Showing papers by "Patoomratana Tuchinda published in 2010"
TL;DR: Two new lupanes, 2 alpha-acetoxy-3 beta-Hydroxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (2- acetoxyalphitolic acid) and 2-acet Oxyalphitol acid (3-acetaldehydealphitolics acid) were isolated from the leaves and twigs of GARCINIA HANBURYI and exhibited anti-inflammatory activity in an ethyl phenylpropiol
Abstract: Two new lupanes, 2 alpha-acetoxy-3 beta-hydroxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (2-acetoxyalphitolic acid) ( 1) and 2 alpha-hydroxy-3 beta-acetoxy-19 beta-hydrogen-lup-20(29)-en-28-oic acid (3-acetoxyalphitolic acid) ( 2), together with the known betulinic acid ( 3), betulin ( 4), and stimasterol-3- O- beta- D-glucopyranoside ( 5), were isolated from the leaves and twigs of GARCINIA HANBURYI. Compounds 1- 3 were also isolated from the resin of this plant. The structure of 2 was confirmed by single-crystal X-ray diffraction analysis. All of the lupanes ( 1- 4) displayed anti-HIV-1 activities in the anti-HIV-1 reverse transcriptase (IC (50) values 16.3-116.9 microg/mL) and syncytium assays (EC (50) 5.6-73.6 microg/mL, SI 1.7-3.3). Moreover compounds 1- 4 exhibited anti-inflammatory activity in an ethyl phenylpropiolate (EPP)-induced ear edema model.
23 citations
TL;DR: Bioassay-guided fractionation and purification of the anti-HIV-1-active MeOH extract from the leaves and twigs of Polyalthia sclerophylla led to the isolation of two new compounds, ENT-kaur-sclerodimer and cyclotucanol 3-palmitate.
Abstract: Bioassay-guided fractionation and purification of the anti-HIV-1-active MeOH extract from the leaves and twigs of Polyalthia sclerophylla led to the isolation of two new compounds, ENT-kaur-sclerodimer ( 1) and cyclotucanol 3-palmitate ( 2), along with the known ENT-kaur-16-en-19-oic acid ( 3), 15 beta-hydroxy- ENT-kaur-16-en-19-oic acid ( 4), 15 beta-acetoxy- ENT-kaur-16-en-19-oic acid ( 5), 15-oxo- ENT-kaur-16-en-19-oic acid ( 6), 16 alpha,17-dihydroxy- ENT-kauran-19-oic acid ( 7), 16 alpha-hydroxy- ENT-kauran-19-oic acid (xylopic acid) ( 8), a pseudodimer (15 alpha-hydroxy- ENT-kaur-16-en-19-oic acid/17-hydroxy- ENT-kaur-15-en-19-oic acid) ( 9), ermanin, nicotiflorin, and allantoin. Among these isolates, compound 3 was the most active in both anti-syncytium (EC (50) 13.7 microg/mL and selectivity index 3.1) and HIV-1 reverse transcriptase (IC (50) 34.1 microg/mL) assays.
17 citations
TL;DR: A synthesis of (+)-4-desoxypentenomycin is reported here; it involves diastereoselective phenylsulfanylpropylation of an enolate anion derived from methyl (2R,5R,6R)-5, 6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carboxylate, obtained from D-mannitol.
Abstract: A synthesis of (+)-4-desoxypentenomycin is reported here; it involves diastereoselective phenylsulfanylpropylation of an enolate anion derived from methyl (2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carboxylate, obtained from D-mannitol, and is followed by sulfide oxidation, intramolecular acylation of the α-sulfinyl carbanion, sulfoxide elimination, and hydrolysis. Straightforward access to substituted analogues of (+)-4-desoxy-pentenomycin was also demonstrated by means of Suzuki-Miyaura, Sonogashira, and Heck coupling reactions.
4 citations
1 citations
TL;DR: In this article, a trialkylaluminum (TAL) was used to protect the glycolysis of protected glycals under very mild conditions, and the reaction of protected glycolysides was achieved under mild conditions.
Abstract: Treatment of glycals with trialkylaluminum in the presence of a catalytic amount of Yb(OTf)3 leads to the corresponding alkyl 2,3-unsaturated glycosides in good to excellent yields. Reactions of protected glycals are achieved under very mild conditions.
01 Jan 2010
TL;DR: Preliminary result demonstrates that the anti-inflammatory activity of the crude extracts of M. oleifera leaves is due partly through the inhibition of NO production and suggests that the plant may have neuroprotective potential in neurodegenerative diseases caused by neuroinflammation.
Abstract: Moringa oleifera Lam(M.oleifera), is generally found in tropical areas, South Asia and Thailand. It has been used for the treatment of various diseases including inflammation. However, little is known about its anti-inflammatory activity. We, therefore studied the effect of crude extracts from leaves (Methanol and hexane fractions) of M. oleifera on the production of nitric oxide (NO), a pro-inflammatory substance in highly aggressively proliferating immortalized (HAPI) microglial cells activated by lipopolysaccharide(LPS) and found that the extracts from M. oleifera significantly suppressed nitric oxide production in a dose dependent manner. This preliminary result demonstrates that the anti-inflammatory activity of the crude extracts of M. oleifera leaves is due partly through the inhibition of NO production and suggests that M. oleifera may have neuroprotective potential in neurodegenerative diseases caused by neuroinflammation.
TL;DR: In this article, a deoxygenative debromination of α-bromo-β-hydroxy (acetoxy) phenyl sulfones with samarium(II) iodide led to substituted α,β-unsaturated sulfones in good to excellent yields.
Abstract: Deoxygenative debromination of α-bromo-β-hydroxy (acetoxy) phenyl sulfones with samarium(II) iodide led to substituted α,β-unsaturated sulfones in good to excellent yields. The E-isomer is the major product. A possible mechanism via an α-sulfonyl radical pathway is proposed.