MWL fraction with a high concentration of lignin-carbohydrate linkages: Isolation and 2D NMR spectroscopic analysis

Holzforschung ◽  
2007 ◽  
Vol 61 (1) ◽  
pp. 1-7 ◽  
Author(s):  
Mikhail Yu. Balakshin ◽  
Ewellyn A. Capanema ◽  
Hou-min Chang
Keyword(s):  
Loblolly Pine ◽  
Spectroscopic Analysis ◽  
Direct Detection ◽  
2D Nmr ◽  
Side Chain ◽  
High Concentration ◽  
Hmbc Correlation ◽  
Nmr Techniques ◽  
C Nmr ◽  
Hmbc Technique

Abstract A preparation enriched in lignin-carbohydrate fragments (LCC-AcOH) was isolated in the course of purification of loblolly pine crude milled wood lignin (MWL). The preparation contained approximately equal amounts of lignin and carbohydrates, with high amounts of arabinose and galactose compared to their levels in wood. LCC-AcOH was investigated by 2D 1H-13C (HMQC and HMBC) correlation NMR techniques and quantitative 13C NMR. The HMQC spectra allowed direct detection of phenyl glycoside, ester and benzyl ether lignin-carbohydrates linkages in high amounts. The assignment of these structures was supported by the HMBC technique. It is noteworthy that in the ester lignin-carbohydrate linkages, a uronic acid residue was attached not to the benzylic position of lignin, as commonly believed, but to the γ-position of the side chain.

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.

Xylogranatin E, a New Phragmalin with a Rare Oxygen Bridge between C1 and C29, from the Fruit of a Chinese Mangrove Xylocarpus granatum

2007 ◽  
Vol 62 (4) ◽  
pp. 569-572 ◽  
Author(s):  
Jun Wu ◽  
Haixin Ding ◽  
Minyi Li ◽  
Si Zhang
Keyword(s):  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Oxygen Bridge ◽  
Nmr Data ◽  
Xylocarpus Granatum ◽  
Complete Assignment ◽  
Nmr Techniques ◽  
Noesy Spectra ◽  
C Nmr

Xylogranatin E, the second phragmalin with a rare oxygen bridge between C1 and C29 found in nature, was isolated from the fruit of a Chinese mangrove, Xylocarpus granatum. Its structure was determined by spectroscopic analysis. Complete assignment of 1H and 13C NMR data of xylogranatin E was achieved by 2D NMR techniques, including 1H-1H COSY, HSQC, HMBC and NOESY spectra.

Isolation of New Glycosides from Anemarrhena Asphodeloides Rhizome and Screening of their Anticancer Activity

2019 ◽  
Vol 16 (6) ◽  
pp. 474-477 ◽  
Author(s):  
Pham Van Khang ◽  
Nguyen Thi Hien Lan ◽  
Le Quang Truong ◽  
Mai Thi Minh Chau ◽  
Mai Xuan Truong ◽  
...  
Keyword(s):  
Anticancer Activity ◽  
Spectral Data ◽  
Cell Lines ◽  
Cancer Cell ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Ic50 Values ◽  
Nmr Techniques ◽  
Inhibitory Activities ◽  
Anemarrhena Asphodeloides

In this report, two new steroidal glycosides were isolated and determined from n-butanol fraction of A.asphodeloides. The structures were confirmed in comparison with the spectral data of known compounds by using different spectroscopic analysis approaches including 1D & 2D-NMR techniques and HRMS. The anti-proliferation screening against cancer cell lines A549 and HeLa indicated that compound 1 exhibited good inhibitory activities with IC50 values of 0.79 and 0.55 µg/mL, respectively.

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

scholarly journals Chemical Constituents of Cordyceps cicadae

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Zhi-Bo Chu ◽  
Jun Chang ◽  
Ying Zhu ◽  
Xun Sun
Keyword(s):  
Amino Acids ◽  
Spectroscopic Analysis ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Cordyceps Cicadae ◽  
Nmr Techniques ◽  
Dopamine Analogues

One new bifuran derivative (1), together with fourteen known compounds, were isolated from Cordyceps cicadae X. Q. Shing. The known compounds included nine nucleosides, uracil (2), uridine (3), 2′-deoxyuridine (4), 2′-deoxyinosine (5), guanosine (6), 2′-deoxyguanosine (7), thymidine (8), adenosine (9), and 2′-deoxyadenosine (10); three amino acids tryptophan (11), phenylalanine (12), and tyrosine (13); and two dopamine analogues N-acetylnoradrenaline (14) and its dimer, trans–2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-( N-acetyl-2″-amino-ethylene)-1,4-benzodioxane (15). Their structures were decisively elucidated by spectroscopic analysis, including 1D and 2D NMR techniques.

scholarly journals Two Novel Norwithasteroids with Unusual Six- and Seven-Membered Ether Rings in Side Chain from Flos Daturae

2013 ◽  
Vol 2013 ◽  
pp. 1-6 ◽  
Author(s):  
Bing-You Yang ◽  
Yong-Gang Xia ◽  
Yan-Yan Wang ◽  
Qiu-Hong Wang ◽  
Hai-Xue Kuang
Keyword(s):  
Carboxylic Acid ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Side Chain ◽  
Macroporous Resin ◽  
Datura Metel ◽  
Naturally Occurring ◽  
The Family ◽  
Proliferation In Vitro

Chemical investigation of 50% ethanol eluate fraction of macroporous resin for the flower of Datura metel L. collected in Jiangsu province of China resulted in the isolation of two novel naturally occurring norwithasteroids, baimantuoluoline I (1) and baimantuoluoside J (2). Their structures were elucidated as 5α, 6β, 12β-trihydroxy-1-oxo-2-en-ergosta-21,24;22,29-diepoxy-26-carboxylic acid (1) and 5α, 6β, 12β, 25-tetrahydroxy-1-oxo-2-en-ergosta-21,24;22,29-diepoxy-26-carboxylic acid (2) on the basis of extensive spectroscopic analysis, including 1D, 2D-NMR, and HR-ESI-MS. According to the literatures, this study represents the first report of the norwithasteroids in the side chain with unusual six- and seven-membered ether rings instead of those with an unmodified skeleton (δ-lactone or δ-lactol side chain) and a modified skeleton (γ-lactone or γ-lactol side chain) in the family of withanolides. Meanwhile, compounds 1 and 2 were evaluated for their immunosuppressive activity against mice splenocyte proliferation in vitro.

scholarly journals A Novel Phenolic Compound from Phyllanthus emblica

2013 ◽  
Vol 8 (4) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Gaimei She ◽  
Ruiyang Cheng ◽  
Lei Sha ◽  
Yixia Xu ◽  
Renbin Shi ◽  
...  
Keyword(s):  
Phenolic Compound ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Phyllanthus Emblica ◽  
Mucic Acid ◽  
Nmr Techniques

A new compound, mucic acid 3- O-gallate (1), was isolated from the fruit of Phyllanthus emblica L, together with 5 known compounds (2-6). Their structures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques, and by comparison with literature data.

Two New Limonoids With A 3-O-β-Tigloyl Group From The Seeds Of The Chinese Mangrove Xylocarpus Granatum

2007 ◽  
Vol 62 (6) ◽  
pp. 859-862 ◽  
Author(s):  
Jun Wu ◽  
Minyi Li ◽  
Si Zhang ◽  
Qiang Xiao ◽  
Qingxin Li
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Nmr Data ◽  
Xylocarpus Granatum ◽  
Nmr Techniques ◽  
Noesy Spectra ◽  
C Nmr

A new mexicanolide and a new phragmalin, named 30α-hydroxyl xylogranatin A and xylogranatin E2, respectively, have been isolated from the seeds of a Chinese mangrove Xylocarpus granatum. Their structures were identified on the basis of spectroscopic data. Each of them has a 3-O-β -tigloyl group. The first complete assignments of 1H and 13C NMR data for these limonoids were achieved by means of 2D NMR techniques, including 1H-1H COSY, HSQC, HMBC and NOESY spectra

Isolation and Structure Determination of Three New Sesquiterpenoids from Achillea millefolium

2012 ◽  
Vol 67 (5) ◽  
pp. 421-425 ◽  
Author(s):  
Umar Farooq ◽  
Afsar Khan ◽  
Saleha Suleman Khan ◽  
Shazia Iqbal ◽  
Rizwana Sarwar ◽  
...  
Keyword(s):  
Sesquiterpene Lactone ◽  
2D Nmr ◽  
Achillea Millefolium ◽  
Two Dimensional ◽  
H Nmr ◽  
Whole Plant ◽  
Phytochemical Investigation ◽  
Nmr Techniques ◽  
C Nmr

Phytochemical investigation of the whole plant of Achillea millefolium led to the isolation of three new sesquiterpenes which were trivially named as sesquiterpene lactone-esters A and B (1 and 2), and sesquiterpene lactone-diol (3). The structures of these compounds were determined with the help of one- and two-dimensional (1D and 2D) NMR techniques including 1H NMR, 13C NMR, HMQC, HMBC, COSY, and NOESY experiments.

Eine Untersuchung der in vivo Oxidation des Capsidiols mit Hilfe der 13C-NMR Spektroskopie / A 13C-NMR Study of the Biological Oxidation of Capsidiol

1978 ◽  
Vol 33 (1-2) ◽  
pp. 149-150 ◽  
Author(s):  
J. B. Stothers ◽  
A. Stoessl ◽  
E. W. B. Ward
Keyword(s):  
13C Nmr ◽  
Side Chain ◽  
Biological Oxidation ◽  
Allylic Rearrangement ◽  
Nmr Study ◽  
Nmr Techniques ◽  
C Nmr

Abstract The mechanism of the biological hydroxylation of the isopropenyl side-chain of the sesquiterpene capsidiol, to give 13-hydroxycapsidiol, has been investigated with 13C-NMR techniques, using capsidiol biogenetically enriched with 13C from [1,2-13C2] acetate. The results indicate that neither an allylic rearrangement nor the formation of an epoxide intervene in the process.

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