (HRESI-MS, 1D and 2D NMR) evidence.

scholarly journals 30-Normedicagenic Acid Glycosides from Chenopodium Foliosum

2012 ◽  
Vol 7 (11) ◽  
pp. 1934578X1200701
Author(s):  
Paraskev T. Nedialkov ◽  
Zlatina Kokanova-Nedialkova ◽  
Daniel Bücherl ◽  
Georgi Momekov ◽  
Jörg Heilmann ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Cell Lines ◽  
Interleukin 2 ◽  
Leukemic Cell ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Dioic Acid ◽  
Leukemic Cell Lines ◽  
Aerial Parts

Two new glycosides of 30-normedicagenic acid, namely 3- O-[ β-D-glucuronopyranosyl methyl ester]-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-D-glucopyranosyl ester, and 3- O-β-D-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid, together with the known 3- O-β-glucopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester, and 3- O-β-glucuronopyranosyl-2 β,3 β-dihydroxy-30-noroleane-12,20(29)-diene-23,28-dioic acid 28- O-β-glucopyranosyl ester were isolated from the aerial parts of Chenopodium foliosum Asch. The structures of the compounds were determined by means of spectroscopic methods (1D and 2D NMR, UV, IR) and HRMS-ESI. The compounds were tested for cytotoxicity on three leukemic cell lines (BV-173, SKW-3, HL-60). In addition, the saponins showed moderate stimulatory effects on interleukin-2 production in PHA/PMA stimulated Jurkat E6.1 cells.

scholarly journals NEW FLAVONOIDS FROM THE AERIAL PARTS OF POLYGONUM EQUISETIFORME SM (POLYGONACEAE)

2017 ◽  
Vol 9 (2) ◽  
pp. 166 ◽  
Author(s):  
Sayed A. El-toumy ◽  
Joslin Y. Salib ◽  
Nabila H. Shafik ◽  
Asmaa S. Abd Elkarim ◽  
Gihan A. Mick
Keyword(s):  
Antioxidant Activity ◽  
Methyl Ester ◽  
Secondary Metabolites ◽  
Gallic Acid ◽  
Total Phenolic ◽  
Flavonoid Content ◽  
Isolation And Identification ◽  
Aerial Parts ◽  
Dpph Method ◽  
Phenolic And Flavonoid

<p><strong>Objective: </strong>The current study was to deal the isolation and identification of secondary metabolites from <em>Polygonum equisetiforme</em> and evaluation of antioxidant activity of its extract.</p><p><strong>Methods: </strong>The methanol-water extract (7:3) of the air-dried aerial parts of <em>Polygonum equisetiforme</em> was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of these compounds were elucidated by UV and 1D⁄2D H⁄ C NMR spectroscopy and compared with the literature data. The crude extract was evaluated for <em>in vitro</em> antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method.</p><p><strong>Results: </strong>Ten secondary metabolites were isolated from <em>Polygonum equisetiforme</em> in this study. Of which three new flavonoids named as 3,5,7,2’,5’ pentahydroxyflavone 3-<em>O</em>-b-D-glucopyranoside (1), 3,5,7,2’,5’ pentahydroxyflavone 3-<em>O</em>-b-D-glucopyranoside 8 C-sulphated (2) and quercetin 3-<em>O-β</em>-D-glucucorinde 6''-methyl ester 8-sulphated (3) as well as quercetin 3-<em>O-β</em>-D-glucucorinde methyl ester (4), quercetin 3-<em>O-</em>β-D-glucopyranoside (5), quercetin 7-<em>O-β-</em>D-glucopyranoside (6),<em> </em>quercetin(7)<sub>, </sub>myricetin (8), <em>P</em><sub>-</sub>methoxy gallic acid methyl ester (9) and gallic acid (10). The antioxidant potential of <em>P. equisetiforme</em> extract was evaluated by investigating it's total phenolic and flavonoid content and DPPH radical scavenging activity whereby the extract showed significant antioxidant activity (IC<sub>50 </sub>= 37.45 μg/ml). The total phenolic and flavonoid content was found to be 130.79±5.502 and 45.8±1.63 μg/ml, respectively.</p><p><strong>Conclusion: </strong><em>Polygonum equisetiforme</em> is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as an antioxidant drug.</p>

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