MIBiG 4.0: advancing biosynthetic gene cluster curation through global collaboration.

Specialized or secondary metabolites are small molecules of biological origin, often showing potent biological activities with applications in agriculture, engineering and medicine. Usually, the biosynthesis of these natural products is governed by sets of co-regulated and physically clustered genes known as biosynthetic gene clusters (BGCs). To share information about BGCs in a standardized and machine-readable way, the Minimum Information about a Biosynthetic Gene cluster (MIBiG) data standard and repository was initiated in 2015.

Napyradiomycin B4 Suppresses RANKL-Induced Osteoclastogenesis and Prevents Alveolar Bone Destruction in Experimental Periodontitis.

The unique structure and beneficial biological properties of marine natural products have drawn interest in drug development. Here, we examined the therapeutic potential of napyradiomycin B4 isolated from marine-derived species for osteoclast-related skeletal diseases. Bone marrow-derived macrophages were treated with napyradiomycin B4 in an osteoclast-inducing medium, and osteoclast formation, osteoclast-specific gene expression, and nuclear factor of activated T-cells cytoplasmic 1 (NFATc1) localization were evaluated using tartrate-resistant acid phosphatase staining, real-time PCR, and immunostaining, respectively.

Antimetastatic activity of seongsanamide B in γ-irradiated human lung cancer.

Lung cancer, which has a high incidence and mortality rates, often metastasizes and exhibits resistance to radiation therapy. Seongsanamide B has conformational features that suggest it has therapeutic potential; however, its antitumor activity has not yet been reported. We evaluated the possibility of seongsanamide B as a radiation therapy efficiency enhancer to suppress γ-irradiation-induced metastasis in non-small cell lung cancer.

Diterpene and biflavone derivatives from Thuja koraiensis and their cytotoxicities against A549 cells.

During the screening of the cytotoxicity of rare Korean endemic plants, the extract of Thuja koraiensis Nakai displayed potent cytotoxicity against the adenocarcinomic human alveolar basal epithelial A549 cell line. Through a series of separations via column chromatography, three undescribed abietanes, an undescribed labdane along with a labdane, and a biflavonoid were purified from methylene chloride (CHCl) fraction possessing a potent cytotoxic effect. Extensive 1D and 2D NMR spectroscopic data analyses, in combination with quantum chemical calculations were conducted to establish the planar and absolute configurations of thujakoraienes A-C.

Ulleungdolin, a Polyketide-Peptide Hybrid Bearing a 2,4-Di--methyl-β-d-antiarose from sp. 13F051 Co-cultured with 15S071.

A new secondary metabolite, ulleungdolin (), was isolated from the co-culture of an actinomycete, sp. 13F051, and a fungus, 15S071. Based on the NMR, UV, and MS data, it was deduced that the planar structure of comprised an isoindolinone (IsoID) with an octanoic acid, a tripeptide, and a sugar.

Marine Depsipeptide Nobilamide I Inhibits Cancer Cell Motility and Tumorigenicity via Suppressing Epithelial-Mesenchymal Transition and MMP2/9 Expression.

A cyclic depsipeptide, nobilamide I (), along with the known peptide A-3302-B/TL-119 (), was isolated from the saline cultivation of the marine-derived bacterium sp., strain CNQ-490. The planar structure of was elucidated by interpretation of 1D and 2D NMR and MS spectroscopic data.

Luquilloamides, Cytotoxic Lipopeptides from a Puerto Rican Collection of the Filamentous Marine Cyanobacterium sp.

Luquilloamides A-G (-) were isolated from a small environmental collection of a marine cyanobacterium found growing on eelgrass ( sp.) near Luquillo, Puerto Rico. Structure elucidation of the luquilloamides was accomplished via detailed NMR and MS analyses, and absolute configurations were determined using a combination of advanced Mosher's method, -based configuration analysis, semisynthetic fragment analysis derived from ozonolysis, methylation, Baeyer-Villiger oxidation, Mosher's esterification, specific rotations, and ECD data.

18:0 Lyso PC Derived by Bioactivity-Based Molecular Networking from Lentil Mutant Lines and Its Effects on High-Fat Diet-Induced Obese Mice.

Lentil (; Fabaceae), one of the major pulse crops in the world, is an important source of proteins, prebiotics, lipids, and essential minerals as well as functional components such as flavonoids, polyphenols, and phenolic acids. To improve crop nutritional and medicinal traits, hybridization and mutation are widely used in plant breeding research. In this study, mutant lentil populations were generated by γ-irradiation for the development of new cultivars by inducing genetic diversity.

Inhibition of A549 Lung Cancer Cell Migration and Invasion by -Caprolactin C via the Suppression of Transforming Growth Factor-β-Induced Epithelial-Mesenchymal Transition.

The epithelial-mesenchymal transition (EMT) of cancer cells is a crucial process in cancer cell metastasis. An sp. MC085 extract was found to inhibit A549 human lung cancer cell invasion, and caprolactin C (), a new natural product, α-amino-ε-caprolactam linked to 3-methyl butanoic acid, was purified through bioactivity-guided isolation of the extract.

Acremonamide, a Cyclic Pentadepsipeptide with Wound-Healing Properties Isolated from a Marine-Derived Fungus of the Genus .

Acremonamide () was isolated from a marine-derived fungus belonging to the genus . The chemical structure of was established using MS, UV, and NMR spectroscopic data analyses. Acremonamide () was found to contain -Me-Phe, -Me-Ala, Val, Phe, and 2-hydroxyisovaleric acid.

Azaphilones from an Endophytic sp. Prevent Neuronal Cell Death via Inhibition of MAPKs and Reduction of Bax/Bcl-2 Ratio.

Fourteen azaphilone-type polyketides (-), including nine new ones (- and -), were isolated from cultures of -associated sp. JVF17, and their structures were determined by spectroscopic analysis together with computational methods and chemical reactions. Neuroprotective effects of the isolated compounds were evaluated against glutamate-induced neurotoxicity.

In Vitro Metabolism Study of Seongsanamide A in Human Liver Microsomes Using Non-Targeted Metabolomics and Feature-Based Molecular Networking.

Seongsanamide A is a bicyclic peptide with an isodityrosine residue discovered in KCTC 12796BP which exhibits anti-allergic activity in vitro and in vivo without significant cytotoxicity. The purpose of this study was to elucidate the in vitro metabolic pathway and potential for drug interactions of seongsanamide A in human liver microsomes using non-targeted metabolomics and feature-based molecular networking (FBMN) techniques. We identified four metabolites, and their structures were elucidated by interpretation of high-resolution tandem mass spectra.

Anticancer Activity of 2--caffeoyl Alphitolic Acid Extracted from the Lichen, 2017-KL-10.

Colorectal cancer is one of the life-threatening ailments causing high mortality and morbidity worldwide. Despite the innovation in medical genetics, the prognosis for metastatic colorectal cancer in patients remains unsatisfactory. Recently, lichens have attracted the attention of researchers in the search for targets to fight against cancer.

Estrogenic Effects of Extracts and Isolated Compounds from Belowground and Aerial Parts of .

Menopause, caused by decreases in estrogen production, results in symptoms such as facial flushing, vaginal atrophy, and osteoporosis. Although hormone replacement therapy is utilized to treat menopausal symptoms, it is associated with a risk of breast cancer development. We aimed to evaluate the estrogenic activities of (SA) and its compounds and identify potential candidates for the treatment of estrogen reduction without the risk of breast cancer.

Antioxidant, Pancreatic Lipase Inhibitory, and Tyrosinase Inhibitory Activities of Extracts of the Invasive Plant (Cord-Grass).

Since 2016, the invasive halophyte has been colonizing mudflats along the western coast of South Korea. In order to minimize costs on expansion management and waste-treatment of collected biomass, the potential application of the collected biomass of was investigated. Ethanolic extracts and subfractions thereof (hexanes, methylene chloride, ethyl acetate, 1-butanol, and water-soluble) of the aerial and belowground parts of showed free radical-scavenging [2,2-diphenyl-1-picrylhydrazyl (DPPH), and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)], tyrosinase inhibitory, and pancreatic lipase inhibitory activities.

Identification and evaluation of a napyradiomycin as a potent Nrf2 activator: Anti-oxidative and anti-inflammatory activities.

Natural products with antioxidant and anti-inflammatory properties are important sources of therapeutic agents. The nuclear factor E2-related factor 2 (Nrf2)/antioxidant response element (ARE) pathway is a well-known defense system against oxidative stress. In this study, a panel of extracts of plants, fungi, and bacteria were screened for Nrf2 activation in a cell-based assay and a crude extract of cultured marine Streptomyces sp.

Androsamide, a Cyclic Tetrapeptide from a Marine sp., Suppresses Motility of Colorectal Cancer Cells.

A cyclic tetrapeptide, androsamide (), was isolated from a marine actinomycete of the genus , strain CNT-189. The planar structure of was assigned by the interpretation of 1D and 2D NMR spectroscopic data. The absolute configurations of constituent amino acids of were determined by application of the Marfey's and advanced Marfey's methods.

Highly oxygenated angucycline from Streptomyces sp. KCB15JA014.

LC/MS-based chemical screening of culture extract led to a new highly oxygenated angucycline derivative, grecocycline D (1), from Streptomyces sp. KCB15JA014, isolated from a soil sample of Oedolgae in Jeju Island, Korea. The planar structure was determined on the basis of spectroscopic analysis, including 1D and 2D NMR techniques as well as HRESIMS and comparison with data from the literature.

A stilbene dimer and flavonoids from the aerial parts of Chromolaena odorata with proprotein convertase subtilisin/kexin type 9 expression inhibitory activity.

Investigation of components of the chloroform-soluble and ethyl acetate-soluble extracts of the aerial parts of Chromolaena odorata L. selected by PCSK9 mRNA expression monitoring assay in HepG2 cells led to the isolation of a new stilbene dimer, (+)-8b-epi-ampelopsin A (1), and 30 known compounds (2-31). The structures of the isolates were established by interpretation of NMR spectroscopic data and the stereochemistry of the new stilbene (1) was proposed based on ECD and NMR calculations.

Isolation of Unstable Isomers of Lucilactaene and Evaluation of Anti-Inflammatory Activity of Secondary Metabolites Produced by the Endophytic Fungus sp. QF001 from the Roots of .

The filamentous fungal pathogen sp. causes several crop diseases. Some sp.

Collismycin C reduces HMGB1-mediated septic responses and improves survival rate in septic mice.

We examined the effects of a 2,2'-bipyridine containing natural product, collismycin C on high mobility group box 1 (HMGB1, septic mediator)-mediated septic responses and survival rate in a mouse sepsis model. Collismycin C inhibited the HMGB1 release and downregulated HMGB1-mediated inflammatory responses in human endothelial cells. Collismycin C also inhibited HMGB1-induced hyperpermeability and leukocyte migration in mice.

Mycousfurans A and B, Antibacterial Usnic Acid Congeners from the Fungus sp., Isolated from a Marine Sediment.

Mycousfurans ( and ), two new usnic acid congeners, along with (-)-mycousnine (), (-)-placodiolic acid (), and (+)-usnic acid (), were isolated using high-performance liquid chromatography-ultraviolet (HPLC-UV)-guided fractionation of extracts of sp. isolated from a marine sediment. The planar structures of and were elucidated using 1D and 2D NMR spectra.

Seongsanamides A-D: Antiallergic Bicyclic Peptides from Bacillus safensis KCTC 12796BP.

Six seongsanamides were isolated from the culture broth of Bacillus safensis KCTC 12796BP, and their structures were elucidated by spectroscopic data analysis combined with Marfey's method, electronic circular dichroism calculations, and biosynthetic gene cluster analysis. Compounds 1-4 were bicyclic peptides with isodityrosine residues; 5 and 6 were monocyclic peptides. Only the bicyclic seongsanamides inhibited degranulation and LTC/PGD generation in IgE/Ag-stimulated bone marrow-derived mast cells.

Biosynthesis of 2-amino-3-hydroxycyclopent-2-enone moiety of bafilomycin in Kitasatospora cheerisanensis KCTC2395.

Bafilomycins produced by Kitasatospora cheerisanensis KCTC- 2395 belong to the 16-membered macrolactone family plecomacrolide antibiotics. Bafilomycin B contains 2-amino- 3-hydroxycyclopent-2-enone (CN), a five membered ring, which gets condensed via an amide linkage to bafilomycin polyketide. To study the biosynthetic pathway of CN during bafilomycin biosynthesis in K.