Feruloyl sucrose derivatives from Bistorta manshuriensis

2010 ◽  
Vol 88 (6) ◽  
pp. 519-523 ◽  
Author(s):  
Ki Hyun Kim ◽  
Sang Wook Chang ◽  
Kang Ro Lee
Keyword(s):  
Medicinal Plant ◽  
2D Nmr ◽  
Aerial Parts ◽  
Extensive Analysis ◽  
Phytochemical Investigation ◽  
New Compounds ◽  
Chemical Evidence

Bistorta manshuriensis is a well-known Korean medicinal plant traditionally used to treat diarrhea. Phytochemical investigation of the aerial parts of B. manshuriensis led to the isolation of two new feruloyl sucrose derivatives, bistoroside A (1) and bistoroside B (2), together with three known compounds, helonioside A (3), helonioside B (4), and smilaside L (5). The structures of the new compounds were elucidated as (3,6-di-O-Z-feruloyl)-β-D-fructofuranosyl-(1→2)-α-D-glucopyranoside (1) and (3,6-di-O-Z-feruloyl)-β-D-fructofuranosyl-(1→2)-(6′-O-acetyl)-α-D-glucopyranoside (2) on the basis of extensive analysis of 1D and 2D NMR (HMQC and HMBC), HR-FAB-MS, and chemical evidence.

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 Unusual derivatives from Hypericum scabrum

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Sara Soroury ◽  
Mostafa Alilou ◽  
Thomas Gelbrich ◽  
Marzieh Tabefam ◽  
Ombeline Danton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Hypericum Scabrum ◽  
New Compounds ◽  
Absolute Structure

AbstractThree new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

scholarly journals Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

2021 ◽  
Author(s):  
Chang-An Geng ◽  
Zhen-Tao Deng ◽  
Qian Huang ◽  
Chun-Lei Xiang ◽  
Ji-Jun Chen
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Cell Protein ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
New Compounds

AbstractTen 3,5-dimethylcoumarins (1–6 and 8‒11) involving six new ones (1–6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro. Graphic Abstract

scholarly journals Hyloglyceride and Hylodiglyceride: Two New Glyceride Derivatives from Hylodendron gabunensis

2010 ◽  
Vol 5 (12) ◽  
pp. 1934578X1000501 ◽  
Author(s):  
Awazi Tengu Nyongha ◽  
Hidayat Hussain ◽  
Etienne Dongo ◽  
Ishtiaq Ahmed ◽  
Karsten Krohn
Keyword(s):  
2D Nmr ◽  
Comprehensive Analysis ◽  
Phytochemical Investigation ◽  
New Compounds

Phytochemical investigation of Hylodendron gabunensis resulted in the isolation of two new glyceride derivatives, hyloglyceride (1) and hylodiglyceride (2). The structures of the two new compounds were determined by comprehensive analysis of their 1D and 2D NMR spectroscopic, and HREIMS data. One known compound was also isolated and identified as β-sitosterol.

scholarly journals Anti-inflammatory Constituents from the Aerial Parts of Iris minutiaurea

2016 ◽  
Vol 11 (6) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Kyeong Wan Woo ◽  
Ki Ho Lee ◽  
Ji Hun Jang ◽  
Min Suk Kim ◽  
Hyun Woo Cho ◽  
...  
Keyword(s):  
Proinflammatory Cytokine ◽  
Fast Atom Bombardment ◽  
Methanol Extract ◽  
2D Nmr ◽  
Flavonoid Glycoside ◽  
Enzyme Hydrolysis ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Tnf Α ◽  
Anti Inflammatory

Phytochemical investigation of the methanol extract of the aerial parts of Iris minutiaurea (Iridaceae) using column chromatography led to the isolation of a new xanthone glycoside, 1-hydroxy-3,5-dimethoxy-xanthone-6- O-β-D-glucoside (1), together with one known flavonoid glycoside (2). The structure of this new compound was elucidated by analysis of spectroscopic, including ID (1H, 13C), 2D NMR (COSY, HMQC, HMBC), and high resolution fast atom bombardment mass spectrometric (HR-FAB-MS) data and enzyme hydrolysis. We found that compounds 1 and 2 significantly suppressed production of NO, and pro-inflammatory cytokine in LPS-induced RAW264.7 cells. These results suggest that compound 1 and 2 have anti-inflammatory activity related with production of TNF-α, IL-6, IL-β, and NO in macrophages, and then compound 1 were more efficient than compound 2 in lowering the level of proinflammatory cytokine.

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.

Dammarane triterpenoid saponins from Bacopa monnieri

2009 ◽  
Vol 87 (9) ◽  
pp. 1230-1234 ◽  
Author(s):  
Pamita Bhandari ◽  
Neeraj Kumar ◽  
Bikram Singh ◽  
Inderjeet Kaur
Keyword(s):  
Medicinal Plant ◽  
2D Nmr ◽  
Bacopa Monnieri ◽  
Spectroscopic Methods ◽  
Triterpenoid Saponins ◽  
Enhancing Effect ◽  
Indian Medicinal Plant ◽  
Aerial Parts ◽  
Memory Enhancer ◽  
Memory Enhancing

Bacopa monnieri is a well-known Ayurvedic Indian medicinal plant traditionally used as a memory enhancer. Its memory-enhancing effect is mainly attributed to dammarane triterpenoid saponins. In the present study, two new dammarane-type triterpenoid saponins, bacopaside-XI (1) and bacopaside-XII (2), together with known compounds, bacopaside IV, bacopaside V, and apigenin, were isolated from the aerial parts of the B. monnieri . The structures of the new saponins were elucidated as 3-O-[α-L-arabinofuranosyl(1→3)]-6-O-sulfonyl-β-D-glucopyranosyl pseudojujubogenin (1) and 3-O-{β-D-glucopyranosyl(1→3)[α-L-arabinofuranosyl(1→2)]-β-D-glucopyranosyl}-20-O-α-L-arabinopyranosyl pseudojujubogenin (2) on the basis of extensive investigations of 1D and 2D NMR (HMQC and HMBC), ESI-QTOF-MS/MS spectroscopic methods, and chemical evidences.

scholarly journals Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3336 ◽  
Author(s):  
Ping-Chen Tu ◽  
Han-Chun Tseng ◽  
Yu-Chia Liang ◽  
Guan-Jhong Huang ◽  
Te-Ling Lu ◽  
...  
Keyword(s):  
2D Nmr ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Isolation And Characterization ◽  
Whole Plant ◽  
Phytochemical Investigation ◽  
Ic50 Value ◽  
Anti Inflammatory ◽  
New Compounds ◽  
First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

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.

A NEW NAPHTHYL SUBSTITUTED Β-SITOSTEROL AND FATTY ACIDS FROM THE BARK OF FICUS RELIGIOSA L.

INDIAN DRUGS ◽  
2017 ◽  
Vol 54 (07) ◽  
pp. 18-22
Author(s):  
A. Ali ◽  
◽  
M. Jameel ◽  
M Ali
Keyword(s):  
Fatty Acids ◽  
Skin Diseases ◽  
Decanoic Acid ◽  
2D Nmr ◽  
Stem Bark ◽  
Gastric Ulcers ◽  
Ficus Religiosa ◽  
Phytochemical Investigation ◽  
Ft Ir ◽  
New Compounds

The stem bark of the holy tree Ficus religiosa L. (family: Moraceae) is traditionally prescribed to treat anxiety, hiccup, burns, scabies and skin diseases, vomiting, gastric ulcers, haemorrhoids, diarrhoea, dysentery, glandular swellings of the neck, gonorrhoea, urinogenital disorders, toothache and for strengthening the gums. Phytochemical investigation of a methanolic extract of the stem bark yielded a β-steryl naphthyl ester, characterized as naphthyl-1',3'-diol-1'-β-sitosteryl-3'-octadec-9′′, 12′′-dienoate (1) and two fatty acids identified as 2β,3β,4β,5β-tetrahydroxy-n-octanoic acid (2) and 2β,3β,4β,5β- tetrahydroxy-n-decanoic acid (3). The structure of isolated compounds was established on the basis of 1D and 2D NMR, FT-IR, UV, and MS data and chemical means. The finding enhance the phytochemical nature of F. religiosa. These new compounds have been isolated for the first time from this plant and may play an important role as chromatographic markers for standardization of crude bark and its marketed herbal formulations.

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