scholarly journals 1H and13C NMR Assignments of Cytotoxic 3S-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic Acid from the Leaves ofCichorium endivia

2012 ◽  
Vol 2012 ◽  
pp. 1-3 ◽  
Author(s):  
Fu-Xin Wang ◽  
An-Jun Deng ◽  
Jin-Feng Wei ◽  
Hai-Lin Qin ◽  
Ai-Ping Wang
Keyword(s):  
Carboxylic Acid ◽  
Nmr Assignments ◽  
Human Cancer ◽  
2D Nmr ◽  
1H And13c Nmr ◽  
Human Cancer Cell Lines ◽  
Complete Assignment ◽  
Isolated Compound ◽  
First Time ◽  
C Nmr

An amino acid, 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, was isolated for the first time from the leaves ofCichorium endivia. The complete assignment of its1H and13C NMR spectroscopic data was carried out also for the first time based on extensive 1D and 2D NMR experiments. Cytotoxicity of this isolated compound against HCT-8 and HepG2 human cancer cell lines was evaluated for the first time, with moderate activities being found.

Cytotoxic constituents of Alocasia macrorrhiza

2017 ◽  
Vol 72 (1-2) ◽  
pp. 21-25 ◽  
Author(s):  
Marwa Elsbaey ◽  
Kadria F.M. Ahmed ◽  
Mahmoud F. Elsebai ◽  
Ahmed Zaghloul ◽  
Mohamed M.A. Amer ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Spectroscopic Data ◽  
Human Cancer ◽  
Indole Alkaloid ◽  
Acid Methyl Ester ◽  
2D Nmr ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Acid Methyl ◽  
First Time

AbstractAn indole alkaloid, 2-(5-hydroxy-1H-indol-3-yl)-2-oxo-acetic acid (1) isolated for the first time from nature, in addition to the nine known compounds 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (2), alocasin B (3), hyrtiosin B (4), α-monopalmitin (5), 1-O-β-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (6), 3-epi-betulinic acid (7), 3-epi-ursolic acid (8),β-sitosterol (9) andβ-sitosterol 3-O-β-D-glucoside (10) were isolated from the rhizomes ofAlocasia macrorrhiza(Araceae). Their structures were elucidated by 1D and 2D NMR spectroscopic data. Of these compounds,6exhibited the strongest cytotoxicity against the four tested human cancer cell lines (IC50of about 10 µM against Hep-2 larynx cancer cells).

scholarly journals Bromotyrosine Alkaloids with Acetylcholinesterase Inhibitory Activity from the Thai Sponge Acanthodendrilla sp

2015 ◽  
Vol 10 (11) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Natchanun Sirimangkalakitti ◽  
Opeyemi J. Olatunji ◽  
Kanokwan Changwichit ◽  
Tongchai Saesong ◽  
Supakarn Chamni ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Nmr Assignments ◽  
Therapeutic Potential ◽  
2D Nmr ◽  
Inhibition Kinetics ◽  
Ache Inhibitory Activity ◽  
First Time ◽  
Kinetics Of ◽  
Resolution Mass ◽  
C Nmr

Twenty bromotyrosine alkaloids, including a new compound, 13-oxosubereamolline D (5), were isolated from the Thai sponge Acanthodendrilla sp. Their structures were determined by analyses of 1D- and 2D-NMR, high-resolution mass, and circular dichroism data. The complete 1H and 13C NMR assignments of 5,7β-dichlorocavernicolin (19) and 5,7α-dichlorocavernicolin (20) are described herein for the first time. The acetylcholinesterase (AChE) inhibitory activity of all isolated compounds was evaluated. Only homoaerothionin (7) and fistularin 1 (10) exhibited inhibitory activity against human recombinant AChE ( hrAChE) with IC50s of 4.5 and 47.5 μM, respectively. The hrAChE inhibition kinetics of 7, the most potent alkaloid, showed increased K m and unchanged V max values, suggesting its competitive mode of inhibition. The spirocyclohexadienylisoxazole and the length of the alkyl diamine linkage were proposed as the crucial parts for its strong inhibitory activity. This finding indicates a therapeutic potential for 7 in acetylcholine-related diseases, most importantly Alzheimer's disease.

Cytotoxic withanolides from Datura innoxia

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Emma Maldonado ◽  
Teresa Ramírez-Apan ◽  
Mahinda Martínez
Keyword(s):  
Lung Adenocarcinoma ◽  
Human Cancer ◽  
2D Nmr ◽  
Datura Innoxia ◽  
Human Cancer Cell Lines ◽  
Aerial Parts ◽  
Adenocarcinoma Cells ◽  
Toxic Plant ◽  
First Time

AbstractChemical investigation of the aerial parts (except fruits) of the medicinal, hallucinogen and toxic plant Datura innoxia Mill. [Solanaceae] led to the isolation of the new withanolide, dinnoxolide A (1), along with the known compounds 21,27-dihydroxy-1-oxowitha-2,5,24-trienolide (2), daturamalakin B (3) and withametelin (4). Their structures were established by analysis of their spectroscopic data, including 1D and 2D NMR experiments and MS. Compounds 2 and 3 were isolated as natural products for the first time and the name dinnoxolide B was given to compound 2. The four withanolides showed in vitro cytotoxic activity against U251 (glioblastoma) and SK-LU-1 (lung adenocarcinoma) human cancer cell lines, with IC50 values ranging from 1.2 to 19.6 µM, and also against the noncancerous monkey kidney cell line (COS-7), with IC50 values ranging from 5.0 to 19.7 µM. Compound 4 was two times more active than the reference compound, etoposide, against lung adenocarcinoma cells.

scholarly journals 1H and13C NMR assignments of dihydropipataline, the main of four long-chain 1-(3,4-methylenedioxyphenyl)-alkanes fromPiper darienenceD.C.

2000 ◽  
Vol 14 (4) ◽  
pp. 195-201
Author(s):  
Myriam Meléndez-Rodríguez ◽  
Willy Rendón ◽  
Galia Chávez ◽  
Gerardo Martínez-Guajardo ◽  
Pedro Joseph-Nathan
Keyword(s):  
Nmr Assignment ◽  
Nmr Assignments ◽  
Chemical Shifts ◽  
2D Nmr ◽  
1H And13c Nmr ◽  
Main Compound ◽  
Nmr Techniques ◽  
Nmr Methods ◽  
Nmr Simulation ◽  
C Nmr

Four 1-(3,4-methylenedioxyphenyl)-alkanes having linear ten, eleven, twelve and fourteen carbon atom chains, found in the roots ofPiper darienenceD.C., were separated by HPLC and their structures determined by mass spectrometry and NMR spectroscopy. Conventional 1D NMR methods were used for1H chemical shifts assignment of the main compound dihydropipataline (3) [1-(3,4-methylenedioxyphenyl)‒dodecane]. The13C NMR assignment was carried out using conventional considerations and 2D NMR techniques (HETCOR and FLOCK) in combination with spectral13C NMR simulation andab initioDFT-GIAO NMR calculations.

scholarly journals ent-Kaurane Diterpenes from Annona glabra and Their Cytotoxic Activities

2014 ◽  
Vol 9 (12) ◽  
pp. 1934578X1400901
Author(s):  
Hoang Le Tuan Anh ◽  
Nguyen Thi Thu Hien ◽  
Dan Thi Thuy Hang ◽  
Tran Minh Ha ◽  
Nguyen Xuan Nhiem ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Human Cancer Cell ◽  
2D Nmr Spectroscopy ◽  
Human Cancer Cell Lines ◽  
Annona Glabra

A new ent-kaurane glycoside, annoglabasin H (1), and three known ent-kauranes, annoglabasin E (2), annoglabasin B (3), and 19-nor- ent-kaurent-4-ol-17-oic acid (4) were isolated from the fruits of Annona glabra. Their structures were determined by the combination of spectroscopic and chemical methods, including 1D- and 2D-NMR spectroscopy, as well as by comparison with the NMR data reported in the literature. The cytotoxic activities of these compounds were evaluated on four human cancer cell lines, LU-1, MCF-7, SK-Mel2, and KB. Compound 1 exhibited significant cytotoxic activity on all tested human cancer cell lines with IC50 values ranging from 3.7 to 4.6 μM.

Flavon- and Flavonolglycosides from Achillea pannonica Scheele

2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  
Keyword(s):  
Methanolic Extract ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Spectroscopic Methods ◽  
Esi Ms ◽  
Aerial Parts ◽  
Nmr Techniques ◽  
Chemotaxonomic Study ◽  
First Time ◽  
C Nmr

The detailed investigation of a methanolic extract of aerial parts of Achillea pannonica SCHEELE. within a chemotaxonomic study led to the isolation of 6 flavonoid glycosides. Besides rutin, apigenin-7-O-glucopyranoside, luteolin-7-O-glucopyranoside, apigenin-7-O-rutinoside and acacetin-7-O-rutinoside, an unusual flavondiglucoside was isolated. Its structure was established by UV, 1HNMR and 13C NMR spectroscopic methods including 2D-NMR techniques and ESI-MS as luteolin-7,4′-O-β-diglucoside. This substance is reported for the first time in the genus Achillea. Chemotaxonomic aspects are discussed briefly

E-Homolupane Derivatives Substituted in Position 17 and 22a. 1H NMR, 13C NMR and IR Spectra

1995 ◽  
Vol 60 (4) ◽  
pp. 619-635 ◽  
Author(s):  
Václav Křeček ◽  
Stanislav Hilgard ◽  
Miloš Buděšínský ◽  
Alois Vystrčil
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Coupling Constants ◽  
Side Chain ◽  
Oxidation Reactions ◽  
H Nmr ◽  
Complete Assignment ◽  
Nmr Techniques ◽  
Intramolecular Association ◽  
C Nmr

A series of derivatives with various oxygen functionalities in positions 17,22a or 19,20 was prepared from diene I and olefin XVI by addition and oxidation reactions. The structure of the obtained compounds was confirmed by 1H NMR, 13C NMR and IR spectroscopy. The kind of intramolecular association of the 17α-hydroxy group was studied in connection with modification of the side chain and substitution in position 22a. Complete assignment of the hydrogen signals and most of the coupling constants was accomplished using a combination of 1D and 2D NMR techniques. The 1H and 13C NMR spectra are discussed.

scholarly journals New 9α-Hydroxy-5α,6α-epoxysterols from the Vietnamese Marine Sponge Ircinia echinata

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 424 ◽  
Author(s):  
Thi Trinh ◽  
Bich Truong ◽  
Arlette Longeon ◽  
Thi Doan ◽  
Alexandre Deville ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Breast Cancer Cells ◽  
Mass Spectra ◽  
Human Cancer ◽  
Selective Inhibition ◽  
2D Nmr ◽  
Human Breast ◽  
Hep G2 ◽  
Human Cancer Cell Lines ◽  
Mcf 7

Chemical investigation of the methanol extract of the Vietnamese marine sponge Ircinia echinata led to the isolation of six new 9α-hydroxy-5α,6α-epoxysterols: 5α,6α-epoxycholesta-7,22(E)-dien-3β,9α-diol (1), 5α,6α-epoxycholesta-7,24(28)-dien-3β,9α-diol (2), (24R)-5α,6α-epoxy-24-ethyl-cholesta-7-en-3β,9α-diol (3), 5α,6α-epoxycholesta-7-en-3β,9α-diol (4), (24S)-5α,6α-epoxyergosta-7,22-dien-3β,9α-diol (5), and (24R)-5α,6α-epoxy-24-methyl-cholesta-7-en-3β,9α-diol (6) along with the known 5α-6α-epoxysterols: 5α,6α-epoxystigmasta-7-en-3β-ol (7), 5α,6α-epoxystigmasta-7,22-dien-3β-ol (8), and 5α,6α-epoxyergosta-7-en-3β-ol (9). Their structures and their configurations were established on the basis of high resolution mass spectra and extensive 1D and 2D NMR spectroscopic data and by comparison with the literature. Their cytotoxic activity, evaluated against three human cancer cell lines, MCF-7, Hep-G2 and LU-1, revealed that only compounds 3 and 4 exhibited significant antiproliferative activity and compound 3 showed a selective inhibition towards the MCF-7 human breast cancer cells.

scholarly journals Conjugated Polyene Ketones From the Marine Sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110437
Author(s):  
Bui H. Tai ◽  
Dan T. Hang ◽  
Do T. Trang ◽  
Pham H. Yen ◽  
Phan T. T. Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Marine Sponge ◽  
Human Cancer ◽  
2D Nmr ◽  
Ionization Mass ◽  
Hep G2 ◽  
Human Cancer Cells ◽  
Resolution Electron ◽  
New Compounds ◽  
First Time

Five conjugated polyene ketones (1-5) were isolated from the methanol extract of the marine sponge Clathria ( Thalysias) reinwardti (Vosmaer, 1880) living in the coastal waters of Vietnam. Their structures were determined to be 8-(2′,3′,4′-trimethylphenyl)-6-methyl-oct-3( E),5( E),7( E)-trien-2-one (1), 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo- β-ionone (4), and 4-(2′,3′,4′-trimethylphenyl)-but-3( E)-en-2-one (5), by extensive analysis of high-resolution electron spray ionization mass spectrum (HR-ESI-MS), one-dimensional, and two-dimensional (2D) nuclear magnetic resonance (NMR) spectra, as well as by comparison of the spectral data with those reported in the literature. Compound 1 was new, compounds 2 to 4 were isolated from nature for the first time, and the chemical structure as well as the NMR assignments, of 5 were indicated by 2D NMR for the first time. Additionally, compound 5 exhibited cytotoxic activity against the human cancer cells SK-LU-1, SK-Mel-2, MCF-7, and Hep-G2 with half-minimal inhibitory concentration (IC50) values of 15.12 ± 3.43, 17.41 ± 2.83, 33.12 ± 3.39, and 34.38 ± 3.52 µM, respectively, but displayed only a weak cytotoxic effect on the normal HEK-239A cells (IC50 64.67 ± 3.67 µM). Compound 5 also significantly increased Caspase-3 activity in SK-LU-1 cells at concentrations of 10, 15, and 20 µM.

scholarly journals Complete NMR Assignments of Tubulosine

2012 ◽  
Vol 7 (1) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Venkata Siva Satyanarayana Kantamreddi ◽  
Colin W. Wright
Keyword(s):  
Nmr Assignments ◽  
2D Nmr ◽  
Structural Elucidation ◽  
First Time ◽  
Unambiguous Assignment

This article reports the structural elucidation of the Alangium alkaloid, tubulosine (1) on the basis of systematic 2D-NMR analyses (DEPT, COSY, TOCSY, NOESY, ROESY, HMQC and HMBC). The data obtained allowed the unambiguous assignment of all proton and carbon signals in 1 for the first time.

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