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.

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 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.

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 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 Three New Iridoid Glucoside Salts from Hedyotis tenelliflora Growing in Vietnam

2013 ◽  
Vol 8 (11) ◽  
pp. 1934578X1300801
Author(s):  
Luu H. Van Long ◽  
Vo Thi Nga ◽  
Nguyen Phuc Dam ◽  
Mai Anh Hung ◽  
Tu Duc Dung ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Methyl Ester ◽  
Acid Methyl Ester ◽  
2D Nmr ◽  
Iridoid Glucoside ◽  
2D Nmr Spectroscopy ◽  
Sodium Salts ◽  
Chemical Structures ◽  
Acid Methyl ◽  
Acid Sodium Salt

Three new sodium salts of iridoid acids, deacetylasperulosidic acid sodium salt (1), teneoside D (2), and teneoside E (3) were isolated from the leaves of Hedyotis tenelliflora Blume (Rubiaceae), together with seven known iridoids, 6α-hydroxygeniposide (4), 6β-hydroxygeniposide (5), 6- O-methyldeacetylasperulosidic acid methyl ester (6), 6- O-methylscandoside methyl ester (7), 6α-methoxygeniposidic acid (8), daphylloside (9), and mollugoside methyl ester (10). Their chemical structures were elucidated by 1D and 2D NMR spectroscopy, as well as HR-ESI-MS analysis.

scholarly journals New Glycosides and Trypanocidal Metabolites from Vangueria edulis

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Shaymaa M. M. Mohamed ◽  
Khaled M. Elokely ◽  
Enaam Y. Bachkeet ◽  
Soad A. L. Bayoumi ◽  
Vincenzo Carnevale ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
Candida Glabrata ◽  
Iridoid Glycosides ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Brucei ◽  
Iridoid Glucoside ◽  
Iridoid Glucosides ◽  
Monoterpene Glycoside ◽  
First Time

A new iridoid glucoside, 10-methoxy apodanthoside (1), and a new monoterpene glycoside, (3S,6S)-cis linalool-3,7-oxide O-β-D-glucopyranosyl-(1′'→5′)-β-D-xylofuranoside (2), were isolated from V. edulis (Rubiaceae), along with eighteen known compounds (3–20), including monoterpenes, iridoid glycosides, and a lignin, which were encountered for the first time in the genus Vangueria,. The structural elucidation of the isolates was based on the analysis of spectroscopic (1D and 2D NMR) and HR-ESI-MS data. Detailed stereochemical studies of 1 and related iridoid glucosides (compounds 3, 4 and 8) were made by matching the calculated ECD peaks with the experimental ones. All isolates were tested for their antiprotozoal, antifungal, and antiplasmodial activities. Compounds 9, 15 and 16 showed good trypanocidal activities against Trypanosoma brucei brucei with IC50 values of 8.18, 9.02 and 7.80 μg/mL, respectively and IC90 values of >10, >10 and 9.76 μg/mL, respectively. Compound 16 showed a moderate activity against Candida glabrata with an IC50 value of 8.66 μg/mL. Compound 20 showed a weak antiplasmodial activity against chloroquine-sensitive (D6) and resistant (W2) Plasmodium falciparum with IC50 values of 3.29 (SI, >1.4) and 4.53 (SI, >1) μg/mL, respectively.

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

Phenylpropanoid and Iridoid Glucosides from the Whole Plant of Hemiphragma heterophyllum and Their alpha-Glucosidase Inhibitory Activities

Planta Medica ◽  
2020 ◽  
Vol 86 (03) ◽  
pp. 205-211
Author(s):  
Yan-Hong Li ◽  
Jia-Meng Dai ◽  
Cui Yang ◽  
Meng-Yuan Jiang ◽  
Yong Xiong ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Iridoid Glucoside ◽  
2D Nmr Spectroscopy ◽  
Whole Plant ◽  
Ic50 Value ◽  
Iridoid Glucosides ◽  
Alpha Glucosidase

AbstractThree phenylpropanoid glucosides (1 – 3) and one iridoid glucoside (11), together with eleven known glucosides, were isolated from the ethanol extract of the whole plant of Hemiphragma heterophyllum. Their structures were elucidated by means of 1D and 2D NMR spectroscopy, HRMS, and chemical methods. All compounds except 11 and 13 – 15 showed varying degrees of α-glucosidase inhibitory activity. Compounds 5, 9, and 12 were marginally active in the bioassay, while compounds 1 – 4, 6 – 8, and 10 exhibited appreciable inhibitory activity with an IC50 value of 33.6 ~ 83.1 µM, which was much lower than that of the positive control acarbose (IC50 = 310.8 µM).

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.

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