Gymnopilus spectabilis, a hallucinogenic mushroom belonging to the family Cortinariaceae, is found growing in dense clusters on stumps and logs of hardwoods and conifers. It contains the hallucinogenic alkaloid psilocybin and its strongly bitter taste makes it undesirable as an edible. In an effort to identify chemical constituents of Korean native wild mushrooms, 4,6-decadiyne-1,3,8-triol (1), ergosta-4,6,8(14), 22-tetraen-3-one (2), bisnoryangonin (3), and hispidin (4) were isolated from the methanolic extract of the fruiting bodies of G. spectabilis. Their structures were assigned on the basis of various spectroscopic studies. Compounds 3 and 4 displayed significant scavenging activity against the ABTS radical cation, DPPH radical, and superoxide radical anion, while 1 and 2 exhibited no antioxidant activity.
Agaricales ; Benzothiazoles ; Coniferophyta ; Fruit ; Humans ; Methanol ; Pyrones ; Sulfonic Acids ; Superoxides

Objective: The present study was undertaken to evaluate the subchronic oral toxicity of sodium dehydroacetate (DHA-Na) and to determine the point of departure (POD), which is a critical factor in the establishment of an acceptable dietary intake. Methods: DHA-Na was administered once daily by gavage to Sprague-Dawley rats at dose levels of 0.0, 31.0, 62.0, and 124.0 mg/kg BW per day for 90 days, followed by a recovery period of 4 weeks in the control and 124.0 mg/kg BW per day groups. The outcome parameters were mortality, clinical observations, body weights, food consumption, hematology and clinical biochemistry, endocrine hormone levels, and ophthalmic, urinary, and histopathologic indicators. The benchmark dose (BMD) approach was applied to estimate the POD. Results: Significant decreases were found in the 62.0 and 124.0 mg/kg BW groups in terms of the body weight and food utilization rate, whereas a significant increase was found in the thyroid stimulating hormone levels of the 124.0 mg/kg BW group. Importantly, the 95% lower confidence limit on the BMD of 51.7 mg/kg BW was modeled for a reduction in body weight. Conclusion The repeated-dose study indicated the slight systemic toxicity of DHA-Na at certain levels (62.0 and 124.0 mg/kg BW) after a 90-day oral exposure.
Animals ; Body Weight ; Organ Size ; Pyrones ; Rats ; Rats, Sprague-Dawley

Melanin is produced in melanocytes and stored in melanosomes. In spite of its beneficial sun-protective effect, abnormal accumulation of melanin results in esthetic problems. Hydroquinone, competing with tyrosine, is a major ingredient in topical pharmacological agents. However, frequent adverse reactions are amongst its major limitation. To solve this problem, several alternatives such as arbutin, kojic acid, aloesin, and 4-n-butyl resorcinol have been developed. Herein, we classify hypopigmenting agents according to their mechanism of action; a) regulation of enzyme, which is subdivided into three categories, i) regulation of transcription and maturation of tyrosinase, ii) inhibition of tyrosinase activity, and iii) post-transcriptional control of tyrosinase; b) inhibition of melanosome transfer, and c) additional mechanisms such as regulation of the melanocyte environment and antioxidant agents.
Arbutin ; Chromones ; Glucosides ; Hydroquinones ; Hypopigmentation ; Melanins ; Melanocytes ; Melanosomes ; Monophenol Monooxygenase ; Pyrones ; Resorcinols ; Tyrosine

OBJECTIVETo study the chemical constituents of the herb of Ludwigia octovalvis.

METHODChemical constituents were isolated by the repeated silica gel column chromatography, and their structures were elucidated by the physicochemical properties and spectral analysis.

RESULTThirteen compounds were obtained and determined as follows: beta-sitosterol (1), oleanolic acid (2), 2alpha-hydroxy ursolic acid (3), tormentic acid (4), daucosterol (5), maltol (6), luteolin (7), quercetin (8), apigenin (9), methyl brevifolincarboxylate (10), gallic acid (11), 3, 4, 8, 9, 10-pentahydroxydibenzo[b, d]pyran-6-one (12), and ellagic acid (13).

CONCLUSIONCompounds 3, 4, 6-13 were isolated from the plant for the first time. And compounds 3, 4, 6, 10, 12 were obtained from the genus for the first time.

Molecular Structure ; Onagraceae ; chemistry ; Plants, Medicinal ; chemistry ; Pyrones ; chemistry ; isolation & purification ; Triterpenes ; chemistry ; isolation & purification

OBJECTIVETo develop an HPLC method for simultaneous determination of swertiamarin, gentiopicroside, sweroside, mangiferin, erythrocentaurin, and to detect these five constituents in eight Qingyedans derived from Swertia mileensis, S. cincta, S. patens, S. punicea, S. delavayi, S. nervosa, S. macrosperma and S. yunnanensis.

METHODThe separation was carried out on a Thermo BDS Hypersil C18 (4. 6 mm x 250 mm, 5 microm) column eluted with mobile phase of water containing 0. 1% phosphoric acid and methanol (B) in gradient program (0-10 min, 18%-20% B; 10-30 min, 20%-35% B; 30-35 min, 35%-60% B). The column temperature was 32 degrees C , and the detection wavelength was set at 250, 260, 225 nm. The flow rate was 0. 7 mL . min-1 from 0 to 30 min, and be increased to 1. 0 mL . min-1 in 35 min.

RESULTThe five compounds were well separated. The linear response ranges of swertiamarin, gentiopicroside, sweroside, mangiferin, erythrocentaurin were 0. 072-13. 39, 0. 1204. 518, 0. 060-5. 050, 0. 025-1. 518, and 0. 031-0. 210 microg, respectively. The mean recoveries of five compounds were 97.03% -102. 7% (RSD 1. 8% -6.2% ). There are swertiamarin, gentiopicroside and sweroside in most samples, and mangiferin in half samples. But erythrocentaurin was only detected in a few samples. The contents of five compounds were different in different samples. The contents of swertiamarin in S. mileensis, S. patens, S. yunnanensis and S. delavayi are up to 34. 47-118.05 mg . g-1, the contents of gentiopicroside are up to 25. 91 mg . g-1 in S. cincta. In S. puncea all contents of swertiamarin, gentiopicroside, sweroside and mangiferin are higher, especially the content of sweroside. There are Xiao-Qingyedans and Da-Qingyedans called in markets, and they can be identified by the contents of swertiamarin, gentiopicroside and sweroside. S. punicea can be identified by the content of sweroside, and the ratio gentiopicroside/total content can be used for identification of S. cincta from other seven Qingyedan species.

CONCLUSIONThe method was certified to be accurate and reliable and can be used for identification and quality evaluation of traditional Chinese medicine Qingyedan derived from Swertia species.

Chromatography, High Pressure Liquid ; methods ; Iridoid Glucosides ; analysis ; Pyrones ; analysis ; Swertia ; chemistry

During the search for neuraminidase inhibitors from medicinal fungi, we found that the culture broth of Phellinus linteus exhibited potent inhibitory activity. Solvent partition, Sephadex LH-20 column chromatography, and high-performance liquid chromatography (HPLC) were performed for purification of two active substances from the culture broth. According to 1H NMR measurements and comparison of HPLC retention times with those of authentic compounds, their chemical structures were identified as hispidin and hypholomine B. Compounds (hispidin) 1 and 2 (hypholomine B) inhibited neuraminidase, with IC50 values of 13.1 and 0.03 microM, respectively.
Chromatography ; Chromatography, High Pressure Liquid ; Chromatography, Liquid ; Dextrans ; Fungi ; Inhibitory Concentration 50 ; Neuraminidase ; Pyrones ; Retention (Psychology)

OBJECTIVE: To investigate the effects of rasfonin, a fungal secondary metabolite, on the proliferation and migration of osteosarcoma 143B cells. METHODS: 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, inner salt (MTS) assay was performed to examine 143B cell viability following treatment of rasfonin. Using dimethyl sulfoxide (DMSO) group as control, cell viability was detected when 143B cells were treated with rasfonin (3 μmol/L and 6 μmol/L) for 12 or 24 hours. The effect of rasfonin on colony forming ability was detected by clone formation assay. 143B cells treated with DMSO or rasfonin (3 μmol/L) for one week, and the number of clones formed in the two groups was counted. Wound healing and transwell assay were employed to analyze cell invasion and migration upon rasfonin challenge. The DMSO group was used as control while rasfonin (3 μmol/L) was used for 24 hours. The wound healing rate and the number of invasive cells were compared between the two groups. The intracellular autophagosomes were monitored by transmission electron microscopy when 143B cells were treated with DMSO or rasfonin (3 μmol/L) for 4 hours. The expression of p62, microtubule-associated protein 1 light chain 3 fusion protein (LC3) and poly (ADP-ribose) polymerase-1 (PARP-1) in response to rasfonin were detected by immunoblotting assay. RESULTS: Rasfonin reduced the viability of 143B cells in a dose-dependent manner (12 h: F=31.36, P<0.01; 24 h: F=67.07, P<0.01). Rasfonin (3 μmol/L) completely inhibited the clonal formation of 143B cells (P<0.01). The wound healing result revealed that rasfonin significantly decreased migratory ability of 143B cells (33.91%±0.83% vs. 65.11%±0.94%, P<0.01), whereas its treatment significantly reduced the number of 143B cells penetrating through Matrigel-containing basement membrane (21.33±1.45 vs. 49.33±2.40, P<0.01). Compared with the control group, rasfonin markedly increased the number of autophagic vacuoles. The immunoblotting results revealed that rasfonin increased LC3-II accumulation and decreased p62 levels. Choloroquine (CQ), an often used autophagic inhibitor, further accumulated rasfonin-induced LC3-II. In addition, rasfonin appeared to cause the cleavage of PARP-1. CONCLUSION Rasfonin induced autophagy and activated caspase-dependent apoptosis in 143B cells concurring with suppressing the proliferation and migration of the cells; these results provide an experimental basis for rasfonin as a potential therapeutic agent for osteosarcoma.
Apoptosis ; Bone Neoplasms ; Cell Line, Tumor ; Cell Proliferation ; Fatty Acids, Unsaturated ; Humans ; Osteosarcoma ; Pyrones

OBJECTIVETo isolate and identify the chemical constituents of 95% alcohol extract from Swertia delavayi.

METHODThe compounds were isolated and purified by column chromatogrphy and their structures were identified by the physicochemical properties and spectral analyses.

RESULTSeven compounds were isolated and identified as oleanolic acid (1), gentiopcroside (2), swertiamarin (3), daucosterol (4), swertiadecoraxanthone-II (5), isovitexin (6), isoorientin (7).

CONCLUSIONCompounds 2-7 were isolated from S. delavayi for the first time. While the compound 6 was firstly reported from the genus Swertia.

Apigenin ; chemistry ; Glucosides ; chemistry ; Iridoid Glucosides ; Iridoids ; chemistry ; Luteolin ; chemistry ; Magnetic Resonance Spectroscopy ; Oleanolic Acid ; chemistry ; Pyrones ; chemistry ; Sitosterols ; chemistry ; Spectrometry, Mass, Electrospray Ionization ; Swertia ; chemistry

OBJECTIVETo develop an HPLC method for the quantification of six active components in three species (Swertia davidi, S. nervosa and S. mussotii) .

METHODThe determination was performed on a Hypersil BDS colunm (4. 6 mm x 200 mm, 5 microm). Acetonitrile and 0.5% phosphoric acid solution were used as the mobile phases with a gradient elution. The flow rate was 1.0 mL x min(-1). The UV detection wavelength was at 240, 274, 325 and 334 nm. The column oven temperature was at 25 degrees C.

RESULTSix components were separated commendably in 60 minutes. The calibration curves of swertiamarin, gentiopicroside, norswertianolin, swertianolin, demethylbellidifolin and bellidifolin were in good linearity over the range of 0.520-20.8, 0.202-8.06, 0.107-4.28, 0.097-3.86, 0.094-3.77, 0.101-4.02 microg, respectively (r = 0.999 9). The average recoveries were 98.7%, 98.1%, 98.3%, 98.8%, 98.1% and 98.6%, respectively, and the RSD were less than 3.0% (n = 6).

CONCLUSIONThe method is accurate,simple and reproducible, and can be used to control the quality of Swertia.

Chromatography, High Pressure Liquid ; instrumentation ; methods ; Drugs, Chinese Herbal ; analysis ; Glucosides ; analysis ; Iridoid Glucosides ; Iridoids ; analysis ; Pyrones ; analysis ; Swertia ; chemistry ; Xanthones ; analysis

AIMTo study the chemical composition of Opuntia dillenii Haw.

METHODSMany kinds of chromatography methods were used to separate the chemical constituents. Their structures were determined by NMR and MS spectral analysis.

RESULTSA new compound, together with five known compounds, were isolated from the 80% ethanolic extract of the stems.

CONCLUSIONThe new compound was identified as 4-ethoxyl-6-hydroxymethyl-alpha-pyrone. Compounds 1, 3, 4 and 5 were obtained for the first time from the genus of Opuntia, and they were: 3-O-methyl isorhamnein, 1-heptanecanol, vanillic acid, isorhamnetin-3-O-beta-D-rutinoside. Ruin was isolated from this plant for the first time.

Molecular Structure ; Opuntia ; chemistry ; Plant Stems ; chemistry ; Plants, Medicinal ; chemistry ; Pyrones ; chemistry ; isolation & purification ; Rutin ; chemistry ; isolation & purification ; Vanillic Acid ; chemistry ; isolation & purification