scholarly journals A New Oleanane Type Saponin from the Aerial Parts of Nigella sativa with Anti-Oxidant and Anti-Diabetic Potential

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2171
Author(s):  
Amna Parveen ◽  
Muhammad Asim Farooq ◽  
Whang Wan Kyunn
Keyword(s):  
Nigella Sativa ◽  
Tyrosine Phosphatase ◽  
Resonance Spectroscopy ◽  
Triterpenoid Saponin ◽  
Aerial Parts ◽  
Anti Oxidant ◽  
Alternate Source ◽  
Innovative Drugs ◽  
New Compounds ◽  
First Time

Natural product studies explore potential and interesting new compounds to discover innovative drugs. Nigella sativa (N. sativa) (Ranunculaceae) is traditionally used to treat diabetes. Flavonoids and triterpenoid mostly show anti-diabetic activity. The current study aim to identify new compounds by a systematic study of the anti-oxidant and anti-diabetic activity of aerial parts of N. sativa concerning. Phytochemicals were isolated from the methanolic extract of aerial parts of the plant by column chromatography and identified by nuclear magnetic resonance spectroscopy and mass spectroscopy. A new triterpenoid saponin glycoside was isolated along with flavonoids. The anti-diabetic study was carried out by DPPH, ABTS, α -glucosidase, and protein tyrosine phosphatase 1B assays at doses of 12.5 to 250 µM. The isolated phytochemicals were identified as 3-O-(β-d-xylopyranosyl-(1-3)-α-l-rhamnopyrnaosyl-(1-2)-α-l-arabinopyranosyl]-28-O-(α-l-rhamno-pyranosyl-(1-4)-β-d-glucopyranosyl-(1-6)-β-d-glucopyranosyl] hederagenin (1), flaccidoside III (2), catechol (3), quercetin-3-gentiobiosides (4), magnoflorine (5), nigelflavonoside B (6), nigelloside (7), quercetin sphorotrioside (8), kaempferol-3, 7-diglucoside (9), kaempferol 3-O-rutinoside (10), rutin (11), 3-O-[α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranpsylhederagenin (12), 3β,23,28-trihydroxyolean-12-ene-3-O-α-l-arabinopyranoside(1→4)-a-rhamnopyranosyl,(1→4)-β-d-gluco-pyranoside (13), 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranpsyl]-28-O-β-d-gluco-pyranosyl hederagenin (14), and α-hederin (15). These were isolated and are reported for the first time in this study. Compared 13 was identified as a new compound. Compound 2 was isolated for first time from the genus Nigella. Compound 6 was found to be the most active in the DPPH, and ABTS assays and compound 10 was found to be the most active in the α-glucosidase assay, with IC50 32.7 ± 0.1, 95.18 ± 0.9, 214.5 ± 0.0 µΜ, respectively. Compound 12, at a dose of 125 µΜ, showed anti-diabetic activity in a PTP1B assay with IC50 91.30 ± 2.5 µΜ. In conclusion, the anti-diabetic activity of N. sativa is due to its flavonoids and TTSGs. Therefore, our studies suggest that the aerial parts of N. sativa are also a valuable and alternate source of valuable phytochemicals that could be used to develop anti-oxidant and anti-diabetic medicines.

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 neo-Clerodane Diterpenoids from Scutellaria galericulata

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Petko I. Bozov ◽  
Plamen N. Penchev ◽  
Josep Coll
Keyword(s):  
Acetone Extract ◽  
Aerial Parts ◽  
Nmr Data ◽  
Clerodane Diterpenoids ◽  
New Compounds ◽  
First Time

Four neo-clerodane diterpenoids, neoajugapyrin A, scutegalerins A and B and scutecolumnin C have been isolated from the acetone extract of the aerial parts of Scutellaria galericulata. Neoajugapyrin A and scutecolumnin C are reported in this species for the first time, whereas scutegalerins A and B are new compounds. NMR data of neoajugapyrin A are discussed in detail to support the proposed revised structure of ajugapyrin A.

scholarly journals neo-Clerodane Diterpenoids from Scutellaria altissima

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Petko I. Bozov ◽  
Josep Coll
Keyword(s):  
Acetone Extract ◽  
Aerial Parts ◽  
Clerodane Diterpenoids ◽  
New Compounds ◽  
First Time

Nine neo-clerodane diterpenoids, scutaltisins B-G, scupolin I, scutecolumnin C and 11- epi-scutecolumnin C have been isolated from the acetone extract of the aerial parts of Scutellaria altissima. Scutaltisins B-G are new compounds, whereas scupolin I, scutecolumnin C and 11- epi-scutecolumnin C are reported in this species for the first time.

scholarly journals Chemical Constituents From the Aerial Part of Tiliacora triandra (Colebr.) Diels and Their α-Glucosidase and α-Amylase Inhibitory Activity

2020 ◽  
Vol 15 (1) ◽  
pp. 1934578X1989959
Author(s):  
Emmanuel Ayobami Makinde ◽  
Chitchamai Ovatlarnporn ◽  
Chonlatid Sontimuang ◽  
Gaëtan Herbette ◽  
Opeyemi Joshua Olatunji
Keyword(s):  
Inhibitory Activity ◽  
Chemical Constituents ◽  
Ethyl Linoleate ◽  
Resonance Spectroscopy ◽  
Ionization Mass ◽  
Pheophorbide A ◽  
Aerial Parts ◽  
Fatty Acid Derivatives ◽  
First Time

Two new fatty acid derivatives identified as 5,7-dihydroxy-6-oxoheptadecanoic acid (1) and ethyl-5,7-dihydroxy-6-oxooctadecanoate (2) together with four known compounds, ethyl linolenate (3), ethyl linoleate (4), ethyl pheophorbide A (5), and pheophorbide A (6), were isolated from the aerial parts of Tiliacora triandra. All the compounds were isolated from T. triandra for the first time. The structures of the compounds were elucidated using high-resolution electrospray ionization mass spectrometry, 1-dimensional and 2-dimensional nuclear magnetic resonance spectroscopy, and comparison with literature data. All the isolated compounds were evaluated for their in vitro inhibitory activity against α-glucosidase and α-amylase. Compounds 1-6 exhibited α-glucosidase inhibitory activity with half-maximal inhibitory concentration values (IC50) values in the range of 11.58-424.06 μM, while only compound 1 displayed inhibitory activity against α-amylase at an IC50 value of 26.27 μM.

scholarly journals New Sulphated Flavonoids and Larvicidal Activity of Helicteres velutina K. Schum (Sterculiaceae)

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2784 ◽  
Author(s):  
Diégina Fernandes ◽  
Maria Souza ◽  
Yanna Teles ◽  
Louise Oliveira ◽  
Jéssica Lima ◽  
...  
Keyword(s):  
Indigenous Peoples ◽  
Larvicidal Activity ◽  
Aliphatic Alcohol ◽  
Ethanolic Extract ◽  
Traditional Use ◽  
Aerial Parts ◽  
Vector Insect ◽  
New Compounds ◽  
First Time ◽  
Chlorophyll Derivatives

Helicteres velutina K. Schum (Sterculiaceae), commonly known in Brazil as ‘pitó’, is traditionally used by indigenous peoples as insecticides and repellents. The present work reports on the the phytoconstituents from aerial parts of H. velutina and evaluation of the larvicidal potential of its extract. The compounds were isolated using chromatographic techniques and identified by NMR, IR and LC-HRMS. This study led to the isolation of a fatty acid, one aliphatic alcohol, four chlorophyll derivatives, one steroid, triterpenes, a lignan, and flavonoids, highlighting the new compounds in the literature, 5,4′-di-hydroxy-7-methoxy-8-O-sulphate flavone (mariahine) (15a) and 5,3′-di-hydroxy-7,4′-dimethoxy-8-O-sulphate flavone (condadine) (15b). The work presented here contributes to the chemotaxonomic knowledge of the Sterculiaceae family by describing the occurrence of sulphated flavonoids in this family for the first time. The crude ethanolic extract of H. velutina featured robust larvicidal activity against Aedes aegypti larvae, showing that the extract can be useful as a domestic larvicide, just as indicated by traditional use, to combat A. aegypti, a vector insect of severe viral diseases, such as dengue and Zika.

scholarly journals New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus

Marine Drugs ◽  
2020 ◽  
Vol 18 (3) ◽  
pp. 132 ◽  
Author(s):  
Jing-Shuai Wu ◽  
Xiao-Hui Shi ◽  
Guang-Shan Yao ◽  
Chang-Lun Shao ◽  
Xiu-Mei Fu ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
Aspergillus Terreus ◽  
Inhibitory Concentration ◽  
Tyrosine Phosphatase ◽  
Inhibitory Effect ◽  
Lipid Lowering ◽  
Ionization Mass ◽  
One Dimensional ◽  
New Compounds ◽  
First Time

Aspergillus terreus has been reported to produce many secondary metabolites that exhibit potential bioactivities, such as antibiotic, hypoglycemic, and lipid-lowering activities. In the present study, two new thiodiketopiperazines, emestrins L (1) and M (2), together with five known analogues (3–7), and five known dihydroisocoumarins (8–12), were obtained from the marine-derived fungus Aspergillus terreus RA2905. The structures of the new compounds were elucidated by analysis of the comprehensive spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), one-dimensional (1D) and two-dimensional (2D) nuclear magnetic resonance (NMR), and electronic circular dichroism (ECD) data. This is the first time that the spectroscopic data of compounds 3, 8, and 9 have been reported. Compound 3 displayed antibacterial activity against Pseudomonas aeruginosa (minimum inhibitory concentration (MIC) = 32 μg/mL) and antifungal activity against Candida albicans (MIC = 32 μg/mL). In addition, compound 3 exhibited an inhibitory effect on protein tyrosine phosphatase 1 B (PTP1B), an important hypoglycemic target, with an inhibitory concentration (IC)50 value of 12.25 μM.

scholarly journals OcUGT1-Catalyzed Glucosylation of Sulfuretin Yields Ten Glucosides

Catalysts ◽  
2018 ◽  
Vol 8 (10) ◽  
pp. 416 ◽  
Author(s):  
Shuai Yuan ◽  
Yan-Li Xu ◽  
Yan Yang ◽  
Jian-Qiang Kong
Keyword(s):  
Trace Amount ◽  
Structural Identification ◽  
The Other ◽  
Nmr Analysis ◽  
Catalytic Behavior ◽  
Innovative Drugs ◽  
New Compounds ◽  
First Time

Sulfuretin glucosides are important sources of innovative drugs. However, few glucosides of sulfuretin have been observed in nature. Therefore, it is urgent to diversify sulfuretin glycosides. Herein, glycosyltransferase (GT)-catalyzed glycodiversification of sulfuretin was achieved. Specifically, a flavonoid GT designated as OcUGT1 was used as a biocatalyst for the glucosylation of sulfuretin with UDP-Glc. The OcUGT1-assisted glucosylation of sulfuretin yielded ten glycosylated products, including three monoglucosides, five diglucosides and two triglucosides. The three monoglucosides were thus identified to be sulfuretin 3′-, 4′- and 6-glucoside according to HR-ESI-TOFMS data and their coelution with respective standards. A major diglucoside was assigned as sulfuretin 4′,6-diglucoside by HR-ESI-TOFMS in conjunction with NMR analysis. The exact structure of the other four diglucosides was not well characterized due to their trace amount. However, they were reasonably inferred as sulfuretin 3′,6-diglucoside, sulfuretin 3′,4′-diglucoside and two disaccharide glucosides. In addition, the structural identification of the remaining two triglucosides was not performed because of their small amount. However, one of the triglucosides was deduced to be sulfuretin 3′,4′,6-triglucoside based on the catalytic behavior of OcUGT1. Of the ten sulfuretin glucosides, at least six were new compounds. This is the first time to obtain monoglucosides, diglucosides and triglucosides of sulfuretin simultaneously by a single glycosyltransferase.

scholarly journals Phytochemical Profile of the Aerial Parts of Sedum sediforme and Anti-inflammatory Activity of Myricitrin

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Daniel Winekenstädde ◽  
Apostolis Angelis ◽  
Birgit Waltenberger ◽  
Stefan Schwaiger ◽  
Job Tchoumtchoua ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Methanol Extract ◽  
2D Nmr ◽  
Prostaglandin E ◽  
Arachidonic Acid Cascade ◽  
Aerial Parts ◽  
Phytochemical Profile ◽  
Anti Inflammatory ◽  
New Compounds ◽  
First Time

The aim of this study was to investigate the phytochemical profile of the methanol extract of the aerial parts of Sedum sediforme and to identify its secondary metabolites. By means of chromatographic separation and enrichment of compounds, HPLC-ESI-MS, HRMS, 1D-, 2D- NMR and/or comparison with reference compounds, three triterpenes, two sterols, ten flavonoids and twelve phenolic compounds were identified, together with two new compounds, i.e. (2 R*, 3 R*)-5,7-dihydroxy-2,3-dimethyl-4-chromanone-7- O-ß-D-glucoside (27) and butan-2- O-rutinoside (28). Out of the 29 identified secondary metabolites, 18 are described as ingredients of S. sediforme herein for the first time. Furthermore, myricitrin, one of the major constituents, was tested for its ability to inhibit different enzymes within the arachidonic acid cascade in order to determine its anti-inflammatory properties. Whereas there was only either weak or no inhibition of the microsomal prostaglandin E2 synthase-1 (mPGES-1) and the soluble epoxide hydrolase (sEH), myricitrin showed strong inhibition of 5-lipoxygenase (5-LO), with an IC50 of 7.8 ± 0.2 μM.

scholarly journals Flavonoids and Terpenoids with PTP-1B Inhibitory Properties from the Infusion of Salvia amarissima Ortega

Molecules ◽  
2020 ◽  
Vol 25 (15) ◽  
pp. 3530
Author(s):  
Eric Salinas-Arellano ◽  
Araceli Pérez-Vásquez ◽  
Isabel Rivero-Cruz ◽  
Rafael Torres-Colin ◽  
Martín González-Andrade ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Performance ◽  
Tyrosine Phosphatase ◽  
Phytochemical Analysis ◽  
Allosteric Site ◽  
Docking Analysis ◽  
Aerial Parts ◽  
Ic50 Values ◽  
Ptp 1B ◽  
First Time

An infusion prepared from the aerial parts of Salvia amarissima Ortega inhibited the enzyme protein tyrosine phosphatase 1B (PTP-1B) (IC50~88 and 33 μg/mL, respectively). Phytochemical analysis of the infusion yielded amarisolide (1), 5,6,4′-trihydroxy-7,3′-dimethoxyflavone (2), 6-hydroxyluteolin (3), rutin (4), rosmarinic acid (5), isoquercitrin (6), pedalitin (7) and a new neo-clerodane type diterpenoid glucoside, named amarisolide G (8a,b). Compound 8a,b is a new natural product, and 2–6 are reported for the first time for the species. All compounds were tested for their inhibitory activity against PTP-1B; their IC50 values ranged from 62.0 to 514.2 μM. The activity was compared to that of ursolic acid (IC50 = 29.14 μM). The most active compound was pedalitin (7). Docking analysis predicted that compound 7 has higher affinity for the allosteric site of the enzyme. Gas chromatography coupled to mass spectrometry analyses of the essential oils prepared from dried and fresh materials revealed that germacrene D (15) and β-selinene (16), followed by β-caryophyllene (13) and spathulenol (17) were their major components. An ultra-high performance liquid chromatography coupled to mass spectrometry method was developed and validated to quantify amarisolide (1) in the ethyl acetate soluble fraction of the infusion of S. amarissima.

scholarly journals Docosahexaenoic Acid Is Naturally Concentrated at the sn-2 Position in Triacylglycerols of the Australian Thraustochytrid Aurantiochytrium sp. Strain TC 20

Marine Drugs ◽  
2021 ◽  
Vol 19 (7) ◽  
pp. 382
Author(s):  
Kim Lee-Chang ◽  
Matthew C. Taylor ◽  
Guy Drummond ◽  
Roger J. Mulder ◽  
Maged Peter Mansour ◽  
...  
Keyword(s):  
Resonance Spectroscopy ◽  
Omega 3 ◽  
Nmr Analysis ◽  
Tuna Oil ◽  
13C Nmr Analysis ◽  
13C Nuclear Magnetic Resonance ◽  
Seal Oil ◽  
Alternate Source ◽  
First Time ◽  
Long Chain

The Labyrinthulomycetes or Labyrinthulea are a class of protists that produce a network of filaments that enable the cells to glide along and absorb nutrients. One of the main two Labyrinthulea groups is the thraustochytrids, which are becoming an increasingly recognised and commercially used alternate source of long-chain (LC, ≥C20) omega-3 containing oils. This study demonstrates, to our knowledge for the first time, the regiospecificity of the triacylglycerol (TAG) fraction derived from Australian thraustochytrid Aurantiochytrium sp. strain TC 20 obtained using 13C nuclear magnetic resonance spectroscopy (13C NMR) analysis. The DHA present in the TC 20 TAG fraction was determined to be concentrated in the sn-2 position, with TAG (16:0/22:6/16:0) identified as the main species present. The sn-2 preference is similar to that found in salmon and tuna oil, and differs to seal oil containing largely sn-1,3 LC-PUFA. A higher concentration of sn-2 DHA occurred in the thraustochytrid TC 20 oil compared to that of tuna oil.

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