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.

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

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 Four New Pterosins from Pteris cretica and Their Cytotoxic Activities

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2767
Author(s):  
Jian Lu ◽  
Caiying Peng ◽  
Shuang Cheng ◽  
Jianqun Liu ◽  
Qinge Ma ◽  
...  
Keyword(s):  
Human Tumor ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Aerial Parts ◽  
Pteris Cretica ◽  
Phytochemical Investigation ◽  
Hct 116 ◽  
Hct 116 Cells ◽  
New Compounds

Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin 3-O-β-d-glucopyranoside (4), together with five known pterosins 5–9. Their structures were identified mainly on the basis of 1D and 2D NMR spectral data, ESI-MS and literature comparisons. Compounds 1 and 3 were new type of petrosins with a six membered ring between C-14 and C-15. The new compounds were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Results showed that compounds 1 and 2 exhibited cytotoxic activity against HCT-116 cells with IC50 value of 22.4 μM and 15.8 μM, respectively.

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.

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.

scholarly journals Three New Cytotoxic Withanolides from the Chinese Folk Medicine Physalis angulata

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Cai-Yun Gao ◽  
Ting Ma ◽  
Jun Luo ◽  
Ling-Yi Kong
Keyword(s):  
Cell Line ◽  
Folk Medicine ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
Physalis Angulata ◽  
The Absolute ◽  
New Compounds

Physagulides M-O, three new withanolides (1–3), were isolated from the aerial parts of Physalis angulata L. Their structures were elucidated through extensive spectroscopic techniques, including 1D and 2D NMR, and HRESIMS. The absolute configurations (22- R) of these new compounds were determined by CD analysis. Compounds 1 and 3 showed significant selective cytotoxic activities on the MG-63 cell line, with IC50 values of 4.28 and 5.44 μM, respectively.

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.

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.

scholarly journals New Rare Ent-Clerodane Diterpene Peroxides from Egyptian Mountain Tea (Qourtom) and Its Chemosystem as Herbal Remedies and Phytonutrients Agents

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2172 ◽  
Author(s):  
Taha A. Hussien ◽  
Ahmed A. Mahmoud ◽  
Naglaa S. Mohamed ◽  
Abdelaaty A. Shahat ◽  
Hesham R. El-Seedi ◽  
...  
Keyword(s):  
Essential Oils ◽  
13C Nmr ◽  
Biosynthetic Pathway ◽  
2D Nmr ◽  
Herbal Remedies ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
The Family ◽  
Carbohydrate Contents

Genus Stachys, the largest genera of the family Lamiaceae, and its species are frequently used as herbal teas due to their essential oils. Tubers of some Stachys species are also consumed as important nutrients for humans and animals due to their carbohydrate contents. Three new neo-clerodane diterpene peroxides, named stachaegyptin F-H (1, 2, and 4), together with two known compounds, stachysperoxide (3) and stachaegyptin A (5), were isolated from Stachys aegyptiaca aerial parts. Their structures were determined using a combination of spectroscopic techniques, including HR-FAB-MS and extensive 1D and 2D NMR (1H, 13C NMR, DEPT, 1H-1H COSY, HMQC, HMBC and NOESY) analyses. Additionally, a biosynthetic pathway for the isolated compounds (1–5) was discussed. The chemotaxonomic significance of the isolated diterpenoids of S. aegyptiaca in comparison to the previous reported ones from other Stachys species was also studied.

scholarly journals Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Antibiotics ◽  
2020 ◽  
Vol 9 (11) ◽  
pp. 753
Author(s):  
Elodie Gisèle M. Anoumedem ◽  
Bel Youssouf G. Mountessou ◽  
Simeon F. Kouam ◽  
Abolfazl Narmani ◽  
Frank Surup
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
In Vitro Cytotoxicity ◽  
Coupling Constants ◽  
Broth Culture ◽  
Spectroscopic Techniques ◽  
Cytotoxic Effects ◽  
Relative Configuration ◽  
Planar Structures

Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.

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