Publications by authors named "Zhong-Bin Cheng"

14 Publications

  • Page 1 of 1

An indole diterpenoid isolated from the fungus sp. and its antimicrobial activity.

Nat Prod Res 2019 Oct 17;33(19):2770-2776. Epub 2018 Sep 17.

b School of Life Science and Biopharmaceutics, Shenyang Pharmaceutical University , Shenyang , China.

One new indole diterpenoid, drechmerin I (), was isolated from the fermentation broth of sp. isolated from the root of . Its structure was elucidated based on 1 D and 2 D nuclear magnetic resonance (NMR), high resolution electrospray ionization mass spectrum (HRESIMS), and electronic circular dichroism (ECD) spectroscopic analyses as well as TD DFT calculations of ECD spectra. Drechmerin I () was assayed for its antimicrobial activity against , , , , , and , respectively. Drechmerin I () showed antimicrobial activities against with an MIC value of 200 μg/mL. The interaction of peptide deformylase with drechmerin I () was investigated by molecular docking.
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http://dx.doi.org/10.1080/14786419.2018.1501050DOI Listing
October 2019

Drechmerin H, a novel 1(2), 2(18)-diseco indole diterpenoid from the fungus Drechmeria sp. as a natural agonist of human pregnane X receptor.

Bioorg Chem 2018 09 9;79:250-256. Epub 2018 May 9.

College of Pharmacy, College (Institute) of Integrative Medicine, College of Medical Laboratory, Advanced Institute for Medical Sciences, Dalian Medical University, Dalian 116044, China. Electronic address:

A novel 1(2), 2(18)-diseco indole diterpenoid, drechmerin H (1), was isolated from the fermentation broth of Drechmeria sp. together with a new indole diterpenoid, 2'-epi terpendole A (3), and a known analogue, terpendole A (2). Their structures were determined by HRESIMS, 1D and 2D NMR, ECD, and X-ray single crystal diffraction analyses as well as quantum chemical calculation. The abosulte configuration of terpendole A (2) was determined for the first time. Compound 1 displayed the significant agonistic effect on pregnane X receptor (PXR) with EC value of 134.91 ± 2.01 nM, and its interaction with PXR was investigated by molecular docking. Meantime, a plausible biosynthetic pathway for compounds 1-3 is also discussed in the present work.
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http://dx.doi.org/10.1016/j.bioorg.2018.05.001DOI Listing
September 2018

Psiguajadials A-K: Unusual Psidium Meroterpenoids as Phosphodiesterase-4 Inhibitors from the Leaves of Psidium guajava.

Sci Rep 2017 04 21;7(1):1047. Epub 2017 Apr 21.

School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, People's Republic of China.

Bioassay-guided fractionation of the ethanolic extract of the leaves of Psidium guajava led to the isolation of 11 new Psidium meroterpenoids, psiguajadials A-K (1-11), along with 17 known ones (12-28). Their structures and absolute configurations were elucidated by spectroscopic methods and comparison of experimental and calculated ECD. Compounds 1 and 2 represent two unprecedented skeletons of 3,5-diformyl-benzyl phloroglucinol-coupled sesquiterpenoid, while 3 is the first example of Psidium meroterpenoids coupling via an oxepane ring. Putative biosynthetic pathways towards 1 and 2 are proposed. Compounds 1-13 and 16-26 exhibited moderate inhibitory activities against phosphodiesterase-4 (PDE4), a drug target for asthma and chronic obstructive pulmonary disease, with IC values in the range of 1.34-7.26 μM.
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http://dx.doi.org/10.1038/s41598-017-01028-4DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5430738PMC
April 2017

Aristoyunnolin H attenuates extracellular matrix secretion in cardiac fibroblasts by inhibiting calcium influx.

Arch Pharm Res 2017 Jan 4;40(1):122-130. Epub 2016 Oct 4.

Guangdong Provincial Key Laboratory of New Drug Design and Evaluation, Guangzhou Higher Education Mega Center, School of Pharmaceutical Sciences, Sun Yat-sen University, 132 East Waihuan Road, Guangzhou, 510006, Guangdong, People's Republic of China.

Aristoyunnolin H is a novel aristophyllene sesquiterpenoid isolated from the traditional Chinese medicine Aristolochia yunnanensis Franch. The present research was designed to explore the anti-fibrotic effects of aristoyunnolin H in adult rat cardiac fibroblasts (CFs) stimulated with angiotensin II (Ang II). Western blot analysis data showed that aristoyunnolin H reduced the upregulation of fibronectin (FN), connective tissue growth factor and collagen I(Col I) production induced by Ang II in CFs. By studying the dynamic intracellular changes of Ca, we further found that while aristoyunnolin H relieved the calcium influx, it has no effect on intracellular calcium store release. Meanwhile, aristoyunnolin H also inhibited the Ang II-stimulated phosphorylation of Ca/calmodulin-dependent protein kinase II. In conclusion, aristoyunnolin H may attenuate extracellular matrix secretion in vitro by inhibiting Ang II-induced calcium signaling.
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http://dx.doi.org/10.1007/s12272-016-0843-4DOI Listing
January 2017

Neolignans from Aristolochia fordiana Prevent Oxidative Stress-Induced Neuronal Death through Maintaining the Nrf2/HO-1 Pathway in HT22 Cells.

J Nat Prod 2015 Aug 30;78(8):1894-903. Epub 2015 Jul 30.

School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou 510006, People's Republic of China.

Bioassay-guided fractionation of the ethanolic extract of the stems of Aristolochia fordiana led to the isolation of six new dihydrobenzofuran neolignans (1-3 and 7-9), three new 2-aryldihydrobenzofurans (4-6), a new 8-O-4' neolignan (10), and 14 known analogues (11-24). The structures of compounds 1-10 were established by spectroscopic methods, and their absolute configurations were determined by analyses of the specific rotation and electronic circular dichroism data. The neuroprotective effects of compounds 1-24 against glutamate-induced cell death were tested in hippocampal neuronal cell line HT22. Compounds 17 and 20-24 exhibited moderate neuroprotective activity by increasing the endogenous antioxidant defense system. In addition, the neolignans activated the Nrf2 (nuclear factor E2-related factor 2) pathway, resulting in the increase of the expression of endogenous antioxidant protein HO-1 (heme oxygenase-1). The active compounds also preserved the levels of antiapoptotic protein Bcl-2 (B cell lymphoma/leukemia-2), which was decreased by glutamate. Collectively, these results suggested that the active neolignans protect neurons against glutamate-induced cell death through maintaining the Nrf2/HO-1 signaling pathway as well as preserving the Bcl-2 protein and might be promising novel beneficial agents for oxidative stress-associated diseases.
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http://dx.doi.org/10.1021/acs.jnatprod.5b00220DOI Listing
August 2015

(±)-Torreyunlignans A-D, rare 8-9' linked neolignan enantiomers as phosphodiesterase-9A inhibitors from Torreya yunnanensis.

J Nat Prod 2014 Dec 12;77(12):2651-7. Epub 2014 Dec 12.

School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou, Guangdong 510006, People's Republic of China.

(±)-Torreyunlignans A-D (1a/1b-4a/4b), four pairs of new 8-9' linked neolignan enantiomers featuring a rare (E)-2-styryl-1,3-dioxane moiety, were isolated from the trunk of Torreya yunnanensis. The structures were determined by combined spectroscopic and chemical methods, and the absolute configurations were elucidated by ECD calculations. The compounds were screened by using tritium-labeled adenosine 3',5'-cyclic monophosphate ([(3)H]-cGMP) as a substrate for inhibitory affinities against phosphodiesterase-9A (PDE9A), which is a potential target for the treatment of diabetes and Alzheimer's disease. All of the enantiomers exhibited inhibition against PDE9A with IC50 values ranging from 5.6 to 15.0 μM. This is the first report of PDE9A inhibitors from nature.
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http://dx.doi.org/10.1021/np500528uDOI Listing
December 2014

Determination of the absolute configuration of two pairs of C-8 - C-9' linked neolignan enantiomers.

Chirality 2014 Dec 29;26(12):825-8. Epub 2014 Oct 29.

School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong, People's Republic of China.

Two pairs of new neolignan enantiomers, (±)-torreyayunan A (1a/1b) and (±)-torreyayunan B (2a/2b), featuring a rare C-8 - C-9' linked skeleton, were isolated from leaves and twigs of Torreya yunnanensis. Their absolute configuration involving two chiral centers was determined by combined spectral and Density Functional Theory (DFT) calculation. This is the first report of the absolute configuration of this group of neolignans.
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http://dx.doi.org/10.1002/chir.22395DOI Listing
December 2014

Prostaglandin Derivatives: Nonaromatic Phosphodiesterase-4 Inhibitors from the Soft Coral Sarcophyton ehrenbergi.

J Nat Prod 2014 Aug;77(8):1928-36

School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou, Guangdong 510006, People's Republic of China.

Ten new prostaglandin derivatives (PGs), sarcoehrendins A-J (1-10), together with five known analogues (11-15) were isolated from the soft coral Sarcophyton ehrenbergi. Compounds 4-8 represented the first examples of PGs featuring an 18-ketone group. The structures including the absolute configurations were elucidated on the basis of spectroscopic analysis and chemical evidence. All of the isolates and six synthetic analogues (3a, 3b, 4a, and 11a-11c) were screened for inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 2, 10, 11a, 11b, and 13-15 exhibited inhibition with IC50 values less than 10 μM, and compound 15 (IC50 = 1.4 μM) showed comparable activity to the positive control rolipram (IC50 = 0.60 μM). The active natural PGs (2, 10, and 13-15) represent the first examples of PDE4 inhibitors without an aromatic moiety, and a preliminary structure-activity relationship is also proposed.
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http://dx.doi.org/10.1021/np500394dDOI Listing
August 2014

Four new cembranoids from the soft coral Sarcophyton sp.

Magn Reson Chem 2014 Sep 10;52(9):515-20. Epub 2014 Jul 10.

School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong, 510006, China.

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http://dx.doi.org/10.1002/mrc.4108DOI Listing
September 2014

Determination of the absolute stereochemistry of two new aristophyllene sesquiterpenes: a combined theoretical and experimental investigation.

Chirality 2014 Apr;26(4):189-93

Aristoyunnolins G (1) and H (2), two new diastereoisomeric sesquiterpenes featuring a rare aristophyllene skeleton, were isolated from the traditional Chinese medicine Aristolochia yunnanensis. Their absolute stereochemistry involving three chiral centers was determined by combined chemical, spectral, and Density Functional Theory (DFT) calculation methods.
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http://dx.doi.org/10.1002/chir.22294DOI Listing
April 2014

Prenylated coumarins: natural phosphodiesterase-4 inhibitors from Toddalia asiatica.

J Nat Prod 2014 Apr 5;77(4):955-62. Epub 2014 Mar 5.

School of Pharmaceutical Sciences, Sun Yat-sen University , Guangzhou, Guangdong 510006, People's Republic of China.

Bioassay-guided fractionation of the ethanolic extract of the roots of Toddalia asiatica led to the isolation of seven new prenylated coumarins (1-7) and 14 known analogues (8-21). The structures of 1-7 were elucidated by spectroscopic analysis, and their absolute configurations were determined by combined chemical methods and chiral separation analysis. Compounds 1-5, named toddalin A, 3‴-O-demethyltoddalin A, and toddalins B-D, represent an unusual group of phenylpropenoic acid-coupled prenylated coumarins. Compounds 1-21 and four modified analogues, 10a, 11a, 13a, and 17a, were screened by using tritium-labeled adenosine 3',5'-cyclic monophosphate ([3H]-cAMP) as substrate for their inhibitory activity against phosphodiesterase-4 (PDE4), which is a drug target for the treatment of asthma and chronic obstructive pulmonary disease. Compounds 3, 8, 10, 10a, 11, 11a, 12, 13, 17, and 21 exhibited inhibition with IC50 values less than 10 μM. Toddacoumalone (8), the most active compound (IC50=0.14 μM), was more active than the positive control, rolipram (IC50=0.59 μM). In addition, the structure-activity relationship and possible inhibitory mechanism of the active compounds are also discussed.
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http://dx.doi.org/10.1021/np401040dDOI Listing
April 2014

Bioactive polyhydroxylated sterols from the marine sponge Haliclona crassiloba.

Steroids 2013 Dec 23;78(14):1353-8. Epub 2013 Oct 23.

School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, PR China.

Four new polyhydroxylated sterols, named halicrasterols A-D (1-4), together with six known analogs (5-10) were isolated from the marine sponge Haliclona crassiloba. Compounds 1 and 2 represented rare examples of steroids featuring 17(20)E-double bonds. The structures of 1-10 were elucidated by spectroscopic analysis and comparison with reported data. This is the first report of a steroid profile for this species. The antimicrobial activities of 1-10 were evaluated against a panel of bacterial and fungal strains in vitro, and compounds 4 and 9 showed moderate activity against some of the Gram-positive strains with MICs ranging from 4 to 32 μg/mL.
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http://dx.doi.org/10.1016/j.steroids.2013.10.004DOI Listing
December 2013

Extracellular signal-regulated kinases (ERK) inhibitors from Aristolochia yunnanensis.

J Nat Prod 2013 Apr 9;76(4):664-71. Epub 2013 Apr 9.

School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, Guangdong 510006, People's Republic of China.

Six new sesquiterpenoids, aristoyunnolins A-F (1-6), an artifact of isolation [7-O-ethyl madolin W (7)], and 12 known analogues were isolated from stems of Aristolochia yunnanensis. The structures were determined by combined chemical and spectral methods, and the absolute configurations of compounds 2, 3, 5-7, 9, 14, and 17 were determined by the modified Mosher's method and CD analysis. Compounds 1-19 were screened using a bioassay system designed to evaluate the effect on mitogen-activated protein kinases (MAPKs) signaling pathways. Among three MAPKs (ERK1/2, JNK, and p38), compounds 1, 4, 10-13, 16, 18, and 19 exhibited selective inhibition of the phosphorylation of ERK1/2. Compounds 16 and 19 were more active than the positive control PD98059, a known inhibitor of the ERK1/2 signaling pathway.
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http://dx.doi.org/10.1021/np300887dDOI Listing
April 2013

Unusual 9,19 : 24,32-dicyclotetracyclic triterpenoids from Lygodium japonicum.

Planta Med 2012 Dec 15;78(18):1971-5. Epub 2012 Nov 15.

School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China.

Lygodipenoids A (1) and B (2), two novel C33 tetracyclic triterpenoids with a new 9,19 : 24,32-dicyclopropane skeleton, were isolated from the whole grass of Lygodium japonicum. Their structures were elucidated by spectroscopic and chemical means. Compounds 1 and 2 were tested in transfected cultured human embryonic kidney 293 HEK293 cells for an agonist assay, and compound 1 was identified as a partial agonist for liver X receptor α.
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http://dx.doi.org/10.1055/s-0032-1327875DOI Listing
December 2012