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 Spirostane-type Saponins from Dracaena fragrans « Yellow Coast »

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000
Author(s):  
Abdelmalek Rezgui ◽  
Anne-Claire Mitaine-Offer ◽  
Tomofumi Miyamoto ◽  
Chiaki Tanaka ◽  
Marie-Aleth Lacaille-Dubois
Keyword(s):  
Mass Spectrometry ◽  
2D Nmr ◽  
Steroidal Glycosides ◽  
Nmr Data ◽  
First Time

Three steroidal glycosides were isolated from the bark of Dracaena fragrans (L.) Ker Gawl. « Yellow Coast », and a fourth from the roots and the leaves. Their structures were characterized on the basis of extensive 1D and 2D NMR experiments and mass spectrometry, and by comparison with NMR data of the literature. These saponins have the spirostane-type skeleton and are reported in this species for the first time.

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 Two New 11(15→1)Abeotaxanes with a 2,20-Epoxy Ring from the Needles of Taxus canadensis

2009 ◽  
Vol 64 (1-2) ◽  
pp. 43-48 ◽  
Author(s):  
Man-Li Zhang ◽  
Jing Zhang ◽  
Mei Dong ◽  
Shu-Hua Feng ◽  
Chang-Hong Huo ◽  
...  
Keyword(s):  
High Resolution ◽  
2D Nmr ◽  
Epoxy Ring ◽  
Taxus Canadensis ◽  
Growth Inhibitory ◽  
Weak Growth ◽  
Inhibitory Activities ◽  
First Time

1Two 11(15→1)abeotaxanes having a tetrahydrofuran ring along the carbon atoms C-2, C-3, C-4, C-20 were identified for the first time from the needles of the Canadian yew, Taxus canadensis. The compounds could be identified as 4α,10β,13α-triacetoxy-15-benzoyloxy-2α,20β- epoxy-11(15→1)abeotax-11-ene-5α,7β,9α-triol () and 4α,7β,9α,10β,15-pentaacetoxy-2α,20β- epoxy-11(15→1)abeotax-11-ene-5α,13α-diol (2) on the basis of 1D-, 2D-NMR evidence and high-resolution FABMS analysis. Compound 1 showed weak growth inhibitory activities against T-98 and MM1-CB cells in vitro.

A New pseudo-Alkaloid Taxane and a New Rearranged Taxane from the Needles of Taxus canadensis

2008 ◽  
Vol 63 (8) ◽  
pp. 1005-1011 ◽  
Author(s):  
Manli Zhang ◽  
Changhong Huo ◽  
Mei Dong ◽  
Ligeng Li ◽  
Françoise Sauriol ◽  
...  
Keyword(s):  
Double Bond ◽  
Nmr Spectroscopy ◽  
High Resolution ◽  
2D Nmr ◽  
Side Chain ◽  
2D Nmr Spectroscopy ◽  
Taxus Canadensis ◽  
First Time

A new taxane with an amino side chain on C-5 and a new 11(15→1)abeotaxane having a tetrahydrofuran ring along carbon atoms C-2, C-3, C-4, C-20 identified for the first time from the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as 2α,7β ,9α,10β ,13-pentaacetoxy-11β -hydroxy-5α-(2´ -hydroxy,3'-N,N-dimethylamino-3´- phenyl)-propionyloxytaxa-4(20),12-diene (1) and 13α,20β -diacetoxy-5α,7β ,9α,10β -tetrahydroxy- 2α,20-epoxy-11(15→1)abeotaxa-11,15-diene (2) on the basis of 1D, 2D NMR spectroscopy and high-resolution FABMS analysis. Taxane 1 contains a rare C-12, C-13 double bond and a basic side chain, while taxane 2 bears a rare isopropenyl group at C-1.

Two New Phytoecdysteroids from the Needles of Taxus canadensis

2010 ◽  
Vol 65 (11) ◽  
pp. 1401-1405 ◽  
Author(s):  
Yu Fang ◽  
Zhi-Yu Ni ◽  
Teiko Yamada ◽  
Yu-Fang Wang ◽  
Man-Li Zhang ◽  
...  
Keyword(s):  
High Resolution ◽  
2D Nmr ◽  
Taxus Canadensis ◽  
First Time ◽  
Acetal Group ◽  
Ponasterone A

Two new phytoecdysteroids with a 20,22-acetal group were identified for the first time from the needles of the Canadian yew, Taxus canadensis. Their structures were characterized as ponasterone A 20,22-p-hydroxybenzylidene acetal (1) and ponasterone A 20,22-acetonide (2) on the basis of 1D, 2D NMR evidence and high-resolution FABMS analysis

scholarly journals Chemical constituents of Chaenomeles sinensis twigs and their biological activity

2020 ◽  
Vol 16 ◽  
pp. 3078-3085
Author(s):  
Joon Min Cha ◽  
Dong Hyun Kim ◽  
Lalita Subedi ◽  
Zahra Khan ◽  
Sang Un Choi ◽  
...  
Keyword(s):  
Biological Activity ◽  
Data Analysis ◽  
Cell Lines ◽  
Chemical Structure ◽  
Biological Effects ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Nmr Data ◽  
Chaenomeles Sinensis ◽  
Modified Mosher’S Method

A new megastigmane-type norsesquiterpenoid glycoside, chaemeloside (1), was isolated from the twigs of Chaenomeles sinensis together with 11 known phytochemicals through chromatographic methods. The chemical structure of the new isolate 1 was determined by conventional 1D and 2D NMR data analysis, ECD experiment, hydrolysis followed by a modified Mosher’s method, and LC–MS analysis. The characterized compounds’ biological effects including cytotoxicity against cancer cell lines, antineuroinflammatory activity, and potential neurotrophic effect were evaluated.

scholarly journals A NEW CYTOTOXIC DOLABELLANE FROM THE INDONESIAN SOFT CORAL Anthelia sp.

2013 ◽  
Vol 13 (3) ◽  
pp. 216-220 ◽  
Author(s):  
Anggia Murni ◽  
Novriyandi Hanif ◽  
Junichi Tanaka
Keyword(s):  
Mass Spectrometry ◽  
Drug Development ◽  
Ethyl Acetate ◽  
Spectroscopic Data ◽  
Soft Coral ◽  
Ethyl Acetate Extract ◽  
2D Nmr ◽  
Cancer Drug ◽  
Nmr Data ◽  
Anti Cancer

One new dolabellane (1) and two known diterpenoids stolonidiol (2) and clavinflol B (3) have been isolated from the ethyl acetate extract of the Indonesian soft coral Anthelia sp. A new compound 1 exhibited a moderate cytotoxicity against NBT-T2 cells at 10 µg/mL, while known compounds 2 and 3 showed cytotoxicity at 1 and 0.5 µg/mL, respectively. Structure of the new compound 1 was elucidated by interpretation of NMR spectroscopic data (1D and 2D NMR data) and mass spectrometry (ESIMS data) as well as comparison with those of related ones. This finding should be useful for anti cancer drug development of the promising dolabellane-types compound.

Acridine Synthesis by the Reaction of 2-(Perfluoroalkyl)aniline with ortho-Alkyl-Substituted Aromatic Grignard Reagent: Mechanistic Studies

2015 ◽  
Vol 68 (2) ◽  
pp. 196
Author(s):  
Lucjan Strekowski ◽  
Jianguo Zhang ◽  
Jaroslaw Saczewski ◽  
Ewa Wolinska
Keyword(s):  
Mass Spectrometry ◽  
Grignard Reagent ◽  
Fast Atom Bombardment ◽  
Ortho Position ◽  
Mechanistic Studies ◽  
Ethyl Group ◽  
Electron Impact Mass ◽  
Perfluoroalkyl Group ◽  
First Time ◽  
Impact Mass

The reaction of 2-(perfluoroethyl)aniline and its higher perfluoroalkyl analogues with an arylmagnesium bromide substituted with a methyl or ethyl group at the ortho position furnishes an acridine containing a shorter perfluoroalkyl group at the 9-position and devoid of the methyl or ethyl group of the Grignard reagent. Yields are in the range of 46–93 %. The intermediary of a substituted aza-ortho-xylylene has been postulated for related transformations in the literature previously, but this intermediate product has never been isolated. As part of this work, the labile product E-27 (half-life of 6 h at 23°C) was isolated for the first time and characterized by infrared spectroscopy, electron impact mass spectrometry, fast atom bombardment mass spectrometry, and 1H NMR. Experimental evidence was also obtained regarding the elimination of the ortho-alkyl group of the Grignard reagent during the course of the reaction as an alcohol.

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.

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