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.

Chemical Constituents of Euphorbia marschalliana Boiss

2004 ◽  
Vol 59 (1-2) ◽  
pp. 15-18 ◽  
Author(s):  
Amir Reza Jassbi ◽  
Simin Zamanizadehnajari ◽  
Satoshi Tahara
Keyword(s):  
Chemical Constituents ◽  
Acetone Extract ◽  
Aerial Parts ◽  
First Time

Acetone extract of aerial parts of Euphorbia marschalliana collected from Iran has been subjected to different chromatography techniques for fractionation and purification. The stereo- structures of the myrsinol esters 15-O-acetyl-3-O-propionyl-5-O-butanoyl-7-O-nicotinoylmyrsinol (1) and 15-O-acetyl-3,5-O-dibutanoyl-7-O-nicotinoylmyrsinol (2) have been probed using ROESY spectroscopy and modified for the stereochemistry at C-6, C-12 and C-13. β-Sitosterol (3), 29-norcycloart-5-ene (4), 5,8-lanostadiene-3β-ol (5), 3β,24(S),25-trihydroxycycloartane (6), 3β,24(R),25-trihydroxycycloartane (7) and 24-methylenecycloartan-3β-ol (8) were identified for the first time in this plant.

Chemical Constituents of the Aerial Parts of Scutellaria lateriflora and their α-Glucosidase Inhibitory Activities

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Minpei Kuroda ◽  
Katsura Iwabuchi ◽  
Yoshihiro Mimaki
Keyword(s):  
Methyl Ester ◽  
Chemical Constituents ◽  
Meoh Extract ◽  
Aerial Parts ◽  
Screening Experiments ◽  
Data Analyses ◽  
Nmr Data ◽  
Scutellaria Lateriflora ◽  
Inhibitory Activities ◽  
First Time

MeOH extracts of 37 herbs were tested in screening experiments for rat intestinal α-glucosidase. The MeOH extract of the aerial parts of Scutellaria lateriflora L. (Lamiaceae) significantly inhibited sucrase and maltase activities, using sucrose and maltase as the substrates. Enzyme inhibition guided-fractionation of the MeOH extract of S lateriflora resulted in the isolation of a new diterpene glucoside, deacetylajugarin-IV 18- O-β-D-glucopyranoside (1), along with 20 known phenolics (2-21). The structures of 1-21 were elucidated on the basis of MS and NMR data analyses. Baicalein (4) and baicalin (10), a glycoside of 4, showed moderate sucrase inhibitory activities at IC50 values of 14.9 and 36.3 μM, respectively, whereas luteolin (3), acteoside (16), leucosceptoside A (18), and isoacteoside (20) showed weak inhibitory activities at IC50 values of 811, 522, 727, and 443 μM, respectively. This is the first report on mammalian α-glucosidase inhibitory activities of S lateriflora extract and identification of the constituents responsible for the activities. Apigenin (2), luteolin (3), 6-methoxyluteolin 4'-methyl ether (6), isoscutellarin 8- O-β-D-glucuronide (7), luteolin 7- O-β-D-glucuronide (9), wogonin 7- O-β-D-glucuronide methyl ester (12), eriodictyol (13), naringenin (14), naringenin 7- O-β-D-glucuronide (15), jionoside D (17), leucosceptoside A (18), and (+)-syringaresinol 4'- O-β-D-glucopyranoside (21) were isolated from this plant for the first time. The inhibitory properties of S lateriflora extract against α-glucosidase provide a prospect for its antidiabetic usage.

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.

Two New Sulfated Furostanol Saponins from Tribulus terrestris

2002 ◽  
Vol 57 (1-2) ◽  
pp. 33-38 ◽  
Author(s):  
Ivanka Kostova ◽  
Dragomir Dinchev ◽  
Gudrun Hopp Rentsch ◽  
Vladimir Dimitrov ◽  
Antoaneta Ivanova
Keyword(s):  
Chemical Transformation ◽  
Sodium Salt ◽  
Mass Spectra ◽  
Tribulus Terrestris ◽  
Furostanol Saponins ◽  
Aerial Parts ◽  
Nmr Data ◽  
New Compounds

The known furostanol saponins methylprotodioscin and protodioscin and two new sulfated saponins, sodium salt of 26-O-β-glucopyranosyl-22α-methoxy-(25R)-furost-5-ene-3β,26-diol- 3-O-α-rhamnopyranosyl-(1→2)-β-4-O-sulfo-glucopyranoside (methylprototribestin) and sodium salt of 26-O-β-glucopyranosyl-22α-hydroxy-(25R)-furost-5-ene-3β,26-diol-3-O-α-rhamnopyranosyl-( 1→2)-β-4-O-sulfo-glucopyranoside (prototribestin) have been isolated from the aerial parts of Tribulus terrestris L. growing in Bulgaria. The structures of the new compounds were elucidated on the basis of 1D and 2D (DQF-COSY, TOCSY, HSQC-TOCSY, HSQC, HMBC, ROESY) NMR data, ESI mass spectra and chemical transformation.

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 Diterpenoid Constituents of Teucrium scordium L. Subsp. scordioides (Shreb.) Maire Et Petitmengin

2020 ◽  
Vol 15 (9) ◽  
pp. 1934578X2095952
Author(s):  
Petko I. Bozov ◽  
Plamen N. Penchev ◽  
Tania D. Girova ◽  
Velizar K. Gochev
Keyword(s):  
Mass Spectrometry ◽  
Acetone Extract ◽  
Ionization Mass ◽  
Gram Negative Bacteria ◽  
Gram Negative ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Nmr Techniques ◽  
Clerodane Diterpenoids ◽  
C Nmr

A new scordidesin А (1) and 2 known furo-clerodane diterpenoids, teucrin A (2) and 6-ketoteuscordin (3), were isolated by the phytochemical investigation of the acetone extract from the aerial parts of Teucrium scordium L. subsp. scordioides (Lamiaceae). The structure and stereochemistry of the compounds were established by high-resolution electrospray ionization mass spectrometry, infrared spectroscopy, and various 1H nuclear magnetic resonance (NMR) and 2-dimensional-NMR techniques. Additionally, we report 13C NMR spectral data of 3 that were not published before. Antimicrobial activity of the compounds was tested against Gram-positive and Gram-negative bacteria belonging to 5 different species and against 2 strains of yeast belonging to 2 different species of the genus Candida.

scholarly journals Carotenoid-Derived Flavor Precursors from Averrhoa carambola Fresh Fruit

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 256 ◽  
Author(s):  
Xuchao Jia ◽  
Dan Yang ◽  
Yue Yang ◽  
Haihui Xie
Keyword(s):  
Spectroscopic Data ◽  
Structure Identification ◽  
Accurate Information ◽  
Phytochemical Study ◽  
Averrhoa Carambola ◽  
Nmr Data ◽  
Star Fruit ◽  
Flavor Precursors ◽  
New Compounds ◽  
First Time

The fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit or carambola, is popular in tropical and subtropical regions. Carotenoid-derived components, mainly C13- and C15-norisoprenoids, contribute greatly to the flavor of star fruit. Previously reported norisoprenoids were tentatively identified by GC-MS analysis after enzymatic hydrolysis. To gain accurate information about glycosidically bound flavor precursors in star fruit, a phytochemical study was conducted, which led to the isolation of 16 carotenoid derivatives—One new C13-norisoprenoid glucoside, (5R,6S,7E,9R)-5,6,9-trihydroxy-7-megastigmene 9-O-β-d-glucoside (1); one new C15-norisoprenoid, (6S,7E,10S)-Δ9,15-10-hydroxyabscisic alcohol (11); and 14 known ones, of which 12 were in glucoside form. The structures of the two new compounds were elucidated on the basis of extensive spectroscopic data analysis and chemical reaction. Compound 11 was a rare C15-norisoprenoid with a double bond between C-9 and C-15, and its possible biogenetic pathway was proposed. The known compounds were identified by comparison of their mass and nuclear magnetic resonance (NMR) data with those reported in the literature. The structure identification of one new (1) and seven known (3–7, 9, and 10) C13-norisoprenoid glucosides from the genus Averrhoa for the first time enriches the knowledge of carotenoid-derived flavor precursors in star fruit.

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 A Bioactive Diterpene from Entada Abyssinica

2007 ◽  
Vol 2 (1) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Alembert T. Tchinda ◽  
Victorine Fuendjiep ◽  
Yalemtsehay Mekonnen ◽  
Bernadette B. Ngo ◽  
Ermias Dagne
Keyword(s):  
Methyl Ester ◽  
Stem Bark ◽  
Acetone Extract ◽  
Clerodane Diterpenoids ◽  
Antileishmanial Activities ◽  
First Time

Three clerodane diterpenoids, 8S-kolavic acid 18-methyl ester (1), 8S-kolavic acid 15-methyl ester (2) and 8S-kolavenol (3) were isolated from the acetone extract of the stem bark of Entada abyssinica along with trans-communic acid (4) and 1-octacosanol. Their structures were established mainly based on 1D (1H, 13C and DEPT) and 2D (1H-1H COSY, HSQC and HMBC) NMR experiments. Compound 1, described here for the first time, showed strong antimicrobial and moderate antileishmanial activities.

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