Molecular networking-guided isolation strategy of a new C-glycosyl flavone rotamer from Stellaria alsine and evaluation of anti-inflammatory and antioxidant activities.

Introduction: Stellaria alsine has traditionally been used as both a famine relief food and an alternative medicine in East Asia. Modern pharmacological studies have revealed that S. alsine has various biological effects such as anticancer, anti-hepatoma, anti-inflammatory, and antioxidative effects.

Molecular Networking-Guided Isolation of a Phenolic Constituent from Seed and Its Antioxidant and Anti-Inflammatory Activities.

(Maesil) is used in health foods and alternative medicine in Korea. In the present study, the anti-inflammatory and antioxidant effects of phenolics from seed extracts were examined. First, the biological activities of various extracts were evaluated, and the profiles of their chemical compounds were investigated by Global Natural Products Social (GNPS)-molecular networking.

Iridoid derivatives from Vitex rotundifolia L. f. with their anti-inflammatory activity.

Three undescribed iridoid glucosides and nine known compounds were isolated from Vitex rotundifolia L. f. Their structural elucidation was performed based on their spectroscopic data or acid hydrolysis followed by HPLC analysis and comparison of their NMR data with those reported in the literature.

Potential function of loliolide as a novel blocker of epithelial-mesenchymal transition in colorectal and breast cancer cells.

Loliolide (LL), a naturally occurring monoterpenoid lactone isolated from Vicia tenuifolia Roth, can exhibit numerous pharmacological effects such as those related to anti-Parkinson, anti-oxidant, anti-cholinesterase, and anti-depressant. Epithelial-mesenchymal transition (EMT) plays a pivotal role in regulating tumor metastasis. CXCR4 and CXCR7 are G-protein-coupled receptors (GPRs), which can be stimulated by CXCL12.

Anti-inflammatory activity of caffeic acid derivatives from Ilex rotunda.

Ilex rotunda Thunb. has been used in traditional medicine for treating rheumatoid arthritis, relieving pain and indigestion. In the present study, we isolated three new caffeic acid benzyl ester (CABE) analogs (1-3) along with eight known compounds (4-11) from the extract of I.

Tolypocladamides A-G: Cytotoxic Peptaibols from .

Seven new peptaibols named tolypocladamides A-G have been isolated from an extract of the fungus , which inhibits the interaction between Raf and oncogenic Ras in a cell-based high-throughput screening assay. Each peptaibol contains 11 amino acid residues, an octanoyl or decanoyl fatty acid chain at the N-terminus, and a leucinol moiety at the C-terminus. The peptaibol sequences were elucidated on the basis of 2D NMR and mass spectral fragmentation analyses.

Analysis of Antioxidant Phytochemicals and Anti-Inflammatory Effect from L.f.

An extraction method using 80% EtOH was selected and applied to obtain the total extracts from leaves, flowers, fruits, twigs, and roots of L.f. based on the antioxidant activity-guided experiments.

Roseabol A, a New Peptaibol from the Fungus .

A new 11 amino acid linear peptide named roseabol A () and the known compound 13-oxo--9,10-epoxy-11()-octadecenoic acid () were isolated from the fungus . Combined NMR and MS analysis revealed that roseabol A () contained amino acid residues characteristic of the peptaibol family of peptides such as isovaline, -aminoisobutyric acid, hydroxyproline, leucinol, and an -terminal isovaleric acid moiety. The amino acid sequence was established by a combination of NMR studies and tandem MS fragmentation analyses, and the absolute configurations of the constituent amino acids of were determined by the advanced Marfey's method.

Identification of natural product modulators of Merkel cell carcinoma cell growth and survival.

Merkel cell carcinoma (MCC) is a rare, but aggressive skin cancer the incidence of which has increased significantly in recent years. The majority of MCCs have incorporated Merkel cell polyomavirus (VP-MCC) while the remainder are virus-negative (VN-MCC). Although a variety of therapeutic options have shown promise in treating MCC, there remains a need for additional therapeutics as well as probes for better understanding MCC.

Neopetrothiazide: An Intriguing Pentacyclic Thiazide Alkaloid from the Sponge sp.

Neopetrothiazide (), a pentacyclic isoquinoline quinone, was isolated from a sp. sponge. The structure elucidation was facilitated by utilizing long-range heteronuclear single quantum multiple bond correlation (LR-HSQMBC) and heteronuclear multiple bond correlation (HMBC) nuclear magnetic resonance (NMR) pulse sequences optimized to detect four- and five-bond H-C heteronuclear correlations.

Denigrins and Dactylpyrroles, Arylpyrrole Alkaloids from a sp. Marine Sponge.

Seven new arylpyrrole alkaloids (-), along with four known compounds, were isolated from an extract of a sp. nov. marine sponge, and their structures were elucidated by interpretation of NMR and MS spectroscopic data.

Suberitamides A-C, Aryl Alkaloids from a sp. Marine Sponge that Inhibit Cbl-b Ubiquitin Ligase Activity.

Three new aryl alkaloids named suberitamides A-C (-), were isolated from an extract of the marine sponge sp. collected along the coast of North Carolina. Their planar structures were established by extensive nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis.

Cytotoxic Scalarane Sesterterpenes from the Sponge .

Twelve new sesterterpenes along with eight known sesterterpenes were isolated from the marine sponge collected off the coast of Chuuk Island, the Federated State of Micronesia. Based upon a combination of spectroscopic and computational analyses, these compounds were determined to be eight glycine-bearing scalaranes (-), a 3-keto scalarane (), two oxidized-furan-bearing scalaranes ( and ), and a salmahyrtisane (). Several of these compounds exhibited weak antiproliferation against diverse cancer cell lines as well as moderate anti-angiogenesis activities.

Swinhopeptolides A and B: Cyclic Depsipeptides from the Sponge That Inhibit Ras/Raf Interaction.

Two new cyclic depsipeptides named swinhopeptolides A () and B () have been isolated from the marine sponge cf. , collected from Papua New Guinea. They each contain 11 diverse amino acid residues and 13-carbon polyketide moieties attached at the -terminus.

Elucidation of Spirodactylone, a Polycyclic Alkaloid from the Sponge Dactylia sp., and Nonenzymatic Generation from the Co-metabolite Denigrin B.

Spirodactylone (1), a hexacyclic indolizidone alkaloid possessing a novel spiro ring system, was isolated from the marine sponge Dactylia sp. The structure was elucidated by extensive spectroscopic methods including application of the LR-HSQMBC NMR pulse sequence. Oxidative cyclization of denigrin B (2), an aryl-substituted 2-oxo-pyrroline derivative that was also isolated from the sponge extract, provided material identical to spirodactylone (1).

Cyclopeptides from the Sponge Stylissa flabelliformis.

Three new cyclopeptides, phakellistatins 20-22 (1-3), as well as 10 known cyclopeptides of the same structural class were isolated from the tropical sponge Stylissa flabelliformis. By a combination of chemical and spectroscopic methods, the structures of the new compounds were determined to be an epimeric mixture of cycloheptapeptides (1) and two epimeric cyclodecapeptides (2 and 3) related to the phakellistatins. The cyclopeptides were evaluated for in vitro cytotoxicity against a variety of cancer cell lines, and compounds 2 and 3 exhibited significant activity.

Inhibitory Effects of Flavonoids from on Sortase A and Sortase A-Mediated Aggregation of .

Seven flavonoids were isolated from via repetitive column chromatography and high-performance liquid chromatography. The chemical structures of these compounds were identified by spectroscopic analysis and comparison with values reported in the literature. Among the flavonoids tested, 7-hydroxy-6-methoxyflavanone () and formononetin () exhibited strong inhibitory activity against SrtA, with IC values of 46.

Manzamine Alkaloids from an Acanthostrongylophora sp. Sponge.

Five new manzamine alkaloids (1-5) and new salt forms of two known manzamines (6 and 7), along with seven known compounds (8-14) of the same structural class, were isolated from an Indonesian Acanthostrongylophora sp. sponge. On the basis of the results of combined spectroscopic analyses, the structure of kepulauamine A (1) was determined to possess an unprecedented pyrrolizine moiety, while others were functional group variants of known manzamines.

Spatholobus suberectus Dunn. constituents inhibit sortase A and Staphylococcus aureus cell clumping to fibrinogen.

Sortases are a family of Gram-positive transpeptidases responsible for anchoring surface protein virulence factors to the peptidoglycan cell wall layer. In Staphylococcus aureus (S. aureus), deletion of sortase isoform results in a significant reduction in virulence and infection potential.

Flavonoid Glycosides Inhibit Sortase A and Sortase A-Mediated Aggregation of Streptococcus mutans, an Oral Bacterium Responsible for Human Dental Caries.

Three flavonoids were isolated from dried flowers of Sophora japonica using repetitive column chromatography and high-performance liquid chromatography. The flavonoids were identified as rutin (1), quercetin-3'-O-methyl-3-O-α-L-rhamnopyranosyl(1 → 6)-β-D-glucopyranoside (2), and quercetin (3) on the basis of spectroscopic analysis and comparison of values reported in the literature. These compounds inhibited the action of sortase A (SrtA) from Streptococcus mutans, a primary etiologic agent of human dental caries.

Callyazepin and (3R)-Methylazacyclodecane, Nitrogenous Macrocycles from a Callyspongia sp. Sponge.

Callyazepin (1) and (3R)-methylazacyclodecane (2), nitrogenous macrocycles, were isolated from a tropical Callyspongia sp. sponge. The combined spectroscopic analyses revealed that the structure of 1 is a bicyclic azepane ammonium salt of a novel structural class derived from mixed biogenetic origins.

Meroterpenoids from a Tropical Dysidea sp. Sponge.

Six new meroterpenoids (1-6), along with arenarol (7), a known rearranged drimane sesquiterpene hydroquinone, were isolated from a Dysidea sp. sponge collected from the Federated States of Micronesia. On the basis of the results of combined spectroscopic analysis, compound 1 was determined to be the cyclic ether derivative of 7, whereas 2 and 3 were assigned as the corresponding sesquiterpene quinones containing taurine-derived substituents.

Amino Acid-Derived Metabolites from the Ascidian Aplidium sp.

Four new iodobenzene-containing dipeptides (1-4), a related bromotryptophan-containing dipeptide (5), and an iodophenethylamine (6) were isolated from the ascidian Aplidium sp. collected off the coast of Chuja-do, Korea. The structures of these novel compounds, designated as apliamides A-E (1-5) and apliamine A (6) were determined via combined spectroscopic analyses.

Additional sesterterpenes and a nortriterpene saponin from the sponge Clathria gombawuiensis.

Three new terpene metabolites (1-3) were isolated from the marine sponge Clathria gombawuiensis collected from Korean waters. On the basis of the results of combined spectroscopic analyses, the structures of phorone B (1) and ansellone C (2) were determined to be the sesterterpenes of the phorone and ansellone classes, respectively, whereas the saponin gombaside A (3) was a nortriterpene sodium O-sulfonato-glucuronide of the rare 4,4,14-trimethylpregnane class. The absolute configuration of the glucuronate of 3 was assigned by an application of the phenylglycine methyl ester (PGME) method.