Cohiro

Plombières-lès-Dijon, France
Plombières-lès-Dijon, France
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Rezgui A.,University of Burgundy | Mitaine-Offer A.-C.,University of Burgundy | Miyamoto T.,Kyushu University | Tanaka C.,Kyushu University | And 3 more authors.
Phytochemistry | Year: 2016

Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, and 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosylhederagenin 28-O-β-d-xylopyranosyl-(1 → 6)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid and 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively. © 2016 Elsevier Ltd. All rights reserved.


Montes E.G.,University of Burgundy | Montes E.G.,University of Los Andes, Venezuela | Mitaine-Offer A.-C.,University of Burgundy | Amaro-Luis J.M.,University of Los Andes, Venezuela | And 8 more authors.
Phytochemistry | Year: 2014

Five oleanane-type saponins, 3-O-β-D-glucuronopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)] -(4-O-acetyl)-β-D-fucopyranosyl ester (1), 3-O-β-D- glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L- rhamnopyranosyl-(1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (2), zanhic acid 28-O-β-D-xylopyranosyl-(1→3)-[α-L-rhamnopyranosyl- (1→2)]-(4-O-acetyl)-β-D-fucopyranosyl ester (3), zanhic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′-hydroxy-2′- methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]-β-D-fucopyranosyl ester (4), medicagenic acid 28-O-α-L-rhamnopyranosyl-(1→2)-4-O-[(3′- hydroxy-2′-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy] -β-D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the β-D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated. © 2013 Elsevier Ltd. All rights reserved.


Pertuit D.,University of Burgundy | Avunduk S.,Muǧla University | Mitaine-Offer A.-C.,University of Burgundy | Miyamoto T.,Kyushu University | And 5 more authors.
Phytochemistry | Year: 2014

Two triterpenoid saponins with two known ones have been isolated from the roots of Gypsophila arrostii var. nebulosa, and two new ones from the roots of Gypsophila bicolor. Their structures were established by extensive NMR and mass spectroscopic techniques as 3-O-β-d-galactopyranosyl-(1→2)-[β-d- xylopyranosyl-(1→3)]-β-d-glucuronopyranosylquillaic acid 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)] -α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)] -β-d-fucopyranosyl ester (1), 3-O-β-d-galactopyranosyl-(1→2)- [β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylgypsogenin 28-O-β-d-xylopyranosyl-(1→4)-[β-d-glucopyranosyl-(1→3)] -α-l-rhamnopyranosyl-(1→2)-[β-d-glucopyranosyl-(1→4)] -β-d-fucopyranosyl ester (2), 3-O-β-d-galactopyranosyl-(1→2)- [β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosylgypsogenin 28-O-β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4) -α-l-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-d-quinovopyranosyl- (1→4)]-β-d-fucopyranosyl ester (3), gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-{6-O-[3-hydroxy-3-methylglutaryl] -β-d-glucopyranosyl-(1→6)}-β-d-galactopyranosyl ester (4). Three compounds were evaluated against one human colon cancer cell line SW480 and one rat cardiomyoblast cell line H9c2. © 2014 Elsevier Ltd. All rights reserved.


Manase M.J.,University of Burgundy | Mitaine-Offer A.-C.,University of Burgundy | Miyamoto T.,Kyushu University | Tanaka C.,Kyushu University | And 3 more authors.
Phytochemistry | Year: 2014

Four triterpenoid saponins (1-4) were isolated from Polycarpaea corymbosa Lamk. var. eriantha Hochst along with the known apoanagallosaponin IV (5). Their structures were elucidated by spectroscopic data analysis. Among the compounds 1, 3-5 which were evaluated for their cytotoxicity against three tumor cell lines (SW480, DU145 and EMT6), compound 1 exhibited cytotoxicity with IC 50 values ranging from 4.61 to 22.61 μM, which was greater than that of etoposide. Compound 2 was tested only against SW480 and a cardiomyoblast cell line (H9c2), and was inactive. © 2013 Elsevier Ltd. All rights reserved.


Rezgui A.,University of Burgundy | Mitaine-Offer A.-C.,University of Burgundy | Paululat T.,University of Siegen | Delemasure S.,Cohiro | And 2 more authors.
Fitoterapia | Year: 2014

Three new spirostane-type glycosides (1-3) were isolated from the whole plant of Allium flavum. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-2α- hydroxyspirost-5-en-3β-yl O-β-d-xylopyranosyl-(1 → 3)-[β-d-galactopyranosyl-(1→2)]-β-d-galactopyranosyl-(1→4) -β-d-galactopyranoside (1), (20S,25R)-2α-hydroxyspirost-5-en-3β- yl O-β-d-xylopyranosyl-(1 → 3)-[β-d-glucopyranosyl-(1→2)]- β-d-galactopyranosyl-(1→4)-β-d-galactopyranoside (2), and (20S,25R)-spirost-5-en-3β-yl O-α-l-rhamnopyranosyl-(1 → 4)-[β-d-glucopyranosyl-(1→2)]-β-d-glucopyranoside (3). The three saponins were evaluated for cytotoxicity against a human cancer cell line (colorectal SW480). © 2013 Elsevier B.V. All rights reserved.


PubMed | University of Bordeaux Segalen, University of Siegen, University of Burgundy, University of Liège and 2 more.
Type: | Journal: Phytochemistry | Year: 2014

Five oleanane-type saponins, 3-O--D-glucuronopyranosylzanhic acid 28-O--D-xylopyranosyl-(13)-[-L-rhamnopyranosyl-(12)]-(4-O-acetyl)--D-fucopyranosyl ester (1), 3-O--D-glucopyranosylzanhic acid 28-O--D-xylopyranosyl-(13)-[-L-rhamnopyranosyl-(12)]-(4-O-acetyl)--D-fucopyranosyl ester (2), zanhic acid 28-O--D-xylopyranosyl-(13)-[-L-rhamnopyranosyl-(12)]-(4-O-acetyl)--D-fucopyranosyl ester (3), zanhic acid 28-O--L-rhamnopyranosyl-(12)-4-O-[(3-hydroxy-2-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]--D-fucopyranosyl ester (4), medicagenic acid 28-O--L-rhamnopyranosyl-(12)-4-O-[(3-hydroxy-2-methyl-butyroyloxy)-3-hydroxy-2-methyl-butyroyloxy]--D-fucopyranosyl ester (5), were isolated from the root barks of Ganophyllum giganteum. Compounds 4 and 5 possessed an unusual substitution of the C-4 position of the -D-fucopyranosyl moiety by a C10 ester group formed by two symmetrical C5 nilic acid. From a chemotaxonomic point of view, their structures are in accordance with the previous saponins isolated from the Doratoxyleae tribe of the Sapindaceae family. Their cytotoxicity and anti-inflammatory activity were also evaluated.


PubMed | Cohiro, University of Burgundy and Kyushu University
Type: | Journal: Phytochemistry | Year: 2016

Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O--D-glucopyranosyl-(1 2)-[-D-xylopyranosyl-(1 4)]--D-xylopyranosyl-(1 4)--D-xylopyranosyl-(1 3)--L-rhamnopyranosyl-(1 2)--L-arabinopyranosyloleanolic acid, 3-O--D-glucopyranosyl-(1 2)-[-D-xylopyranosyl-(1 4)]--D-xylopyranosyl-(1 4)--D-xylopyranosyl-(1 3)--L-rhamnopyranosyl-(1 2)--D-xylopyranosyloleanolic acid, 3-O--D-glucopyranosyl-(1 2)-[-D-glucopyranosyl-(1 4)]--D-xylopyranosyl-(1 4)--D-xylopyranosyl-(1 3)--L-rhamnopyranosyl-(1 2)--D-xylopyranosyloleanolic acid, 3-O--D-glucopyranosyl-(1 2)-[-D-xylopyranosyl-(1 4)]--D-xylopyranosyl-(1 4)--D-xylopyranosyl-(1 3)--L-rhamnopyranosyl-(1 2)--L-arabinopyranosyloleanolic acid 28-O--D-glucopyranosyl-(1 6)--D-glucopyranosyl ester, and 3-O--D-glucopyranosyl-(1 2)--L-arabinopyranosylhederagenin 28-O--D-xylopyranosyl-(1 6)-[-L-rhamnopyranosyl-(1 2)]--D-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O--D-glucopyranosyl-(1 2)-[-D-xylopyranosyl-(1 4)]--D-xylopyranosyl-(1 4)--D-xylopyranosyl-(1 3)--L-rhamnopyranosyl-(1 2)--L-arabinopyranosyloleanolic acid and 3-O--D-glucopyranosyl-(1 2)-[-D-xylopyranosyl-(1 4)]--D-xylopyranosyl-(1 4)--D-xylopyranosyl-(1 3)--L-rhamnopyranosyl-(1 2)--D-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1 production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.


PubMed | Cohiro, University of Siegen and University of Burgundy
Type: | Journal: Fitoterapia | Year: 2014

Three new spirostane-type glycosides (1-3) were isolated from the whole plant of Allium flavum. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20S,25R)-2-hydroxyspirost-5-en-3-yl O--D-xylopyranosyl-(13)-[-D-galactopyranosyl-(12)]--D-galactopyranosyl-(14)--D-galactopyranoside (1), (20S,25R)-2-hydroxyspirost-5-en-3-yl O--D-xylopyranosyl-(13)-[-D-glucopyranosyl-(12)]--D-galactopyranosyl-(14)--D-galactopyranoside (2), and (20S,25R)-spirost-5-en-3-yl O--L-rhamnopyranosyl-(14)-[-D-glucopyranosyl-(12)]--D-glucopyranoside (3). The three saponins were evaluated for cytotoxicity against a human cancer cell line (colorectal SW480).


PubMed | Cohiro, University of Burgundy and Kyushu University
Type: | Journal: Phytochemistry | Year: 2014

Four triterpenoid saponins (1-4) were isolated from Polycarpaea corymbosa Lamk. var. eriantha Hochst along with the known apoanagallosaponin IV (5). Their structures were elucidated by spectroscopic data analysis. Among the compounds 1, 3-5 which were evaluated for their cytotoxicity against three tumor cell lines (SW480, DU145 and EMT6), compound 1 exhibited cytotoxicity with IC50 values ranging from 4.61 to 22.61 M, which was greater than that of etoposide. Compound 2 was tested only against SW480 and a cardiomyoblast cell line (H9c2), and was inactive.


PubMed | Annaba University, Cohiro, University of Burgundy, Kyushu University and Alger University
Type: | Journal: Fitoterapia | Year: 2016

From the aerial parts, pericarps and roots of Solenostemma argel, three new pregnane glycosides (1-3) with two known ones and a new phenolic glycoside (4) have been isolated. Their structures were established by extensive 1D - and 2D NMR and mass spectroscopic analysis. The cytotoxicity of all compounds was evaluated against two human tumor cell lines (SW 480, MCF-7), but none of them was active in the concentration range 0.9-59.0M. Compounds 2 and the known argeloside F at non toxic concentrations for the PBMCs (27.3M and 27.6M, respectively) significantly decreased the Il-1 production by LPS-stimulated PBMCs. All isolated compounds showed a significant antioxidant potential with ORAC values in the concentration range 3481-9617moleq. Trolox/100g.

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