A new flavonol glycoside from Millettia speciosa

A new flavonol triglycoside, millettiaspecoside D, was isolated from the caulis of Millettia speciosa Champ. Its structure was elucidated on the basis of spectroscopic analysis.     

Cytotoxic constituents from Anagyris foetida leaves

Anagyris foetida extracts were investigated in preliminary cytotoxic tests against two tumour cell lines. Chromatographic separations on active extracts led to the isolation of two alkaloids, anagyrine (1) and baptifoline (2), as well of isorhamnetin (3) and syringin 4-O-beta-D-glucopyranoside (4). In vitro cytotoxicity of compounds 1-3 was also evaluated.     

Anti-inflammatory constituents from Tabebuia avellanedae

Five novel compounds were isolated from the water extract of Tabebuia avellanedae, and their structures were established by analysis of NMR spectroscopy and mass spectrometry. Compounds 1–5 at 25 μM showed strong inhibitory activity on the inflammatory cytokine, tumor-necrosis factor-α and interleukin-1β production in cultured human myeloma THP-1 cells co-stimulated with lipopolysaccharide without any significant cytotoxicity, and their anti-allergic and antioxidant activities were evaluated.     

Sesquiterpenes from the aerial part of Chloranthus japonicus and their cytotoxicities

Four new sesquiterpenes, chlorajapolides F–I (1–4), along with nine known terpenoids (5–13) were isolated from the aerial part of Chloranthus japonicus. Their structures were elucidated on the basis of spectroscopic analysis, and a lindenane sesquiterpene, named 9-hydroxy-heterogorgiolide, previously isolated from the C. japonicus, was revised as its 8-epimer (1a). Moreover, methanol extract (ME), EtOAc fraction (EF), water fraction (WF), and all isolates (1a, 1–13) were evaluated for their cytotoxicities using two human cancer cell lines.     

Cytotoxic sesquiterpenes and lignans from Saussurea deltoidea

Two new sesquiterpenes deltoiden A (1) and deltoiden B (2), and two new lignans deltoignan A (9) and deltoignan B (10), together with 14 known compounds, including six sesquiterpenes 3-8 and three lignans 11-13, were isolated from the whole plant of Saussurea deltoidea. Compounds 3-8 and 11-17 were isolated for the first time from this plant. Their structures were established by spectroscopic analysis, including 2D-NMR spectroscopic techniques. Cytotoxicities of compounds 1-13 were tested against three cancer cell lines A549, Hela and SMMC-7721. Results showed that 5, 6 and 7 exhibited cytotoxicity against SMMC-7721 with the IC(50) values of 6.49, 9.53, 1.23 μg/ml, 5 and 7 against A549 with the IC(50) values of 4.99 and 5.35 μg/ml, 5, 6, 7, 13 against Hela with the IC(50) values of 1.40, 4.75, 0.93 and 5.42 μg/ml, respectively. The structure-activity relationships of sesquiterpenes 1-8 were discussed on the base of cytotoxic results.     

Cytotoxic nor-dammarane triterpenoids from Dysoxylum hainanense

Four new nor-dammarane triterpenoids, 12β-O-acetyl-15α,28-dihydoxy-17β-methoxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanran (1), 12β-O-acetyl-15α,17β,28-trihydoxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanran (2), 12β-O-acetyl-15α,28-dihydoxy-3-oxo-17-en-20,21,22-23,24,25,26,27-octanordammanran (3), and 12β,15α,17β,28-tetrahydoxy-3-oxo-20,21,22-23,24,25,26,27-octanordammanran (4), were isolated from the 70% EtOH extract of Dysoxylum hainanense. The structures of the new compounds were elucidated by spectral methods. All the triterpenoids were in vitro evaluated for their cytotoxic activities against four tumor cell lines (A549, SK-OV-3, SKMEL-2 and HCT15).     

Cytotoxic taraxerane triterpenoids from Saussurea graminea

Four new taraxerane triterpenoids, 1β,3β-dihydroxy-11α,12α-oxidotaraxerane (1), 28-hydroxy-11α,12α-oxidotaraxerane-3-one (2), 3β-hydroxy-11α,12α-oxidotaraxerane-28-al (3), and 3-O-acetyl-11α,12α-oxidotaraxerane-28-al (4), together with three known compounds 3β-hydroxy-11α,12α-oxidotaraxerane (5), 3β,28-dihydroxy-11α,12α-oxidotaraxerane (6), and 11α,12α-oxidotaraxerane-3-one (7), were isolated from the 70% EtOH extract of Saussurea graminea. Their structures were elucidated on the basis of extensive 1D and 2D NMR (COSY, HMQC, HMBC and NOESY) analyses. The isolated compounds were evaluated in vitro for cytotoxic properties against eight tumor cell lines (A-549, BGC-823, HCT15, HeLa, HepG2, MCF-7, SGC-7901 and SK-MEL-2).     

Cytotoxic triterpene glycosides from the sea cucumber Pseudocolochirus violaceus

A new triterpene glycoside (1) along with the known intercedenside B (2) was isolated from the sea cucumber Pseudocolochirus violaceus. Glycoside 1 was elucidated as 3-O-{6-O-sodiumsulfate-3-O-methyl-beta-D-glucopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta-D-xylopyranosyl(1-->2)]-beta-D-quinovopyranosyl-(1-->2)-4-O-sodiumsulfate-beta-D-xylopyranosyl}-16beta-acetoxy-holosta-7, 24-diene-3beta-ol on the basis of extensive spectral studies and chemical evidence. Both the glycosides exhibited significant cytotoxicity against cancer cell lines MKN-45 and HCT-116.     

Sesquiterpenoids from Carpesium divaricatum and their cytotoxic activity

In the course of searching for cytotoxic terpenoids from medicinal plants in China, two new eudesmane sesquiterpenoids, 5α-hydroxy-13-methoxy-7αH,11αH-eudesm-4(15)-en-12,8β-lactone (1) and 1β-hydroxy-7αH,11αH-eudesm-4(15)-en-12,8β-lactone (2), along with fourteen known sesquiterpenoids were isolated from the whole plant of Carpesium divaricatum. The structures of new compounds were determined using spectroscopic methods, including IR, HRESIMS, and 1D and 2D NMR spectroscopy. The cytotoxicity of selected sesquiterpene lactones against human oral epidermoid carcinoma (KB), human breast cancer (MCF-7) and human hepatoma (HepG-2) cells was also evaluated by MTT method.     

Cytotoxic alkoxylated xanthones from the resin of Garcinia hanburyi

Three new xanthones, garcinolic acid (1), 10α-ethoxy-9,10-dihydromorellic acid (2), and 10α-ethoxy-9,10-dihydrogambogenic acid (3), along with six known compounds were isolated from the resin of Garcinia hanburyi. These compounds were tested for their cytotoxicities against A549, HCT116, SK-BR-3 and HepG2, and showed high inhibitory effects on the cell lines.     

Prenylated phloroglucinol derivatives from Hypericum sampsonii

Six new acylphloroglucinol derivatives, sampsonols A-F (1–6), were isolated from the petroleum ether extract of the aerial parts of Hypericum sampsonii. The structures and relative configurations of sampsonols A-F were elucidated by extensive spectroscopic analyses. All these compounds were tested for their in vitro cytotoxic and anti-inflammatory activities. Sampsonols A and B (1 and 2) showed significant cytotoxicity against four human tumor cell lines with IC₅₀ values in the range of 13–28 μM, whereas sampsonols C and F (3 and 6) showed potent inhibitory activities against LPS-induced NO production in RAW 264.7 macrophages with IC₅₀ values of 27.3 and 29.3 μM, respectively.     

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).     

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.     

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.     

Cytotoxic dimeric indole alkaloids from Catharanthus roseus

Three new dimeric indole alkaloids (1-3), together with five known ones (4-8), were isolated from the whole plants of Catharanthus roseus. The structures and absolute configurations of new compounds were elucidated by means of NMR and CD analyses. All these compounds were evaluated for their in vitro cytotoxic activities against human breast cancer cell line MDA-MB-231.     

Anti-inflammatory,cyclooxygenase (COX)-2, COX-1 inhibitory and antioxidant effects of Dysophylla stellata Benth.

The n-hexane and ethyl acetate extracts of whole plants of Dysophylla stellata significantly inhibited edema when applied topically at doses of 0.5 and 1 mg/ear in TPA-induced ear edema assay in mice. Further, both the extracts were evaluated for COX-1 and COX-2 inhibitory activities and showed 85.42 and 57.38%; and 71.79 and 89.27% inhibition at 50 µg/ml, respectively. Chromones (1 and 2) present in these extracts could be responsible for their COX-1 and COX-2 inhibitory and anti-inflammatory activities. The ethyl acetate extract showed antioxidant activity in DPPH and ABTS radical scavenging assay where as n-hexane extract found to be inactive.     

Chemical constituents from Delphinium chrysotrichum and their biological activity

A new diterpene alkaloid named delphatisine C (1) has been isolated from aerial parts of Delphinium chrysotrichum along with three known norditerpenoid alkaloids delpheline (2), delbrunine (3), and delectinine (4). Their structures were characterized on the basis of their spectral data. All of them were determined by SRB assay for their cytotoxicity, and compound (1) showed significant cytotoxic activities (IC₅₀ = 2.36 μmol/L) against the A549 cell line.     

A new cytotoxic 1-azaanthraquinone from the stems of Goniothalamus laoticus

A new 1-azaanthraquinone, named laoticuzanone A (1), and a synthetically known 3-methyl-1H-1-azaanthracene-2,9,10-trione (2), together with four known compounds, Griffithazanone A (3), methyl sinapate (4), methyl p-coumarate (5), and p-hydroxyphenylethyl p-coumarate (6) were isolated from the stems of Goniothalamus laoticus. Their structures were established on the basis of spectroscopic data as well as comparisons with the previous literature data. Compound 1 showed the highest cytotoxicity against KB and HeLa cells with IC₅₀ values of 0.68 and 0.50 μg/ml, respectively.     

Chemical constituents of the Vietnamese liverwort Porella densifolia

From the ether extract of Porella densifolia, the first liverwort collected and chemically investigated in Vietnam, a kaurane diterpenoid, ent-kauren-15-one (1) and two sesquiterpene norpinguisone (2) and norpinguisone methyl ester (3) have been purified. Their structures were elucidated by spectroscopic analysis. In addition, an X-ray crystal structure of norpinguisone was obtained, allowing to determine its stereochemistry. Furthermore, the inhibitory activity of nitric oxide (NO) production in RAW 264.7 cells stimulated by lipopolysaccharide (LPS) of compounds 1–3 was examined with their IC₅₀ values of 69.4, 45.5 and 1.68 μM, 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.