Sesquiterpenes and α-pyrones from an endophytic fungus Xylaria curta YSJ-5.

Chemical investigation of the culture extract of an endophyte Xylaria curta YSJ-5 from Alpinia zerumbet (Pers.) Burtt. et Smith resulted in the isolation of eight previously undescribed compounds including five eremophilane sesquiterpenes xylarcurenes A-E, one norsesquiterpene xylarcurene F, and two α-pyrone derivatives xylarpyrones A-B together with eight known related derivatives. Their chemical structures were extensively established based on the 1D- and 2D-NMR spectroscopic analysis, modified Mosher's method, electronic circular dichroism calculations, single-crystal X-ray diffraction experiments, and the comparison with previous literature data. All these compounds were tested for in vitro cytotoxic, anti-inflammatory, α-glucosidase inhibitory, and antibacterial activities. As a result, 6-pentyl-4-methoxy-pyran-2-one was disclosed to display significant antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with minimal inhibitory concentration value of 6.3 µg/mL.

Chemical Constituents and Bioactivities of the Plant-Derived Fungus Aspergillus fumigatus.

A new bergamotane sesquiterpenoid, named xylariterpenoid H (1), along with fourteen known compounds (2-15), were isolated from the crude extract of Aspergillus fumigatus, an endophytic fungus isolated from Delphinium grandiflorum L. Their structures were elucidated mainly by extensive analyses of NMR and MS spectroscopic data. In addition, the screening results of antibacterial and cytotoxic activities of compounds 1-15 showed that compound 4 displayed antibacterial activities against Staphylococcus aureus and MRSA (methicillin-resistant S. aureus) with an MIC value of 3.12 µg/mL.

Rosemary: Unrevealing an old aromatic crop as a new source of promising functional food additive-A review.

Rosemary (Rosmarinus officinalis L.) is one of the most famous spice plants belonging to the Lamiaceae family as a remarkably beautiful horticultural plant and economically agricultural crop. The essential oil of rosemary has been enthusiastically welcome in the whole world for hundreds of years. Now, it is wildly prevailing as a promising functional food additive for human health. More importantly, due to its significant aroma, food, and nutritional value, rosemary also plays an essential role in the food/feed additive and food packaging industries. Modern industrial development and fundamental scientific research have extensively revealed its unique phytochemical constituents with biologically meaningful activities, which closely related to diverse human health functions. In this review, we provide a comprehensively systematic perspective on rosemary by summarizing the structures of various pharmacological and nutritional components, biologically functional activities and their molecular regulatory networks required in food developments, and the recent advances in their applications in the food industry. Finally, the temporary limitations and future research trends regarding the development of rosemary components are also discussed and prospected. Hence, the review covering the fundamental research advances and developing prospects of rosemary is a desirable demand to facilitate their better understanding, and it will also serve as a reference to provide many insights for the future promotion of the research and development of functional foods related to rosemary.

Isolation, identification, and antibacterial evaluation of endophytic fungi from Gannan navel orange.

Gannan navel orange is a famous brand in China but the isolation of its endophytic fungi was rarely reported. In this study, a total of 54 strains of endophytic fungi were successfully isolated from the pulp, peel, twig, and leaf of Gannan navel orange; they were successfully identified to belong to 17 species of 12 genera. All these strains were fermented using potato-dextrose agar (PDA) medium, and their secondary metabolites were then extracted with ethyl acetate (EtOAc). The antibacterial assays of Escherichia coli (E. coli), methicillin-resistant Staphylococcus aureus (MRSA), and Xanthomonas citri subsp. citri (Xcc) were also performed for the EtOAc extracts of these strains. As a result, the extracts of both Geotrichum sp. (gc-1-127-30) and Diaporthe biconispora (gc-1-128-79) demonstrated significant antibacterial activities against Xcc, and the MIC value for the extract of Colletotrichum gloeosporioides against MRSA was low to 62.5 µg/mL. Moreover, the chemical components of the extracts of Colletotrichum sp., Diaporthe biconispora, and Annulohypoxylon atroroseum were primarily investigated, and they successfully led to the isolation of 24 compounds involving a new botryane sesquiterpene. Among the isolated products, compound 2 showed significant inhibitory activities toward SA, MRSA, E. coli, and Xcc with MIC values of 12.5, 3.1, 125, and 12.5 µg/mL, respectively. This study revealed that the endophytic fungi of Gannan navel orange showed high potency to produce secondary metabolites with significant antibacterial effects.

Two new secondary metabolites isolated from the fungus Penicillium virgatum T49-A.

The extensively chemical investigation of the EtOAc extract of the soil fungus Penicillium virgatum T49-A has successfully led to the isolation of two undescribed secondary metabolites penivirtone A (1) and peniviramide B (2) together with six known compounds. Their chemical structures including the absolute configurations of the two new compounds were comprehensively established by extensive analyses of NMR and HRESIMS spectra as well as ECD powered by theoretical calculations. Moreover, the cytotoxic and antibacterial activities of compounds 1-2 were also evaluated, whereas the two novel compounds showed no notable cytotoxic and antibacterial activities.

Alkyl aromatic derivatives from the endophytic fungus Cytospora rhizophorae.

Two new alkylresorcinols named herein 5'-methoxy-integracins A-B (1-2), two new monomeric alkyl aromatic derivatives 3-(7-hydroxyheptyl)-5-methoxyphenol (5) and 7-(3,5-dihydroxyphenyl) heptyl acetate (6), along with four known compounds including integracins A-B (3-4), 2,4-dihydroxy-6-(8-hydroxyoctyl) benzene (7), and cytosporone B (8) were isolated from the endophytic fungus Cytospora rhizophorae A761. The structures of the four new compounds were elucidated by NMR, HRESIMS data, and electronic circular dichroism (ECD) calculations, whereas the compounds 1 and 2 were disclosed as a class of the natural rare-occurring dimeric alkylresorcinol derivatives. Moreover, the bioassays of the new compounds clarified that compound 1 was a potent inhibitor for the α-glucosidase, and compound 2 showed relatively good activity against the tumor cell lines. It is worth mentioning that the known compound integracin B (4) was first reported to display significant antibacterial activity against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA) with MIC values of 6.25 µg ml-1.

The chemical constituents of endophytic fungus Nigrospora chinensis of Gannan navel orange.

A new drimane sesquiterpene 11-methoxyl-danilol (1) was obtained from endophytic fungus Nigrospora chinensis of Gannan navel orange pulp. Its structure was established to possess a natural rarely-occurring tricyclic acetal fused ring system by means of spectroscopic data analyses. Meanwhile, five known compounds danilol (2), redoxcitrinin (3), euphorbol (4), ergosta-7,24(24')-dien-3ß-ol (5), and ergosta-4,6,8(14),22-tetraen-3-one (6) were also co-isolated in this fungus. The results of antibacterial and cytotoxic activity screenings showed that compound 5 displayed antibacterial activities against Staphylococcus aureus and MRSA (methicillin-resistant S. aureus) with MIC value of 50 µg/mL.

3,4-Dimethoxycinnamic Acid as a Novel Matrix for Enhanced In Situ Detection and Imaging of Low-Molecular-Weight Compounds in Biological Tissues by MALDI-MSI.

Low-molecular-weight (low-MW) compounds have many essential functions in biological processes, and the molecular imaging of as many low-MW compounds as possible is critical for understanding complex biological processes. Matrix-assisted laser desorption/ionization mass spectrometry imaging (MALDI-MSI) is an emerging molecular-imaging technology that enables determination of the spatial distributions and the relative abundances of diverse endogenous compounds in tissues. New matrices suitable for the imaging of low-MW compounds by MALDI-MSI are important for the technological advancement of tissue imaging. In this study, 3,4-dimethoxycinnamic acid (DMCA) was evaluated as a new matrix for enhanced low-MW compound detection by MALDI-MSI because of its strong ultraviolet absorption, low matrix-ion related interferences below m/ z 500, and high ionization efficiency for the analysis of low-MW compounds. DMCA was successfully used for improved in situ detection of low-molecular-weight metabolites ( m/ z < 500) and lipids in rat liver, rat brain, and germinating Chinese-yew seed tissue sections. The use of DMCA led to the successful in situ detection of 303, 200, and 248 low-MW compound ion signals from these three tissues, respectively. Both MALDI-MS/MS and LC-MS/MS were used to identify these ion signals, leading to the identification of 115 low-MW compounds from rat liver (including 53 lipids, 29 oligopeptides, and 33 metabolites), 130 low-MW compounds from rat brain (including 104 lipids, 5 oligopeptides, and 21 metabolites), and 111 low-MW compounds from germinating Chinese-yew seeds (including 77 lipids, 22 oligopeptides, 8 flavonoids, and 4 alkaloids). A larger number of low-MW compounds could be detected and imaged when DMCA was used as the MALDI matrix than with other commonly used MALDI matrices such as 2,5-dihydroxybenzoic acid, α-cyano-4-hydroxycinnamic acid, 2-mercaptobenzothiazole, graphene oxide, and silver nanoparticles. Our work provides a new and powerful matrix for enhanced MALDI-MS profiling of low-MW compounds in both animal and plant tissues.