Biomedical subjects

Chatchanok Karalai

Publications and source records attributed to Chatchanok Karalai.

15 recordsLinked to original sources

PubMed2006

Potential anti-allergic ent-kaurene diterpenes from the bark of Suregada multiflora.

Two ent-kaurene diterpenes, ent-16-kaurene-3beta,15beta,18-triol (1) and ent-3-oxo-16-kaurene-15beta,18-diol (2), were isolated from a dichloromethane extract of the bark of Suregada multiflora along with five known diterpenes:ent-16-kaurene-3beta,15beta-diol (3), abbeokutone (4), helioscopinolide A (5), helioscopinolide C (6) and helioscopinolide I (7). Their structures were elucidated on the basis of spectroscopic analysis. Compounds 1-7 possessed appreciable anti-allergic activities in RBL-2H3 cells model with IC50 values ranging from 22.5 to 42.2 microM.

Animals↗

PubMed2006

Antibacterial and cytotoxic xanthones from the roots of Cratoxylum formosum.

Chemical investigation of the roots of Cratoxylum formosum has resulted in the isolation and characterization of xanthones: three new, named formoxanthone A-C and three known together with three known anthraquinones. Their structures were established on the basis of analysis of spectroscopic evidence. In addition, antibacterial and cytotoxic activities of the isolates were also evaluated.

Anthraquinones↗

PubMed2005

Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata.

Searching for anti-HIV-1 protease (PR) inhibitors of Thai medicinal plants led to the isolation of a new cyclohexenyl chalcone named panduratin C (1) and chalcone derivatives (2-6) from the methanol extract of Boesenbergia pandurata rhizomes. The known compounds were identified to be panduratin A (2), hydroxypanduratin A (3), helichrysetin (4), 2',4',6'-trihydroxyhydrochalcone (5), and uvangoletin (6). The structures of all compounds were elucidated on the basis of chemical and spectroscopic methods. It was found that 3 possessed the most potent anti-HIV-1 PR activity with an IC50 value of 5.6 microM, followed by 2 (IC50 = 18.7 microM), whereas other compounds exhibited only mild activity. Structure-activity relationships of these compounds on anti-HIV-1 PR activity are summarized as follows: (1) hydroxyl moiety at position 4 conferred higher activity than methoxyl group; (2) prenylation of dihydrochalcone was essential for activity; (3) hydroxylation at position 4''' reduced activity; and (4) introduction of double bond at C1' and C6' of chalcone gave higher activity. As regards active constituents contained in B. pandurata rhizomes, hydroxypanduratin A (3) and panduratin A (2) are active principles against HIV-1 PR.

Chalcones↗

PubMed2005

Dammarane triterpenes from the hypocotyls and fruits of Ceriops tagal.

Three new dammarane triterpenes, cereotagaloperoxide, cereotagalol A, and cereotagalol B, together with four known dammarane triterpenes, an oleanane triterpene, and 13 known lupane triterpenes were isolated from the hypocotyls and fruits of Ceriops tagal. The structures of 1-3 were characterized on the basis of their spectroscopic data.

Fruit↗

PubMed2004

Cytotoxic cardenolide glycoside from the seeds of Cerbera odollam.

A cardenolide glycoside, 3 beta-O-(2'-O-acetyl-l- thevetosyl)-15(14-->8)-abeo-5 beta-(8R)-14-oxo-card-20(22)-enolide (2'-O-acetyl cerleaside A), was isolated from a methylene chloride extract of the seeds of Cerbera odollam, together with four known compounds: cerleaside A, 17 alpha-neriifolin, 17 beta- neriifolin and cerberin. Their structures were elucidated by spectroscopic methods. All compounds except cerleaside A exhibited cytotoxic activities against oral human epidermoid carcinoma (KB), human breast cancer cell (BC) and human small cell lung cancer (NCI-H187).

Antineoplastic Agents, Phytogenic↗

PubMed2004

Pentacyclic triterpenoid esters from the fruits of Bruguiera cylindrica.

Six new pentacyclic triterpenoid esters (1-6) together with 3alpha- and 3beta-taraxerol were isolated from the fruits of Bruguiera cylindrica. The structures of the new compounds were characterized as 3alpha-E-feruloyltaraxerol (1), 3alpha-Z-feruloyltaraxerol (2), 3beta-E-feruloyltaraxerol (3), 3beta-Z-feruloyltaraxerol (4), 3alpha-E-coumaroyltaraxerol (5), and 3alpha-Z-coumaroyltaraxerol (6), respectively. Compounds 2 and 6 exhibited weak cytotoxicity against the NCI-H187 cell line.

Antineoplastic Agents, Phytogenic↗

PubMed2004

New cytotoxic cardenolide glycoside from the seeds of Cerbera manghas.

A new cytotoxic cardenolide glycoside, 3beta-O-(2'-O-acetyl-alpha-L-thevetosyl)-14beta-hydroxy-7-en-5beta-card-20(22)-enolide, (7,8-dehydrocerberin), together with five known cardenolides, 17beta-neriifolin, deacetyltanghinin, tanghinin, cerberin and 2'-O-acetyl-cerleaside A were isolated from the seeds of Cerbera manghas L. Their structures were elucidated by 1D- and 2D-NMR techniques as well as UV, IR and mass spectral data. 7,8-Dehydrocerberin, deacetyltanghinin and tanghinin exhibited cytotoxic activities against oral human epidermoid carcinoma (KB), human breast cancer cell (BC) and human small cells lung cancer (NCI-H187).

Antineoplastic Agents, Phytogenic↗

PubMed2004

New sesquiterpenoid and triterpenoids from the fruits of Rhizophora mucronata.

A new sesquiterpene (1) and two new pentacyclic triterpenoid esters (2, 3) together with three known compounds (4-6) were isolated from the fruits of Rhizophora mucronata. Their structures were elucidated by analysis of their spectroscopic data. The new compounds were characterized as 3-hydroxy-3,7,11-trimethyl-9-oxododeca-1,10-diene (mucronatone, 1), 3beta-E-caffeoyltaraxerol (2) and 3beta-Z-caffeoyltaraxerol (3).

Fruit↗

PubMed2003

Bis[14beta-hydroxy-3beta-O-(L-thevetosyl)-5beta-card-20(22)-enolide] methanol solvate monohydrate and 3beta-O-(L-2'-o-acetylthevetosyl)-14beta-hydroxy-5beta-card-20(22)-enolide.

The title compounds, 2C(30)H(46)O(8).CH(3)OH.H(2)O, (I), and C(32)H(48)O(9), (II), respectively, are cardenolide glycosides which were isolated from the seeds of Cerbera odollam. There are two crystallographically independent cardenolide molecules in (I), together with one methanol and one water solvate molecule. In both (I) and (II), the steroid nuclei are in cis/trans/cis configurations, with the cyclopentane rings showing conformational flexibility, viz. an envelope conformation in (I) and a twisted conformation in (II). In both compounds, the lactone ring is nearly orthogonal to the cyclopentane ring. The packing of (I) is composed of molecular layers stabilized by five O-H...O hydrogen bonds. In the packing of (II), the molecules are packed into columns by one O-H...O hydrogen bond, and are further interconnected into a three-dimensional network by one O-H...O and three C-H...O interactions.

Apocynaceae↗

PubMed2003

Antimycobacterial activity of phorbol esters from the fruits of Sapium indicum.

Three new phorbol esters, 12-(2-N-methylaminobenzoyl)-4beta,5,20-trideoxyphorbol-13-acetate (1), 12-(2-N-methylaminobenzoyl)-4alpha,5,20-trideoxyphorbol-13-acetate (2), and 12-(2-N-methylaminobenzoyl)-4alpha, 20-dideoxy-5-hydroxyphorbol-13-acetate (6), together with six known compounds (3-5 and 7-9), were isolated from the fruits of Sapium indicum. The chemical structures of 1, 2, and 6 were elucidated by analysis of their spectroscopic data. Compounds 1-3, 5, and 7-9 exhibited antimycobacterial activity with minimum inhibitory concentrations (MIC) between 3.12 and 200 microg/mL, but compounds 4 and 6 were inactive (MIC >200 microg/mL).

Antitubercular Agents↗

PubMed2002

Hexamethylenetetramine-4-nitrocatechol-water (1/2/1).

In the title adduct, 1,3,5,7-tetraazatricyclo[3.3.1.1(3,7)]decane-4-nitrobenzene-1,2-diol-water (1/2/1), C(6)H(12)N(4).2C(6)H(5)NO(4).H(2)O, the hexamethylenetetramine molecule acts as an acceptor of intermolecular O-H.N hydrogen-bonding interactions from the water molecule and the hydroxy groups of one of the two symmetry-independent 4-nitrocatechol molecules. The structure is built from molecular layers which are stabilized by three intermolecular O-H.O, two intermolecular O-H.N and four intermolecular C-H.O hydrogen bonds. The layers are further interconnected by one additional intermolecular O-H.N and two intermolecular C-H.O hydrogen bonds.

Journal Article↗

PubMed2002

The ternary complex 4-(2-pyridyl)pyridinium-3,5-dinitrobenzoate-3,5-dinitrobenzoic acid (1/1/1).

In the title ternary complex, C(10)H(9)N(2)(+).C(7)H(3)N(2)O(6)(-).C(7)H(4)N(2)O(6), the pyridinium cation adopts the role of the donor in an intermolecular N-H.O hydrogen-bonding interaction with the carboxylate group of the 3,5-dinitrobenzoate anion. The molecules of the ternary complex form molecular ribbons perpendicular to the b direction, which are stabilized by one N-H.O, one O-H.O and five C-H.O intermolecular hydrogen bonds. The ribbons are further interconnected by three intermolecular C-H.O hydrogen bonds into a three-dimensional network.

Journal Article↗

PubMed2002

Piperazine-1,4-diium--2,4-dinitrophenolate--water (1/2/2).

In the title 1/2/2 adduct, C(4)H(12)N(2)(2+) x 2C(6)H(3)N(2)O(5)(-) x 2H(2)O, the dication lies on a crystallographic inversion centre and the asymmetric unit also has one anion and one water molecule in general positions. The 2,4-dinitrophenolate anions and the water molecules are linked by two O-H...O and two C-H...O hydrogen bonds to form molecular ribbons, which extend along the b direction. The piperazine dication acts as a donor for bifurcated N-H...O hydrogen bonds with the phenolate O atom and with the O atom of the o-nitro group. Six symmetry-related molecular ribbons are linked to a piperazine dication by N---H.O and C---H.O hydrogen bonds.

Journal Article↗

PubMed2001

Hexamethylenetetraminium 2,4,6-trinitrophenolate.

In the title complex, the 1:1 ionic adduct of hexamethylenetetraminium and 2,4,6-trinitrophenolate, C6H13N4+*C6H2N3O7-, the cation acts as a donor for bifurcated hydrogen bonds to the O atoms of the phenolate and one of the nitro groups of the 2,4,6-trinitrophenolate anion. The crystal structure is built from sheets of cations and anions, and is stabilized by intermolecular C-H...O and C-H...pi interactions.

Journal Article↗

PubMed2001

A 1:1 adduct of hexamethylenetetramine and 4-hydroxy-3-methoxybenzaldehyde.

In the title complex, C6H12N4*C8H8O3, the hexamethylenetetramine molecule accepts a single intermolecular O-H...N hydrogen bond from the hydroxy group of the 4-hydroxy-3-methoxybenzaldehyde moiety. The non-centrosymmetric crystal structure is built from alternating molecular sheets of 4-hydroxy-3-methoxybenzaldehyde and hexamethylenetetramine molecules, and is stabilized by intermolecular O-H...N, C-H...O and C-H...pi interactions.

Journal Article↗