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 ◽  
...  

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.

2014 ◽  
Vol 9 (3) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Petko I. Bozov ◽  
Plamen N. Penchev ◽  
Josep Coll

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.


2012 ◽  
Vol 7 (12) ◽  
pp. 1934578X1200701 ◽  
Author(s):  
Jian Chen ◽  
Sven Mangelinckx ◽  
An Adams ◽  
Wei-lin Li ◽  
Zheng-tao Wang ◽  
...  

Gynura bicolor (Willd.) DC., is used in folk recipes for the treatment of diabetes mellitus in Jiangsu, Zhejiang and Sichuan province in the south of China. A previous pharmacological study proved that the plant showed significant hypoglycemic activity on normal and alloxan-diabetic mice. In this study, two terpenes, four megastigmane-type norisoprenoids and two glycosides were isolated from the aqueous ethanolic extract of the aerial parts of Gynura bicolor and characterized mainly by NMR spectroscopy and mass spectrometry. These compounds were isolated for the first time from this plant, and no evidence could be found for the previous reported presence of megastigmane-type norisoprenoids in the genus Gynura.


2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Petko I. Bozov ◽  
Josep Coll

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.


2017 ◽  
Vol 6 (12) ◽  
pp. 1868
Author(s):  
Chiranjit Paul ◽  
Amal Debnath ◽  
Rahul Chanda ◽  
Bimal Debnath

The existence of Dioscorea wallichii Hook. f. (Dioscoreaceae) is noted first time from the forest floor of Tripura, North East India. The tuber of this plant is used as a vegetable as well as a medicinal purpose by the indigenous peoples of the state. Reang communities of Tripura used tuber of this plant for stomach pain and Jamatia community have eaten this tuber with honey for refreshment and also increase physical fitness. It is widely distributed throughout forest floor as well as the degraded land of the state.


2015 ◽  
Vol 10 (8) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Yan Zhang ◽  
Hang Ma ◽  
Tao Yuan ◽  
Navindra P. Seeram

The bark and stems of red maple ( Acer rubrum) are reported to contain bioactive phenolics but its aerial parts, namely, flowers and leaves, remain largely unexplored. This is unfortunate considering that various parts of the red maple were used for traditional medicinal purposes by the indigenous peoples of eastern North America, where this species is found. Herein, we report the identification of twenty-five (1–25) phenolics, including two new galloyl derivatives (1 and 2), from red maple flowers and leaves. Of these, ten compounds (1–10), including the new compounds, were isolated and identified by NMR and HRESIMS data while the remaining fifteen compounds (11–25) were identified by HPLC-DAD analyses (by comparison with chemical standards). The isolates (1–10), along with the clinical drug, acarbose, were evaluated for their α-glucosidase enzyme inhibitory activities.


Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2171
Author(s):  
Amna Parveen ◽  
Muhammad Asim Farooq ◽  
Whang Wan Kyunn

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.


Molecules ◽  
2018 ◽  
Vol 23 (7) ◽  
pp. 1723 ◽  
Author(s):  
Xiu-Qing Song ◽  
Kongkai Zhu ◽  
Jin-Hai Yu ◽  
Qianqian Zhang ◽  
Yuying Zhang ◽  
...  

In this study, 19 octadecanoid derivatives—four pairs of enantiomers (1–8), two racemic/scalemic mixtures (9–10), and nine biosynthetically related analogues—were obtained from the ethanolic extract of a Chinese medicinal plant, Plantago depressa Willd. Their structures were elucidated on the basis of detailed spectroscopic analyses, with the absolute configurations of the new compounds assigned by time-dependent density functional theory (TD-DFT)-based electronic circular dichroism (ECD) calculations. Six of them (1, 3–6, and 9) were reported for the first time, while 2, 7, and 8 have been previously described as derivatives and are currently obtained as natural products. Our bioassays have established that selective compounds show in vitro anti-inflammatory activity by inhibiting lipopolysaccharide-induced nitric oxide (NO) production in mouse macrophage RAW 264.7 cells.


2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Daniel Winekenstädde ◽  
Apostolis Angelis ◽  
Birgit Waltenberger ◽  
Stefan Schwaiger ◽  
Job Tchoumtchoua ◽  
...  

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.


2015 ◽  
Vol 10 (7) ◽  
pp. 1934578X1501000
Author(s):  
Paraskev T. Nedialkov ◽  
Georgi Momekov ◽  
Zlatina K. Kokanova-Nedialkova ◽  
Jörg Heilmann

A detailed phytochemical investigation of the dichloromethane extract of the aerial parts of Hypericum maculatum Crantz. led to the isolation of four new (2-5) and six known (1a/b, 6-10) polyprenylated phloroglucinol derivatives. The new compounds were identified by means of spectral methods (MS, NMR, IR, UV) as ( E)-4-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-2-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl isobutyrate (2), ( E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-4-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl isobutyrate (3), ( E)-4-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-2-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylbutanoate (4) and ( E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-4-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylbutanoate (5). The known compounds have been identified as hyperpolyphyllirin/hyperibine J (1a/b), erectquione A (6), ( E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one (7), ( E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one (8), 1-(5,7-dihydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)chroman-8-yl)-2-methylpropan-1-one (9) and 1-(6,8-dihydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-5-yl)-2-methylpropan-1-one (10). The stereochemistry of 1a is described for the first time. The cytotoxicity of 1-6 on SKW-3, BV-173 and K-562 tumor cell lines was determined using MTT based assays.


2014 ◽  
Vol 2014 ◽  
pp. 1-7 ◽  
Author(s):  
Sayed A. Ahmed ◽  
Emadeldin M. Kamel

Phytochemical studies on the ethanolic extract of the aerial parts ofCentaurea scoparialed to the isolation of two new flavonoids, 3′,4′-dihydroxy-(3′′,4′′-dihydro-3′′-hydroxy-4′′-acetoxy)-2′′,2′′-dimethylpyrano-(5′′,6′′:7,8)-flavone-3-O-β-D-glucopyranoside (1) and 3,3′,4′-trihydroxy-(3′′,4′′-dihydro-3′′,4′′-dihydroxy)-2′′,2′′-dimethylpyrano-(5′′,6′′:7,8)-flavone (2), along with eight known flavonoids isolated for the first time from this plant, cynaroside (3), Apigetrin (4), centaureidin (5), oroxylin A (6), 5,7-dihydroxy-3′,4′,5′-trimethoxyflavone (7), atalantoflavone (8), 5-hydroxy-3′,4′,8-trimethoxy-2′′,2′′-dimethylpyrano (5′′,6′′:6,7)-flavone (9), and 3′,4′,5,8-tetramethoxy-2′′,2′′-dimethylpyrano (5′′,6′′:6,7)-flavone (10). The structures of the isolated compounds were elucidated by means of spectroscopic tools including 1D and 2D NMR, UV, IR, and mass spectroscopy. Cytotoxic activities of the isolated compounds were evaluated against human cervical carcinoma HeLa, human hepatocellular carcinoma HepG2, and human breast carcinoma MCF-7. Compound2was the most potent cytotoxic agent against HeLa cells with an IC500.079 μM.


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