scholarly journals FLAVONOL AND LIGNAN GLYCOSIDES FROM Datura metel L.

2017 ◽  
Vol 55 (3) ◽  
pp. 263
Author(s):  
Nguyen Thi Mai ◽  
Nguyen Thi Cuc ◽  
Tran Hong Quang ◽  
Phan Van Kiem
Keyword(s):  
Methanol Extract ◽  
2D Nmr ◽  
Chemical Investigation ◽  
Cd Spectra ◽  
Datura Metel ◽  
Spectroscopic Analyses ◽  
The Absolute ◽  
Lignan Glycosides ◽  
Whole Plants ◽  
First Time

Chemical investigation of an acidic methanol extract of the whole plants of D. metel resulted in the isolation of five compounds, including kaempferol 3-O-beta-D-glucosyl(1->2)-beta-D-galactoside 7-O-beta-D-glucoside (1), kaempferol 3-O-beta-glucopyranosyl(1->2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside (2), pinoresinol O-beta-D-glucopyranoside (3), (7R,8S,7'S,8'R)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside (4), and (7S,8R,7'S,8'S)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside (5). Their structures were elucidated by 1D and 2D NMR and MS spectroscopic analyses as well as comparing with the data reported in the literature. The absolute configurations of compounds 4 and 5 were determined by CD spectra. It is noted that (7R,8S,7'S,8'R)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside and (7S,8R,7'S,8'S)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside were isolated for the first time from the Datura genus.

Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta

2015 ◽  
Vol 70 (11) ◽  
pp. 837-842 ◽  
Author(s):  
Jean Pierre Longue Ekon ◽  
Achille Nouga Bissoue ◽  
Marie Fomani ◽  
Flavien Aristide Alfred Toze ◽  
Alain François Waffo Kamdem ◽  
...  
Keyword(s):  
Methanol Extract ◽  
2D Nmr ◽  
Adenocarcinoma Cell Line ◽  
2D Nmr Spectroscopy ◽  
Spectrometric Data ◽  
Spectroscopic Analyses ◽  
Paper Disk ◽  
Standard Doxorubicin ◽  
First Time ◽  
Diffusion Assay

AbstractTwo new 24-nor-ursane-type triterpenoids, 2α,3β,19α-trihydroxy-24-norurs-4(23),12-dien-28-oic acid (1) and 3β-acetoxy-2α,19α-dihydroxy-24-norurs-4(23),12-dien-28-oic acid (2), along with 15 known compounds were isolated from the methanol extract of the twigs of Mostuea hirsuta. While 2-hydroxymethylbenzamide (13) was isolated for the first time from the natural source, compounds 3–12 are reported here for the first time from the genus Mostuea. Their structures were elucidated by means of spectroscopic analyses including 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometric data as well as comparison with data from the literature. Compounds 1, 2, 4–9 and 13 were tested against bacteria, fungi and plant pathogen oomycetes by the paper disk agar diffusion assay resulting in missing to low activities corresponding with minimum inhibitory concentrations (MICs) > 1 mg mL–1. However, the respective compounds 1, 2, 8, 9 and 13 exhibited moderate cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC50 10.6–16.5 μm compared to the standard doxorubicin with IC50 0.9 μm.

A Novel Phenylethanoid Dimer and Flavonoids from Jacaranda mimosaefolia

2007 ◽  
Vol 62 (9) ◽  
pp. 1213-1220 ◽  
Author(s):  
Fatma A. Moharram ◽  
Mohamed S. A. Marzouk
Keyword(s):  
Methyl Ester ◽  
Methanol Extract ◽  
2D Nmr ◽  
Aqueous Methanol ◽  
Esi Ms ◽  
Spectroscopic Analyses ◽  
First Time

A novel phenylethanoid dimer, namely, jacraninoside A (1) and the five known constituents E/Z-acetoside (2), isoacetoside (3), cistanoside E (4), 6 '-acetylacetoside (5), and campneoside I (6) together with the seven flavonoids isoquercitrin (7), scutellarein 7-O-β -D-glucuronopyranoside methyl ester (8), apigenin 7-O-β -D-galacturonopyranoside (9), luteolin 7-O-β -D-glucuronopyranoside methyl ester (10), apigenin 7-O-β -D-glucuronopyranoside methyl ester (11), luteolin 7-O-β -Dglucopyranoside (12), and isovitexin (13) were isolated from the aqueous methanol extract of Jacaranda mimosaefolia D. Don. leaves. All known metabolites have been identified in this genus for the first time except for 2 and 12 which had been isolated once before from the leaves and twigs of Jacaranda mimosaefolia. Their structures were elucidated based on chemical evidences and spectroscopic analyses (1D and 2D NMR, HRMS ((-)-ESI)/MS, UV).

scholarly journals Trogopterins A–C: Three new neolignans from feces of Trogopterus xanthipes

2014 ◽  
Vol 10 ◽  
pp. 2955-2962 ◽  
Author(s):  
Soyoon Baek ◽  
Xuikui Xia ◽  
Byung Sun Min ◽  
Chanil Park ◽  
Sang Hee Shim
Keyword(s):  
2D Nmr ◽  
Cytotoxic Activities ◽  
Cd Spectra ◽  
The Absolute ◽  
Optical Rotations ◽  
First Time

Seven compounds, including three neolignans 1–3, a norlignan 4, and three diterpenoids 5–7, were isolated from the feces of Trogopterus xanthipes. Structures of these compounds were identified by 1D and 2D NMR as well as MS. The absolute configurations of compounds 1, 2, and 4 were determined by comparing CD spectra and optical rotations. Among the isolated compounds, 1–3 were novel and subsequently named trogopterins A, B, and C, respectively. Likewise, compound 4 was isolated from nature for the first time. Cytotoxic activities of compounds 1–4 were evaluated. Compounds 1–3 exhibited moderate cytotoxic activities against HL-60 cells with IC50 values of 34.77–45.68 μM.

scholarly journals tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1951 ◽  
Author(s):  
Thi-Bach-Le Nguyen ◽  
Olivier Delalande ◽  
Isabelle Rouaud ◽  
Solenn Ferron ◽  
Laura Chaillot ◽  
...  
Keyword(s):  
Bacterial Strain ◽  
2D Nmr ◽  
One Dimensional ◽  
Spectroscopic Analyses ◽  
Human Keratinocyte ◽  
Rhizocarpon Geographicum ◽  
Ionisation Mass Spectrometry ◽  
Keratinocyte Cell ◽  
Ic50 Values ◽  
First Time

Two compounds (1) and (2) containing tert-butylphenol groups were, for the first time, produced during the culture of Paenibacillus odorifer, a bacterial strain associated with the crustose lichen, Rhizocarpon geographicum. Their entire structures were identified by one-dimensional (1D) and two-dimensional (2D) NMR and high-resolution electrospray ionisation mass spectrometry (HRESIMS) spectroscopic analyses. Among them, Compound 1 exhibited significant cytotoxicity against B16 murine melanoma and HaCaT human keratinocyte cell lines with micromolar half maximal inhibitory concentration (IC50) values. Furthermore, after supplementation studies, a putative biosynthesis pathway was proposed for Compound 1 throughout a bioconversion by this bacterial strain of butylated hydroxyanisole (BHA), an antioxidant polymer additive.

scholarly journals Absolute Configuration of Cembrane Diterpenoids from Bursera multijuga

2014 ◽  
Vol 9 (9) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Juan D. Hernández-Hernández ◽  
Hugo A. García-Gutiérrez ◽  
Luisa U. Román-Marín ◽  
Yunuen I. Torres-Blanco ◽  
Carlos M. Cerda-García-Rojas ◽  
...  
Keyword(s):  
Molecular Modeling ◽  
Absolute Configuration ◽  
2D Nmr ◽  
Vibrational Circular Dichroism ◽  
Conformational Preference ◽  
X Ray Diffraction ◽  
X Ray ◽  
The Absolute ◽  
First Time ◽  
Good Agreement

The stems of Bursera multijuga afforded (-)-(1 S,3 E,7 R,8 R,11 E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate 2, together with cembrene A (3), nephthenol (4), and cembrenol (5). The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRESIMS, and X-ray diffraction. The conformational preference of flexible 1 was studied by molecular modeling at the DFT B3LYP/DGDZVP level of theory. Good agreement between calculated and experimental vibrational circular dichroism curves established the absolute configuration of 1. This is the first time that cembrane derivatives have been isolated from the genus Bursera.

scholarly journals A HOPANE TRITERPENOID FROM THE MYCELIUM OF Isaria japonica IN VIETNAM

2017 ◽  
Vol 55 (5) ◽  
pp. 535
Author(s):  
Nguyen Ngoc Tuan ◽  
Tran Thi Kim Anh ◽  
Ping-Chung Kuo ◽  
Tran Dinh Thang
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Methanol Extract ◽  
2D Nmr ◽  
1H And 13C Nmr ◽  
Nmr Techniques ◽  
First Time

A hopane triterpenoid (11b, 22-dihydroxyhopane) was isolated from the methanol extract of the mycelium of Isaria japonica in Vietnam. The structure of this compound was elucidated using a combination of 1D and 2D NMR techniques (1H-, 13C-NMR, COSY, HSQC and HMBC). In the study, we reported the comprehensive 1H- and 13C-NMR spectral data of 11b, 22-dihydroxyhopane for the first time.

scholarly journals Antialactone: A New γ-Lactone from Antiaris Africana, and its Absolute Configuration Determined from TDDFT CD Calculations

2008 ◽  
Vol 3 (2) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Vouffo Bertin ◽  
Hidayat Hussain ◽  
Simeon F. Kouam ◽  
Etienne Dongo ◽  
Gennaro Pescitelli ◽  
...  
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Betulinic Acid ◽  
Spectroscopic Data ◽  
Nmr Spectra ◽  
2D Nmr ◽  
Stem Bark ◽  
Cd Spectra ◽  
2D Nmr Spectra ◽  
First Time

Four compounds were isolated from the stem bark of Antiaris africana. One of them, a γ-lactone named antialactone (1a), is reported for the first time as a natural product. The structures were determined by comprehensive analyses of their 1D and 2D NMR spectra and EI MS data. The absolute configuration of antialactone acetate (1b) was established by TDDFT CD calculations and comparison with measured CD spectra. The remaining three known compounds were identified, by comparing their spectroscopic data with those reported in the literature, as lichenxanthone, β-sitosterol, and betulinic acid.

scholarly journals Saracoside: A New Lignan Glycoside from Saraca indica, a Potential Inhibitor of DNA Topoisomerase IB

2012 ◽  
Vol 7 (6) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Tulika Mukherjee ◽  
Sayan Chowdhury ◽  
Ashish Kumar ◽  
Hemanta K Majumder ◽  
Parasuraman Jaisankar ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Stem Bark ◽  
Chemical Investigation ◽  
Dna Topoisomerase ◽  
Potential Inhibitor ◽  
Topoisomerase Ib ◽  
Lignan Glycoside ◽  
Lignan Glycosides ◽  
First Time

Chemical investigation of the stem bark of Saraca indica has resulted in the isolation of a new lignan glycoside, saracoside, along with four known lignan glycosides lyoniside, icariside E3, (+)5′methoxyisolarciresinol-9′- O-β-D-glucopyranoside and nudiposide, and a phenolic glucopyranoside, 3,4,5– trimethoxyphenyl-β-D-glucopyranoside, which has been isolated for the first time from this species. The isolated lignan glycosides exhibit potent DNA topoisomerase IB inhibitory activity.

scholarly journals Triterpenes from the Mushroom Hypholoma lateritium: Isolation, Structure Determination and Investigation in Bdelloid Rotifer Assays

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 301 ◽  
Author(s):  
Bayar Chuluunbaatar ◽  
Zoltán Béni ◽  
Miklós Dékány ◽  
Bernadett Kovács ◽  
András Sárközy ◽  
...  
Keyword(s):  
Natural Products ◽  
Structure Determination ◽  
Methanol Extract ◽  
Bdelloid Rotifer ◽  
Spectroscopic Analyses ◽  
Experimental Environment ◽  
Low Toxicity ◽  
First Time ◽  
Decadienoic Acid

Twelve compounds (1–12) were isolated from the methanol extract of brick cap mushroom (Hypholoma lateritium (Schaeff.) P. Kumm.). The structures of the compounds were elucidated using extensive spectroscopic analyses, including NMR and MS measurements. Lanosta-7,9(11)-diene-12β,21α-epoxy-2α,3β,24β,25-tetraol (1) and 8-hydroxy-13-oxo-9E,11E-octa-decadienoic acid (2) were identified as new natural products, together with ten known compounds, from which 3β-hydroxyergosta-7,22-diene (4), demethylincisterol A2 (5), cerevisterol (6), 3β-O-glucopyranosyl-5,8-epidioxyergosta-6,22-diene (7), fasciculol E (9), and uridine (12) were identified in this species for the first time. The isolated triterpenes (1, 3–11) were investigated for their toxicity in vivo using bdelloid rotifer assays. Most of the examined steroids in general showed low toxicity, although the effects of the compounds varied in a wider range from the non-toxic lanosta-7,9(11)-diene-12β,21α-epoxy-2α,3β,24β,25-tetraol (1) to the significantly toxic cerevisterol (6), with substantial dependence in some cases on the presence of nutrient in the experimental environment.

Four New 2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis and Their Inhibitory Activities on Neutrophil Pro-Inflammatory Responses

Planta Medica ◽  
2018 ◽  
Vol 84 (18) ◽  
pp. 1340-1347 ◽  
Author(s):  
Sin-Ling Wang ◽  
Hsiang-Ruei Liao ◽  
Ming-Jen Cheng ◽  
Chih-Wen Shu ◽  
Chun-Lin Chen ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Inflammatory Responses ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Aquilaria Sinensis ◽  
Superoxide Anion Generation ◽  
Spectroscopic Analyses ◽  
Inhibitory Activities ◽  
New Compounds ◽  
First Time

AbstractFour new 2-(2-phenylethyl)-4H-chromen-4-one derivatives, 6-hydroxy-5-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (1), 6,7-dimethoxy-2-[2-(2′-hydroxyphenyl)ethyl]chromone (2), 5-hydroxy-6-methoxy-2-[2-(3′-methoxyphenyl)ethyl]-chromone (3), and 7-chloro-8-hydroxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (4), have been isolated from the resinous wood of Aquilaria sinensis, together with 16 known compounds (5–20). Among these, 7-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (5) was isolated from a natural source for the first time. The structures of the new compounds were established by spectroscopic analyses (1D and 2D NMR, HR-ESI-MS, IR, UV). Nine compounds, including 1 showed more than 80% inhibition of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine at 50 µM.

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