Surat Laphookhieo

Bioactive Carbazole Alkaloids from Clausena wallichii Roots

Four new carbazole alkaloids, clausenawallines C-F (1-4), along with 18 known compounds (5-22) were isolated from the roots of Clausena wallichii. Compounds 3, 9, and 22 exhibited significant antibacterial activity against methicillin-resistant Staphylococcus aureus SK1 (MRSA SK1) and Staph. aureus TISTR 1466 with MIC values in the range 4-16 μg/mL, whereas compound 4 showed the highest cytotoxicity against oral cavity cancer (KB) and small-cell lung cancer (NCI-H187) with IC(50) values of 10.2 and 4.5 μM, respectively.

Antimalarial, antimycobacterial and cytotoxic limonoids from Chisocheton siamensis.

Five limonoids isolated from the seeds of Chisocheton siamensis were tested for their antimalarial activity against Plasmodium falciparum, antimycobacterial activity against Mycobacterium tuberculosis and cytotoxic activity against NCI-H187 (human small cell lung cancer), KB (oral human epidermal carcinoma) and MCF-7 (breast cancer) cancer cell lines. All limonoids (1-5) showed inhibitory effect against Plasmodium falciparum with IC(50) values ranging from 2.06 to 6.31 microg/ml. Only azadiradione (2) exhibited strong inhibitory effect against Mycobacterium tuberculosis with the MIC of 6.25 microg/ml. Compounds 1-4 also showed cytotoxic activity against NCI-H187, KB and MCF-7 cancer cell lines and dysobinine (1) had the highest activity with IC(50) of 1.67, 3.17 and 2.15 microg/ml, respectively.

New coumarins from Clausena lansium twigs

Two new coumarins namely Clausenalansimin A (5) and B (9) together with seven known coumarins (1-4 and 6-8), were isolated from twigs of Clausena lansium. All compounds were determined by spectroscopic methods. Some of isolates had cytotoxicity against human cancer cell lines (KB, MCF7 and NCI-H187).

Antitumoral alkaloids from Clausena lansium

Three new carbazole alkaloids, mafaicheenamine A-C (1-3), along with five know compounds (4-8) were isolated from the twigs of Clausena lansium. All compounds were characterized by the analysis of spectroscopic methods. In addition, the evaluation of antitumoral activity against three human cancer cell lines, KB, MCF-7 and NCI-H187, of compounds 1, 2 and 4-8 were also reported.

Antibacterial carbazole alkaloids from Clausena harmandiana twigs.

Three new carbazole alkaloids, harmandianamines A-C (1-3), together with fifteen known compounds (4-18) were isolated from the twigs of Clausena harmandiana. The structures were elucidated by spectroscopic methods, including UV, IR, NMR, and MS. The antibacterial activity against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphylococcus aureus TISTR 1466 and methicillin-resistant S. aureus (MRSA) SK1 of some isolated compounds was also evaluated. Compound 6 exhibited significant antibacterial activity against MRSA SK1 with an MIC value of 0.25 μg/mL which higher than that of standard drug, vancomycin (MIC value=1 μg/mL) whereas compounds 14 and 5 showed strong activity with MIC values of 4 and 8 μg/mL, respectively. Only compound 14 showed strong antibacterial activity against S. aureus TISTR 1466 with an MIC value of 4 μg/mL.

Carbazole alkaloids from the stems of Clausena excavata

A new carbazole alkaloid, sansoakamine (8), together with 11 known compounds, was isolated from the stems of Clausena excavata. All structures were elucidated by spectroscopic methods. Compound 7 showed moderate anti-malarial activity against Plasmodium falciparum with a MIC value of 6.74 μg/ml.

Antimalarial and Cytotoxic Phenolic Compounds from Cratoxylum maingayi and Cratoxylum cochinchinense

Nine phenolic compounds isolated from Cratoxylum maingayi and C. cochinchinense were evaluated for anti-malarial activity against Plasmodium falciparum, and for cytotoxic activity against the NCI-H187 (human small cell lung cancer) cancer cell line. Formoxanthone C (3) was found to be the most active against the NCI-H187 cancer cell line, with an IC50 of 0.22 μg/mL, while vismione B (7) had the highest activity against Plasmodium falciparum, with an IC50 of 0.66 μg/mL.

Semisynthetic and biotransformation studies of (1S,2E,4S,6R,7E,11E)-2,7,11-cembratriene-4,6-diol.

Tobacco-derived (1 S,2 E,4 S,6 R,7 E,11 E)-2,7,11-cembratriene-4,6-diol (1) and (1 S,2 E,4 R,6 R,7 E,11 E)-2,7,11-cembratriene-4,6-diol (2) were first shown to display potential antitumor-promoting activity in the mid-1980s. However, very little is currently understood regarding the structural activity relationships of tobacco cembranoids. The aim of this present study was to explore antiproliferative activity of various derivatives of (1 S,2 E,4 S,6 R,7 E,11 E)-2,7,11-cembratriene-4,6-diol (1) using semisynthetic and biotransformation approaches. Derivatives of 1 include esterified, oxidized, halogenated, and nitrogen- and sulfur-containing compounds (3-17). Biotransformation of 1 using Mucor ramannianus ATCC 9628 and Cunninghamella elegans ATCC 7929 afforded the known 10 S,11 S-epoxy analogue of 1 (4) as the main metabolite. Biotransformation of the 6-O-acetyl analogue (3) using the marine symbiotic Bacillus megaterium strain MO31 afforded (1 S,2 E,4 S,6 R,7 E,11 E,10 R)-2,7,11-cembratriene-4,6,10-triol (18). (1 S,2 E,4 S,6 R,7 E,11 E,13 R)-2,7,11-Cembratriene-4,6,13-triol-6-O-acetate (6), (1 S,2 E,4 S,6 R,7 E,11 E,13 S)-2,7,11-cembratriene-4,6,13-triol-6-O-acetate (7), the rearranged alpha-ketol (1 S,2 E,4 S,7 Z,11 E)-2,7,11-cembratrien-4-ol-6-one (11), and the secocembranoid 12 showed antiproliferative activity against highly malignant +SA mammary epithelial cells with an IC50 range of 15-30 microM.

Chemical constituents from Aegle marmelos

A new natural product oxazoline derivative named aeglemarmelosine (1) along with eight known compounds (2-9) were isolated from roots and twigs of Aegle marmelos. Compounds 1-6 were isolated from the roots whereas compounds 7-9 were obtained from twigs. Compounds 5 and 6 were also detected from the twigs. All structures were characterized by extensive 1D and 2D NMR spectroscopic methods.

Bioactive Prenylated Xanthones from the Young Fruits and Flowers of Garcinia cowa

Five new xanthones, garciniacowones A-E (1-5), together with 14 known xanthones, 6-19, were isolated from the young fruits and fresh flowers of Garcinia cowa. The structures of 1-5 were elucidated by analysis of their 1D and 2D NMR spectra and mass spectrometric data. The compounds 1-19 were tested in vitro for their antimicrobial activity and for their ability to inhibit α-glucosidase. Compounds 16 and 17 showed the most potent α-glucosidase inhibitory activity, with IC50 values of 7.8 ± 0.5 and 8.7 ± 0.3 μM, respectively. Compounds 8, 9, and 19 showed antibacterial activity against Bacillus subtilis TISTR 088 with identical MIC values of 2 μg/mL, while 8, 10, and 19 exhibited antibacterial activity against Bacillus cereus TISTR 688 with identical MIC values of 4 μg/mL.