scholarly journals UPLC-PDA-QTOFMS-guided isolation of prenylated xanthones and benzoylphloroglucinols from the leaves of Garcinia oblongifolia and their migration-inhibitory activity

2016 ◽  
Vol 6 (1) ◽  
Author(s):  
Hong Zhang ◽  
Dan Zheng ◽  
Zhi-Jie Ding ◽  
Yuan-Zhi Lao ◽  
Hong-Sheng Tan ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Soluble Fraction ◽  
2D Nmr ◽  
Acetone Extract ◽  
Cancer Cell Migration ◽  
Transwell Migration Assay ◽  
Migration Assay ◽  
Protein Levels ◽  
Snail Protein ◽  
New Compounds

Abstract A UPLC-PDA-QTOFMS-guided isolation strategy was employed to screen and track potentially new compounds from Garcinia oblongifolia. As a result, two new prenylated xanthones, oblongixanthones D and E (1–2), six new prenylated benzoylphloroglucinol derivatives, oblongifolins V–Z (3–7) and oblongifolin AA (8), as well as a known compound oblongifolin L (9), were isolated from the EtOAc-soluble fraction of an acetone extract of the leaves of Garcinia oblongifolia guided by UPLC-PDA-QTOFMS analysis. The structures of the new compounds were elucidated by 1D- and 2D-NMR spectroscopic analysis and mass spectrometry. Experimental and calculated ECD spectra were used to determine the absolute configurations. The results of wound healing and transwell migration assay showed that oblongixanthones D (1), E (2), and oblongifolin L (9) have the ability to inhibit cancer cell migration in lower cytotoxic concentrations. Western blotting results showed that these compounds exhibited an anti-metastasis effect mainly through downregulating RAF protein levels. In addition, 2 and 9 could inhibit phospho-MEK and phospho-ERK at downstream. Moreover, 1, 2, and 9 could inhibit snail protein level, suggesting that they could regulate the EMT pathway.

scholarly journals New Cyclopentyl Fatty Acid and Cyanohydrin Glycosides from Fruits of Hydnocarpus hainanensis

2017 ◽  
Vol 12 (2) ◽  
pp. 1934578X1701200
Author(s):  
Thanh Tra Nguyen ◽  
Bich Ngan Truong ◽  
Huong Doan Thi Mai ◽  
Marc Litaudon ◽  
Van Hung Nguyen ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Cytotoxic Activity ◽  
Cell Line ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
New Compounds ◽  
Line Compound

Three new compounds, hydnohainanic acid (1), and hydnohainanin A (2) and B (3) were isolated from the fruits of Hydnocarpus hainanensis (Achariaceae). Their structures were determined by spectroscopic analysis, including 2D NMR, and MS. Compounds 1-3 were evaluated for their cytotoxic activity against the KB cell line. Compound 1 had a moderate cytotoxicity with an IC50 value of 32.5 μg/mL, while the two remaining compounds did not exhibit inhibition, even at a concentration of 128 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.

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).

scholarly journals Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 69 ◽  
Author(s):  
Kazuki Watanabe ◽  
Yoshihiro Mimaki ◽  
Haruhiko Fukaya ◽  
Yukiko Matsuo
Keyword(s):  
Spectroscopic Analysis ◽  
Apoptotic Cell ◽  
2D Nmr ◽  
Phytochemical Analysis ◽  
X Ray ◽  
C 23 ◽  
The Family ◽  
Ic50 Values ◽  
Cycloartane Glycosides ◽  
New Compounds

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

Cornus sanguinea Fruits: a Source of Antioxidant and Antisenescence Compounds Acting on Aged Human Dermal and Gingival Fibroblasts

Planta Medica ◽  
2021 ◽  
Author(s):  
Anna Maria Iannuzzi ◽  
Chiara Giacomelli ◽  
Marinella De Leo ◽  
Lara Russo ◽  
Fabiano Camangi ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Human Fibroblasts ◽  
2D Nmr ◽  
Mass Spectrometry Data ◽  
Flavonoid Glycosides ◽  
Gingival Fibroblasts ◽  
Cellular Models ◽  
Collagen Expression ◽  
Aging Properties ◽  
New Compounds

AbstractFive new compounds, a flavonol glycoside (1), a megastigmane (2), 2 cyclohexylethanoids (3, 4), and a phenylethanoid derivative (5), together with 15 known compounds (6–20) including flavonoid glycosides, cyclohexylethanoids, and phenolic compounds, have been isolated from Cornus sanguinea drupes. All the structures have been determined by 1D and 2D NMR spectroscopic analysis and mass spectrometry data. The antioxidant capability of the most representative isolated compounds was evaluated in the hydrogen peroxide (H2O2)-induced premature cellular senescence model of human dermal and gingival fibroblasts. Several derivatives counteracted the increase of reactive oxigen species (ROS) production in both cellular models. Among the most promising, compounds 8, 14, and 20 were able to counteract cell senescence, decreasing the expression of p21 and p53. Furthermore, compound 14 decreased the expression of inflammatory cytokines (IL-6) in both cell models and counteracted the decrease of collagen expression induced by the H2O2 in dermal human fibroblasts. These data highlight the anti-aging properties of several isolated compounds from C. sanguinea drupes, supporting its possible use in the cure of skin or periodontitis lesions.

scholarly journals Acylated Aminooligosaccharides with Inhibitory Effects against α-Amylase from Streptomyces sp. HO1518

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 403 ◽  
Author(s):  
Hai-Li Liu ◽  
Heng-Chao E ◽  
Ding-An Xie ◽  
Wen-Bo Cheng ◽  
Wan-Qi Tao ◽  
...  
Keyword(s):  
Type Ii Diabetes ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Ionization Mass ◽  
Inhibitory Effects ◽  
Streptomyces Sp ◽  
Nmr Data ◽  
New Compounds ◽  
Drug Leads ◽  
Clinical Drug

Five new acylated aminooligosaccharides (1–5), together with one known related analogue (6), were isolated from Streptomyces sp. HO1518. Their structure was identified by extensive spectroscopic analysis, including 1D and 2D NMR data and high resolution electrospray ionization mass spectrometry (HRESIMS), and by comparison with those reported in the literature. All of the new compounds showed more promising porcine pancreatic α-amylase (PPA) inhibitory activities than the clinical drug acarbose, indicating them as potential pharmaceutical drug leads toward type II diabetes.

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 Three New Compounds from the Actinomycete Actinocorallia aurantiaca

2019 ◽  
Vol 9 (5) ◽  
pp. 351-354 ◽  
Author(s):  
Kai-Yue Han ◽  
Xing Wu ◽  
Chenglin Jiang ◽  
Rong Huang ◽  
Zheng-Hui Li ◽  
...  
Keyword(s):  
Influenza A ◽  
Sika Deer ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
No Production ◽  
Raw 264.7 ◽  
Spectroscopic Methods ◽  
Raw 264.7 Macrophages ◽  
Optical Rotations ◽  
New Compounds

Abstract Aurantiadioic acids A (1) and B (2), two new furan-containing polyketides, and aurantoic acid A (3), a new natural product, were isolated from the liquid fermentation of the sika deer dung-derived actinomycete Actinocorallia aurantiaca. The structures of the new compounds were established by extensive spectroscopic methods, including 1D & 2D NMR, HRESIMS spectroscopic analysis. The absolute configuration of 3 was assigned by comparison of the specific optical rotations with the reported derivatives. Biological activity evaluations suggested that compounds 1–3 showed weak inhibition on NO production in the murine monocytic RAW 264.7 macrophages with IC50 values of 35.8, 41.8, 45.2 μM, respectively. Compound 3 showed weak inhibition on influenza A virus (A/PuertoRico/8/1934, H1N1) with an EC50 value of 35.9 μM, and a selective index higher than 13.3.

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.

Cotonoates A and B, New Aromatic Esters from Cotoneaster racemiflora

2008 ◽  
Vol 63 (10) ◽  
pp. 1219-1222 ◽  
Author(s):  
Shafiullah Khan ◽  
Shazia Yasmeen ◽  
Nighat Afza ◽  
Abdul Malik ◽  
Lubna Iqbal ◽  
...  
Keyword(s):  
Spectral Analysis ◽  
Methanolic Extract ◽  
Soluble Fraction ◽  
2D Nmr ◽  
Aromatic Esters ◽  
Phytochemical Investigation ◽  
Nmr Techniques ◽  
Inhibitory Activities ◽  
New Compounds

AbstractPhytochemical investigation of the chloroform soluble fraction of the methanolic extract of Cotoneaster racemiflora resulted in the isolation of two new aromatic esters named cotonoates A (1) and B (2) along with the known compound methyl 3,4-dihydroxy-5-methoxybenzoate (3). The structures of the new compounds have been assigned on the basis of spectral analysis including 1D and 2D NMR techniques. Compound 3 shows significant antioxidant and lipoxygenase inhibitory activities.

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