This study identified six novel azaphilones, isochromophilones G-L (1-6), and three novel biosynthetically related congeners (7-9) from Diaporthe sp. SCSIO 41011. The structures and absolute configurations were elucidated through comprehensive spectroscopic analyses combined with experimental and calculated electronic circular dichroism (ECD) spectra. Significantly, three highly oxygenated azaphilones contain an acetyl group at the terminal chain (4) or linear conjugated polyenoid moieties (5 and 6), which occur infrequently in the azaphilone family. Additionally, several compounds demonstrated inhibition of lipopolysaccharide (LPS)-induced nuclear factor kappa-B (NF-κB) activation in RAW 264.7 macrophages at 20 μmol·L^-1. The novel compound (1) effectively inhibited receptor activator of NF-κB ligand (RANKL)-induced osteoclast differentiation without exhibiting cytotoxicity in bone marrow and RAW 264.7 macrophages, indicating its potential as a promising lead compound for osteolytic disease treatment. This research presents the first documented evidence of azaphilone derivatives as inhibitors of RANKL-induced osteoclastogenesis.
Animals ; Mice ; RANK Ligand/genetics* ; RAW 264.7 Cells ; Osteoclasts/metabolism* ; Benzopyrans/isolation & purification* ; Osteogenesis/drug effects* ; Macrophages/metabolism* ; Molecular Structure ; Pigments, Biological/isolation & purification* ; Ascomycota/chemistry* ; NF-kappa B/genetics* ; Cell Differentiation/drug effects*

Ten flavonoids were isolated from the 95% ethanol extract of the seeds of Alpinia galanga Willd. with a combination of various chromatographic techniques, including silica gel, Sephadex LH-20 and preparative HPLC. On the basis of spectroscopic data analysis, they were elucidated as (2R, 3S)-pinobaksin-3-cinnamate (1), (2R, 3R)-pinobaksin-3-cinnamate (2), pinocembrin (3), pinobaksin (4), 3-O-acetylpinobaksin (5), galangin (6), galangin-3-methylether (7), kumatakenin (8), 3-methylkaempferol (9) and (2R, 3R)-3, 5-dihydroxy-7-methoxyflavanone (10). Among them, compound 1 is a new compound, compounds 2, 5 and 10 were isolated from the genus Alpinia for the first time, and others were isolated from this plant for the first time.
Alpinia ; chemistry ; Benzopyrans ; chemistry ; isolation & purification ; Cinnamates ; chemistry ; isolation & purification ; Flavanones ; chemistry ; isolation & purification ; Flavonoids ; chemistry ; isolation & purification ; Kaempferols ; chemistry ; isolation & purification ; Molecular Structure ; Plants, Medicinal ; chemistry ; Seeds ; chemistry

A novel lactone, tripterospermumcins E (1), along with four known compounds, sweroside (2), loganic acid (3), 8-epi-kingiside (4) and bergenin (5), were isolated from the aerial parts of Tripterospermum chinense. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and chemical methods. Compound 1 is rare beta-lactone with a glucoside.
Benzopyrans ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Gentianaceae ; chemistry ; Iridoid Glucosides ; chemistry ; isolation & purification ; Iridoids ; chemistry ; isolation & purification ; Lactones ; chemistry ; isolation & purification ; Molecular Structure ; Plant Components, Aerial ; chemistry ; Plants, Medicinal ; chemistry

To study the chemical constituents of Saxifraga stolonifera (L.) Meeb., chromatographic techniques were applied to separate and purify the compounds, and their structures were confirmed on the basis of physicochemical properties and spectral data. Ten compounds were isolated and identified as 5-O-methylnorbergenin (1), 3, 4-dihydroxyallylbenzene-4-O-beta-D-glucopyranoside (2), (7R, 8S)-4, 9, 9'-trihydroxyl-3-methoxyl-7, 8-dihydrobenzofuran-1'-propylneolignan-3'-O-beta-D-glucopyranoside (3), quercetin-3-O-beta-D-xylopyranosyl-(1 --> 2)-beta-D-galactopyranoside (4), kaempferol-3-O-alpha-L-rhamnopyranoside (5), (3S, 5R, 6R, 7E, 9R)-3, 5, 6, 9-tetrahydroxy-7-megastigmane (6), benzyl-O-alpha-L-rhamnopyranosyl-(1 --> 6)-beta-D-glucopyranoside (7), p-hydroxyacetophenone (8), pyrogallic acid (9) and p-hydroxyphenol (10). Compound 1 is a new compound. Compounds 2-10 were isolated from this plant for the first time.
Acetophenones ; chemistry ; isolation & purification ; Benzofurans ; chemistry ; isolation & purification ; Benzopyrans ; chemistry ; isolation & purification ; Glycosides ; chemistry ; isolation & purification ; Molecular Structure ; Plants, Medicinal ; chemistry ; Pyrogallol ; chemistry ; isolation & purification ; Saxifragaceae ; chemistry

OBJECTIVETo study the chemical constituents of Adenanthera pavanina.

METHODVarious chromatographic techniques were used to isolate and purify the constituents. The structures were elucidated by chemical evidence and spectroscopic methods.

RESULTNine compounds were isolated from the 95% ethanol extract of the stems and leaves of A. pavanina and their structures were elucidated as aridanin (1), 3-[(2-Acetamido-2-deoxy-beta-D-glucopyranosyl)oxy]-16alpha-hydroxyolean-12-en-28-oic acid (2), (+)-pinitol (3), sucrose (4), (-)-butin (5), apigenin (6), isoliquiritigenin 4-methyl ether (7), oleanolic acid (8), daucosterol (9).

CONCLUSIONCompounds 1-7 were isolated from this plant for the first time.

Apigenin ; chemistry ; isolation & purification ; Benzopyrans ; chemistry ; isolation & purification ; Fabaceae ; chemistry ; Oleanolic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Plant Leaves ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry

OBJECTIVETo study the chemical constituents of the roots of Euphorbia soongarica (Xinjiang origin).

METHODCompounds were isolated and purified by repeated normal column chromatography, preparative thin layer chromatography and Sephadex LH - 20 chromatography. The chemical structures were elucidated by NMR and MS spectra.

RESULTSTen chemical constituents were isolated from the n-BuOH fraction and identified as ellagic acid (1) , 3, 3'-di-O-methylellagic acid (2) , 3, 3'-di-O-methylellagic acid-4'-O-alpha-D-arabinfuranoside (3), 3, 3'-di-O-methylellagic acid-4'-O-beta-D-xylopyranoside (4), 3, 3'-di-O-methylellagic acid-4-O-beta-D-glucopyranoside (5), 3, 3', 4'-tri-O-methylellagic acid (6), 3-O-methylellagic acid-4'-O-beta-D-xylopyranoside (7), 3, 3', 4-tri-O-methylellagic acid-4'-O-beta-D-glucopyranoside (8), brevifolin (9) and ethyl brevifolin carboxylate (10).

CONCLUSIONAll of above compounds were obtained from this plant for the first time.

Benzopyrans ; chemistry ; isolation & purification ; Ellagic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Euphorbia ; chemistry ; Plant Roots ; chemistry ; Plants, Medicinal ; chemistry

AIMTo establish the method of HPLC-fingerprint analysis for the quality control of Dalbergia odorifera and identify its main constituents by HPLC-MS.

METHODSThe 37 hatches of samples were analyzed on a Phenomenex Luna C18 column with a gradient of acetonitrile and 0.3% aqueous acetic acid at a flow rate of 1.0 mL x min(-1) and detected at 275 nm. Furthermore, the typical samples were detected by HPLC-DAD-MS under negative ion mode.

RESULTS37 batches of D. odorifera samples were classified into three types based on the results of similarity analysis. According to the comparison of the tR, MS data and UV maximum absorbance (gamma(max)) values with the standards, 10, 7 and 2 phenolic components were identified in three types of D. odorifera extracts, separately.

CONCLUSIONThe method is repeatable and reliable, and it is capable of effectively controlling the quality of D. odorifera.

Benzopyrans ; chemistry ; isolation & purification ; China ; Chromatography, High Pressure Liquid ; methods ; Chromones ; chemistry ; isolation & purification ; Dalbergia ; chemistry ; Flavanones ; isolation & purification ; Isoflavones ; Molecular Structure ; Plants, Medicinal ; chemistry ; Quality Control ; Reproducibility of Results ; Spectrometry, Mass, Electrospray Ionization

OBJECTIVETo investigate the flavonoid constituents of Ipomoea batatas.

METHODThe leaf was extracted with EtOH and partitioned with CHCl3, EtOAc and n-BuOH respectively. The chemical components of EtOAc fraction were isolated by silica gel and sephadex LH-20 column chromatography. The chemical structures were elucidated on the basis of physic-chemical properties and spectral data.

RESULTFive compounds were isolated and identified as: tiliroside (I), astragalin (II), rhamnocitrin (III), rhamnetin (IV) and kaempferol (V).

CONCLUSIONAll of these five compounds were obtained from this plant for the first time.

Benzopyrans ; chemistry ; isolation & purification ; Flavonoids ; Ipomoea batatas ; chemistry ; Kaempferols ; chemistry ; isolation & purification ; Plant Leaves ; chemistry ; Plants, Medicinal ; chemistry ; Quercetin ; analogs & derivatives ; chemistry ; isolation & purification

OBJECTIVETo study the chemical constituents in rhizome of Astilbe chinensis.

METHODThe constituents were isolated with column chromatographies and the structures were identified by physicochemical properties and spectral analysis (UV, IR, MS, 1H-NMR, 13C-NMR and 2D-NMR).

RESULTThe structures were identified as bergenin (1), 11-O-galloylbergenin (2), 4-O-galloylbergenin (3), catechin (4), respectively.

CONCLUSIONCompound 3 was isolated from Astilbe for the first time.

Benzopyrans ; chemistry ; isolation & purification ; Catechin ; chemistry ; isolation & purification ; Gallic Acid ; analogs & derivatives ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Rhizome ; chemistry ; Saxifragaceae ; chemistry

AIMTo isolate polyphenols from grape seeds and to evaluate their antioxidant effects.

METHODSPure compounds were isolated by using Diaion HP20, Toyopearl HW40 chromatography repeatedly, as well as semi-preparative RP-HPLC, from ethyl acetate extract of grape seeds. IR, MS, NMR, CD, X-Ray crystal diffraction spectral analysis were used to identify the structures. The antioxidant effects of different type of structures were screened by reducing power and DPPH (alpha,alpha-diphenyl-beta-picrylhydrazyl) free radical scavenging tests. Then, SCGE (single cell gel-electrophoresis) technique was used to investigate the effects of these potent antioxidant phytochemicals on cellular DNA oxidative damage with mice spleen cells, damage was induced by H2O2.

RESULTSEleven compounds were obtained including 3 novel structures, viniferones A, B and C. Proanthocyanidin B4, catecin, epicatechin and gallic acid showed strong antioxidant power, and at lower concentration (10 micromol x L(-1), 25 micromol x L(-1)), they can prevent cellular DNA damage, while 150 micromol x L(-1) catechin induced damage by itself.

CONCLUSIONViniferones A, B and C were reported for the first time. That polyphenols investigated were shown to be good cellular DNA oxidative damage-preventing phytochemicals at lower concentration, could be used to explain the nutrient effect of grape seed polyphenols at certain degree. At the same time, higher concentration of polyphenols can induce oxidative damage, suggesting that dose is one factor to determine the nutrient effects.

Animals ; Antioxidants ; isolation & purification ; pharmacology ; Benzopyrans ; chemistry ; isolation & purification ; pharmacology ; Cell Separation ; DNA Damage ; drug effects ; Dose-Response Relationship, Drug ; Flavonoids ; isolation & purification ; pharmacology ; Gallic Acid ; pharmacology ; Mice ; Molecular Conformation ; Molecular Structure ; Phenols ; isolation & purification ; pharmacology ; Polyphenols ; Seeds ; chemistry ; Spleen ; cytology ; Vitis ; chemistry