On the Reaction of Deacetylvindoline with Thionyl Chloride

2000 ◽  
Vol 65 (5) ◽  
pp. 789-796 ◽  
Author(s):  
Josef Hájíček ◽  
Vladimír Hanuš
Keyword(s):  
Thionyl Chloride ◽  
Mass Spectra ◽  
2D Nmr ◽  
Single Product ◽  
Complex Transformation ◽  
Excess Thionyl Chloride

Reaction of deacetylvindoline (2) with excess thionyl chloride gave rise to hexacyclic 6,10-dichloro-6,17-epithio-11-methoxy-1-methyltabersonine (4) as a single product in 43.5% yield. The structure was deduced from 1H and 13C 1D and 2D NMR experiments as well as from mass spectra. A tentative mechanism of this complex transformation was also proposed.

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 Salaramides A and B; Two α-Oxoamides Isolated from the Marine Sponge Hippospongia sp. (Porifera, Dictyoceratida)

2010 ◽  
Vol 5 (2) ◽  
pp. 1934578X1000500
Author(s):  
Julia Bensemhoun ◽  
Amira Rudi ◽  
Yoel Kashman ◽  
Emile M. Gaydou ◽  
Jean Vacelet ◽  
...  
Keyword(s):  
Chemical Transformation ◽  
Marine Sponge ◽  
Mass Spectra ◽  
Nmr Spectra ◽  
2D Nmr ◽  
2D Nmr Spectra

Two novel α-oxoamides, salaramide A (1) and its homologue salaramide B (2), were isolated from the Madagascar marine sponge, Hippospongia sp., collected in Salary Bay, north of Tulear. The structures of 1 and 2 were elucidated by interpretation of mass spectra, 1D and 2D NMR spectra, and confirmed by chemical transformation.

scholarly journals A New Isocoumarin from Cajanus cajan (Fabaceae)

2014 ◽  
Vol 9 (4) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Virginia F. Rodrigues ◽  
Rodrigo R. Oliveira ◽  
Maria Raquel G. Vega
Keyword(s):  
Spectral Data ◽  
Cajanus Cajan ◽  
Mass Spectra ◽  
2D Nmr ◽  
C Nmr

A new isocoumarin, 3-phenyl-8-hydroxy-6-methoxy-5-γ, γ-dimethylallyl-isocoumarin, named cajavilmina (1) and eight known compounds: α-amirenone (2), β-amirenone (3), lupenone (4), 5-hydroxy-7-methoxydihydroflavone (5), longistilin C (6), 3-hydroxy-5-methoxystilbene (7), β-sitosterol (8) and stigmasterol (9) were identified in a dichloromethane fraction from Cajanus cajan leaves. Structures were elucidated by analysis of spectral data, mainly those afforded by 1H, NOEDIFF and 13C NMR (1D and 2D NMR HMQC, HMBC and COSY) and mass spectra.

Juglomycins G-J: Isolation from Streptomycetes and Structure Elucidation

2005 ◽  
Vol 60 (2) ◽  
pp. 183-188 ◽  
Author(s):  
R. P. Maskey ◽  
H. Lessmann ◽  
S. Fotso ◽  
I. Grün-Wollny ◽  
H. Lackner ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Absolute Configuration ◽  
Structure Elucidation ◽  
Mass Spectra ◽  
2D Nmr ◽  
Cd Spectra ◽  
Streptomyces Spp ◽  
Nmr Data ◽  
Related Compounds ◽  
Weak Antibacterial Activity

From the Streptomyces spp. 815 and GW4184, four new 4-juglon-2-ylbutyric acid derivatives, the juglomycins G - J (3a, 4a, 4c, 5c), have been isolated and characterised. The structures were derived from the 1D and 2D NMR data and mass spectra and confirmed by comparison with structurally related compounds. The absolute configuration was deduced from the CD spectra. The new natural products exhibited weak antibacterial activity similar to juglomycin A (5a).

scholarly journals Identification of Two New Phenanthrenes from Dendrobii Herba and Their Cytotoxicity towards Human Hypopharynx Squamous Carcinoma Cell (FaDu)

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2339 ◽  
Author(s):  
Bomi Nam ◽  
Seung Mok Ryu ◽  
Dongho Lee ◽  
Chan-Hun Jung ◽  
Chang Hyun Jin ◽  
...  
Keyword(s):  
Mass Spectra ◽  
Carcinoma Cell ◽  
Soluble Fraction ◽  
Spectroscopic Method ◽  
Squamous Carcinoma ◽  
2D Nmr ◽  
Ionization Mass ◽  
One Dimensional ◽  
Ic50 Values ◽  
Squamous Carcinoma Cell

Two new phenanthrenes, (1R,2R)-1,7-hydroxy-2,8-methoxy-2,3-dihydrophenanthrene-4(1H)-one (1) and 2,7-dihydroxy-phenanthrene-1,4-dione (2), were isolated from the ethyl acetate-soluble fraction of Dendrobii Herba, together with seven known phenanthrenes (3–9), two bibenzyls (10–12), and a lignan (13). Structures of 1 and 2 were elucidated by analyzing one-dimensional (1D) and two-dimensional (2D)-NMR and High-resolution electrospray ionization mass spectra (HR-ESI-MS) data. The absolute configuration of compound 1 was confirmed by the circular dichroism (CD) spectroscopic method. In cytotoxicity assay using FaDu human hypopharynx squamous carcinoma cell line, compounds 3–6, 8, 10, and 12 showed activities, with IC50 values that ranged from 2.55 to 17.70 μM.

scholarly journals Prenylated Flavones from Artocarpus Lanceifolius and their Cytotoxic Properties against P-388 Cells

2009 ◽  
Vol 4 (7) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Iqbal Musthapa ◽  
Jalifah Latip ◽  
Hiromitsu Takayama ◽  
Lia D. Juliawaty ◽  
Euis H. Hakim ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
Mass Spectra ◽  
Cytotoxic Effect ◽  
Methanol Extract ◽  
2D Nmr ◽  
Tree Bark ◽  
Prenylated Flavones ◽  
Murine Leukemia

New prenylated flavones, artoindonesianins Z-4 and Z-5, together with four known prenylated flavones, artonin E, 12-hydroxyartonin E, artobiloxanthone, and cycloartobiloxanthone, have been isolated from the methanol extract of the tree bark of Artocarpus lanceifolius. The structures of these compounds were determined on the basis of spectroscopic data, including UV, IR, 1D and 2D NMR, and mass spectra. The cytotoxic effect of the isolated compounds against murine leukemia P-388 cells is described.

Reactions of the tetrasulfur pentanitride(-1) ion with halogens: synthesis, spectroscopic characterization, and crystal structure of pentasulfur hexanitride

1979 ◽  
Vol 57 (11) ◽  
pp. 1286-1293 ◽  
Author(s):  
T. Chivers ◽  
J. Proctor
Keyword(s):  
Crystal Structure ◽  
Thionyl Chloride ◽  
Mass Spectra ◽  
Methylene Chloride ◽  
Spectroscopic Characterization ◽  
The Other ◽  
X Ray ◽  
Yellow Orange ◽  
Uv Visible ◽  
Single Bonds

Pentasulfur hexanitride, S5N6, has been prepared in good yield by the reaction of [n-Bu4N+][S4N5−] with bromine (or iodine) in methylene chloride at 0 °C. In contrast, the tetrasulfur pentanitride(−1) ion reacts smoothly with chlorine to give S4N5Cl, while the reaction with sulfuryl chloride produces S4N5Cl and S5N6 and the reaction with thionyl chloride produces a mixture of S3N2O, S3N2O2, S4N4, and S5N6. Pentasulfur hexanitride is an air-sensitive, explosive, yellow-orange solid which sublimes at ca. 45 °C/10−2 Torr without significant decomposition. It has been characterised by infrared, Raman, uv–visible, and mass spectra and by a single crystal X-ray structure determination. The crystals are monoclinic and belong to the space group C2/c, a = 8.787(2), b = 11.190(2), c = 7.427(2) Å, β = 106.46(2)°, V = 700.3(5) Å3, Z = 4, Dc = 2.317 g cm−3. The refined structure (Rw = 0.040) has twofold symmetry and resembles a basket in which an —N=S=N— unit (d(S—N) = 1.54 Å) is the handle which bridges an S4N4 cradle via S—N single bonds (d(S—N) = 1.70 Å). The introduction of this bridge widens one of the [Formula: see text] transannular separations in S4N4 to 3.94 Å while the other is shortened to 2.43 Å. Thus, the S4N4 cradle can be viewed as two five-membered rings fused at the S—S bond.

scholarly journals 3-Alkylpyridinium salts from Haplosclerida marine sponges: Isolation, structure elucidations, and biosynthetic considerations

2009 ◽  
Vol 81 (6) ◽  
pp. 1033-1040 ◽  
Author(s):  
Rémi Laville ◽  
Philippe Amade ◽  
Olivier P. Thomas
Keyword(s):  
High Resolution ◽  
Mass Spectra ◽  
Biosynthetic Pathway ◽  
2D Nmr ◽  
Marine Sponges ◽  
Structure Characterization ◽  
Ionization Mass ◽  
Family Structures ◽  
Resolution Electron

A very little studied marine sponge Callyspongia sp. collected off the coast of Martinique was chemically investigated. The study led to the isolation and structure characterization of two new 3-alkylpyridinium salts which belonged to the recently isolated pachychaline family. Structures were elucidated by 1D, 2D NMR and detailed high-resolution electron spray ionization mass spectra (HRESIMS)-MS studies. The use of HRESIMS-MS studies proved to be highly efficient to identify two other close derivatives in a mixture. Finally, these studies allowed us to propose a general biosynthetic pathway leading to important 3-alkylpyridinium salts.

scholarly journals New triterpene isolated from Eschweilera longipes (Lecythidaceae)

2003 ◽  
Vol 75 (1) ◽  
pp. 21-25 ◽  
Author(s):  
PATRÍCIA M. DA COSTA ◽  
MÁRIO G. DE CARVALHO
Keyword(s):  
Mass Spectra ◽  
Acetyl Derivative ◽  
2D Nmr ◽  
Natural Substances ◽  
Phytochemical Studies

The phytochemical studies of Eschweilera longipes Miers (Lecythidaceae) have led to the identification of a new triterpene 3beta, 24-dihydroxyfriedelane, the known 1beta, 2beta, 3beta, 19beta-tetrahydroxyurs-12-en-28-oic acid (1beta-hydroxyeucaphic acid) besides the saponin sitosterol 3betaO-betaD-glucopyranoside. The structures were established from the IR, NMR and mass spectra data including 2D NMR experiments of natural substances and of the acetyl derivative of the new triterpene.

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