Seven novel acylphloroglucinol-sesquiterpenoid adducts, designated as dryatraols J-P (1-7), were isolated from the rhizomes of Dryopteris atrata (Wall. ex Kunze) Ching. The structures, including absolute configurations, were elucidated using comprehensive spectroscopic data, calculated ¹³C Nuclear Magnetic Resonance-Diastereotopic Probability Assignment Plus (¹³C NMR-DP4+) probability analysis, and ECD calculations. These structures represent a rare subclass of carbon skeleton of acylphloroglucinol-sesquiterpenoid adducts with a furan ring connecting the acylphloroglucinol and sesquiterpenoid moieties. Notably, compounds 1-6 are the first reported examples of acylphloroglucinol-sesquiterpenoid adducts with dimeric acylphloroglucinol incorporated into the aristolane- or rulepidanol-type sesquiterpene, while compound 7 features a hydroxylated monomeric acylphloroglucinol motif. A preliminary evaluation of their antiviral activities revealed that compounds 1-6 exhibited more potent activities against respiratory syncytial virus (RSV) with IC₅₀ values ranging from 0.75 to 3.12 μmol·L^-1 compared to the positive control (ribavirin).
Antiviral Agents/isolation & purification* ; Phloroglucinol/isolation & purification* ; Sesquiterpenes/isolation & purification* ; Molecular Structure ; Dryopteris/chemistry* ; Respiratory Syncytial Viruses/drug effects* ; Humans ; Rhizome/chemistry* ; Drugs, Chinese Herbal/pharmacology*

The aim of this study was to look for the chemical constituents from the rhizomes of Dryopteris sublaeta. The fresh plant was extracted twice with boiling water, the extract was concentrated to small volume under reduced pressure at 50 degrees C. The concentrated material was partitioned with ether, ethyl acetate and n-butanol. The fraction of ethyl acetate was repeatedly chromatographied over silica gel and Sephadex LH-20 columns. Structures of pure compounds were established on the basis of their physiochemical and spectral data. Nine compounds were obtained and identified as sublaetentin A (1), sublaetentin B (2), sublaetentin C (3), sublaetentin D (4), matteuorienate A (5), matteuorienate C (6), arbutin (7), 3-methoxy-4-hydroxyphenyl-1-O-beta-D-glucopyranoside (8) and 3,4-dimethoxyphenyl-1-O-beta-D-glucopyranoside (9). Compounds 1 - 4 are new compounds, the others were isolated from this plant for the first time.
Arbutin ; chemistry ; isolation & purification ; Dryopteris ; chemistry ; Flavanones ; chemistry ; isolation & purification ; Flavonoids ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Glycosides ; chemistry ; Molecular Structure ; Plant Extracts ; chemistry ; Plants, Medicinal ; chemistry ; Rhizome ; chemistry

OBJECTIVETo investigate the behavioral changes and the levels of monoamine neurotransmitters in the anterior cortex in the olfactory bulb damage rats after being treated with Guanyu capsules (GYC).

METHODOpen-field test and step-down passive avoidance test were used to observe the behavior in model rats. HPLC-ECD was used to analyze the influences of GYC on the levels of monoamine neurotransmitters.

RESULTIn the model rats, there was a characteristic hyperactivity in the Open-field and learning deficits in step-down passive avoidance (P < 0.01). The contents of 5-HT reduced, and the rate of DOPAC/DA increased significantly (P < 0.01). GYC 1.2, 0.6 g x kg(-1) could correct behavioral changes increase the contents of 5-HT, and decrease DOPAC/DA level (P < 0.01).

CONCLUSIONGYC can correct behavioral changes in rats model of olfactory bulb damage, and regulating 5-HT and DA metabolism in cortex is one of the antidepressive mechanisms of GYC.

3,4-Dihydroxyphenylacetic Acid ; metabolism ; Animals ; Behavior, Animal ; drug effects ; Biogenic Monoamines ; metabolism ; Cerebral Cortex ; metabolism ; Curcuma ; chemistry ; Depression ; etiology ; metabolism ; Dopamine ; metabolism ; Drugs, Chinese Herbal ; isolation & purification ; pharmacology ; Dryopteris ; chemistry ; Male ; Olfactory Bulb ; pathology ; Plants, Medicinal ; chemistry ; Random Allocation ; Rats ; Rats, Sprague-Dawley ; Serotonin ; metabolism

AIMTo study the chemical constituents of Dryopteris sublaeta Ching et Hsu.

METHODSFresh plant of Dryopteris sublaeta Ching et Hsu was extracted twice with boiling water, the extract was concentrated to small volume under reduced pressure at 50 degrees C. The concentrated material was partitioned with ether, ethyl acetate, and n-butanol. The fraction of ether extract was chromatographed over silica gel column. The compounds were identified on the basis of their physiochemical and spectral data.

RESULTSFour compounds were obtained and identified as 2 (S)-5, 7, 3'-trihydroxy-6, 8-dimethyl-5'-methoxyflavanone (1), matteucinol (2), desmethoxymatteucinol (3) and 5, 7, 2'-trihydroxy-6, 8-dimethylflavanone (4).

CONCLUSIONCompound 1 is a new one, the others were isolated from Dryopteris for the first time.

Chromones ; chemistry ; isolation & purification ; Dryopteris ; chemistry ; Flavanones ; chemistry ; isolation & purification ; Molecular Conformation ; Molecular Structure ; Plants, Medicinal ; chemistry

AIMTo study the chemical constituents of Dryopteris sublaeta Ching et Hsu.

METHODSFresh plant of Dryopteris sublaeta ching et hsu was extracted twice with boiling water, concentrated to small volume under reduced pressure at 50 degrees C. The concentrated material was partitioned with ether, ethyl acetate, and n-butanol. The fraction of ethyl acetate extract was chromatographed over macroporous adsorption resin (Diaion HP-20) eluted with a mixture of H2O and MeOH in increasing MeOH content. Their fractions from resin were repeatedly chromatographed over Toyopearl HW-40, Sephadex LH-20 and silica gel column chromatography. The compounds were identified on the basis of their physiochemical and spectral data.

RESULTSFour compounds were obtained and identified as 3,5-dihydroxy-stilbene-3-O-neohesperidoside (1), 3,5-dihydroxy-stilbene-3-O-beta-D-glucoside (2), polydotin peceid (3) and 3,5,4'-trihydroxy-bibenzyl-3-O-beta-D-glucoside (4).

CONCLUSIONCompound 1 is a new compound, the others were isolated from Dryopteris for the first time.

Dryopteris ; chemistry ; Glycosides ; chemistry ; isolation & purification ; Molecular Structure ; Plants, Medicinal ; chemistry ; Stilbenes ; chemistry ; isolation & purification