Neolignans and polyoxygenated seco-cyclohexenes from the stems and leaves of Piper suipigua Buch.-Ham. ex D. Don.

Five new compounds including, a neolignan, eupomatenoid-19 (1) and four polyoxygenated seco-cyclohexenes, artahongkongenes G-J (2-5), together with fifteen known compounds (6-20) were isolated from the stems and leaves of Piper suipigua Buch.-Ham. ex D. Don. Their structures were determined by spectroscopic evidence (IR, UV, 1H NMR, 13C NMR and 2 D NMR) as well as MS. The absolute configurations of polyoxygenated seco-cyclohexenes 2-8 were identified by NOESY data and by comparison of their experimental and calculated ECD spectral data. Neolignans, eupomatenoid-19 (1) and eupomatenoid-7 (10), displayed cytotoxicity against several cancer cell lines. In addition, eupomatenoid-7 (10) showed antibacterial activity against Bacillus cereus, Bacillus subtilis and Staphylococcus aureus.

Ethanolic extract of Ya-nang (Tiliacora triandra) leaf powder induces apoptosis in cholangiocarcinoma cell lines via induction of hyperacetylation and inhibition of growth signaling.

Objective: To develop alternative medicine for reducing undesired side effects of chemotherapy in CCA patients, the anticancer activity of Tiliacora triandra leaf powder ethanolic (TLPE) extract against cholangiocarcinoma cell lines was investigated. Methods: Antiproliferation was studied using the MTT assay while apoptosis induction and cell cycle arrest were analyzed by flow cytometry. The levels of key proteins and phenolic acid content were analyzed by western blotting and reversed-phase HPLC, respectively. Results: TLPE extract inhibited CCA cell growth in a dose- and time-dependent manner, with IC50 values of 7.86 ± 0.05 µg/ml for KKU-M213B cells and 8.59 ± 0.36 µg/ml for KKU-100 cells at an exposure time of 72 h. TLPE extract inhibited the growth of CCA cell lines by inducing apoptosis of both cell lines and causing an increased population of KKU-100 cells at G0/G1 phase. TLPE extract up-regulated Ac-H3 but down-regulated p-ERK, p53, Bax, CDK4 and Bcl2 expressions in KKU-M213B cells. TLPE extract up-regulated Ac-H3, p21 and Bax but down-regulated p-ERK, p53, CDK4 and Bcl2 expressions in KKU-100 cells. Additionally, phenolic acids including p-hydroxybenzoic, vanillic, syringic, p-coumaric, ferulic and sinapinic acids were identified. Conclusion: These results suggest the possibility of developing T. triandra leaf powder ethanolic extract as a chemotherapeutic or chemoprevention agent for cholangiocarcinoma.

Cytotoxic and antibacterial xanthones from the roots of Maclura cochinchinensis.

Three new furanoxanthones, macochinxanthones A-C (1-3) and sixteen known xanthones (4-19) were isolated from the roots of Maclura cochinchinensis. Their structures were elucidated by spectroscopic analysis including NMR, UV and IR, as well as mass spectrometry. Chiral-phase HPLC analysis of 1-3 revealed that they were scalemic mixtures with an enantiomeric excess (ee) of 0.05%, 36.8% and 8%, respectively. Most of the isolated xanthones exhibited potent cytotoxicity against four cancer cell lines (KB, HelaS3, A549 and HepG2) with IC50 values in the range of 1.29-90.15 µM. In addition, many of them displayed antibacterial activity against Gram-positive bacteria and Methicillin resistant Stephylococus aureus (MRSA) with MIC values in the range of 4-128 µg/mL.

Four New Anthraquinones with Histone Deacetylase Inhibitory Activity from Ventilago denticulata Roots.

Chromatographic separation of the crude extracts from the roots of Ventilago denticulata led to the isolation of four new anthraquinones, ventilanones L-O (1-4), together with eight known anthraquinones (5-12). Their structures were elucidated by spectroscopic methods (UV, IR, 1H NMR, 13C NMR, and 2D NMR) and mass spectrometry (MS), as well as comparison of their spectroscopic data with those reported in the literature. HDACs inhibitory activity evaluation resulted that compound 2 exhibited moderate antiproliferative activity against HeLa and A549 cell lines but nontoxic to normal cell. Molecular docking indicated the phenolic functionality of 2 plays crucial interactions with class II HDAC4 enzyme.

Phytochemicals from twigs of Afzelia xylocarpa and their antioxidation kinetics of oxymyoglobin.

The phytochemical investigation of crude n-hexane and ethyl acetate extracts from twigs of Afzelia xylocarpa (Kurz) led to the isolation of 14 known compounds. Their structures were elucidated by spectroscopic techniques (IR, 1H NMR, 13C NMR, and 2D NMR) as well as mass spectrometry. These structures were characterized as ß-sitosterol (1), lupeol (2), vanilic acid (3), 5,7-dihydroxychromone (4), (+)-mellein (5), isoliquiritigenin (6), 7-hydroxyemodin (7), physion (8), aromadendrin (9), naringenin (10), apigenin (11), luteolin (12), chrysoeriol (13) and kaempferol (14). Compounds 4-7 and 12-13 were isolated from the genus Afzelia for the first time. The selected compounds 5, 8, 9 and 12 exhibited potent activity for antioxidation kinetics of oxymyoglobin.

Chemical constituents and antibacterial activity from the stems and leaves of Piper wallichii.

A phytochemical investigation of the stems and leaves of Piper wallichii led to the isolation of two new compounds, an aryl alkanone, piwalkanone (1) and a dioxoaporphine alkaloid, piwallidione (2), together with nine known compounds, a dioxoaporphine alkaloid, cepharadione A (3); two aristolactams, piperolactam A (4) and stigmalactam (5); a piperidine, piperine (6); four isobutylamides, piperlonguminine (7), pellitorine (8), N-isobutyl-2E,4E-octadecadienamide (9), and guineensine (10); and a tyramine, N-trans-feruloyltyramine (11). Their structures were elucidated on the basis of spectroscopic evidence (IR, 1H NMR, 13C NMR and 2 D NMR) and MS. Compounds 2 and 3 showed inhibitory activities against pathogenic bacteria, Bacillus cereus, Bacillus subtilis and Staphylococcus aureus.

ent-Clerodane diterpenoids from the stems of Croton krabas.

The first phytochemical investigation from the stems of Croton krabas resulted in the isolation of three new ent-clerodane diterpenoids, crotonkrabases A-C (1-3), along with two known compounds, 12-oxohardwickiic acid (4) and crotonpyrone B (5). Their structures were elucidated using extensive spectroscopic methods. The structure of 3 was unambiguously proven by X-ray crystallography. Furthermore, the absolute configurations of compounds 1-3 were identified by NOESY and the comparison of their experimental ECD spectra with those of calculated ECD spectra reported in the literature. Compounds 1, 2, and 5 showed antibacterial activities against two Gram-positive bacteria (Bacillus cereus and Bacillus subtilis); whereas compound 4 exhibited weak antibacterial against B. cereus. In addition, compound 4 showed potent α-glucosidase inhibitory activity, which was lower than the reference standard acarbose.

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus.

Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A - C (1:  - 3: ), together with fourteen known compounds (4:  - 17: ), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1:  - 3: were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1: showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC50 values of 7, 11, 10, 12, and 10 µM, respectively. Compounds 1: and 14: showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1:  - 3: and 14: showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1: showed weak antibacterial activity against Escherichia coli.

A new antibacterial tirucallane from Walsura trichostemon roots.

Phytochemical investigation of the roots of Walsura trichostemon, a Thai medicinal plant, provided a new tirucallane, 3-epimesendanin S 12-acetate (1), together with four known compounds, 3-epimesendanin S (2), meliasenin G (3), ß-sitosterol (4) and ß-sitosterol glucoside (5). Their structures were characterized by intensive spectroscopy including 1 D and 2 D NMR, UV, IR and MS spectrometric analysis. The isolated compounds were evaluated for antibacterial and acetylcholinesterase inhibitory activities. Compounds 1-2 showed antibacterial activity against Bacillus cereus and Bacillus subtilis with MIC values ranging from 16-128 µg/mL. In addition, compound 3 was active against Pseudomonas aeruginosa and Escherichia coli with MIC values of 64 and 128 µg/mL, respectively.

A new cytotoxic plumbagin derivative from roots of Diospyros undulata.

A new plumbagin derivative, 3-(5-oxohexyl)plumbagin (1), together with six known benzoquinone derivatives (2-7), four known triterpenoids (8-11) and coniferyl aldehyde (12) were isolated from Diospyros undulata roots. Their structures were elucidated by intensive spectroscopy including 1 D and 2 D NMR, UV, IR and MS spectrometric analysis. Compound 1 exhibited strong cytotoxicity against three cancer cell lines as lung cancer (NCI-H187), breast cancer (MCF-7), and oral cancer (KB) with IC50 values of 7.16, 12.85 and 28.67 µM, respectively. Moreover, it did not showed cytotoxicity to Vero cells. In addition, the antimicrobial activity of compound 1 was moderate that kill only S. aureus with MBC of 250 µg/mL while other compounds especially compound 4 showed a broader activity that kill all tested bacteria.

Spirosteroids and α-glucosidase inhibitory norlignans from Asparagus racemosus Willd. roots.

Three undescribed spirosteroids, asparacemosones A-C, an undescribed spiro-21-norsteroid, asparacemosone D, along with seven known compounds were isolated from Thai herbal plant Asparagus racemosus Willd. roots. Their structures were elucidated by spectroscopic analysis including NMR, UV, IR and mass spectrometry. The absolute configurations of asparacemosones A, B, and D were determined by single crystal X-ray diffraction using CuKα radiation. Among the isolated compounds, the norlignan nyasol and three acetylenic norlignans demonstrated potent α-glucosidase inhibition, with IC50 values ranging from 0.003 to 0.004 µM which is 5 × 104 fold more potent than the standard acarbose.

Meroterpenoid pyrones, alkaloid and bicyclic brasiliamide from the fungus Neosartorya hiratsukae.

Two new meroterpenoid pyrones, chevalone G (1) and aszonapyrone C (2), a new indole alkaloid, 7-chlorofischerindoline (3) and a new bicyclic brasiliamide, brasiliamide H (4), together with sixteen known compounds, 5-20 were isolated from the fungus Neosartorya hiratsukae. Their structures were established on the basis of spectroscopic evidence. The antibacterial activity and the cytotoxic activity of new compounds were evaluated.

Two new bioactive triterpenoids from the roots of Colubrina asiatica.

Two new ceanothane triterpenes, 3,7-O,O-dibenzoyl ceanothic acid methylester (1) and 3-O-acetyl-7-O-benzoyl ceanothic acid methylester (2), along with nine known compounds (3-11), were isolated from the roots of Colubrina asiatica. The isolated compounds were identified by spectroscopic evidence. Compounds 1 and 2 showed antimalarial activity against Plasmodium falciparum with IC50 values of 4.67 and 3.07 µg/mL, respectively. Compound 2 also showed antimycobacterial activity against Mycobacterium tuberculosis (MIC 6.25 µg/mL). In addition, compounds 1, 2, 10 and 11 showed cytotoxicity against three cancer cell lines (KB, NCI-H187 and MCF-7) with IC50 values ranging from 8.32 to 46.72 µg/mL.

Meroditerpene pyrone, tryptoquivaline and brasiliamide derivatives from the fungus Neosartorya pseudofischeri.

Two new meroditerpene pyrones, chevalone F (1) and 11-hydroxychevalone E (2), a new tryptoquivaline analog, tryptoquivaline V (3) and a new brasiliamide analog, brasiliamide G (4), together with thirteen known compounds, chevalones A-C (5-7), chevalone E (8), 11-hydroxychevalone C (9), pyripyropene A (10), isochaetominine C (11), pyrrolobenzoxazine terpenoids CJ-12662 (12) and CJ-12663 (13), fischerindoline (14), eurochevalierine (15), 1,4-diacetyl-2,5-dibenzylpiperazine-3,7''-oxide (16) and lecanorin (17) were isolated from the fungus Neosartorya pseudofischeri. Their structures were established on the basis of spectroscopic evidence. Compound 2 showed weak antibacterial activity against Escherichia coli and Salmonella enterica serovar Typhimurium, whereas compounds 7, 12, 13 and 15 showed antibacterial activity against Bacillus cereus and Staphylococcus aureus. In addition, compounds 13 and 14 showed cytotoxicity against KB and MCF-7 cancer cell lines, as well as the Vero cell line.

Types A and D Trichothecene Mycotoxins from the Fungus Myrothecium roridum.

Chromatographic separation of extracts from the fungal biomass of a plant pathogenic fungus, Myrothecium roridum, yielded 8 trichothecene toxins including 6 type D trichothecenes (1: -6: ) and 2 type A trichothecenes (7: -8: ). 6',12'-Epoxymyrotoxin A (1: ) and 7'-hydroxymytoxin B (2: ) were new macrocyclic trichothecenes, while the other trichothecenes were identified as myrotoxin B (3: ), myrotoxin D hydrate (4: ), 2',3'-epoxymyrothecine A (5: ), miotoxin A (6: ), and 2 trichothecenes lacking the macrocyclic lactone system, roridin L-2 (7: ) and trichoverritone (8: ). The structures of these mycotoxins were characterized using spectroscopic methods. The absolute configurations of 1: and 2: were determined by NOESY and a comparison of their experimental and calculated ECD spectra. Most of these mycotoxins (1: -4: and 6: ) exhibited highly potent antimalarial activity against Plasmodium falciparum. They also showed strong cytotoxicity towards KB and NCI-H187 cell lines (IC50 0.60 - 112.28 nM), as well as the Vero cell line (IC50 1.50 - 46.51 nM).

Bioactive oxaphenalenone dimers from the fungus Talaromyces macrosporus KKU-1NK8.

Six new polyketide-derived oxaphenalenone dimers, talaromycesone C (1) and macrosporusones A-E (2-6), together with eight known analogs, were isolated from the mycelium of the fungus Talaromyces macrosporus KKU-1NK8. Their structures were established based on their spectroscopic data and MS. The absolute configurations of new compounds 1-6 were determined by ECD analyses. Compounds 3 and 8 exhibited antimalarial activity against Plasmodium falciparum. Compound 3 showed activity against NCI-H187 cells, while compound 8 displayed activity against KB, MCF-7 and NCI-H187 cell lines. In addition, compound 11 showed antibacterial activity against Bacillus cereus, Staphylococcus aureus and MRSA.

Bioactive homogentisic acid derivatives from fruits and flowers of Miliusa velutina.

Chromatographic separation of fruits and flowers of the Thai medicinal plant, Miliusa velutina, resulted in the isolation of five new rare homogentisic acid derivatives, miliusanal (1) and miliusanones A-D (2-5), together with fifteen known secondary metabolites (6-20). Their structures were determined through the use of extensive spectroscopic data. The absolute configurations of homogentisic acid derivatives 2-7 were identified using NOESY data and a comparison of experimental and calculated ECD spectral data. Compounds 2, 3, 6, and 7 showed antimalarial activity with IC50 values in the range of 3.3-5.2 µg/mL. Compound 6 also showed activity against Mycobacterium tuberculosis with an MIC value of 50 µg/mL. Compounds 1-3, 6 and 7 exhibited cytotoxicity againt KB, MCF-7, NCI-H187 and Vero cell lines with IC50 values in the range of 5.8-40.4 µg/mL. In addition, compounds 1, 2 and 6 showed moderate antibacterial activities against three Gram-positive bacteria (Bacillus cereus, Staphylococcus aureus, and Methicillin resistant S. aureus) with MICs in the range of 32-64 µg/mL.

Antimalarial polyoxygenated cyclohexene derivatives from the roots of Uvaria cherrevensis.

Three new polyoxygenated cyclohexene derivatives named cherrevenisyls A and B (1 and 2), and ellipeiopsol E (3), along with fifteen known compounds, were isolated from the roots of Uvaria cherrevensis. Their structures were determined by spectroscopic methods including 2D NMR techniques and mass spectrometry. The absolute configurations of 1 and 2 were assigned. Compounds 1, 2 and 5 showed antimalarial activity against Plasmodium falciparum with IC50 ranging from 3.34-7.34µg/mL. Compounds 5-18 exhibited cytotoxicity against three cancer cell lines (KB, MCF-7 and NCI-H187) with IC50 values in ranging from 1.26-49.03µg/mL.

Chemical constituents and biological activities from branches of Colubrina asiatica.

Sixteen compounds were isolated from a Thai medicinal plant, Colubrina asiatica. The isolated compounds were elucidated on the basis of spectroscopic methods (IR, 1D and 2D NMR) as six triterpene acids (1-6), five steroids (7-11), one benzoic acid derivative (12), two peptides (13 and 14), one sesquiterpenoid (15) and one jujubogenin (16). Compounds 3 and 10 showed antimalarial activity against Plasmodium falciparum. Compound 5 showed antimycobacterial activity. Moreover, compounds 3, 5, 6, 10 and 14 exhibited weak cytotoxicity against cancer cell lines. Compounds 1-15 have been isolated for the first time from this plant.

A new coruleoellagic acid derivative from stems of Rhodamnia dumetorum.

A new coruleoellagic acid derivative, 3,3',4,4',5'-pentamethylcoruleoellagic acid (1) together with nine known compounds, hexamethylcoruleoellagic acid (2), 3,4,3'-tri-O-methylellagic acid (3), heptaphylline (4), 7-methoxymukonal (5), dentatin (6), sinapaldehyde (7), gallic acid (8), 2,6-dimethoxy-4H-pyran-4-one (9) and ß-sitosterol (10) were isolated from the stems of Rhodamnia dumetorum. Their structures were identified by physical and spectroscopic data (IR, 1D and 2D NMR, and MS). Compounds 1, 2 and 7-10 were tested for antibacterial activity against six pathogenic bacterial strains (Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica serovar Typhimurium, Staphylococcus aureus, and Methicillin resistant S. aureus (MRSA)).