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1.
J Asian Nat Prod Res ; : 1-10, 2019 Dec 03.
Artigo em Inglês | MEDLINE | ID: mdl-31791147

RESUMO

Various bioactive polyketides have been found in Aloe barbadensis. However, the polyketide synthases (PKSs), which participate in biosynthesis of polyketides in A. barbadensis remain unknown. In this study, two type III PKSs (AbPKS1 and AbPKS2) were identified from A. barbadensis. AbPKS1 and AbPKS2 were able to utilize malonyl-CoA to yield heptaketides (TW93a and aloesone) and octaketides (SEK4 and SEK4b), respectively. AbPKS1 also exhibited catalytic promiscuity in recognizing CoA thioesters of aromatics to produce unusual polyketides. What Is more, a whole cell biocatalysis system with the capability of producing 26.4 mg/L of SEK4/SEK4b and 2.1 mg/L of aloesone was successfully established.

2.
J Asian Nat Prod Res ; : 1-7, 2019 Nov 18.
Artigo em Inglês | MEDLINE | ID: mdl-31738087

RESUMO

Bistachybotrysin K (1), one new phenylspirodrimane dimer with a central 6/7 oxygen heterocycle core, was isolated from the fungus Stachybotrys chartarum CGMCC 3.5365. Its structure was elucidated by extensive spectroscopic data and single-crystal X-ray diffraction. Compound 1 showed significant cytotoxicity against human tumor cell lines HCT116, NCI-H460, BGC823, Daoy, and HepG2 with IC50 values in the range of 1.1-4.7 µM.

3.
J Asian Nat Prod Res ; 21(9): 887-894, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-30614271

RESUMO

Three new phenylspirodrimanes derivatives named stachybotrysins H and I (1 and 2) and stachybotrin E (3), together with one known compound stachybotrylactam (4), were isolated from Stachybotrys chartarum CGMCC 3.5365. Their structures were determined by extensive NMR data and mass spectroscopic analysis. Compounds 1 and 2 showed inhibitory effect towards potassium channel Kv1.3 with IC50 values of 13.4 and 10.9 µM, respectively.


Assuntos
Canal de Potássio Kv1.3/antagonistas & inibidores , Compostos de Espiro/química , Stachybotrys/química , Animais , Células CHO , Linhagem Celular , Cricetinae , Cricetulus
4.
J Asian Nat Prod Res ; 20(7): 605-614, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29989425

RESUMO

Glucuronidation is an important and popular metabolic reaction in vivo of drugs. The further evaluation of biological activity and toxicity of glucuronides is necessary in the course of the drug research and development. However, the synthesis of glucuronides is limited by the lack of efficient approach. Herein, we have developed a new glucuronide synthesis method using plant uridine diphosphate-dependent glucuronosyltransferases (UGTs), UGT88D4, UGT88D7, and EpGT8, enabling the convenient preparation for corresponding O-glucuronide metabolites (1a, 2a, 3a, and 3b) in milligram scale of two neurological active agents, IMM-H004 (1) and FLZ (2). Their structures were characterized by spectroscopic data analyses.


Assuntos
Glucuronídeos/síntese química , Glucuronosiltransferase/metabolismo , Plantas/enzimologia , Clonagem Molecular , Glucuronosiltransferase/química , Glucuronosiltransferase/genética , Concentração de Íons de Hidrogênio , Espectroscopia de Ressonância Magnética , Metais/química , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Temperatura Ambiente
5.
J Asian Nat Prod Res ; 20(9): 844-851, 2018 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-29119831

RESUMO

Two new lanostane triterpenoids (1 and 2), two new ergostane-type steroids (3 and 4) together with two known lanostane triterpenoids (5 and 6) and one known steroid (7) were isolated from the cultured mycelia of Ganoderma capense (CGMCC 5.71). Their structures were determined on the basis of extensive spectroscopic (HRESIMS, 1D NMR, 2D NMR) data analyses. Compound 1 exhibited moderate cytotoxic activity against the human cancer cell line NCI-H1650 with an IC50 value of 22.3 µM, and 7 displayed cytotoxic activity against the human cancer cell line HCT116 with an IC50 value of 17.4 µM. In addition, compounds 2, 3, 5, and 6 displayed weak anti-HIV activity with IC50 values of 23.5, 46.7, 21.6, and 30.1 µM, respectively.


Assuntos
Ganoderma/química , Micélio/química , Esteroides/química , Triterpenos/química , Ganoderma/metabolismo , Estrutura Molecular , Micélio/metabolismo , Esteroides/metabolismo
6.
Zhongguo Zhong Yao Za Zhi ; 42(12): 2323-2328, 2017 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-28822187

RESUMO

The glycosides of 4'-demethylepipodophyllotoxin (DMEP) possess various pharmacological activities; however, the chemical synthesis of these glycosides faces challenges in regioselectivity, stereoselectivity, and the protection and de-protection of functional groups. In this work, a novel glycosyltransferase (GT) gene AbGT5 from Aloe barbadensis was successfully cloned, heterogeneously expressed and purified. Recombinant AbGT5 was able to catalyze the glycosylation of DMEP and the glycosylated product, which was separated from the preparative scale reaction, was characterized as DMEP 4'-O-ß-D-glucoside via MS, 1H-NMR, 13C-NMR, HSQC and HMBC. According to the investigations of enzyme properties, AbGT5 show the highest activity around 20 ℃ in the buffer of pH 9.0, and it was independent of divalent metal ions. Under the optimum conditions, the conversion rate of DMEP can reach 80%. Above all, in this work the enzymatic glycosylation of DMEP was achieved with high efficiency by the novel GT AbGT5.


Assuntos
Glucosídeos/química , Glicosídeos/química , Glicosiltransferases/metabolismo , Podofilotoxina/análogos & derivados , Aloe/enzimologia , Aloe/genética , Glicosilação , Glicosiltransferases/genética , Podofilotoxina/química
7.
J Asian Nat Prod Res ; 19(6): 541-549, 2017 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-28395517

RESUMO

Five monoterpenoids were isolated from the endophytic fungus Periconia sp. F-31, including three new carene-type monoterpenoids, 2-carene-5,8-diol (1), 2-carene-8,10-diol (2), 2-carene-8-acetamide (3), one new menthene-type monoterpenoid 8-hydroxy-1,7-expoxy-2-menthene (4), and one known monoterpenoid anethofuran (5). The structures of all compounds were elucidated based on a comprehensive spectroscopic data analysis, electronic circular dichroism (ECD), and calculated ECD.


Assuntos
Antineoplásicos/isolamento & purificação , Ascomicetos/química , Monoterpenos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/farmacologia , Dicroísmo Circular , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Estrutura Molecular , Monoterpenos/química , Monoterpenos/farmacologia , Ressonância Magnética Nuclear Biomolecular
8.
J Asian Nat Prod Res ; 19(10): 1028-1035, 2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28145126

RESUMO

A new steroid glucoside (1), along with nine known steroids (2-10) and four known sorbicillinoids (11-14), were isolated from the endophytic fungus Trichoderma sp. Xy24. Their structures were elucidated on the basis of spectroscopic data analyses and by comparison with reported data. Compounds 3, 5-7, 9, 10, and 13 exhibited significant inhibitory effects on HIV-1 virus with IC50 values ranging 1.9-9.3 µM; compounds 10, 13, and 14 showed potent inhibitory activity on LPS-induced NO production in BV2 microglia cells with inhibitory rates of 108.2, 100, and 75.1% at 10 µM, respectively. In addition, compound 10 displayed moderate cytotoxicity against BCG823 and HePG2 cell lines with IC50 values of 11.1 and 17.7 µM, respectively.


Assuntos
Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Esteroides/isolamento & purificação , Esteroides/farmacologia , Trichoderma/química , Anti-Inflamatórios não Esteroides/farmacologia , Glucosídeos/química , Células HCT116 , HIV-1/efeitos dos fármacos , Células Hep G2 , Humanos , Concentração Inibidora 50 , Microglia/efeitos dos fármacos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Paclitaxel/farmacologia , Esteroides/química
9.
J Asian Nat Prod Res ; 19(7): 651-658, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27835936

RESUMO

Three new sesquiterpenoids trichoacorenols B-C and cyclonerodiol B (1-3), along with three known ones (4-6), were isolated from the mangrove plant endophytic fungus Trichoderma sp. Xy24 using various column chromatography techniques. The structures of these compounds were determined on the basis of extensive spectroscopic data analyses. Compounds 1, 2, 4, and 5 were four acorane sesquiterpenes, 3 and 6 were two monocyclic sesquiterpenediols. Compounds 3 and 5 exhibited significant neural anti-inflammatory activity by inhibiting LPS-induced NO production in BV2 cells with the inhibitory rates of 75.0% and 39.2% at 0.1 µM, respectively, which are more potent than curcumin, a positive control with the inhibitory rate of 21.1% at 0.1 µM.


Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Trichoderma/química , Animais , Anti-Inflamatórios/química , Curcumina/farmacologia , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Rhizophoraceae/microbiologia , Sesquiterpenos/química
10.
Zhongguo Zhong Yao Za Zhi ; 41(1): 87-91, 2016 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-28845646

RESUMO

Various chromatographic techniques, including silica gel column chromatography, Sephadex LH-20, preparative thin-layer chromatography, and preparative HPLC, were employed to isolate the chemical constituents from callus cultures of Dysosma versipellis. Structures of the compounds were elucidated based on UV, IR, MS and NMR spectroscopic data analysis. Totally, seven flavonoid glycosides were isolated from the 95% ethanol extract of the callus cultures and identified as kaempferol-3-O-[6″-(3″'-methoxy)-malonyl]-ß-D-glucopyranoside(1), kaempferol-3-O-(6″-O-acetyl)-ß-D-glucopyranoside(2), kaempferide-3-O-ß-D-glucopyranoside(3), kaempferol-3-O-ß-D-glucopyranoside(4), isoquercitrin(5), quercetin-4'-O-ß-D-glucopyranoside(6) and kaempferol-3-(6″-malonyl)-ß-D-glucopyranoside(7), respectively.All these compounds were isolated from callus cultures of D. versipellis for the first time.Compounds 1, 2, 3, 6 and 7 were firstly obtained from plant materials of D. versipellis, and compound 1 was a new compound.


Assuntos
Berberidaceae/química , Flavonoides/análise , Flavonoides/isolamento & purificação , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray
11.
J Asian Nat Prod Res ; 18(3): 253-9, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-26465203

RESUMO

Two new flavonoids (1 and 2), along with 14 known ones (3-16), were isolated from the cultured cells of Glycyrrhiza uralensis. Most of them were prenylated flavonoids. Their structures were elucidated on the basis of spectroscopic data analysis. All compounds showed non-cytotoxicity against five human tumor cell lines. The results suggest that plant cultured cells can yield the secondary metabolites that have not been found in parent plant.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Flavonoides/isolamento & purificação , Glycyrrhiza uralensis/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Células Cultivadas , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/química , Flavonoides/farmacologia , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
12.
Zhongguo Zhong Yao Za Zhi ; 41(24): 4568-4571, 2016 Dec.
Artigo em Chinês | MEDLINE | ID: mdl-28936839

RESUMO

Secoisolariciresinol dehydrogenase (SDH) is a key enzyme involved in the biosynthetic pathway of podophyllotoxin.In this study, two SDH candidate genes,SO282 and SO1223, were cloned from callus of Dysosma versipellis by homology-based PCR and rapid amplification of cDNA end (RACE).The SDH candidate genes were expressed in Escherichia coli and the subsequent enzyme assay in vitro showed that recombinant SO282 had the SDH activity. These results pave the way to the follow-up investigation of the biosynthetic of podophyllotoxin.


Assuntos
Berberidaceae/enzimologia , Álcool Oxidorredutases Dependentes de NAD(+) e NADP(+)/genética , Proteínas de Plantas/genética , Berberidaceae/genética , Clonagem Molecular , DNA Complementar , Podofilotoxina/biossíntese
13.
Zhongguo Zhong Yao Za Zhi ; 40(12): 2349-51, 2015 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-26591523

RESUMO

To investigate the secondary metabolites of endophytic fungi Pericinia sp. F-31. Column chromatography on silica gel, Sephadex LH-20 and semi-preparative HPLC were used to separate and purify the compounds. Two compounds were isolated from the fermentation broth of Periconia sp. Their structures were identified as 5-(1-hydroxyhexyl) -6-methyl-2H-pyran-2-one (1) and 2-(3-hydroxy-4-methylphenyl) -propanoic acid (2). Compound 1 was a new lactone compound, compound 2 was new natural product, and the NMR data of compound 2 was reported for the first time.


Assuntos
Annona/microbiologia , Ascomicetos/metabolismo , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Endófitos/metabolismo , Lactonas/química , Lactonas/isolamento & purificação , Ascomicetos/química , Ascomicetos/genética , Ascomicetos/isolamento & purificação , Medicamentos de Ervas Chinesas/metabolismo , Endófitos/química , Endófitos/genética , Endófitos/isolamento & purificação , Lactonas/metabolismo , Espectrometria de Massas , Estrutura Molecular
14.
J Asian Nat Prod Res ; 17(6): 656-61, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-26074011

RESUMO

Biotransformations of icariin (1) by cell suspension cultures of Glycyrrhiza uralensis and Morus alba yielded two new metabolites, icaruralins A and B (2 and 3), and one known metabolite, baohuoside I (4). Their structures were determined on the basis of extensive spectroscopic analysis. This is the first report that the cell suspension cultures of G. uralensis and M. alba possess deglycosylation functionality.


Assuntos
Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Glycyrrhiza uralensis/química , Morus/química , Biotransformação , Flavonoides/química , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química
15.
Zhongguo Zhong Yao Za Zhi ; 39(11): 2039-42, 2014 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-25272838

RESUMO

Naringenin (1) was transformed to three metabolites (2-4) by Mucor sp. Based on LCMS(n)-IT-TOF and NMR spectroscopic data, 2-4 were identified as naringenin-7-O-sulphate, naringenin-4'-O-sulphate, and naringenin-5-O-sulphate, respectively. These results might provide hints to the mammalian/human metabolism of naringenin.


Assuntos
Medicamentos de Ervas Chinesas/metabolismo , Flavanonas/metabolismo , Mucor/metabolismo , Sulfatos/metabolismo , Biotransformação , Medicamentos de Ervas Chinesas/química , Flavanonas/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular
16.
Zhongguo Zhong Yao Za Zhi ; 39(12): 2275-80, 2014 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-25244758

RESUMO

Syringin, chlorogenic acid and 1,5-dicaffeoylquinic acid are three main bioactive ingredients in herbs of Saussurea involucrata with various pharmacological properties, while their contents are very low. In this study, the biosynthesis of syringin, chlorogenic acid and 1,5-dicaffeoylquinic acid in the cell suspension cultures of S. involucrata were regulated by feeding carbon sources and precursors, which resulted in a great increase of the contents and yields of the above three bioactive ingredients. After 16 days of fermentation, the yields of syringin, chlorogenic acid and 1,5-dicaffeoylquinic acid reached 339.0, 225.3, 512.7 mg x L(-1), respectively. Meanwhile, their contents increased up to 67.9, 1.9, 10.6 times of wild medicinal material, respectively. The results provided a solid basis for further studies on application of cell suspension cultures of S. involucrata for large-scale production of bioactive compounds syringin, chlorogenic acid and 1,5-dicaffeoylquinic acid.


Assuntos
Ácido Clorogênico/metabolismo , Cinamatos/metabolismo , Glucosídeos/biossíntese , Saussurea/metabolismo , Técnicas de Cultura de Células , Células Cultivadas , Ácido Clorogênico/análise , Cinamatos/análise , Glucosídeos/análise , Fenilpropionatos/análise , Saussurea/química , Saussurea/crescimento & desenvolvimento
17.
Yao Xue Xue Bao ; 49(6): 913-20, 2014 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-25212040

RESUMO

Seven meroterpenoids and five small-molecular precursors were isolated from Penicillium sp., an endophytic fungus from Dysosma versipellis. The structures of new compounds, 11beta-acetoxyisoaustinone (1) and isoberkedienolactone (2) were elucidated based on analysis of the spectral data, and the absolute configuration of 2 was established by TDDFT ECD calculation with satisfactory match to its experimental ECD data. Meroterpenoids originated tetraketide and pentaketide precursors, resepectively, were found to be simultaneously produced in specific fungus of Penicillium species. These compounds showed weak cytotoxicity in vitro against HCT-116, HepG2, BGC-823, NCI-H1650, and A2780 cell lines with IC 50 > 10 micromol x L(-1).


Assuntos
Lactonas/farmacologia , Monoterpenos/farmacologia , Penicillium/química , Berberidaceae/microbiologia , Linhagem Celular , Linhagem Celular Tumoral , Humanos , Lactonas/isolamento & purificação , Monoterpenos/isolamento & purificação
18.
Zhongguo Zhong Yao Za Zhi ; 38(14): 2282-6, 2013 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-24199555

RESUMO

A total of 24 biologically pure entophytic fungal strains were isolated from stems, leaves, and seed coats of Xylocarpus plants by repeated purification, and identified with Internal Transcribed Spacer (ITS) rDNA molecular method, which belonging to 14 genera, 11 families, 9 orders and 3 classes. There were differences in genus and species levels among three plant materials from different habitats and species, and it was found that the strains of Phomopsis and Colletotrichum existed in all three plant materials. In vitro assay of antitumor activity by MTT method revealed that the EtOAc extracts of 15 strains exhibited potent antitumor activity. These results suggest that it is of value for further investigation on the above fungal strains.


Assuntos
Antineoplásicos/isolamento & purificação , Fungos/química , Fungos/isolamento & purificação , Meliaceae/microbiologia , Antineoplásicos/farmacologia , Biodiversidade , Linhagem Celular Tumoral , Endófitos/química , Endófitos/classificação , Endófitos/genética , Endófitos/isolamento & purificação , Fungos/classificação , Fungos/genética , Células HCT116 , Humanos , Filogenia
19.
Yao Xue Xue Bao ; 48(2): 161-9, 2013 Feb.
Artigo em Chinês | MEDLINE | ID: mdl-23672011

RESUMO

The prenylation of aromatic compounds plays an important role in the natural product research because it not only gives rise to an astounding diversity of primary and secondary metabolites in plants, fungi and bacteria but also enhances the bioactivities and bioavailabilities of these compounds. However, further investigation of prenylated aromatic compounds is frequently hindered due to their low content in nature and difficulties in chemical synthesis. Cloning aromatic prenyltransferase genes followed by heterologous expression would be attractive tools for the chemoenzymatic synthesis of bioactive molecules. This review summarizes the classifications, structural investigations, enzymatic catalysis and other progress in aromatic prenyltransferases originated from microorganisms.


Assuntos
Bactérias/enzimologia , Dimetilaliltranstransferase/biossíntese , Fungos/enzimologia , Biologia Sintética , Dimetilaliltranstransferase/química , Dimetilaliltranstransferase/classificação , Estrutura Molecular , Especificidade por Substrato
20.
Zhongguo Zhong Yao Za Zhi ; 37(24): 3734-7, 2012 Dec.
Artigo em Chinês | MEDLINE | ID: mdl-23627169

RESUMO

Ten compounds were isolated and purified from cell suspension cultures of Cudrania tricuspidata with silica-gel column chromatography, semi-preparative HPLC and Sephadex LH-20. On the base of their physicochemical properties and spectral data, their structures were identified as 1, 3, 5-trihydroxy4-(3, 3-dimethylallyl) xanthone (1), wighteone (2), 6-prenylapigenin (3), licoflavone C(4), cudraflavanone C(5), erythrivarone A (6), derrone (7), carthamidin (8), genistein (9) and aromadendrin (10). Among them, compounds 2-10 were flavonoids, and compound 1 was a xanthone which was isolated from the plant for the first time.


Assuntos
Técnicas de Cultura de Células/métodos , Moraceae/química , Folhas de Planta/química , Plantas Medicinais/química , Cromatografia Líquida de Alta Pressão , Flavanonas/isolamento & purificação , Flavonas/isolamento & purificação , Flavonoides/isolamento & purificação , Genisteína/isolamento & purificação , Moraceae/citologia , Folhas de Planta/citologia , Xantonas/isolamento & purificação
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