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 New Diterpenes with a Fused 6-5-6-6 Ring System Isolated from the Marine Sponge-Derived Fungus Trichoderma harzianum

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 480 ◽  
Author(s):  
Takeshi Yamada ◽  
Ayano Fujii ◽  
Takashi Kikuchi
Keyword(s):  
Mass Spectrometry ◽  
Marine Sponge ◽  
Trichoderma Harzianum ◽  
Fast Atom Bombardment ◽  
2D Nmr ◽  
Cd Spectroscopy ◽  
Ring System ◽  
Chemical Structures ◽  
Modified Mosher’S Method ◽  
Halichondria Okadai

New diterpenes, namely, trichodermanins F–H, with a fused 6-5-6-6 ring system were isolated from the fungus Trichoderma harzianum OUPS-111D-4 separated from a marine sponge Halichondria okadai. These chemical structures were elucidated by 1D and 2D NMR as well as high-resolution fast atom bombardment mass spectrometry (HRFABMS) spectral analyses. We established their absolute stereostructures by application of the modified Mosher’s method or circular dichroism (CD) spectroscopy. In addition, their cytotoxicities were assessed using several cancer cell lines, with 1 and 2 exhibiting modest activities.

scholarly journals Four New Acyclic Diterpenes From Siegesbeckia orientalis

2021 ◽  
Vol 16 (11) ◽  
pp. 1934578X2110561
Author(s):  
Do Thi Trang ◽  
Phan Thi Thanh Huong ◽  
Nguyen Thi Cuc ◽  
Duong Thi Dung ◽  
Bui Thi Thu Trang ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
High Resolution ◽  
Xanthine Oxidase ◽  
Ionization Mass ◽  
Oxidative Reaction ◽  
Chemical Structures ◽  
Aerial Parts ◽  
Extensive Analysis ◽  
Siegesbeckia Orientalis

Four new acyclic diterpenes, siegetalises A-D (1-4), were isolated from the aerial parts of Siegesbeckia orientalis. Their chemical structures were elucidated by extensive analysis of high-resolution electrospray ionization mass spectrometry and nuclear magnetic resonance spectral data. The effects of the isolated compounds on the activity of xanthine oxidase were evaluated by the oxidative reaction with xanthine as a substrate. At a concentration of 50 µM, compounds 1-4 exhibited xanthine oxidase inhibitory activity at levels of 13.59% ± 0.51%, 19.64% ± 1.54%, 17.45% ± 1.26%, and 21.36% ± 1.40%, respectively.

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 Struthiolanone: A Flavanone-Resveratrol Adduct from Struthiola Argentea

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300
Author(s):  
Sloan Ayers ◽  
Deborah L. Zink ◽  
Robert Brand ◽  
Seef Pretorius ◽  
Dennis Stevenson ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Absolute Configuration ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Cd Spectrum ◽  
High Resolution Mass ◽  
The Absolute ◽  
Resolution Mass

Struthiolanone (1), a flavanone-resveratrol adduct, was isolated from Struthiola argentea. Its structure was determined by high-resolution mass spectrometry and 1D- and 2D-NMR spectroscopic techniques. The absolute configuration was determined by comparison of the CD spectrum of biflavonoids. This compound appears to be the first example of a flavanoid-stilbene adduct.

New Constituents from Gymnocarpos decander

Planta Medica ◽  
2017 ◽  
Vol 83 (14/15) ◽  
pp. 1200-1206 ◽  
Author(s):  
Houria Bechlem ◽  
Teresa Mencherini ◽  
Mohamed Bouheroum ◽  
Samir Benayache ◽  
Roberta Cotugno ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Antiproliferative Activity ◽  
High Resolution Mass Spectrometry ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Nmr Analysis ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Resolution Mass

AbstractThe phytochemical investigation of Gymnocarpos decander aerial parts extract afforded two new saponins, 3-O-β-D-glucuronopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-O-β-D-apiofuranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester (1), 3-O-β-D-glucuronopyranosyl-2β,3β,16α-trihydroxyolean-12-en-28-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester (2), and three new flavonol glycosides, isorhamnetin 3-O-2′′′′-O-acetyl−β-D-xylopyranosyl-(1 → 6)-[β-D-apiofuranosyl-(1 → 2)]-β-D-glucopyranoside (3), isorhamnetin 3-O-2‴-O-acetyl−β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside (4), and quercetin 3-O-2‴-O-acetyl−β-D-xylopyranosyl-(1 → 6)-β-D-glucopyranoside (5), together with three known compounds. Their structures were determined by spectroscopic methods including 1D and 2D NMR analysis and high-resolution mass spectrometry. The new isolates were investigated for their potential cytotoxic activity on three cancer cell lines. Compounds 1 and 2 showed moderate antiproliferative activity.

scholarly journals Polyoxygenated Klysimplexane- and Eunicellin-Based Diterpenoids from the Gorgonian Briareum violaceum

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3276
Author(s):  
Atallah F. Ahmed ◽  
Yang Cheng ◽  
Chang-Feng Dai ◽  
Jyh-Horng Sheu
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Cytotoxic Activity ◽  
Electrospray Ionization ◽  
Cell Lines ◽  
Cancer Cell ◽  
Electrospray Ionization Mass Spectrometry ◽  
Biosynthetic Pathway ◽  
Ionization Mass ◽  
Chemical Structures

Three new polyoxygenated diterpenoids with a rare 4-isopropyl-1,5,8a-trimethylperhydrophenanthrane structure of the klysimplexane skeleton, briarols A‒C (1‒3), and one eunicellin-based diterpenoid, briarol D (4), were isolated from Briareum violaceum, a gorgonian inhabiting Taiwanese waters. The chemical structures of these compounds were determined by employing extensive analyses of NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) data. Metabolites 1‒3 were found to possess the rarely found skeleton of the diterpenoid klysimplexin T. All isolated compounds showed very weak cytotoxic activity against the growth of three cancer cell lines. A plausible biosynthetic pathway for briarols A‒C from the coexisting eunicellin diterpenoid briarol D (4) was postulated.

Two new taxane-glycosides from the needles of Taxus canadensis

2015 ◽  
Vol 70 (11) ◽  
pp. 829-835 ◽  
Author(s):  
Nan Li ◽  
Jin Wang ◽  
Hui-Min Yan ◽  
Man-li Zhang ◽  
Qing-Wen Shi ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Data Analysis ◽  
High Resolution ◽  
Fast Atom Bombardment ◽  
2D Nmr ◽  
Taxus Canadensis ◽  
Nmr Data ◽  
First Time

AbstractTwo minor taxane glycosides were isolated for the first time from the needles of Taxus canadensis. Their structures were characterized as 2α,5α-diacetoxy-10β-(6′-O-acetyl-β-d-glucopyranosyl)oxy-14β-[(2′R,3′S)-3′-hydroxy-2′-methylbutanoyl]oxytaxa-4(20),11-diene (1) and 2α,14β-diacetoxy-10β-(β-d-glucopyranosyl)oxytaxa-4(20),11-dien-5β-ol (2) on the basis of 1D and 2D NMR data analysis and confirmed by high-resolution fast atom bombardment mass spectrometry.

scholarly journals Two New Oleanane-type Saponins from Hydrocotyle multifida

2018 ◽  
Vol 13 (11) ◽  
pp. 1934578X1801301
Author(s):  
Mayra Rengifo Carrillo ◽  
Anne-Claire Mitaine-Offer ◽  
Thomas Paululat ◽  
Laurent Pouységu ◽  
Stéphane Quideau ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Phytochemical Study

A phytochemical study of a Venezuelan species Hydrocotyle multifida led to the isolation of five oleanane-type glycosides: two previously undescribed and three known ones. Their structures were established by 2D NMR spectroscopic techniques and mass spectrometry as 3- O-β-D-galactopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucuronopyranosyloleanolic acid and 3- O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-glucuronopyrano-syloleanolic acid. These results represent a significative contribution to the chemotaxonomy of the Hydrocotyle genus.

Tannins and Flavonoids from the Erodium cicutarium Herb

2005 ◽  
Vol 60 (5) ◽  
pp. 555-560 ◽  
Author(s):  
Izabela Fecka ◽  
Wojciech Cisowski
Keyword(s):  
Phenolic Acids ◽  
2D Nmr ◽  
Methyl Gallate ◽  
Esi Ms ◽  
Chemical Structures ◽  
Erodium Cicutarium ◽  
Aerial Parts ◽  
Acid Methyl

A new depside, erodiol, was isolated and identified from the aerial parts of Erodium cicutarium (Geraniaceae), together with essential compounds such as: geraniin, didehydrogeraniin, corilagin, (-) 3-O-galloylshikimic acid, methyl gallate 3-O-β -D-glucopyranoside, rutin, hyperin, quercetin 3- O-(6”-O-galloyl)-β -D-galactopyranoside, isoquercitrin and simple phenolic acids. Their chemical structures were elucidated by means of spectroscopic (ESI MS, HRESI MS, 1D and 2D NMR) evidence.

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