scholarly journals New Rare Ent-Clerodane Diterpene Peroxides from Egyptian Mountain Tea (Qourtom) and Its Chemosystem as Herbal Remedies and Phytonutrients Agents

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2172 ◽  
Author(s):  
Taha A. Hussien ◽  
Ahmed A. Mahmoud ◽  
Naglaa S. Mohamed ◽  
Abdelaaty A. Shahat ◽  
Hesham R. El-Seedi ◽  
...  
Keyword(s):  
Essential Oils ◽  
13C Nmr ◽  
Biosynthetic Pathway ◽  
2D Nmr ◽  
Herbal Remedies ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
The Family ◽  
Carbohydrate Contents

Genus Stachys, the largest genera of the family Lamiaceae, and its species are frequently used as herbal teas due to their essential oils. Tubers of some Stachys species are also consumed as important nutrients for humans and animals due to their carbohydrate contents. Three new neo-clerodane diterpene peroxides, named stachaegyptin F-H (1, 2, and 4), together with two known compounds, stachysperoxide (3) and stachaegyptin A (5), were isolated from Stachys aegyptiaca aerial parts. Their structures were determined using a combination of spectroscopic techniques, including HR-FAB-MS and extensive 1D and 2D NMR (1H, 13C NMR, DEPT, 1H-1H COSY, HMQC, HMBC and NOESY) analyses. Additionally, a biosynthetic pathway for the isolated compounds (1–5) was discussed. The chemotaxonomic significance of the isolated diterpenoids of S. aegyptiaca in comparison to the previous reported ones from other Stachys species was also studied.

scholarly journals Guaianolide Sesquiterpene Lactones from Centaurothamnus maximus

Molecules ◽  
2021 ◽  
Vol 26 (7) ◽  
pp. 2055
Author(s):  
Taha A. Hussien ◽  
Tarik A. Mohamed ◽  
Abdelsamed I. Elshamy ◽  
Mahmoud F. Moustafa ◽  
Hesham R. El-Seedi ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Biosynthetic Pathway ◽  
Fast Atom Bombardment ◽  
Arabian Peninsula ◽  
Sesquiterpene Lactones ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Chemical Structures ◽  
Aerial Parts

Centaurothamnus maximus (family Asteraceae), is a leafy shrub indigenous to the southwestern Arabian Peninsula. With a paucity of phytochemical data on this species, we set out to chemically characterize the plant. From the aerial parts, two newly identified guaianolides were isolated: 3β-hydroxy-4α(acetoxy)-4β(hydroxymethyl)-8α-(4-hydroxy methacrylate)-1αH,5αH, 6αH-gual-10(14),11(13)-dien-6,12-olide (1) and 15-descarboxy picrolide A (2). Seven previously reported compounds were also isolated: 3β, 4α, 8α-trihydroxy-4-(hydroxymethyl)-lαH, 5αH, 6βH, 7αH-guai-10(14),11(13)-dien-6,12-olide (3), chlorohyssopifolin B (4), cynaropikrin (5), hydroxyjanerin (6), chlorojanerin (7), isorhamnetin (8), and quercetagetin-3,6-dimethyl ether-4’-O-β-d-pyranoglucoside (9). Chemical structures were elucidated using spectroscopic techniques, including High Resolution Fast Atom Bombardment Mass Spectrometry (HR-FAB-MS), 1D NMR; 1H, 13C NMR, Distortionless Enhancement by Polarization Transfer (DEPT), and 2D NMR (1H-1H COSY, HMQC, HMBC) analyses. In addition, a biosynthetic pathway for compounds 1–9 is proposed. The chemotaxonomic significance of the reported sesquiterpenoids and flavonoids considering reports from other Centaurea species is examined.

scholarly journals Two New Prenylated Isoflavonoids from Erinacea anthyllis with Antioxidant and Antibacterial Activities

2017 ◽  
Vol 12 (7) ◽  
pp. 1934578X1701200 ◽  
Author(s):  
Soumia Mouffouk ◽  
Laurence Marcourt ◽  
Mohammed Benkhaled ◽  
Kaouthar Boudiaf ◽  
Jean-Luc Wolfender ◽  
...  
Keyword(s):  
Antioxidant Activities ◽  
Optical Rotation ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Total Phenolic ◽  
Aerial Parts ◽  
Whole Plant ◽  
The Family ◽  
Chemotaxonomic Markers ◽  
Phenolic And Flavonoid

Two new prenylated isoflavonoids, namely Erinasone A and Erinasone B along with 19 known secondary metabolites, including twelve isoflavonoids, three polyphenols, one flavonol, two flavanones and three steroids, were isolated from the whole plant (roots and aerial parts) of Erinacea anthyllis. Structures of all isolated compounds were elucidated by spectroscopic analysis, including 1D and 2D NMR (1H, 13C, COSY, HSQC, TOCSY, HMBC and NOESY), mass spectrometry (ESI-MS), UV-Vis, measurement of optical rotation [α]D and by comparison with the literature data. The total phenolic and flavonoid contents were determined in this study. Furthermore, the antioxidant and antibacterial activities of the EtOAc and n-BuOH extracts of E. anthyllis were evaluated. These extracts exhibited moderate antibacterial and antioxidant activities. Their IC50 values were approximately 0.04 mg/mL ( n-BuOH) and 0.037 mg/mL (EtOAc). Consequently, Erinacea anthyllis is a rich source of polyphenolic compounds particularly isoflavonoids used as chemotaxonomic markers for the subfamily Papilionoideae of the family Fabaceae.

scholarly journals Two Distinct Essential Oil Bearing Races of Tanacetum nubigenum Wallich ex DC from Kumaon Himalaya

2007 ◽  
Vol 2 (7) ◽  
pp. 1934578X0700200 ◽  
Author(s):  
Chandan S. Chanotiya ◽  
Chandra S. Mathela
Keyword(s):  
Essential Oil ◽  
Essential Oils ◽  
Plant Material ◽  
2D Nmr ◽  
Bornyl Acetate ◽  
2D Nmr Spectroscopy ◽  
Aerial Parts ◽  
Kumaon Himalaya ◽  
Linalool Oxide ◽  
Total Oil

The essential oil from the aerial parts of Tanacetum nubigenum Wallich ex DC collected from the Milam glacier moraine showed the presence of 73 compounds, of which 69, representing 87.9% of the total oil, have been identified, with bornyl acetate (39.7%), borneol (10.6%), ( E)-β-farnesene (6.6%) and 1,8-cineole (5.8%) as major constituents, while the oil from the plant material from the Pindari glacier area contained a total of 81 compounds, of which 77 have been identified. This oil was characterized by the presence of (3 R, 6 R)-linalool oxide acetate (69.4%), β-eudesmol (3.2%), selin-11-en-4α-ol (3.2%) and (3.2% and 1.2%, respectively) for compounds ( E) and ( Z)-2-(2,4-hexadiynylidene)-1,6-dioxospiro [4,4] non-3-ene, respectively. The major constituents of the essential oils from the aerial parts were separated and characterized by GC, GC/MS and 1D- and 2D-NMR spectroscopy. The chemical differences between the two essential oils place them as distinct chemical races or chemotypes.

scholarly journals Isolation and Quantification of Pinitol, a Bioactive Cyclitol, in Retama spp

2016 ◽  
Vol 11 (3) ◽  
pp. 1934578X1601100 ◽  
Author(s):  
Nuria H. González-Mauraza ◽  
Antonio J. León-González ◽  
José L. Espartero ◽  
Juan B. Gallego-Fernández ◽  
Marina Sánchez-Hidalgo ◽  
...  
Keyword(s):  
Mediterranean Region ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Aqueous Extracts ◽  
Aerial Parts ◽  
The Mediterranean ◽  
Anti Inflammatory ◽  
Identification And Quantification

The genus Retama (Fabaceae) is widely distributed in the Mediterranean region. In the present study, pinitol (3- O-methyl- chiro-inositol), an anti-inflammatory and antidiabetic molecule, was isolated from aerial parts of R. monosperma, and its structure established on the basis of spectroscopic techniques (1D/2D NMR) and MS. Identification and quantification of pinitol in R. raetam and R. sphaerocarpa were also performed. R. monosperma had the highest concentration of pinitol (2.3%). The presence of pinitol in aqueous extracts of Retama spp. may explain the adaptation of these plants to drought and salinity. Furthermore, pinitol could be considered as a mediator in the anti-inflammatory and hypoglycemic activities of Retama spp., which are traditionally used to treat diabetes.

scholarly journals Three New Cytotoxic Withanolides from the Chinese Folk Medicine Physalis angulata

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Cai-Yun Gao ◽  
Ting Ma ◽  
Jun Luo ◽  
Ling-Yi Kong
Keyword(s):  
Cell Line ◽  
Folk Medicine ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
Physalis Angulata ◽  
The Absolute ◽  
New Compounds

Physagulides M-O, three new withanolides (1–3), were isolated from the aerial parts of Physalis angulata L. Their structures were elucidated through extensive spectroscopic techniques, including 1D and 2D NMR, and HRESIMS. The absolute configurations (22- R) of these new compounds were determined by CD analysis. Compounds 1 and 3 showed significant selective cytotoxic activities on the MG-63 cell line, with IC50 values of 4.28 and 5.44 μM, respectively.

Biological Activity of a Phloroglucinol Glucoside Derivative from Conyza aegyptiaca

2009 ◽  
Vol 64 (7-8) ◽  
pp. 513-517 ◽  
Author(s):  
Ahmed A. Mahmoud ◽  
Shar S. Al-Shihry ◽  
Mohamed-Elamir F. Hegazy
Keyword(s):  
2D Nmr ◽  
Raw 264.7 ◽  
Spectroscopic Techniques ◽  
Hep G2 ◽  
Dpph Assay ◽  
Cytotoxic Effects ◽  
Aerial Parts ◽  
Different Types ◽  
Hct 116 ◽  
C Nmr

The phloroglucinol glucoside derivative [2,4-dihydroxy-6-(β-D-glucopyranosyloxy)phenyl]- butan-1-one (1), roseoside (2), and kaempferol-3-O-β-D-glucopyranoside (3) were isolated from the aerial parts of Conyza aegyptiaca (L.). To the best of our knowledge, this is the first isolation of compounds 1 - 3 from C. aegyptiaca. Their structures were determined by spectroscopic techniques including, IR, HR-EIMS, and extensive 500 MHz 1D- and 2D-NMR analyses (1H, 13C NMR, DEPT, 1H-1H COSY, HMQC and HMBC experiments). The antioxidant activity of 1, using the DPPH assay, was investigated; in addition, 1 was investigated against different types of cell lines, including Hep-G2, HCT-116, and RAW 264.7 for its cytotoxic effects. Also, this is the first report on the activity of 1.

scholarly journals Chemical Constituents of Cichorium intybus and their Inhibitory Effects against Urease and α-Chymotrypsin Enzymes

2011 ◽  
Vol 6 (8) ◽  
pp. 1934578X1100600
Author(s):  
Sumayya Saied ◽  
Shazia Shah ◽  
Zulfiqar Ali ◽  
Ajmal Khan ◽  
Bishnu P. Marasini ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
Cichorium Intybus ◽  
Spectroscopic Techniques ◽  
Inhibitory Effects ◽  
Isolation And Identification ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Hydroxyphenylacetic Acid ◽  
First Time

Phytochemical investigation of the aerial parts of Cichorium intybus L. resulted in the isolation and identification of two new natural metabolites, 2,6-di[but-3( E)-en-2-onyl]naphthalene (1), and 3,3′,4,4′-tetrahydroxychalcone (2), along with nine known compounds. Their structures were determined by spectroscopic techniques including 1D and 2D NMR. The known compounds were identified as scopoletin (3), 4-hydroxyphenylacetic acid (4), 3-hydroxy-4-methoxybenzoic acid (5), 4,4′-dihydroxychalcone (6), 6,7-dihydroxycoumarine (7), 1-triacontanol (8), lupeol (9), β-sitosterol (10), and β-sitosterol-3- O-β-glucopyranoside (11). Compounds 4-6 and 8 are reported for the first time from C. intybus. Compounds 2 and 3 showed weak inhibitory activities against urease and α-chymotrypsin enzymes, respectively.

scholarly journals New Natural Oxygenated Sesquiterpenes and Chemical Composition of Leaf Essential Oil from Ivoirian Isolona dewevrei (De Wild. & T. Durand) Engl. & Diels

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5613
Author(s):  
Didjour Albert Kambiré ◽  
Jean Brice Boti ◽  
Thierry Acafou Yapi ◽  
Zana Adama Ouattara ◽  
Ange Bighelli ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Essential Oil ◽  
13C Nmr ◽  
2D Nmr ◽  
Integrated Analysis ◽  
Spectroscopic Techniques ◽  
Germacrene D ◽  
Leaf Essential Oil ◽  
Main Components ◽  
First Time

This study aimed to investigate the chemical composition of the leaf essential oil from Ivoirian Isolona dewevrei. A combination of chromatographic and spectroscopic techniques (GC(RI), GC-MS and 13C-NMR) was used to analyze two oil samples (S1 and S2). Detailed analysis by repetitive column chromatography (CC) of essential oil sample S2 was performed, leading to the isolation of four compounds. Their structures were elucidated by QTOF-MS, 1D and 2D-NMR as (10βH)-1β,8β-oxido-cadin-4-ene (38), 4-methylene-(7αH)-germacra-1(10),5-dien-8β-ol (cis-germacrene D-8-ol) (52), 4-methylene-(7αH)-germacra-1(10),5-dien-8α-ol (trans-germacrene D-8-ol) (53) and cadina-1(10),4-dien-8β-ol (56). Compounds 38, 52 and 53 are new, whereas NMR data of 56 are reported for the first time. Lastly, 57 constituents accounting for 95.5% (S1) and 97.1% (S2) of the whole compositions were identified. Samples S1 and S2 were dominated by germacrene D (23.6 and 20.5%, respectively), followed by germacrene D-8-one (8.9 and 8.7%), (10βH)-1β,8β-oxido-cadin-4-ene (7.3 and 8.7), 4-methylene-(7αH)-germacra-1(10),5-dien-8β-ol (7.8 and 7.4%) and cadina-1(10),4-dien-8β-ol (7.6 and 7.2%). Leaves from I. dewevrei produced sesquiterpene-rich essential oil with an original chemical composition, involving various compounds reported for the first time among the main components. Integrated analysis by GC(RI), GC-MS and 13C-NMR appeared fruitful for the knowledge of such a complex essential oil.

scholarly journals Chemical Constituents of the Aerial Parts ofDaucus carotasubsp.hispidusGrowing in Tunisia

2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1986351
Author(s):  
Saoussen Hammami ◽  
Abdelsamed I. Elshamy ◽  
Ridha El Mokni ◽  
Ali Snene ◽  
Kanako Iseki ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
Squamous Carcinoma ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
Weak Activity ◽  
Cervical Cells ◽  
Antimicrobial And Antioxidant Activity ◽  
First Time ◽  
High Resolution Mass Spectroscopy

Three known polyol menthane monoterpenoids, namely, (4 R)-1- p-menthen-6,8-diol (1), (4 R)-1- p-menthen-4,7-diol (2), and (1 R,2 R,4 R)- p-menthane-1,2,4-triol (3), and 6 known phenolics (4-9), in addition to β-sitosterol 3- O-glucoside (10), were isolated from the aerial parts of Daucus carota subsp. hispidus (Ball) Heywood (Family: Apiaceae) growing in Tunisia. The structures of the isolated compounds were established depending upon the spectroscopic techniques including one and two-dimensional nuclear magnetic resonance (1D, and 2D NMR) and high resolution mass spectroscopy (HRMS). The absolute configuration of the compounds 1 to 3 was determined using experimental circular dichroism (CD) for the first time. Compounds 1 to 3 were reported for the first time from this plant. Compounds 1 to 3 exhibited no antimicrobial and antioxidant activity using superoxide dismutase-like activities. Compounds 2 and 3 exhibited weak activity, while 1 showed negative cytotoxic activity against human mouth squamous carcinoma (HSC-2) and human cervical cells (HeLa) cancer cells.

scholarly journals Naphthoquinone-Based Meroterpenoids from Marine-Derived Streptomyces sp. B9173

Biomolecules ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 1187
Author(s):  
Xinqian Shen ◽  
Xiaozheng Wang ◽  
Tingting Huang ◽  
Zixin Deng ◽  
Shuangjun Lin
Keyword(s):  
Antibacterial Activity ◽  
Biosynthetic Pathway ◽  
Biological Activities ◽  
Structural Diversity ◽  
2D Nmr ◽  
Chemical Diversity ◽  
Spectroscopic Techniques ◽  
Amino Group ◽  
Streptomyces Sp ◽  
Resolution Mass

Naphthoquinone-based meroterpenoids are hybrid polyketide-terpenoid natural products with chemical diversity and a broad range of biological activities. Here, we report the isolation of a group of naphthoquinone-containing compounds from Streptomyces sp. B9173, and their structures were elucidated by using a combination of spectroscopic techniques, including 1D, 2D NMR, and high-resolution mass (HRMS) analysis. Seven flaviogeranin congeners or intermediates, three of which were new, have been derived from common naphthoquinone backbone and subsequent oxidation, methylation, prenylation, and amino group incorporation. Both flaviogeranin B1 (1) and B (2) contain an amino group which was incorporated into the C8 of 1,3,6,8-terhydroxynaphthalene (THN). Flaviogeranin D (3) contains an intact C-geranylgeranyl residue attached to the C2 of THN, while the O-geranylgeranyl group of 2 links with the hydroxyl on the C2 site of THN. Four compounds were selected and tested for antibacterial activity and cytotoxicity, with 3 and flaviogeranin C2 (5) displaying potent activity against selected bacteria and cancer cell lines. In light of the structure features of isolated compounds and the biosynthetic genes, a biosynthetic pathway of naphthoquinone-based flaviogeranins has been proposed. These isolated compounds not only extend the structural diversity but also represent new insights into the biosynthesis of naphthoquinone-based meroterpenoids.

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