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Xie Z.-L.,Sun Yat Sen University | Li H.-J.,Sun Yat Sen University | Wang L.-Y.,Guangdong Pharmaceutical University | Liang W.-L.,Sun Yat Sen University | And 4 more authors.
Natural Product Communications | Year: 2013

Trichodermaerin (1), a novel diterpenoid lactone, together with the known compound, harziandione (2) were isolated from the culture broth of the fungus Trichoderma erinaceum associated with the sea star Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. 1 was the Baeyer-Villiger monooxygenase catalyzed oxidation product of 2. Compound 2 did not show cytotoxic activities against various cancer cell lines.


Liu W.,Sun Yat Sen University | Liu W.,Guangdong Pharmaceutical University | Li H.-J.,Sun Yat Sen University | Xu M.-Y.,Sun Yat Sen University | And 7 more authors.
Organic Letters | Year: 2015

Pseudellones A and B (1 and 2), a pair of irregularly bridged epimonothiodiketopiperazine diastereomers constructed from unusual 3-indolylglycine and alanine residues, and an alkaloid pseudellone C (3) possessing a unique skeleton were isolated from the marine-derived fungus Pseudallescheria ellipsoidea F42-3. Their structures were determined by spectroscopic data, ECD calculation, and X-ray single crystal diffraction. The biogenetic pathways of 1-3 were proposed, and 1H-indole-3-carboxylic acid (4), a plausible biosynthetic intermediate, was coisolated. © 2015 American Chemical Society.


Lan W.-J.,Sun Yat Sen University | Lan W.-J.,Guangdong Technology Research Center for Advanced Chinese Medicine | Liu W.,Sun Yat Sen University | Liu W.,Guangdong Pharmaceutical University | And 9 more authors.
Marine Drugs | Year: 2014

Two novel isobenzofuranone derivatives, pseudaboydins A ( 1) and B ( 2), along with five known compounds, including ( R)-2-(2-hydroxypropan-2-yl)-2,3- dihydro-5-hydroxybenzofuran (3), (R)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-5- methoxybenzofuran (4), 3,3′-dihydroxy-5,5′-dimethyldiphenyl ether (5), 3-(3-methoxy-5-methylphenoxy)-5-methylphenol (6) and (-)-regiolone (7), were isolated from the culture broth of the marine fungus, Pseudallescheria boydii, associated with the starfish, Acanthaster planci. Their structures were elucidated primarily based on NMR and MS data. The absolute configurations of 1-4 were determined by CD spectroscopy and single-crystal X-ray diffraction studies. The cytotoxic and antibacterial activities of 1-4 were evaluated. Pseudaboydin A (1) showed moderate cytotoxic activity against human nasopharyngeal carcinoma cell line HONE1, human nasopharyngeal carcinoma cell line SUNE1 and human glandular lung cancer cell line GLC82 with IC50 values of 37.1, 46.5 and 87.2 μM, respectively. © 2014 by the authors; licensee MDPI.


Liang Z.,Sun Yat Sen University | Liang Z.,Guangdong Technology Research Center for Advanced Chinese Medicine | Xie Z.,Sun Yat Sen University | Xie Z.,Guangdong Technology Research Center for Advanced Chinese Medicine | And 4 more authors.
Journal of Separation Science | Year: 2014

A consecutive preparation method for the isolation and purification of paclitaxel from the Taxus Chinensis cell culture was developed in this study. The process involved alkaline Al2O3 chromatography, fractional precipitation, and high-speed countercurrent chromatography. The original cell culture materials were first extracted with methanol using ultrasound-assisted extraction, and then the extract (the content of paclitaxel is 1.5%) was separated by alkaline Al2O3 column chromatography. Subsequently, fractional precipitation was used to obtain paclitaxel. In particular, response surface methodology was used to optimize the factors of fractional precipitation (methanol concentration, material-to-solvent ratio, and precipitating time were optimized as 48.14%, 8.85 mg/mL, and 48.71 h, respectively) and the yield of fractional precipitation product was 30.64 ± 0.60 mg (the content of paclitaxel is 89.3%, 27.37 ± 0.54 mg) from a 100 mg fraction by Al2O3 column separation (the content of paclitaxel is 32.4%). Then, the product was used for further isolation by high-speed countercurrent chromatography. About 1.00 g paclitaxel (200 ± 2 mg in each loading) with a purity up to 99.61% was isolated from 1.25 g of fractional precipitation product with a solvent system of n-hexane/ethyl acetate/methanol/water (1.2:1.8:1.5:1.5, v/v/v/v) in one run of five consecutive sample loadings without exchanging a new solvent system. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Leung D.,Sun Yat Sen University | Yang D.,Sun Yat Sen University | Yang D.,Guangdong Technology Research Center for Advanced Chinese Medicine | Li Z.,Sun Yat Sen University | And 4 more authors.
Industrial and Engineering Chemistry Research | Year: 2012

The advancement of biodiesel production emphasizes the finding of new, low-cost, and plentiful raw materials. Insects, as one of the most plentiful biological resources worldwide, could be potential candidates for biodiesel production. In this study, Zophobas morio (Coleoptera: Tenebrionidae) was evaluated as an insect feedstock, attempting to prove the feasibility of producing qualified biodiesel. The oil content in dried Z. morio larvae was found to be 33.80 wt %. Biodiesel from Z. morio larva oil was prepared by acid esterification followed by alkaline transesterification. The parameters of the reaction were optimized at 1.25 wt % potassium hydroxide catalyst, a 5:1 methanol to oil ratio, a reaction temperature of 50 °C, and a reaction time of 45 min. Under these conditions, the maximum fatty acid methyl ester yield was 92.35 wt %. The biodiesel obtained was verified to be in compliance with the ASTM D6751 standard. This study supports the use of Z. morio larva oil as a viable and valuable raw feedstock for biodiesel production and indicates the potential use of insects as feedstock for applications in energy production. © 2011 American Chemical Society.


Xie Z.,Sun Yat Sen University | Xie Z.,Guangdong Technology Research Center for Advanced Chinese Medicine | Sun Y.,Quality Administration and Risk Control Center Biozen Pharmaceutical | Lam S.,Sun Yat Sen University | And 11 more authors.
Journal of Separation Science | Year: 2014

A method of ultrasonic-assisted extraction followed by high-speed countercurrent chromatography was established for the extraction and isolation of three flavonoid glycosides, i.e. rutin, narcissin, and nicotiflorin from Flos Sophorae Immaturus. The effects of ultrasonic-assisted extraction factors for the main flavonoid compound (rutin) from Flos Sophorae Immaturus were optimized using Box-Behnken design combined with response surface methodology. The optimum conditions were determined as ultrasonic power 83% (600 W), solvent-to-material ratio 56:1, methanol concentration 82% v/v, and extraction time 60 min. Three bioactive flavonol glucosides, rutin, narcissin, and nicotiflorin were isolated from Flos Sophorae Immaturus using high-speed countercurrent chromatography. The separation was performed with a two-phase solvent system containing ethyl acetate/n-butanol/methanol/water (4:0.9:0.2:5, v/v). Amounts of 87 mg of rutin, 10.8 mg of narcissin, and 1.8 mg of nicotiflorin were isolated from 302 mg of crude extract of Flos Sophorae Immaturus in a one-step separation within 160 min with purities of 99.3, 98.0, and 95.1%, respectively, as determined by HPLC with diode array detection. Their structures were characterized by UV, MS, and NMR spectroscopy. It was demonstrated that the established method was simple, fast, and convenient, which was feasible to extract and isolate active flavonoid glycosides from Flos Sophorae Immaturus. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Xiong Y.,Sun Yat Sen University | Zhao Z.,Sun Yat Sen University | Zhao Z.,Guangdong Technology Research Center for Advanced Chinese Medicine | Zhu L.,Sun Yat Sen University | And 5 more authors.
LWT - Food Science and Technology | Year: 2013

The removal of phthalates from essential oils is necessary due to the wide use of plastic products in daily life and severe adverse effects. In this study, molecular distillation techniques were used to remove phthalates from sweet orange oil (. Citrussinensis (L.) Osbeck). Three parameters were investigated to optimize this process. An evaporation temperature of 50°C, evaporator pressure of 5kPa and a feed flow rate of 0.75ml/min were identified as optimal parameters for this method. After distillation, obvious decreases in bis (2-ethylhexyl) phthalate (DEHP), diisobutyl phthalate (DIBP) and dibutyl phthalate (DBP) levels were observed. Phthalates were efficiently removed from sweet orange oil using the developed molecular distillation technique indicating that this approach is suitable for the effective removal of harmful substances from essential oils. © 2013 Elsevier Ltd.


Xie Z.,Sun Yat Sen University | Xie Z.,Guangdong Technology Research Center for Advanced Chinese Medicine | Lam S.,Sun Yat Sen University | Lam S.,Guangdong Technology Research Center for Advanced Chinese Medicine | And 6 more authors.
Analytical Methods | Year: 2014

A simple and efficient HPLC method is developed for the fingerprint analysis of Flos Sophorae Immaturus and for the simultaneous determination of three flavonoids in Flos Sophorae Immaturus, namely rutin, narcissin and quercetin. The separation of analytes is conducted on a Dikma Diamonsil C 18 column (250 mm × 4.6 mm, 5 μm) at 35 °C; the wavelength of UV detector was set at 254 nm; the mobile phases were composed of acetonitrile and aqueous acetic acid (0.5%, v/v). A gradient elution was carried out at a flow rate of 1.0 mL min-1. A common chromatographic fingerprint consisting of 9 characteristic peaks is established among 14 batches of Flos Sophorae Immaturus samples, which were collected from different source areas of China. The constituents in Flos Sophorae Immaturus were further identified by HPLC-DAD-ESI-MS/MS and most of them were flavonoids. Multiple chemometrics analysis, including similarity analysis (SA), hierarchical cluster analysis (HCA) and principal component analysis (PCA) were performed to classify samples. In quantitative analysis, all of the calibration curves showed good linear regression (R2 ≥ 0.9991) within the tested ranges, and the mean recoveries ranged from 100.28% to 101.08%. Three flavonoid compounds in Flos Sophorae Immaturus were simultaneously quantified by the established method. The results demonstrate that the developed method is accurate and effective, and could be readily utilized for the comprehensive quality control of Flos Sophorae Immaturus. © 2014 the Partner Organisations.


Zhao Y.,Sun Yat Sen University | Li S.-Q.,Sun Yat Sen University | Li H.-J.,Sun Yat Sen University | Lan W.-J.,Sun Yat Sen University | Lan W.-J.,Guangdong Technology Research Center for Advanced Chinese Medicine
Chemistry of Natural Compounds | Year: 2013

Under chemical prescreening by direct infusion electrospray ionization mass spectrometry, three new lanostane triterpenoids, 3β-acetoxy-15α- hydroxylanosta-8,24-dien-21-oic acid (1), 1β,3β-dihydroxylanosta-8,24- dien-21-oic acid (2), and 15α-hydroxy-3-oxolanosta-8,24-dien-21-oic acid (3), together with two known lanostane triterpenoids, 3β,15α- dihydroxylanosta-8,24-dien-21-oic acid (4) and 3β-hydroxylanosta-8,24-dien- 21-oic acid (5), were isolated from the marine fungus Ceriporia lacerate derived from Acanthaster planci. Their structures were established by MS and 1D and 2D NMR spectroscopic techniques. © 2013 Springer Science+Business Media New York.


Lan W.-J.,Sun Yat Sen University | Lan W.-J.,Guangdong Technology Research Center for Advanced Chinese Medicine | Zhao Y.,Sun Yat Sen University | Xie Z.-L.,Sun Yat Sen University | And 7 more authors.
Natural Product Communications | Year: 2012

Two novel sorbicillinoid analogues, (4'Z)-sorbicillin (1) and (2S)-2,3-dihydro-7-hydroxy-6-methyl-2-[(E)-prop-1-enyl]-chroman-4-one (2), together with three known compounds, (2S)-2,3-dihydro-7-hydroxy-6,8-dimethyl-2- [(E)-prop-1-enyl]-chroman-4-one (3), sorbicillin (4), and 2′,3′- dihydrosorbicillin (5), were isolated from the culture broth of the fungus Trichoderma sp. associated with the seastar Acanthaster planci. Their structures were determined by analysis of the NMR and MS data. Compound 1 was the first example with a Z-configuration of the C-4′/C-5′ double bond in the sorbyl side chain. Compounds 2 and 3 were uncommon monomeric sorbicillinoids with a cyclic sorbyl chain. 2, 3 and 5 showed moderate cytotoxic activities against various cancer cell lines.

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