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ABSTRACT: In this paper, microbial transformation of kurarinone (1) by Cunninghamella echinulata AS 3.3400 was investigated and four transformed products were isolated and identified as 6″-hydroxykurarinone (2), 4″,5″,8″-trihydroxynorkurarinone (3), norkurarinone (4), and kurarinone-7-O-β-glucoside (5), respectively. Among them, 3 and 5 are new compounds, and the rare glycosylation in microbial transformation was observed. In addition, the cytotoxicities of transformed products (2-5) were also investigated.
Journal of Asian natural products research 09/2012; · 0.61 Impact Factor
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ABSTRACT: In the crystal of the title compound, C(17)H(17)N(3)O(2), the mol-ecules exist in the keto-enamine form. The pyrazole ring is oriented at 10.59 (4) and 57.98 (5)° to the phenyl and furyl rings, respectively, and the dihedral angle between phenyl and furyl rings is 73.30 (11)°. An intra-molecular N-H⋯O hydrogen bond occurs between imino and carbonyl groups. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into supra-molecular chains along the b axis.
Acta Crystallographica Section E Structure Reports Online 05/2012; 68(Pt 5):o1277. · 0.35 Impact Factor
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ABSTRACT: A series of analogues of deoxyandrographolide (1) transformed by Cunninghamella blakesleana AS 3.2004 were isolated and identified by spectral methods including 2D NMR. Among them, 3-oxo-17,19-dihydroxy-7,13-ent-labdadien-15,16-olide (9), 3-oxo-19-hydroxy-1,13-ent-labdadien-15,16-olide (16), 3-oxo-1β-hydroxy-14-deoxy-andrographolide (17) and 3-oxo-2β-hydroxy-14-deoxyandrographolide (18) are new compounds. And their structure-activity relationships (SAR) of inhibitory activity on LPS-induced NO production in RAW 264.7 macrophage cells were also discussed.
Bioorganic & medicinal chemistry letters 02/2012; 22(4):1615-8. · 2.65 Impact Factor
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ABSTRACT: In this paper, microbial transformation of resibufogenin by Fusarium solani AS 3.1829 was investigated, and five transformed products were isolated and identified as 3-ketone-resibufogenin (2), 3-one-cyclic 3-(1,2-dimethyl-1,2-ethanediylacetal)-resibufogenin (3), 3-dimethoxyl-resibufogenin (4), 3-epi-resibufogenin (5), and 3-epi-15α-hydroxy-7βH-bufalin (6), respectively. Among them, 3, 4, and 6 are new compounds, and the rare double oxidization of C-3 was reported. In addition, the cytotoxicities of transformed products were also investigated.
Journal of Asian natural products research 09/2011; 13(9):831-7. · 0.61 Impact Factor
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ABSTRACT: In the title compound, C(16)H(16)N(2)O(5)·CH(4)O, the two benzene rings in the Schiff base mol-ecule form a dihedral angle of 17.1 (1)°. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the components into corrugated sheets parallel to the (101) plane.
Acta Crystallographica Section E Structure Reports Online 08/2011; 67(Pt 8):o2189. · 0.35 Impact Factor
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ABSTRACT: Biotransformation of deoxyandrographolide (1) by Alternaria alternata AS 3.4578 gave five derivatives identified by spectral methods including 2D NMR as the known dehydroandrographolide (2) and 9beta-hydroxy-dehydroandrographolide (3) and the new compounds 9beta-hydroxy-deoxyandrographolide (4), 3alpha,17,19-trihydroxy-8,13-ent-labdadien-15,16-olide (5) and 3-oxo-9beta-hydroxy-deoxyandrographolide (6).
Natural product communications 06/2011; 6(6):781-4. · 1.24 Impact Factor
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ABSTRACT: Biotransformation of deoxyandrographolide (1) by Fusarium graminearum AS 3.4598 was investigated in this paper. And five transformed products of 1 by F. graminearum AS 3.4598 were obtained. Their chemical structures were characterized as 3-oxo-8α,17β-epoxy-14-deoxyandrographolide (2), 3-oxo-14-deoxyandrographolide (3), 3-oxo-17,19-dihydroxyl-8,13-ent-labdadien-15,16-olide (4), 1β-hydroxyl-14-deoxyandrographolide (5), and 7β-hydroxyl-14-deoxyandrographolide (6) by spectral methods including 2D NMR. Among them, products 2, 4, and 5 are new.
Journal of Asian natural products research 04/2011; 13(4):350-5. · 0.61 Impact Factor
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ABSTRACT: The title compound, C(14)H(10)BrFN(2)O, adopts an E geometry about the C=N bond. The dihedral angle between the mean planes of the two benzene rings is 81.5 (6)°. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the b axis.
Acta Crystallographica Section E Structure Reports Online 04/2011; 67(Pt 4):o940. · 0.35 Impact Factor
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ABSTRACT: Cinobufagin (CB), a major bioactive component of the traditional Chinese medicine Chansu, has been reported to have potent antitumor activity. In this study, in vitro metabolism of CB among species was compared with respect to metabolic profiles, enzymes involved, and catalytic efficiency by using liver microsomes from human (HLM), mouse (MLM), rat (RLM), dog (DLM), minipig (PLM), and monkey (CyLM). Significant species differences in CB metabolism were revealed. In particular, species-specific deacetylation and epimerization combined with hydroxylation existed in RLM, whereas hydroxylation was a major pathway in HLM, MLM, DLM, PLM, and CyLM. Two monohydroxylated metabolites of CB in human and animal species were identified as 1α-hydroxylcinobufagin and 5β-hydroxylcinobufagin by using liquid chromatography-mass spectrometry and two-dimensional NMR techniques. CYP3A4 was identified as the main isoform involved in CB hydroxylation in HLM on the basis of the chemical inhibition studies and screen assays with recombinant human cytochrome P450s. Furthermore, ketoconazole, a specific inhibitor of CYP3A, strongly inhibited CB hydroxylation in MLM, DLM, PLM, and CyLM, indicating that CYP3A was responsible for CB hydroxylation in these animal species. The apparent substrate affinity and catalytic efficiency for 1α- and 5β-hydroxylation of CB in liver microsomes from various species were also determined. PLM appears to have K(m) and total intrinsic clearance value (V(max)/K(m)) similar to those for HLM, and the total microsomal intrinsic clearance values for CB obeyed the following order: mouse > dog > monkey > human > minipig. These findings provide vital information to better understand the metabolic behaviors of CB among various species.
Drug metabolism and disposition: the biological fate of chemicals 01/2011; 39(4):675-82. · 3.74 Impact Factor
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ABSTRACT: A high-performance liquid chromatographic method was applied to the determination of gamabufotalin, telocinobufagin, bufotalin, cinobufotalin, bufalin, cinobufagin and resibufogenin in three traditional Chinese medicinal preparations containing ChanSu. The compounds were separated on a YMC-C18 column (250 x 4.6 mm, 5 um) with a gradient of acetonitrile and 0.3% aqueous acetic acid (v/v) at a flow rate of 0.8 mL min(-1) and detected at 296 nm. Complete separation was obtained within 35 min for the seven bufadienolides. The calibration curves showed good linearity (r2 > 0.999) within the test range. The recovery was 95.5% - 105.9%. The assay could simultaneously determine seven major bufadienolides of the three Chinese medicinal preparations of ChanSu in 35 min. The results obtained suggested that the developed HPLC assay could be comprehensively utilized for the quality control of the three traditional Chinese medicinal preparations of ChanSu used in the clinic.
Natural product communications 02/2009; 4(2):179-84. · 1.24 Impact Factor
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ABSTRACT: In the mixed-ligand metal-organic polymeric compound poly[[mu(2)-1,4-bis(imidazol-1-yl)benzene](mu(2)-terephthalato)dizinc(II)], [Zn(2)(C(8)H(4)O(4))(2)(C(12)H(10)N(4))](n) or [Zn(2)(bdc)(2)(bib)](n) [H(2)bdc is terephthalic acid and bib is 1,4-bis(imidazol-1-yl)benzene], the asymmetric unit contains one Zn(II) ion, with two half bdc anions and one half bib molecule lying around inversion centers. The Zn(II) ion is in a slightly distorted tetrahedral environment, coordinated by three carboxylate O atoms from three different bdc anions and by one bib N atom. The crystal structure is constructed from the secondary building unit (SBU) [Zn(2)(CO(2))(2)N(2)O(2)], in which the two metal centers are held together by two bdc linkers with bis(syn,syn-bridging bidentate) bonding modes. The SBU is connected by bdc bridges to form a two-dimensional grid-like (4,4)-layer, which is further pillared by the bib ligand. Topologically, the dinuclear SBU can be considered to be a six-connected node, and the extended structure exhibits an elongated primitive approximately cubic framework. The three-dimensional framework possesses a large cavity with dimensions of approximately 10 x 13 x 17 A in cross-section. The potential porosity is filled with mutual interpenetration of two identical equivalent frameworks, generating a novel threefold interpenetrating network with an alpha-polonium topology [Abrahams, Hoskins, Robson & Slizys (2002). CrystEngComm, 4, 478-482].
Acta crystallographica. Section C, Crystal structure communications 02/2009; 65(Pt 2):m82-5. · 0.78 Impact Factor
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ABSTRACT: In the title compound, C(17)H(18)N(2)O(6), the mol-ecule is slightly twisted, with a dihedral angle of 18.1 (2)° between the two benzene rings. In the crystal structure, mol-ecules are linked into a network by inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds. An intra-molecular O-H⋯O hydrogen bond is also present.
Acta Crystallographica Section E Structure Reports Online 01/2009; 65(Pt 10):o2412. · 0.35 Impact Factor
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ABSTRACT: In the title compound, C(14)H(11)BrN(2)O(3)·H(2)O, the dihedral angle between the two benzene rings of the Schiff base is 22.7 (2)° and an intra-molecular O-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked into layers parallel to the ab plane by O-H⋯O and N-H⋯O hydrogen bonds.
Acta Crystallographica Section E Structure Reports Online 01/2009; 65(Pt 10):o2489. · 0.35 Impact Factor
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ABSTRACT: In the title compound, C(14)H(11)ClN(2)O(4)·H(2)O, the dihedral angle between the two benzene rings is 8.5 (2)° and an intra-molecular O-H⋯N hydrogen bond is observed in the Schiff base mol-ecule. In the crystal structure, the water mol-ecule accepts an N-H⋯O hydrogen bond and makes O-H⋯O hydrogen bonds to two further Schiff base mol-ecules. Further inter-molecular O-H⋯O hydrogen bonds lead to the formation of layers parallel to the bc plane.
Acta Crystallographica Section E Structure Reports Online 01/2009; 65(Pt 4):o721. · 0.35 Impact Factor
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ABSTRACT: The title compound, C(14)H(10)ClN(3)O(4)·CH(4)O, was synthesized from the reaction of 5-chloro-salicylaldehyde with 4-nitro-benzohydrazide in methanol. The Schiff base mol-ecule is nearly planar, with a dihedral angle of 9.1 (3)° between the two benzene rings. The methanol solvent mol-ecules are linked to the Schiff base mol-ecules by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds, forming chains running parallel to the a axis.
Acta Crystallographica Section E Structure Reports Online 01/2008; 64(Pt 5):o781. · 0.35 Impact Factor
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ABSTRACT: The mol-ecule of the title compound, C(15)H(14)N(2)O(4), displays a trans configuration with respect to the hydrazide C=N bond. The dihedral angle between the two benzene rings is 15.0 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯N and O-H⋯O hydrogen bonds, forming layers parallel to the ab plane; an intramolecular N-H⋯O hydrogen bond is also present.
Acta Crystallographica Section E Structure Reports Online 01/2008; 64(Pt 2):o470. · 0.35 Impact Factor
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ABSTRACT: In the mol-ecule of the title compound, C(20)H(18)N(2)O(4), the dihedral angle between the benzene ring and the naphthyl ring system is 8.5 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds, forming chains running along the b axis.
Acta Crystallographica Section E Structure Reports Online 01/2008; 64(Pt 5):o909. · 0.35 Impact Factor
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ABSTRACT: The asymmetric unit of the title compound, C(14)H(12)N(2)O(4)·0.5CH(4)O·1.5H(2)O, consists of two Schiff base mol-ecules, three water mol-ecules and one methanol mol-ecule. The dihedral angle between the two benzene rings is 7.8 (2)° in one of the mol-ecules and 4.0 (2)° in the other. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds are observed. Mol-ecules are linked into a three-dimensional network by O-H⋯O and N-H⋯O inter-molecular hydrogen bonds.
Acta Crystallographica Section E Structure Reports Online 01/2007; 64(Pt 1):o210. · 0.35 Impact Factor
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ABSTRACT: The capabilities of twenty strains of filamentous fungi (from 9 genera) to transform deoxyandrographolide (1) were screened. And eleven derivatives of 1 transformed by Cunninghamella echinulata AS 3.3400 were isolated. Their chemical structures were identified by spectral methods including 2D NMR. Among them, 3-oxo-7α-hydroxy-14-deoxyandrographolide (2), 3-oxo-8β,17α-epoxy-14-deoxyandrographolide (3), 8α-formyl-14-deoxyandrographolide (4), 8β-methoxyl-17α-hydroxyl-14-deoxyandro-grapholide (5) and 3α,17,19-trihydroxyl-7,13-ent-labdadien-15,16-olide (6), are new compounds. And their structure–activity relationships (SAR) were also discussed.Graphical abstractResearch highlights▶ Eleven transformed products from biotransformation of deoxyandrographolide by C. echinulata. And Five of them were novel compounds. ▶ The structure-activity relationships (SAR) of bioconversion products and proposed biosynthetic pathways were listed. ▶ Hydroxylation was the main biotransformation reaction which providing more functional hydroxyl groups for semi-synthesis of ester derivatives.
Journal of Molecular Catalysis B Enzymatic 68(2):187-191. · 2.73 Impact Factor
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ABSTRACT: A new isoflavone was obstained from the medicinal herb Amorpha fruticosa. It was elucidated asbenzopyran-12-one,1,4,10,11-tetrahydro-6′-[8′-(hydroxymethyl)ethenyl]-2,3-dimethoxy-8′-O-β-d-glucopyranosyl-O-α-d-arabinoside by spectroscopic methods including UV, IR, 1D NMR and 2D NMR techniques. And the activity against acetaminophen-induced hepatotoxicity of this compound was also studied, and found this compound can protect liver obviously from hepatotoxicity induced by acetaminophen (AAP).
Chinese Chemical Letters.
