Antifungal New Oxepine-Containing Alkaloids and Xanthones from the Deep-Sea-Derived Fungus Aspergillus versicolor SCSIO 05879.

Phytopathogenic fungi remain a continuous and huge threat in the agricultural fields. The agrochemical industry has made great development of the use of microbial natural products, which has been regarded as an effective strategy against phytopathogenic fungi. Antifungal bioassay-directed fractionation was used to isolate two new oxepine-containing alkaloids (1 and 2), two new 4-aryl-quinolin-2-one alkaloids (3 and 4), and four new prenylated xanthones (5-8) from the deep-sea-derived fungus Aspergillus versicolor SCSIO 05879. Extensive NMR spectroscopic analysis, quantum mechanical calculations, and X-ray single-crystal diffraction were used to elucidate their structures, including their absolute configurations. Versicoloids A and B, versicone A, and cottoquinazoline A showed antifungal activities against three phytopathogenic fungi. The antifungal activities of these bioactive compounds strongly depend on the fungal species. Especially versicoloids A and B showed strong fungicidal effect (MIC of 1.6 µg/mL) against Colletotrichum acutatum, compared with that of the positive control cycloheximide (MIC of 6.4 µg/mL). The results of antifungal experiments indicated that versicoloids A and B may be regarded as candidate agents of antifungal agrochemicals.

HPLC isolation of antioxidant constituents from Xanthoparmelia spp.

A chromatographic method is described for the purification and characterization of secondary lichen substances with biological activity. A simple reversed-phase high-performance liquid chromatography method with gradient elution has been developed that allows the determination and isolation of salazinic, usnic and stictic acids from lichen samples in a single run and the quantification of every acid in the tested extracts. The antioxidant activity of both the isolated compounds and the respective lichen belonging to Xanthoparmelia genus was determined by the Oxygen Radical Absorbance Capacity (ORAC) assay; their effect as free radical scavengers, effect on cell survival by the 3(4,5-dimethyltiazol-2-yl)-2,5-diphenyltetrazolium reduction assay and 2',7'-dichlorofluorescin diacetate method were tested on U373 MG human astrocytome cell line. Both lichens extracts and all isolated compounds protected U373 MG cells from hydrogen peroxide-induced damage, suggesting that they could act as antioxidant agents in those neurodegenerative disorders associated with oxidative damage, such as Alzheimer's disease and Parkinson's disease.

The use of LC/MS, GC/MS, and LC/NMR hyphenated techniques to identify a drug degradation product in pharmaceutical development.

Understanding drug degradation in the formulated product is critical in pharmaceutical development as it has significant impacts on drug efficacy, safety profile and storage conditions. As a result, identification of degradation compounds has taken an important role in the drug development process. In this study, various hyphenated analytical techniques, such as liquid chromatography mass spectrometry (LC/MS), gas chromatography mass spectrometry (GC/MS), and liquid chromatography nuclear magnetic resonance with a solid phase extraction interface (LC/SPE/NMR), have been applied to the identification of a drug degradation product which grew over time in the stability study of the drug product. The target unknown is less polar and more unsaturated than the drug substance based upon reverse phase HPLC relative retention time and UV spectra. It is not ionizable by electrospray ionization (ESI) or atmospheric pressure chemical ionization (APCI) in either a positive or a negative mode. The unknown was isolated by an HPLC fraction collector and enriched by solid phase extraction. GC/MS with chemical ionization (CI) was employed to determine the molecular weight of this compound. Its fragmentation pattern was determined by CI-MS/MS using an ion trap mass spectrometer. The isolated material was also analyzed by LC/SPE/NMR, from which the structure of this compound was further characterized. The study utilizes a combination of various hyphenated analytical techniques to obtain complimentary information for structure elucidation of the unknown. The combination approach is critical for unambiguous impurity structure elucidation in drug degradation studies of pharmaceutical drug products.

Separación de la tríada de zoapatanol y montanol obtenida de Montanoa tomentosa s.s.p. tomentosa por cromatografía de líquidos de alta exactitud en fase inversa / Separation of \"triplet\" zoapatanol and montanol obtained from Montanoa tomentosa s.s.p. tomentosa by revers-plase high perfomance liquid chromatography

Se ha aislado a partir de hojas y flores de Montanoa tomentosa s.s.p. tomentosa un material homogéneo biológicamente activo conocido como "tríada"; en este artículo se describe la separación de los tres componentes por cromatografía líquida de alta presión. Este método es más sencillo, rápido y barato que cualquier otro publicado hasta la fecha. Este procedimiento permite la separación preparativa de zoapatanol y montanol. También se comprueba que la "tríada" está formada por zoapatanol, montanol y otro compuesto estrechamente relacionado con el último

The zoapatle I--a traditional remedy from Mexico emerges to modern times.

A review of publications from 1529 to 1982 related to the zoapatle was made. Historical, biological, ethnobotanical, agricultural, clinical and chemical studies were noted; most of the early publications were written by Mexican scientists, in Spanish. More recent ones appear in the form of patents dealing with the isolation, characterization and total synthesis of some of its constituents. From this review, ideas emerged that might contribute to the understanding and rational use of this plant, or its chemical constituents, as a new, safe, reliable, inexpensive and - hopefully soon - a widely used interceptive agent.

PIP: Zoapatle, the common name for Montanoa tomentosa, is a well-known plant in Mexico that has been used since the 16th century to induce labor or to increase both the tone and frequency of uterine contractions during labor. Since 1866, the plant has been recognized as a potential menses inducer. Pharmacological observations of zoapatle were made in Mexico in 1945 and focused on the administration of zoapatle aqueous crude extract (ZACE). Animal studies demonstrated increased uterine contractility. 9 compounds have been isolated from zoapatle. Much of the recent work with the material has been detailed in several patent applications. In 2 of 4 clinical studies on the use of ZACE, an increase in uterine contractility and cervical dilation among pregnant women was noted, and in another study, a cramping sensation was reported by nonpregnant women. The need to control for ecological variables which effect the plants seasonally was mentioned by 1 researcher who found working with the crude extract difficult and unpredictable. The lack of toxic effects was demonstrated in a study using animal models. Different effects were noted in a study which used zoapatanol obtained by total synthesis, including the lack of uterotonic response in rabbit tissue which warrants further investigation. The plant or its derivatives are potentially useful as interceptive agents but further research under controlled conditions is needed.