scholarly journals Triterpenoid Glycosides from Olax imbricata

2019 ◽  
Vol 22 (3) ◽  
pp. 324-334
Author(s):  
Nga Thi Vo ◽  
Suong Thi Minh Huynh ◽  
Huong Thi My Nguyen ◽  
Huy Thuc Duong ◽  
Phung Kim Phi Nguyen
Keyword(s):  
Oleanolic Acid ◽  
Inhibitory Activity ◽  
Methanol Extract ◽  
Colorimetric Method ◽  
2D Nmr ◽  
Pure Compound ◽  
Ic50 Value ◽  
2D Nmr Spectra ◽  
Pure Compounds ◽  
Triterpenoid Glycosides

Introduction: Olax imbricata, owning antibacterial, antioxidant, and anti-inflammatory activities, has been investigated as one of traditional diabetic plants in Vietnam. In our previous publications on Olax imbricata, the structure analysis of the isolated compounds were reported, including two phenolic compounds, three phenolic glycosidic compounds, a sesquiterpenoid tropolone and 1,2,3,4-tetrahydronaphthalene derivatives. This article described the isolation and structure elucidation of three triterpenoid glycosides isolated from the methanol extract of Olax imbricata growing in Phu Yen province. Additionally, the evaluation of inhibitory activity for a-glucosidase was performed on a pure compound. Method: The methanol extract of this plant applied the chromatographic techniques, including thin-layer chromatography and silica gel column chromatography, led to the isolation of three pure compounds. The structures of three isolated compounds were elucidated by the spectroscopic data, including 1D and 2D NMR spectra in a combination of HRESIMS, and the sugar moieties were elucidated by acid hydrolysis. The a-glucosidase inhibitory assay was applied to a pure compound by the colorimetric method. Results: Three triterpenoid glycosides, namely 3-O-a-L-rhamnopyranosyl-(1->4)-b -D-glucopyranosyl-(1->3)-6′- O-ethyl-b -Dglucuronyl oleanolic acid (1), oleanolic acid 28-O-b -D-glucopyranoside (2) and spergulacin (3) were isolated and elucidated. The compound 2 showed its strong potentiala-glucosidase inhibitory activity with the IC50 value of 56.15+/-1.31 mM. Conclusion: Among them, compound 1 is a new one, the compounds 2 and 3 were isolated for the first time from the genus Olax. The compound 2 exhibited the potential a-glucosidase inhibition activity, contributing to demonstrating the diabetes treatment ability of Olax imbricata in the folklore.  

Inhibition of Protein Tyrosine Phosphatase 1B by Lutein Derivatives isolated from Mexican Oregano (Lippia graveolens)

2018 ◽  
Vol 17 (3) ◽  
pp. 134-139
Author(s):  
R.M. Perez-Gutierrez
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Methanol Extract ◽  
Tyrosine Phosphatase ◽  
Positive Control ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Ic50 Value ◽  
Ic50 Values

Methanol extract from Lippia graveolens (Mexican oregano) was studied in order to identify inhibitory bioactives for protein tyrosine phosphatase 1B (PTP1B). Known flavone as lutein (1), and another flavone glycoside such as lutein-7-o-glucoside (2), 6-hydroxy-lutein-7-ohexoside (3) and lutein-7-o-ramnoide (4) were isolated from methanol extract of aerial parts of the Lippia graveolens. All isolates were identified based on extensive spectroscopic data analysis, including UV, IR, NMR, MS and compared with spectroscopic data previously reported. These flavones were evaluated for PTP1B inhibitory activity. Among them, compounds 1 and 3 displayed potential inhibitory activity against PTP1B with IC50 values of 7.01 ± 1.25 μg/ml and 18.4 μg/ml, respectively. In addition, compound 2 and 4 showed moderate inhibitory activity with an IC50 value of 23.8 ± 6.21 and 67.8 ± 5.80 μg/ml respectively. Among the four compounds, luteolin was found to be the most potent PTP1B inhibitor compared to the positive control ursolic acid, with an IC50 value of 8.12 ± 1.06 μg/ml. These results indicate that flavonoids constituents contained in Lippia graveolens can be considered as a natural source for the treatment of type 2 diabetes.

LC-MS- and NMR-Guided Isolation of Monoterpene Dimers from Cultivated Thymus vulgaris Varico 3 Hybrid and Their Antityrosinase Activity

Planta Medica ◽  
2019 ◽  
Vol 85 (11/12) ◽  
pp. 941-946 ◽  
Author(s):  
Ilias Stefanis ◽  
Dimitra Hadjipavlou-Litina ◽  
Anna-Rita Bilia ◽  
Anastasia Karioti
Keyword(s):  
Ursolic Acid ◽  
Oleanolic Acid ◽  
Inhibitory Activity ◽  
Kojic Acid ◽  
2D Nmr ◽  
Thymus Vulgaris ◽  
Reference Compound ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
Antityrosinase Activity

AbstractTargeted isolation based on a combination of NMR and HPLC-PDA-MS of a dichloromethane extract of Thymus vulgaris Varico 3 aerial parts afforded one new p-cymene dimer, 6,3′,4′-trihydroxy-5,5′-diisopropyl-2,2′-dimethylbiphenyl (1), together with two known p-cymene derivatives (2 and 3), as well as five known compounds, namely, thymol (4), oleanolic acid (5), ursolic acid (6), cirsimaritin (7), and xanthomicrol (8). The structural elucidation of all compounds was performed by spectroscopic analyses, including 1D and 2D NMR, and HRESIMS experiments. The biphenyls were assayed for their inhibitory activity on tyrosinase. Compounds 2 and 3 showed negligible activity on tyrosinase, while compound 1 effectively inhibited the enzyme with 35% (± 0.3) inhibitory activity, higher than the inhibition of the reference compound kojic acid (18.6 ± 0.02).

scholarly journals POLYHYDROXYPREGNANE GLYCOSIDES FROM DREGEA VOLUBILIS

2020 ◽  
Vol 58 (4) ◽  
pp. 426
Author(s):  
Phan Van Kiem ◽  
Phan Tuan Phuong
Keyword(s):  
Nmr Spectra ◽  
Methanol Extract ◽  
2D Nmr ◽  
2D Nmr Spectra

Four known polyhydroxypregnane glycosides, dregeoside Da1 (1), volubiloside A (2), drevoluoside N (3), and volubiloside C (4) were isolated from the methanol extract of the leaves of Dregea volubilis. Their structures were elucidated by 1D-, 2D-NMR, spectra and comparing with those reported in the literature.

Phenylpropanoid and Iridoid Glucosides from the Whole Plant of Hemiphragma heterophyllum and Their alpha-Glucosidase Inhibitory Activities

Planta Medica ◽  
2020 ◽  
Vol 86 (03) ◽  
pp. 205-211
Author(s):  
Yan-Hong Li ◽  
Jia-Meng Dai ◽  
Cui Yang ◽  
Meng-Yuan Jiang ◽  
Yong Xiong ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Iridoid Glucoside ◽  
2D Nmr Spectroscopy ◽  
Whole Plant ◽  
Ic50 Value ◽  
Iridoid Glucosides ◽  
Alpha Glucosidase

AbstractThree phenylpropanoid glucosides (1 – 3) and one iridoid glucoside (11), together with eleven known glucosides, were isolated from the ethanol extract of the whole plant of Hemiphragma heterophyllum. Their structures were elucidated by means of 1D and 2D NMR spectroscopy, HRMS, and chemical methods. All compounds except 11 and 13 – 15 showed varying degrees of α-glucosidase inhibitory activity. Compounds 5, 9, and 12 were marginally active in the bioassay, while compounds 1 – 4, 6 – 8, and 10 exhibited appreciable inhibitory activity with an IC50 value of 33.6 ~ 83.1 µM, which was much lower than that of the positive control acarbose (IC50 = 310.8 µM).

scholarly journals Two New Compounds from the Leaves of Glochidion obliquum

2016 ◽  
Vol 11 (4) ◽  
pp. 1934578X1601100
Author(s):  
Vu Kim Thu ◽  
Nguyen Van Thang ◽  
Nguyen Xuan Nhiem ◽  
Hoang Le Tuan Anh ◽  
Pham Hai Yen ◽  
...  
Keyword(s):  
Nmr Spectra ◽  
Methanol Extract ◽  
2D Nmr ◽  
Chromatographic Methods ◽  
2D Nmr Spectra ◽  
New Compounds

Using combined chromatographic methods, two new compounds, 6β,9β:9,13-diepoxymegastig-4-en-3β-ol (1), 5α,6α-epoxy D:C-friedoolean-8-en-3β-ol (2) were isolated from the methanol extract of the leaves of Glochidion obliquum Decne. Their structures were elucidated by 1D- and 2D-NMR spectra and in comparison with those reported in the literature.

scholarly journals Assessment of Total Phenolic, Flavonoid Content and Antioxidant Activity of Ocimum sanctum Linn

2019 ◽  
Vol 40 ◽  
pp. 30-35
Author(s):  
Ishwor Pathak ◽  
Muna Niraula
Keyword(s):  
Antioxidant Activity ◽  
Methanol Extract ◽  
Colorimetric Method ◽  
Radical Scavenging ◽  
Hexane Extract ◽  
Ocimum Sanctum ◽  
Total Phenolic ◽  
Flavonoid Content ◽  
Ic50 Value ◽  
Phenolic And Flavonoid

Ocimum sanctum, commonly known as Tulasi in Nepal, is a pharmacologically important plant due to its active constituents. In this work, extraction was carried out in hexane, chloroform and methanol solvents and their phytochemical screening was performed. Total phenolic and flavonoid contents in the plant were measured by Folin-Ciocalteu colorimetric method and aluminum chloride colorimetric method respectively. Antioxidant activity of the extracts was evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. Alkaloids, flavonoids, tannins, glycosides, polyphenols, terpenoids, tannins and steroids are mainly found in the extracts. Based on the result obtained, the plant posses a significant amount of total phenolic and total flavonoid content. Both phenolic and flavonoid contents were highest in methanol extract, followed by chloroform and hexane extract. Antioxidant activity of the extracts as ascorbic acid standard (IC50 value = 41.34 µg/mL) was in the order of methanol extract (IC50 value = 47.73 µg/mL) > chloroform extract (IC50 value = 79.46 µg/mL) > hexane extract (IC50 value = 94.68 µg/mL). The extent of the antioxidant activity of the plant is following the number of total phenolics and flavonoids present in it.

scholarly journals Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

2012 ◽  
Vol 8 ◽  
pp. 763-775 ◽  
Author(s):  
Elena A Khatuntseva ◽  
Vladimir M Men’shov ◽  
Alexander S Shashkov ◽  
Yury E Tsvetkov ◽  
Rodion N Stepanenko ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Antifungal Activity ◽  
Methanol Extract ◽  
Keyhole Limpet Hemocyanin ◽  
2D Nmr ◽  
2D Nmr Spectroscopy ◽  
Triterpenoid Saponins ◽  
Pure Compounds ◽  
Ester Linkage ◽  
Quillaic Acid

Two new triterpenoid saponins 1 and 2 were isolated from the methanol extract of the roots of Acanthophyllum gypsophiloides Regel. These saponins have quillaic acid or gypsogenin moieties as an aglycon, and both bear similar sets of two oligosaccharide chains, which are 3-O-linked to the triterpenoid part trisaccharide α-L-Arap-(1→3)-[α-D-Galp-(1→2)]-β-D-GlcpA and pentasaccharide β-D-Xylp-(1→3)-β-D-Xylp-(1→3)-α-L-Rhap-(1→2)-[β-D-Quip-(1→4)]-β-D-Fucp connected through an ester linkage to C-28. The structures of the obtained saponins were elucidated by a combination of mass spectrometry and 2D NMR spectroscopy. A study of acute toxicity, hemolytic, anti-inflammatory, immunoadjuvant and antifungal activity was carried out. Both saponins 1 and 2 were shown to exhibit immunoadjuvant properties within the vaccine composition with keyhole limpet hemocyanin-based immunogen. The availability of saponins 1 and 2 as individual pure compounds from the extract of the roots of A. gypsophiloides makes it a prospective source of immunoactive agents.

scholarly journals A New Cytotoxic Evodiamine Derivative From Tetradium ruticarpum (A. Jussieu) T. G. Hartley

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110403
Author(s):  
Jing Qin ◽  
Da-Wei Kang ◽  
Xue-mei Zhang ◽  
Li-ling Mo ◽  
Ying-dong Zhang ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Inhibitory Activity ◽  
Nmr Spectra ◽  
Human Tumor ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Nitric Oxide Production ◽  
Biosynthetic Pathways ◽  
Chromatographic Separations ◽  
2D Nmr Spectra

1-Hydroxymethyl goshuyuamide II (1), a new derivative of evodiamine with a quinazolinocarboline skeleton, along with nine known evodiamine derivatives were isolated from the dried and nearly ripe fruits of Tetradium ruticarpum (A. Jussieu) T. G. Hartley using several different chromatographic separations. Their structures were elucidated on the basis of extensive spectroscopic techniques, including 1D and 2D NMR spectra. Putative biosynthetic pathways toward 1 are proposed. Compounds 1 and 2 and 4 to 10 exhibited cytotoxic activity against six human tumor lines, and compounds 4 and 7 to 10 exhibited moderate inhibitory activity against nitric oxide production in LPS-activated RAW264.7 cells.

scholarly journals Three New 2-(2-Phenylethyl)chromone Derivatives of Agarwood Originated from Gyrinops salicifolia

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 576 ◽  
Author(s):  
Wen-Hua Dong ◽  
Hao Wang ◽  
Feng-Juan Guo ◽  
Wen-Li Mei ◽  
Hui-Qin Chen ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Line ◽  
Inhibitory Activity ◽  
Leukemia Cell ◽  
2D Nmr ◽  
Leukemia Cell Line ◽  
Chromone Derivatives ◽  
Ache Inhibitory Activity ◽  
2D Nmr Spectra ◽  
Derivatives Of

Two new 2-(2-phenylethyl)chromone derivatives (1–2), comprising 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone and benzylacetone moieties, together with one new 2-(2-phenylethenyl)chromone (3) were isolated from the ethyl acetate extraction of agarwood originated from Gyrinops salicifolia Ridl. All structures were unambiguously elucidated on the basis of 1D and 2D NMR spectra as well as by HRESIMS data. All isolated compounds were tested for acetylcholinesterase (AChE) inhibitory activity and cytotoxic activity against human myeloid leukemia cell line (K562). However, none of the compounds displayed AChE inhibitory activity at a concentration of 50 µg mL−1 or cytotoxic activity against K562 cell line.

scholarly journals SOME GLYCOSIDES ISOLATED FROM DESMODIUM GANGETICUM (L.) DC. OF VIET NAM

2018 ◽  
Vol 56 (2A) ◽  
pp. 99-103
Author(s):  
Le Minh Ha
Keyword(s):  
Nmr Spectra ◽  
Protocatechuic Acid ◽  
Methanol Extract ◽  
2D Nmr ◽  
The Other ◽  
Viet Nam ◽  
2D Nmr Spectra ◽  
First Time

From the methanol extract of the leaves of Desmodium gangeticum collected in Me Linh, Ha Noi, we isolated 5 compounds. In which, there are four glycosides including (6S,9R)-roseoside (1), kaempferol-3-O-rutinoside (nicotiflorin) (2),  quercetin-3-O-rutinoside (rutin) (3), β-sitosterol-3-O- β-D-glucopyranoside (4), and the other is protocatechuic acid (5). Kaempferol-3-O-rutinoside (2) was isolated from Desmodium gangeticum for the first time while (6S,9R)-roseoside (1) was isolated from the genus Desmodium for the first time. Their structures were determined by 1D and 2D NMR spectra.

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