scholarly journals New Lupane-type Triterpenoid Saponins from Leaves of Oplopanax horridus (Devil's Club)

2010 ◽  
Vol 5 (7) ◽  
pp. 1934578X1000500
Author(s):  
Pei-Pei Liu ◽  
Mo Li ◽  
Ting-Guo Kang ◽  
De-Qiang Dou ◽  
David C Smith
Keyword(s):  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Dioic Acid ◽  
Triterpenoid Saponins ◽  
Oplopanax Horridus ◽  
New Compounds ◽  
First Time ◽  
Chemical Evidence

Two new lupane type saponins, along with one known saponin were isolated from leaves of Oplopanax horridus (Devil's Club). The structures of the two new compounds were elucidated as 3α-hydroxy-lup-20(29)-ene-23, 28-dioic acid-3- O-β-D-glucopyranoside (2) and 24-nor-3-oxo-lup-20(29)-en-28-oic acid-28- O-α-L-rhamnopyranosyl(1″′→4′)-β-D-glucopyranosyl(1″→6′)-β-D-glucopyranoside (3) on the basis of spectroscopic analysis and chemical evidence. The known compound was identified as 3α-hydroxy-lup-20(29)-ene-23, 28-dioic acid (1) by comparison of its spectral data with those reported. Compound 1 was isolated for the first time from the title plant.

scholarly journals New Compounds from Leaves of Smallanthus sonchifolius

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400
Author(s):  
Xiang Zheng ◽  
Gai Kuo ◽  
Dou De-Qiang ◽  
Kang Ting-Guo ◽  
Shi Yu-Yuan ◽  
...  
Keyword(s):  
Benzyl Alcohol ◽  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Trienoic Acid ◽  
Octadecatrienoic Acid ◽  
Smallanthus Sonchifolius ◽  
New Compounds ◽  
First Time ◽  
Chemical Evidence

A new octadecatrienoic acid and a new benzyl glycoside, along with a known compound, were isolated from the leaves of Smallanthus sonchifolius. The structures of the two new compounds were elucidated as 13(R)-hydroxy-octadeca-(9E,11E,15Z)-trienoic acid (1) and benzyl alcohol 7-O-α-L-arabinopyranosyl(1″→2′)-β-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence. The known compound was identified as 13(R)-hydroxy-octadeca-(9Z,11E,15Z)-trienoic acid (3) by comparison of its spectral data with that reported. Compound 3 was isolated for the first time from the title plant.

scholarly journals Structures of New Phenolic Glycosides from the Seeds of Cucurbita Moschata

2009 ◽  
Vol 4 (4) ◽  
pp. 1934578X0900400
Author(s):  
Li Fa-Sheng ◽  
Xu Jing ◽  
Dou De-Qiang ◽  
Chi Xiao-Feng ◽  
Kang Ting-Guo ◽  
...  
Keyword(s):  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Phenolic Glycosides ◽  
Phenolic Glycoside ◽  
Cucurbita Moschata ◽  
Reported Data ◽  
First Time ◽  
Chemical Evidence

A new phenolic glycoside and three known compounds were isolated from the seeds of Cucurbita moschata. The structures of the new compound was elucidated as phenylcarbinyl 5-O-(4-hydroxy)benzoyl-β-D-apiofuranosyl (1→2)-β-D-glucopyranoside on the basis of spectroscopic analysis and chemical evidence. Three known compounds were identified as 1-O-benzyl[5-O-benzoyl-β-D-apiofuranosyl(1→2)]-β-D-glucopyranoside 2, cucurbitosides C 3 and A 4, by comparison of the spectral data with reported data. Compound 2 was isolated from this plant for the first time.

scholarly journals Flavonoid Glycosides and their p-Coumaroyl Esters from Campylospermum calanthum Leaves

2012 ◽  
Vol 67 (5-6) ◽  
pp. 233-243 ◽  
Author(s):  
Savio S. Elo Manga ◽  
Anastasie E. Tih ◽  
Bintou Abderamane ◽  
Raphael T. Ghogomu ◽  
Alain Blond ◽  
...  
Keyword(s):  
Spectral Data ◽  
Spectroscopic Analysis ◽  
Methanol Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Flavonoid Aglycones ◽  
New Compounds ◽  
Related Compounds ◽  
Chemical Evidence

Six new compounds, comprising three flavonoid glycosides and their respective coumaroyl esters, have been isolated and characterized from the methanol extract of the leaves of Campylospermum calanthum, along with three known flavonoid aglycones, 7-O-methyl apigenin (1), 7-O-methyl luteolin (2), and 7-O-methyl quercetin (3). Their structures were elucidated based on chemical evidence as well as spectroscopic analysis including 1D and 2D NMR (1H-1H COSY, HSQC, HMBC, and NOESY) spectroscopy and by comparing their spectral data with those reported for related compounds

scholarly journals Triterpene Bisdesmosides from the Stems of Akebia Quinata

2008 ◽  
Vol 3 (6) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Yoshihiro Mimaki ◽  
Saya Doi
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Triterpene Saponins ◽  
Nmr Data ◽  
New Compounds ◽  
Chemical Evidence

Five new triterpene saponins (1–5) were isolated from the stems of Akebia quinata. On the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence, the structures of the new compounds were determined to be 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (1), 3β-[( O-β-D-glucopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (2), 3β-[( O-β-D-glucuronopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-29-hydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (3), 3β-[( O-β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl)oxy]-23,29-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (4), and 3β-[( O-β-D-glucopyranosyl-(1→3)- O-[α-L-rhamnopyranosyl-(1→2)]-α-L-arabinopyranosyl)oxy]-23,29-dihydroxy-olean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1→4)- O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (5), respectively.

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).

New lupan-type triterpenoids

2016 ◽  
Vol 71 (11-12) ◽  
pp. 381-386 ◽  
Author(s):  
Pierre Mkounga ◽  
Hermine L.D. Maza ◽  
Blandine M.W. Ouahouo ◽  
Lydie N. Tyon ◽  
Hayato Ishikawa ◽  
...  
Keyword(s):  
Spectral Data ◽  
Manihot Esculenta ◽  
2D Nmr ◽  
Antimicrobial Activities ◽  
Wide Range ◽  
New Compounds ◽  
Chemical Evidence

Abstract Three new lupan-type triterpernoid derivatives, namely globimetulin A (1), B (2) and C (3), were isolated from the shoot of Globimetula dinklagei (Loranthaceae), a hemiparasitic plant growing on Manihot esculenta, along with five known compounds: friedelin (4), friedelan-3-ol (5), 28-hydroxyfriedelin (6), 4-hydroxy-3,5-dimethoxybenzoic acid (7) and (1R,5S,7S)-7-[2-(4-hydroxyphenyl)ethyl]-2,6-dioxabicyclo[3.3.1]nonan-3-one (8). The structures of the new compounds were elucidated by detailed analyses of their MS, IR, 1D and 2D NMR spectral data and chemical evidence. Some of these compounds were evaluated in vitro for their antimicrobial activities against a wide range of microorganisms, but none of them exhibited noticeable activity.

scholarly journals Diketopiperazine and Diphenylether Derivatives from Marine Algae-Derived Aspergillus versicolor OUCMDZ-2738 by Epigenetic Activation

Marine Drugs ◽  
2018 ◽  
Vol 17 (1) ◽  
pp. 6 ◽  
Author(s):  
Wen Liu ◽  
Liping Wang ◽  
Bin Wang ◽  
Yanchao Xu ◽  
Guoliang Zhu ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Specific Rotation ◽  
Crystallographic Analysis ◽  
Aspergillus Versicolor ◽  
X Ray ◽  
Naturally Occurring ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time ◽  
Optically Pure

A chemical-epigenetic method was used to enhance the chemodiversity of a marine algicolous fungus. Apart from thirteen known compounds, (+)-brevianamide R ((+)-3), (‒)-brevianamide R ((‒)-3), (+)-brevianamide Q ((+)-4), (‒)-brevianamide Q ((‒)-4), brevianamide V ((+)-5), brevianamide W ((‒)-5), brevianamide K (6), diorcinol B (7), diorcinol C (8), diorcinol E (9), diorcinol J (10), diorcinol (11), 4-methoxycarbonyldiorcinol (12), two new compounds, (+)- and (‒)-brevianamide X ((+)- and (‒)- 2)), as well as a new naturally occurring one, 3-[6-(2-methylpropyl)-2-oxo-1H-pyrazin-3-yl]propanamide (1), were isolated from chemical-epigenetic cultures of Aspergillus versicolor OUCMDZ-2738 with 10 µM vorinostat (SAHA). Compared to cultures in the same medium without SAHA, compounds 1–4, 8, 9, 11, and 12 were solely observed under SAHA condition. The structures of these compounds were elucidated based on spectroscopic analysis, specific rotation analysis, ECD, and X-ray crystallographic analysis. (±)-3, (±)-4, and (±)-5 were further resolved into the corresponding optically pure enantiomers and their absolute configurations were determined for the first time. Compounds 11 and 12 showed selective antibacterial against Pseudomonas aeruginosa with a minimum inhibitory concentration (MIC) of 17.4 and 13.9 μM, respectively. Compound 10 exhibited better α-glucosidase inhibitory activity than the assay control acarbose with IC50 values of 117.3 and 255.3 μM, respectively.

scholarly journals Two Compounds from the Endophytic Colletotrichum sp. of Ginkgo biloba

2011 ◽  
Vol 6 (8) ◽  
pp. 1934578X1100600
Author(s):  
Sheng-Liang Zhou ◽  
Song-Lin Zhou ◽  
Mei-Xia Wang ◽  
Shuang-Lin Chen
Keyword(s):  
Spectral Data ◽  
Ginkgo Biloba ◽  
Endophytic Fungus ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Fermentation Products ◽  
First Time

Two compounds, apigenin-8- C-β-D-glucopyranoside and 2-(hydroxymethylthio)ethanol, were extracted from the fermentation products of a strain of endophytic fungus, Colletotrichum sp. NTB-2, isolated from the leafstalk of Ginkgo biloba. The structures of the two compounds were determined on the basis of extensive spectroscopic analysis, including 1D and 2D NMR spectral data. The compounds were obtained from microorganisms for the first time.

scholarly journals Triterpenoids and Their Glycosides from Glinus Oppositifolius with Antifungal Activities against Microsporum Gypseum and Trichophyton Rubrum

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2206 ◽  
Author(s):  
Dongdong Zhang ◽  
Yao Fu ◽  
Jun Yang ◽  
Xiao-Nian Li ◽  
Myint Myint San ◽  
...  
Keyword(s):  
Trichophyton Rubrum ◽  
Microsporum Gypseum ◽  
Dioic Acid ◽  
Triterpenoid Saponins ◽  
Methyl Group ◽  
Antifungal Activities ◽  
One Dimensional ◽  
Inhibitory Activities ◽  
Whole Plants ◽  
New Compounds

Four new triterpenoids, 3β,12β,16β,21β,22-pentahydroxyhopane (1), 12β,16β,21β,22-tetrahydroxyhopan-3-one (2), 3-oxo-olean-12-ene-28,30-dioic acid (3), and 3β-hydroxyoleana-11,13(18)-diene-28,30-dioic acid 30-methyl ester (4); 21 new triterpenoid saponins, glinusopposides A–U (5–25); and 12 known compounds (26–37) were isolated from the whole plants of Glinus oppositifolius. The structures of the new compounds were elucidated based on the analysis of one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR) and mass spectrometry (MS) data. All compounds from the plants were measured for antifungal activities against Microsporum gypseum and Trichophyton rubrum. Glinusopposide B (6), glinusopposide Q (21), glinusopposide T (24), and glinusopposide U (25) showed strong inhibitory activities against M. gypseum (MIC50 7.1, 6.7, 6.8, and 11.1 μM, respectively) and T. rubrum (MIC50 14.3, 13.4, 11.9, and 13.0 μM, respectively). For those active compounds with an oleanane skeleton, glycosylation (21–26) or oxidation (3) of 3-OH was helpful in increasing the activity; replacement of the 30-methyl group (29) by a carboxymethyl group (26) enhanced the activity; the presence of 11,13(18) double bonds (20) decreased the activity.

scholarly journals Steroidal Saponins from the Rhizomes of Ruscus Hypophyllum

2008 ◽  
Vol 3 (10) ◽  
pp. 1934578X0800301 ◽  
Author(s):  
Yoshihiro Mimaki ◽  
Tsukasa Aoki ◽  
Maki Jitsuno ◽  
Akihito Yokosuka ◽  
Ceyda Sibel Kiliç ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Promyelocytic Leukemia ◽  
Leukemia Cells ◽  
Steroidal Saponins ◽  
Furostanol Saponins ◽  
Nmr Data ◽  
Spirostanol Saponins ◽  
New Compounds ◽  
Chemical Evidence

Phytochemical screening of the rhizomes of Ruscus hypophyllum (Liliaceae) has resulted in the isolation of five spirostanol saponins (1-5) including a new saponin (4) and nine furostanol saponins (6–14) including three new saponins (9–11), together with a known cholestane glycoside (15) and a new cholestane glycoside (16). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR data, and chemical evidence. The spirostanol saponins 1, 2, and 5 showed moderate cytotoxic activity against HL-60 human promyelocytic leukemia cells.

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