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 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.

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 Two New Isomers of Palmityl-4-hydroxycinnamate from Flowers of Taraxacum Species

2016 ◽  
Vol 11 (6) ◽  
pp. 1934578X1601100
Author(s):  
Matej Dudáš ◽  
Mária Vilková ◽  
Tibor Béres ◽  
Miroslav Repčák ◽  
Pavol Mártonfi
Keyword(s):  
Nmr Spectroscopy ◽  
Pollen Grains ◽  
2D Nmr ◽  
Male Sterile ◽  
2D Nmr Spectroscopy ◽  
First Time

Two isomers, (Z)- and (E)-palmityl 4-hydroxycinnamate [hexadecyl(2Z)-3-(4-hydroxyphenyl)prop-2-enoate and hexadecyl(2E)-3-(4-hydroxyphenyl)prop-2-enoate] were isolated for the first time from ligulate flowers of Taraxacum linearisquameum Soest (sect. Taraxacum). The highest amount of these compounds was detected in pollen grains; 0.26 mg/100 mg DW of the (E)-isomer and 0.096 mg/100 mg DW of the (Z)-isomer. The structures of these compounds were elucidated by a combination of HPLC-ESI-Qtof-MS and ID and 2D NMR spectroscopy. Their presence was confirmed in other species of Taraxacum, but they were not found in the male-sterile triploid agamospermous taxon T. parnassicum.

scholarly journals A Phenylpropanoid and Biflavonoids from the Needles of Cephalotaxus harringtonia var. harringtonia

2017 ◽  
Vol 12 (11) ◽  
pp. 1934578X1701201 ◽  
Author(s):  
Anju Mendiratta (Nee Chugh) ◽  
Rameshwar Dayal ◽  
John P. Bartley ◽  
Graham Smith
Keyword(s):  
Nmr Spectroscopy ◽  
Oral Dose ◽  
Spectral Data ◽  
2D Nmr ◽  
Hepatoprotective Activity ◽  
X Ray Diffraction ◽  
Soluble Extract ◽  
2D Nmr Spectroscopy ◽  
X Ray ◽  
First Time

A phenylpropanoid [2-(3-methoxy-4-hydroxyphenyl)-propane-1,3-diol] (1) together with four known biflavonoids namely 7, 4′, 7′″, 4′″-tetra- O-methyl amentoflavone (2); 7, 4′, 7″-tri- O-methyl amentoflavone (3); ginkgetin (4); sequoiaflavone (5) were isolated from the acetone soluble extract of needles of Cephalotaxus harringtonia var. harringtonia. Their structures were elucidated mainly on the basis of interpretation of 1D and 2D NMR spectroscopy and X-ray diffraction studies. The detailed spectral data of phenylpropanoid have been described for the first time. Ginkgetin (4) exhibited significant hepatoprotective activity in rat at 6 mg/kg oral dose level.

Structural Studies of Chelirubine and Chelilutine Free Bases

1998 ◽  
Vol 63 (7) ◽  
pp. 1045-1055 ◽  
Author(s):  
Jiří Dostál ◽  
Jiří Slavík ◽  
Milan Potáček ◽  
Radek Marek ◽  
Otakar Humpa ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Quantum Chemical ◽  
2D Nmr ◽  
Molecular Symmetry ◽  
Structural Studies ◽  
Free Base ◽  
2D Nmr Spectroscopy ◽  
Sanguinaria Canadensis ◽  
First Time

The structures of chelirubine and chelilutine free bases have been examined by 2D NMR spectroscopy and mass spectrometry. Chelirubine chloride (1a) upon treatment with Na2CO3 yielded free base which possessed the constitution of bis(5,6-dihydrochelirubin-6-yl) ether (2a). The free base of chelilutine (1b) was determined to be bis(5,6-dihydrochelilutin-6-yl) ether (2b). The aqueous NH3 treatment of chelilutine (1b) produced bis(5,6-dihydrochelilutin-6-yl)amine (3b). 6-Hydroxy-5,6-dihydrochelirubine (4a) and 6-hydroxy-5,6-dihydrochelilutine (4b) were detected only in CDCl3 solution by NMR spectroscopy. In CDCl3, the compound 2b underwent hydrolysis to 4b that was immediately followed by the reverse condensation to a diastereomer of 2b. Pseudokinetics of this reaction was followed by NMR spectroscopy and quantum chemical calculations were carried out to support the suggested type of molecular symmetry alteration. The known alkaloid dihydrochelirubine (5) was isolated for the first time from Sanguinaria canadensis.

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 Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai

Marine Drugs ◽  
2019 ◽  
Vol 17 (11) ◽  
pp. 605 ◽  
Author(s):  
Li ◽  
Li ◽  
Yang ◽  
Meng ◽  
Li ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Density Functional ◽  
Aspergillus Terreus ◽  
Optical Rotation ◽  
2D Nmr ◽  
Red Alga ◽  
Spectrometric Data ◽  
Phenol Derivatives ◽  
First Time ◽  
Laurencia Okamurai

Three new prenylated phenol derivatives, terreprenphenols A–C (1–3), along with four known related compounds (4–7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, and optical rotation (OR). The corresponding relationship between absolute configuration and optical rotation for known compounds anodendroic acid (4) and asperterreusine C (5) was ambiguous in literature, and their absolute configurations were therefore discussed and confirmed for the first time by time-dependent density functional (TDDFT) ECD and OR calculations. Compounds 1–7 inhibited some common aquatic bacteria with MIC values ranging from 2 to 64 μg/mL.

New polysubstituted monoterpenic thiazolidinones: synthesis, spectroscopic and crystal structure studies

2018 ◽  
Vol 74 (12) ◽  
pp. 1629-1634 ◽  
Author(s):  
Abdellah N'ait Ousidi ◽  
Moulay Youssef Ait Itto ◽  
Aziz Auhmani ◽  
Abdelkhalek Riahi ◽  
Anthony Robert ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Nmr Spectroscopy ◽  
2D Nmr ◽  
Asymmetric Unit ◽  
2D Nmr Spectroscopy ◽  
X Ray ◽  
X Ray Crystallography ◽  
Naturally Occurring ◽  
Spectroscopic Analyses ◽  
Graph Set

The synthesis of three new polysubstituted monoterpenic thiazolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C14H21N3OS (2), (2Z,5Z)-5-[(dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C16H24N4OS (3), and (2Z,5Z)-5-[(dimethylamino)methylidene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C17H26N4OS (4), is reported, starting from the corresponding thiosemicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thiazolidin-4-ones have been fully characterized by HRMS and 1H and 13C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical molecules within the asymmetric unit with the same absolute configuration. These two molecules are linked through N—H...O hydrogen bonds, building an R 2 2(8) graph-set motif.

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.

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