Chemical constituents from endophytic fungus Fusarium oxysporum

A new oxysporidinone analogue (1) and a new 3-hydroxyl-2-piperidinone derivative (2), along with the known compounds (−)-4,6′-anhydrooxysporidinone (3), (+)-fusarinolic acid (4), gibepyrone D (5), beauvercin (6),cerevisterol (7), fusaruside (8), and (2S,2′R,3R,3′E,4E,8E)-1-O-D-glucopyranosyl-2-N-(2′-hydroxy-3′-octadecenoyl)-3-hydroxy-9-methyl-4,8-sphingadienine (9) were isolated from Fusarium oxysporum. Compounds 1-9 were evaluated for cytotoxicity using the MTT method against cancer cell lines, PC-3, PANC-1, and A549. Beauvericin showed cytotoxicity against PC-3, PANC-1, and A549 with IC₅₀ value of 49.5 ± 3.8, 47.2 ± 2.9, and 10.4 ± 1.6 μM, respectively. Beauvericin also exhibited anti-bacterial activity towards methicillin-resistant Staphylococcus aureus (MIC = 3.125 μg/mL) and Bacillus subtilis (MIC = 3.125 μg/mL).     

Two new cytotoxic isomeric indole alkaloids from the roots of Nauclea orientalis

A pair of new isomeric indole alkaloids, naucleaorals A (1) and B (2) were isolated from the roots of Nauclea orientalis. The structures of compounds 1 and 2 were fully characterized using spectroscopic data, and were tested for their cytotoxicity (HeLa and KB cells) and antimalarial activity. Compound 1 showed significant cytotoxicity to HeLa cells with an IC₅₀ value of 4.0 µg/mL, while compound 2 exhibited very modest cytotoxicity to both cell lines with IC₅₀ values of 7.8 and 9.5 µg/mL, respectively. Both compounds proved to be inactive in antimalarial assays (IC₅₀ > 10.00 µg/mL).     

Sesquiterpenoids and norterpenoids from Vitex negundo

Chemical investigation on the seeds of Vitex negundo has afforded a new furan-containing sesquiterpenoid, negunfurol (1), a new norlabdane-type diterpenoid, negundoal (2), and two new norursane-type triterpenoids, negundonorins A (3) and B (4), together with two know compounds, 3-formyl-4,5-dimethyl-8-oxo-5H-6,7-dihydronaphtho[2,3-b]furan (5) and 3-epi-corosolic acid (6). Their structures and configurations were elucidated by detailed spectroscopic analyses on the basis of NMR, IR, and MS data. Compound 3 was strongly cytotoxic against ZR-75-30 cell line with IC₅₀ value of 0.56 ± 0.19 μg/mL, whereas compound 1 was most active against HL-60 cell line with IC₅₀ value of 0.94 ± 0.26 μg/mL.     

Comparative analysis of the chemical constituents of two varieties of Pueraria candollei

A high-performance liquid chromatography (HPLC) method was developed to determine the contents of miroestrol and deoxymiroestrol in the tubers of Pueraria candollei var. mirifica and P. candollei var. candollei. The linear detection ranges were 0.78-25.00 μg/mL for miroestrol and 1.56-25.00 μg/mL for deoxymiroestrol. The limit of detection (LOD) and limit of quantification (LOQ) were 0.2 and 0.78 μg/mL, respectively, for miroestrol and 0.78 and 1.56 μg/mL, respectively, for deoxymiroestrol. Our results suggest that both varieties of P. candollei can produce miroestrol and deoxymiroestrol and that the developed HPLC method can be applied for quality control of plants and their products.     

Novel indole C-glycosides from Isatis indigotica and their potential cytotoxic activity

Two novel indole C-glycosides, which were the first reported alkaloids C-glycosides from Isatis indigotica, together with five known alkaloids were isolated. The novel alkaloids were elucidated to be indole-3-acetonitrile-4-methoxy-2-C-β-D-glucopyranoside (1) and N-methoxy-indole-3-acetonitrile-2-C-β-D-glucopyranoside (2) on the basis of spectroscopic analysis. 1 exhibited significant cytotoxic activities against human myeloid leukemia HL-60 and human liver cancer HepG2 cells with the IC₅₀ of 1.3 ± 0.1 and 2.1 ± 0.3 μM, respectively. 2 showed potential cytotoxic activities against HL-60 and human myeloid leukemia Mata cells with the IC₅₀ of 5.1 ± 0.4 and 12.1 ± 0.8 μM, respectively.     

Three new antibacterial active diarylheptanoids from Alpinia officinarum

Three new diarylheptanoids, together with ten known ones, were isolated from the ethanol extract from the rhizomes of Alpinia officinarum Hance. The structural identification of these compounds was mainly achieved by spectroscopic methods. The new compounds were elucidated as 7-(4″, 5″-dihydroxy-3″-methoxyphenyl)-1-phenyl -4-heptene-3-one (1), 1, 7-diphenyl-5-heptene-3-one (2) and 4-phenethyl-1, 7-diphenyl -1-heptene-3, 5-dione (3), respectively. All of the compounds showed antibacterial activity against Helicobactor pylori. Especially, the three new compounds showed strong antibacterial activity against Hp-Sydney strain 1 with the MIC values of 9–12 μg/mL, and against Hp-F44 with the MIC values of 25–30 μg/mL.     

A new dimeric resveratrol from the roots of Shorea roxburghii

A new resveratrol dimer, roxburghiol A (1) together with eleven known compounds were isolated from the roots of Shorea roxburghii. Their structures were identified on the basis of spectroscopic evidence and physicochemical properties. All isolated compounds were evaluated for their cytotoxicity (KB and HeLa cells). Compounds 8 and 9 showed potent cytotoxicity against both KB and HeLa cell lines with IC₅₀ values of 6.5, 8.5 and 8.7, 10.1 μg/mL, respectively.     

Bioactive flavones and biflavones from Selaginella moellendorffii Hieron

Three new flavones named 5-carboxymethyl-4′,7-dihydroxyflavone (1), its ethyl ester (2) and butyl ester (3) were isolated from the herb Selaginella moellendorffii Hieron., together with ten known compounds. Their structures were elucidated on the basis of spectroscopic and chemical analysis. Selected compounds were evaluated for their anti-HBV and cytotoxic activity. Among them, compounds 2 and 3 displayed inhibitory activity in vitro on hepatitis B virus (HBV) surface antigen (HBsAg) secretion of the Hep G2.2.15 cell line with IC₅₀ values of 0.17 mg/ml and 0.46 mg/ml, and on HBV e antigen (HBeAg) secretion with IC₅₀ values of 0.42 mg/ml and 0.42 mg/ml, respectively. Compounds 7, 8, 10 and 12 exhibited selective cytotoxicity against the three human cancer cell lines tested.     

Antibacterial dihydrobenzopyran and xanthone derivatives from Garcinia cowa stem barks

Two new compounds, garciniacowol (1) and garciniacowone (2) along with 15 known compounds were isolated from the stem barks of Garcinia cowa. Their structures were determined by intensive spectroscopic methods. The structure of 1 was a symmetrical dimeric dihydrobenzopyran derivative, whereas the framework of 2 was a triprenyl caged-xanthone precursor. The antibacterial activities against Escherichia coli TISTR 780, Salmonella typhimurium TISTR 292, Staphylococcus aureus TISTR 1466, and methicillin-resistant S. aureus (MRSA) SK1 of the isolated compounds were also evaluated. Compounds 2 and 9 exhibited good antibacterial activity against MRSA SK1 with the same minimum inhibitory concentration (MIC) value of 2 μg/mL. Moreover, compound 2 also showed good antibacterial activity against S. aureus with an MIC value of 2 μg/mL.     

Antioxidant flavanes from Livistona chinensis

Three new flavanes and eight known flavonoids were isolated from the fruits of Livistona chinensis. The structure of the new flavanes were established as 2S,3S-3,5,7,3′,5′-pentahydroxyflavane (1), 2R,3R-3,5,6,7,8,4′-hexahydroxyflavane (2) and 2R,3R-3,5,6,7,8,3′,5′-heptahydroxyflavane (3), respectively, on the basis of chemical and spectroscopic data. The antiproliferative activity against four human tumor cell lines (HL-60, Mata, HepG2 and CNE-1) was evaluated. 1 had significantly antiproliferative effects against HL-60 and CNE-1 with the IC₅₀ of 0.2 ± 0.01 and 1.0 ± 0.1 μM, respectively, overpowering the reference compound in the assay (cisplatin). Most compounds also exhibited potent antioxidant activity.     

Cytochrome P450 1 enzyme inhibition and anticancer potential of chromene amides from Amyris plumieri

Cytochrome P450 (CYP) enzyme inhibitory properties of six chromenylated amide compounds (CAs) from Amyris plumieri are described. Inhibition of CYP microsomes (CYP1A1, CYP1A2, CYP1B1, CYP2D6, CYP3A4 and CYP2C19) was monitored using a fluorescent assay. Potent inhibition was found against CYP1A1 with IC₅₀ and K_i for CA1 (acetamide), being the lowest at 1.547 ± 1.0 μM and 0.37 μM respectively, displaying non-competitive kinetics. The selectivity for CYP1A1 was increased in CA3 (butanamide), which also exhibited cytotoxicity against breast cancer cells, MCF7 with an IC₅₀ of 47.46 ± 1.62 μM. Structure-activity relationship studies provide insight at a molecular level for CAs with implications in chemoprevention and chemotherapy.     

New diterpenoids and cytotoxic and anti-inflammatory diterpenoids from Amentotaxus formosana

Two new abietane diterpenoids, ramentoxide (1) and ramentoxidone (2) and a new icetexane diterpenoid, amentonone (3) were isolated from the barks of Amentotaxus formosana. The structures of 1-3 were determined by spectroscopic methods. Known compounds brevitaxin (4), and (+)-ferruginol (5) and ent-kaur-16-en-15-one (6) isolated from this plant revealed potent cytotoxic activity against human breast adenocarcinoma cells, MCF-7 cells with an IC₅₀ value of 0.08 ± 0.05 μg/mL, and significant anti-inflammatory activities, respectively.     

Two new prenylated xanthones and a new prenylated tetrahydroxanthone from the pericarp of Garcinia mangostana

Two new prenylated xanthones and a new prenylated tetrahydroxanthone, garcimangosxanthone A–C (1–3), along with fourteen known xanthones were isolated from the pericarp of Garcinia mangostana. Their structures were elucidated on the basis of spectroscopic data. Compounds 1 and 2 exhibited in vitro cytotoxicity against A549, LAC and A375 cell lines with IC₅₀ values of 5.7–24.9 μM, which were comparable to those of doxorubicin.     

Anti-inflammatory, cyclooxygenase inhibitory and antioxidant activities of standardized extracts of Tridax procumbens L.

The standardized EtOAc, MeOH and 70% EtOH extracts of Tridax procumbens aerial parts showed significant inhibition of rat paw edema at a medium dose of 200 mg/kg and the EtOAC extract was the most active. These extracts were standardized by HPLC with the help of chemical markers. Further, the extracts were evaluated for COX-1 and COX-2 inhibitory activity and EtOAc extract exhibited the highest inhibition of COX-1 and COX-2 at 50 μg/mL. Cent aurein, centaureidin and bergenin were isolated as COX-1 and COX-2 inhibitory principles from the EtOAc extract. The extracts also exhibited antioxidant activity against DPPH and ABTS free radicals. The anti-inflammatory activity of T. procumbens aerial parts could be at least in part due to COX-1, COX-2 enzyme inhibition and free radical-scavenging activities which may be attributed to the presence of flavonoids and other polyphenols in the extracts.     

Anticholinesterase activity of standardized extract of Illicium verum Hook. f. fruits

Illicium verum is a well known spice in traditional Indian system for its therapeutic potential. The present study was aimed to evaluate the acetylcholinesterase (AChE) and butyrylcholinesterase inhibitory (BChE) activity of standardized extracts of I. verum and its oil. Present study confirmed that anethole contributed to the anticholinesterase activity of I. verum, with more specificity towards AChE. IC₅₀ for AChE and BChE inhibitory activity of anethole was 39.89 ± 0.32 μg/mL and 75.35 ± 1.47 μg/mL, whereas for the oil, 36.00 ± 0.44 μg/mL and 70.65 ± 0.96 μg/mL respectively. Therefore I. verum can be a good lead as anti-cholinesterase agent from natural resources.     

Inhibitory components from the buds of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells

In the course to find a new whitening agent, we evaluated the methanol extract from bud of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells. Eugenol and eugenol acetate were isolated as the active compounds and showed melanin inhibition of 60% and 40% in B16 melanoma cell with less cytotoxicity at the concentration of 100 and 200 μg/mL, respectively. Furthermore, an essential oil prepared from the bud of clove, which contain eugenol and eugenol acetate as dominant components, showed melanin inhibition of 50% and 80% in B16 melanoma cells at the concentration of 100 and 200 μg/mL, respectively.     

Antituberculosis activity of alkylated mulinane diterpenoids

Natural azorellane and mulinane diterpenoids show antituberculosis activity, which is increased by methylation of their free carboxyl group. We have systematically investigated the effect of alkylation in this class of diterpenoids and found that the profile of bioactivity is relatively unaffected by the introduction of short alkyl groups, both linear and branched. In this investigation, three semisynthetic diterpenoids, 13 hydroxy-mulin-11-en-20-oic acid n-propyl ester (3) and the n-propyl (19) and n-butyl (20) esters of isomulinic acid, showed the strongest antituberculosis activity (MIC = 6.25 μg/mL) against a drug-resistant strain of Mycobacterium tuberculosis.     

Two new benzofuran derivatives with anti-inflammatory activity from Liriope spicata var. prolifera

Two new benzofuran derivatives, 2-(4′-hydroxybenzyl)-5,6-methylenedioxy-benzofuran () and 2-(4′-hydroxybenzoyl)-5,6-methylenedioxy-benzofuran (), along with 8 known compounds were isolated from 60% EtOH extract of the fibrous roots of Liriope spicata var. prolifera. Their structures were elucidated on the basis of extensive spectroscopic analysis. In an in vitro bioactive assay, the two new benzofuran derivatives showed anti-inflammatory activity. Compounds 1 and 2 exhibited significant inhibitory activity against neutrophil respiratory burst stimulated by phorbol 12-myristate 13-acetate (PMA) with IC₅₀ value of 4.15 ± 0.07 and 5.96 ± 0.37 μM, respectively.     

Acetylcholinesterase and butyrylcholinesterase inhibition of ethanolic extract and monoterpenes from Pimpinella anisoides V Brig. (Apiaceae)

Ethanolic extract from the fruits of Pimpinella anisoides, an aromatic plant and a spice, exhibited activity against AChE and BChE, with IC₅₀ values of 227.5 and 362.1 μg/ml, respectively. The most abundant constituents of the extract were trans-anethole, (+)-limonene and (+)-sabinene. trans-Anethole exhibited the highest activity against AChE and BChE with IC₅₀ values of 134.7 and 209.6 μg/ml, respectively. The bicyclic monoterpene (+)-sabinene exhibited a promising activity against AChE (IC₅₀ of 176.5 μg/ml) and BChE (IC₅₀ of 218.6 μg/ml).     

Photosynthetic characteristics of Fagus sylvatica and Quercus robur established for stand conversion from Picea abies

Efforts in Europe to convert Norway spruce (Picea abies) plantations to broadleaf or mixed broadleaf-conifer forests could be bolstered by an increased understanding of how artificial regeneration acclimates and functions under a range of Norway spruce stand conditions. We studied foliage characteristics and leaf-level photosynthesis on 7-year-old European beech (Fagus sylvatica) and pedunculate oak (Quercus robur) regeneration established in open patches and shelterwoods of a partially harvested Norway spruce plantation in southwestern Sweden. Both species exhibited morphological plasticity at the leaf level by developing leaf blades in patches with an average mass per unit area (LMA) 54% greater than of those in shelterwoods, and at the plant level by maintaining a leaf area ratio (LAR) in shelterwoods that was 78% greater than in patches. However, we observed interspecific differences in photosynthetic capacity relative to spruce canopy openness. Photosynthetic capacity (A₁₆₀₀, net photosynthesis at a photosynthetic photon flux density of 1600 μmol photons m⁻² s⁻¹) of beech in respect to the canopy gradient was best related to leaf mass, and declined substantially with increasing canopy openness primarily because leaf nitrogen (N) in this species decreased about 0.9 mg g⁻¹ with each 10% rise in canopy openness. In contrast, A₁₆₀₀ of oak showed a weak response to mass-based N, and furthermore the percentage of N remained constant in oak leaf tissues across the canopy gradient. Therefore, oak photosynthetic capacity along the canopy gradient was best related to leaf area, and increased as the spruce canopy thinned primarily because LMA rose 8.6 g m⁻² for each 10% increase in canopy openness. These findings support the premise that spruce stand structure regulates photosynthetic capacity of beech through processes that determine N status of this species; leaf N (mass basis) was greatest under relatively closed spruce canopies where leaves apparently acclimate by enhancing light harvesting mechanisms. Spruce stand structure regulates photosynthetic capacity of oak through processes that control LMA; LMA was greatest under open spruce canopies of high light availability where leaves apparently acclimate by enhancing CO₂ fixation mechanisms.