scholarly journals Triterpenes from Maytenus macrocarpa and Evaluation of Their Anti-HIV Activity

2006 ◽  
Vol 1 (12) ◽  
pp. 1934578X0600101 ◽  
Author(s):  
Sonia Piacente ◽  
Lourdes Campaner Dos Santos ◽  
Naheed Mahmood ◽  
Cosimo Pizza

A set of pentacyclic triterpenes has been isolated from the bark of Maytenus macrocarpa (Celastraceae). It includes two new olean-12-ene derivatives, namely 3β, 22α-dihydroxy-olean-12-en-30-oic acid (1) and 22α-hydroxy-olean-12-en-3-oxo-30-oic acid (2), and the new urs-12-ene derivative 3-(E)-coumaroyluvaol (7), along with 10 known compounds possessing olean-12-ene, urs-12-ene, lupane and friedelane skeletons. The structures have been elucidated by extensive spectroscopic methods including 1D- and 2D-NMR experiments, as well as ESI-MS analysis. All isolated compounds were tested for anti-HIV activity in C8166 cells infected with HIV-1MN. The most active compound was 22α-hydroxy-12-en-3-oxo-29-oic acid (triterpenonic acid A, 4), with an EC50 value of 1 μg/mL and a selectivity index of 35.

2013 ◽  
Vol 8 (4) ◽  
pp. 1934578X1300800
Author(s):  
Guang-Yu Yang ◽  
Rui-Rui Wang ◽  
Zhong-Hua Gao ◽  
Yin-Ke Li ◽  
Liu-Meng Yang ◽  
...  

Three new dibenzocyclooctadiene lignans, marlignans M–O (1–3), together two known ones, were isolated from the leaves and stems of Schisandra wilsoniana. The structures of 1–3 were elucidated by spectroscopic methods, including extensive 1D- and 2D-NMR techniques. Compound 2 showed anti-HIV-1 activity with an EC50 value of 5.82 μg/mL and a therapeutic index (TI) of more than 12.8. Compound 3 showed obvious bioactivity in inhibiting Epstein-Barr virus early antigen (EBV-EA) activation.


2001 ◽  
Vol 56 (7-8) ◽  
pp. 521-525 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
Shi Shan Yuc ◽  
...  

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


2016 ◽  
Vol 11 (7) ◽  
pp. 1934578X1601100
Author(s):  
Ahmed A. Zaki ◽  
Zulfiqar Ali ◽  
Yasser A. El-Amier ◽  
Ikhlas A. Khan

A new neolignan, paniculignan (1), and a known lignan, tetracentronside B (2), were isolated from Panicum turgidum. The structure of 1 was elucidated by extensive spectroscopic methods including 1D and 2D NMR and HR-ESI-MS. The relative configuration of 1 was determined on the basis of circular dichroism spectroscopy, optical rotation, and NOESY correlations.


2010 ◽  
Vol 63 (6) ◽  
pp. 877 ◽  
Author(s):  
Rabab Mohammed ◽  
Jiangnan Peng ◽  
Michelle Kelly ◽  
Muhammad Yousaf ◽  
Eustace Winn ◽  
...  

A new cyclic peroxide plakortisinic acid (1), and a new ketone derivative (2), in addition to six known compounds, an α,β-unsaturated ester (3), plakortide N (4), plakortide F (5) and its free acid (6), plakortone D (7), and a furan-containing molecule (8), were isolated from a species of Plakortis from Jamaica. The structures were elucidated by interpretation of 1D and 2D NMR spectra, and mass spectrometry data and by comparison with data from the literature. Comparison between experimental and calculated optical rotations allowed the assignment of absolute configuration of 1 and 2. The isolated compounds have been evaluated for their antimicrobial, antimalarial, anticancer, anti-Mtb, and anti HIV-1 activity.


2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800
Author(s):  
Chun-Yan Zhang ◽  
Xiao Ji ◽  
Xuan Gui ◽  
Bao-Kang Huang

A new ergosterol, 15β-hydroxyl-(22 E,24 R)-ergosta-3,5,8,22-tetraen-one (1), along with three known ergosterols, two known cytochalasins, and two known azapholines were isolated from Chaetomium globosum Z1. The structures of these compounds were elucidated on the basis of spectroscopic methods (HR-ESI-MS, 1D NMR, and 2D NMR). Compound 6 showed significant cytotoxic activity against A-549 and MG-63 cell lines with IC50 values of 6.96 and 1.73 μg/mL, respectively.


2012 ◽  
Vol 7 (5) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Alexandra Marchenko ◽  
Pavel Kintya ◽  
Bozena Wyrzykiewicz ◽  
Elena Gorincioi

Two new spirostane glycosides, chamaedrosides C (1) and C1 (2), two new furostane glycosides, chamaedrosides E (4) and E1 (5), and two new furospirostane glycosides, chamaedrosides C2 (3) and E2 (6), have been isolated from Veronica chamaedrys L. plants. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D- and 2D-NMR experiments, as well as MS analysis. The given compounds have been found for the first time.


2015 ◽  
Vol 10 (2) ◽  
pp. 1934578X1501000
Author(s):  
QingHu Wang ◽  
Nayintai Dai ◽  
Narenchaoketu Han ◽  
Wuliji Ao

Two new compounds, namely 5-methyl-4,2′,3′,5′-tetrahydroxy-4′-methoxy-2-aldehyde biphenyl (1) and 1,8-dioxo-1,8-dihydropyrano[3,4-c]pyran-3,6-dicarboxyl acid, diethyl ester (2), were isolated from the 95% ethanol extract of the roots of Paeonia lactiflora Pall. The structures of 1 and 2 were elucidated by spectroscopic methods, including UV, IR, HR-ESI-MS and extensive 1D and 2D NMR techniques.


2008 ◽  
Vol 3 (10) ◽  
pp. 1934578X0800301
Author(s):  
Xia-Chang Wang ◽  
Shi-Ping Ma ◽  
Jing-Han Liu ◽  
Li-Hong Hu

Two new guaiane sesquiterpenoids named jatrophaols A and B (1, 2), along with three known analogues, were isolated from the roots of Jatropha curcas. Their structures were determined by spectroscopic methods, including 1D and 2D NMR spectroscopy, HR-EI-MS, HR-ESI-MS, and X-ray diffraction, as well as by comparison of their spectral data with those of related compounds.


2001 ◽  
Vol 69 (1) ◽  
pp. 75-83 ◽  
Author(s):  
Denata Kasaj ◽  
Liselotte Krenn ◽  
Gottfried Reznicek ◽  
Sonja Prinz ◽  
Antje Hüfner ◽  
...  

In a detailed study on the flavonoid pattern of Achillea collina BECKER ten flavonoids were isolated from a methanolic extract of aerial parts of the plant. Their structures were determined by UV, ESI-MS, GC-MS and NMR spectroscopic methods including 2D-NMR. Apigenin-7-O-rutinoside was proven for the first time in the genus Achillea.


1998 ◽  
Vol 9 (4) ◽  
pp. 21-27
Author(s):  
P Franchetti ◽  
P Perlini ◽  
G Abu Sheikha ◽  
L Cappellacci ◽  
M Grifantini ◽  
...  

A series of human immunodeficiency virus (HIV) protease inhibitors, which are analogues of N-[2( R)-hydroxy-1( S)-indanyl]-5( S)-[( tert-butyloxycarbonyl)amino]-4( S)-hydroxy-6-phenyl-2-( R)-[[4-(carboxymethoxy)phenyl]methyl]hexanamide (L-694,746), a metabolite of the anti-HIV agent L-689,502, were synthesized. In these compounds, the acetic group linked to the para position of the P1′ phenyl in the reference inhibitor was replaced either by the bioisosteric phosphonomethoxy group and its diisopropyl/dibenzyl derivatives, or the 1H-tetrazol-5-yl-methoxy group and its 1-benzyl derivative. In enzyme assays, phosphonomethoxy and tetrazolmethoxy analogues proved to be potent inhibitors of the HIV-1 protease, with IC50 values as low as 0.04 nM. When tested for anti-HIV-1 activity in cell-based assays, most of the new derivatives proved active, with benzyl derivatives being more active than their highly polar, unsubstituted counterparts. The dibenzylphosphonomethoxy analogue was the most active compound, with an EC50 value of 10 nM and a selectivity index of 20 000. When compounds were examined for their capability to reduce p24 levels in both acutely and chronically infected MT-4 and H9/IIIB cells, all of them were found to be active at concentrations close to those capable of preventing HIV-1-induced cytopathic effect.


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