Ophiobolins P–T,five new cytotoxic and antibacterial sesterterpenes from the endolichenic fungus Ulocladium sp.

Five ophiobolane sesterterpenes, ophiobolins P–T, and three known compounds, 6-epi-21,21-O-dihydroophiobolin G, 6-epi-ophiobolin G and 6-epi-ophiobolin K, were isolated from the acetone extract of the endolichenic fungus Ulocladium sp. by using OSMAC method. Their structures were elucidated on the basis of spectroscopic analysis. The absolute configuration of the 18,19-diol moieties in ophiobolin Q was assigned using the Frelek's method. The cytotoxic effects on KB and HepG2 cell lines, antibacterial activity against Bacillus subtilis, methicillin-resistant Staphylococcus aureus, and Bacille Calmette–Guerin were evaluated for all isolated compounds. Ophiobolin T and 6-epi-ophiobolin G exhibited the most potent cytotoxic activity against HepG2 with IC₅₀ of 0.24 and 0.37 μM, respectively. In antibacterial assay, ophiobolins P and T showed moderate antibacterial activity against B. subtilis and meticillin-resistant S. aureus. Ophiobolin T also displayed moderate antibacterial activity against the Bacille Calmette–Guerin strain.     

Sibiricasaponins A–E,five new triterpenoid saponins from the aerial parts of Polygala sibirica L.

Five new triterpenoid saponins, named as sibiricasaponins A–E (1–5), were isolated and identified from the aerial parts of Polygala sibirica L., together with nine known triterpenoid saponins (6–14). The chemical structures of the five new triterpenoid saponins (1–5) were elucidated as 3β,19α-dihydroxyurso-12-ene-23,28-dioic acid 3-O-β-d-glucuronopyranoside (1), pomolic acid 3-O-(3-O-sulfo)-α-l-arabinopyranoside (2), pomolic acid 3-O-(4-O-sulfo)-β-d-xylopyranoside (3), pomolic acid 3-O-(2-O-acetyl-3-O-sulfo)-α-l-arabinopyranoside (4), and 3-O-β-d-glucopyranosyl medicagenic acid 28-O-β-d-galactopyranosyl (1 → 4)-β-d-xylopyranosyl (1 → 4)-α-l-rhamnopyranosyl (1 → 2)-(4-O-acetyl)-[β-d-apiofuranosyl (1 → 3)]-β-d-fucopyranosyl ester (5), respectively, on the basis of spectroscopic data and physicochemical evidences. These isolated compounds (1–14) were evaluated for their anti-ischemic effects on oxygen/glucose deprivation (OGD) model in vitro, and only compound 7 showed a weak anti-ischemia effect, with EC₅₀ value of 46.7 μM.     

Coniochaetones E–I,new 4H-chromen-4-one derivatives from the Cordyceps-colonizing fungus Fimetariella sp.

Five new 4H-chromen-4-one derivatives coniochaetones E–I (1–5), along with the known compounds coniochaetones B (6) and A (7) have been isolated from solid cultures of the Cordyceps-colonizing fungus Fimetariella sp. Their structures were elucidated primarily by NMR spectroscopy and the absolute configurations of compounds 1–3 were assigned using the modified Mosher's method. Compound 4 showed weak cytotoxic activity against HeLa cells with IC₅₀ values of 72.8 μM. The co-isolated known compound 6 showed modest inhibitory effects against Aspergilus fumigates, Fusarium oxysporum and Fusarium nivale.     

Astershionones A–F,six new anti-HBV shionane-type triterpenes from Aster tataricus

Six new shionane-type triterpenes, astershionones A–F (1–6), were obtained from the roots and rhizomes of Aster tataricus. Their structures were elucidated on the basis of spectroscopic data, mainly NMR and MS data. The absolute configuration of 1 was determined by single crystal X-ray diffraction analysis and CD analysis. 3 showed inhibitory activity against HBsAg and HBeAg secretion with IC₅₀ values of 23.0 and 23.1 μM, and cytotoxicity against HepG 2.2.15 cells with a CC₅₀ value of 170.5 μM. 3 also exhibited inhibitory activity against HBV DNA replication with an IC₅₀ value of 22.4 μM.     

Fuscacarpans A–C,new pterocarpans from the stems of Erythrina fusca

Chemical investigation of the stems of Erythrina fusca Lour. led to the isolation of three new pterocarpans, named fuscacarpans A–C (1−3), together with fourteen known compounds, sandwicensin (4), erythribyssin A (5), erythrabissin I (6), demethylmedicarpin (7), eryvarin D (8), erypoegin I (9), hydroxycristacarpone (10), orientanol A (11), scandenone (12), genistein (13), liquiritigenin (14), isoliquiritigenin (15), vestitone (16) and 3,7,4′-trihydroxyflavone (17). Structures 1−3 were elucidated by spectroscopic and chemical methods. The isolates were evaluated for antibacterial, antiplasmodial and cytotoxic activities.     

Andirolides Q–V from the flower of andiroba (Carapa guianensis,Meliaceae)

Two new gedunins, an andirobin, two mexicanolides, and a phragmalin-type limonoid, named Andirolides Q (1), R (2), S (3), T (4), U (5), and V (6), were isolated from an oil of the flower of Carapa guianensis AUBLET (Meliaceae). Their structures have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Andirolide S (3) and Andirolide T (4) showed significant cytotoxic activity against the murine P388 leukemia cell line (IC₅₀ of 1.4 μM for 3; 1.8 μM for 4) and the human HL-60 leukemia cell line (IC₅₀ of 1.3 μM for 3 and 4).     

Three new secoiridoids,swermacrolactones A–C and anti-hepatitis B virus activity from Swertia macrosperma

Three new secoiridoids, swermacrolactones A–C (1–3), together with fourteen known compounds were isolated from Swertia macrosperma. Their structures were elucidated based on extensive spectroscopic analyses (IR, UV, MS, 1D and 2D NMR). By anti-HBV assay on the Hep G 2.2.15 cell line in vitro, the most active compound, luteolin (9), inhibited the secretion of hepatitis B virus surface antigen (HBsAg) and hepatitis B virus e antigen (HBeAg) with IC₅₀ values of 0.02 and 0.02 mM, respectively.     

Leiyemudanosides A–C,three new bidesmosidic triterpenoid saponins from the roots of Caulophyllum robustum

Three new oleanane bidesmosidic triterpenoid saponins, named leiyemudanosides A–C (1–3) were isolated from the roots of Caulophyllum robustum Maxim. Their structures were established by chemical and detailed spectroscopic analysis as 3-O-α-l-arabinopyranosyl-caulophyllogenin-28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (1), 3-O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl-caulophyllogenin-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (2), and 3-O-β-d-glucopyranosyl-(1 → 3)-α-l-arabinopyranosyl-echinocystic acid-28-O-α-l-rhamnopyranosyl-(1 → 4)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester (3), respectively.     

Lessons from long-term studies of harvest methods in southwestern ponderosa pine–Gambel oak forests on the Fort Valley Experimental Forest,Arizona, U.S.A.

The Fort Valley Experiment Station (now Fort Valley Experimental Forest) has contributed many long-term studies to forest research. This paper focuses on a “Methods of Cutting” study initiated in 1913 on the Coulter Ranch Unit of Fort Valley and how that long-term study yielded important ecological and management lessons. We quantified the historical and contemporary forest patterns at this ponderosa pine–Gambel oak site, which was harvested using three different harvesting systems in 1913 (seed tree, group selection, and light selection) and was partially excluded from livestock browsing in 1919. Using nine historically stem-mapped permanent plots for the following three stand structural scenarios: 1913 pre-harvest (modeled), post-harvest (actual), and 2003–2006 (actual) conditions, we examined the short- and long-term consequences of harvest and livestock grazing land-use and stand dynamics. We assessed changes in spatial pattern under each harvesting system and in each structural scenario, and lastly, we examined spatial and temporal tree recruitment patterns as observed in the contemporary (2003–2006) conditions. The seed tree harvests effectively converted the spatial patterns from aggregated to random and left few trees, while the group selection and light selection had varying effects, but consistently exaggerated the spatial patchiness of the stand. By 2003–2006, all plots were aggregated at all scales and were one large patch of predominately small trees. Sites that were harvested, but excluded from livestock browsing had 40% more trees in 2003–2006. Contemporary recruitment patterns were significantly aggregated under all harvesting systems, but were most strongly aggregated if the site received a group selection or light selection cut. For group and light selection, pine seedlings initially established in stump patches created by harvesting and then proceeded to fill-in the remaining area, with recruitment rarely found under the residual pine or oak trees. Long-term data sets, such as these established by the Fort Valley Experimental Forest in 1913, are essential for quantifying the impact of historical land-use practices on contemporary forest composition and structure. Ignoring land-use legacies may lead to the misinterpretation of stand dynamics and development, and therefore should be explicitly quantified and incorporated into future management and restoration activities.