Publications by authors named "Zhang-Hua Sun"

25 Publications

  • Page 1 of 1

Asymmetric Total Synthesis of the Highly Strained 4β-Acetoxyprobotryane-9β,15α-diol.

J Am Chem Soc 2020 11 11;142(47):19868-19873. Epub 2020 Nov 11.

Shenzhen Grubbs Institute, Department of Chemistry, Guangdong Provincial Key Laboratory of Catalytic Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.

The first and asymmetric total synthesis of 4β-acetoxyprobotryane-9β,15α-diol, containing a rare and highly strained -fused bicyclo[3.3.0]octane ring system, has been achieved. The synthetically challenging [6-5-5] tricyclic ring system in the final product was efficiently and diastereoselectively synthesized via an asymmetric rhodium-catalyzed [4 + 2] cycloaddition reaction, followed by a unique benzilic acid type rearrangement under very mild conditions. The seven contiguous stereocenters were installed efficiently and diastereoselectively.
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http://dx.doi.org/10.1021/jacs.0c10116DOI Listing
November 2020

Tigliane Diterpenoids as a New Type of Antiadipogenic Agents Inhibit GRα-Dexras1 Axis in Adipocytes.

J Med Chem 2019 02 15;62(4):2060-2075. Epub 2019 Feb 15.

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

The phytochemical study of Euphorbia prolifera led to the isolation of two tiglianes (1 and 2) and 23 mysrinanes (3-25). Most of these isolates showed significant antiadipogenic activity in 3T3-L1 adipocyte without apparent cytotoxicity. Subsequent structural modification yielded 10 derivatives, among which 1a, the 5- O-acetyl derivative of 1, turned out to be the most active compound with improved triglyceride-lowering activity (EC for 1 and 1a: 0.61 and 0.32 μM, respectively) and reduced cytotoxicity (selectivity index for 1 and 1a: 28 and 312, respectively). The structure-activity relationship study revealed that the trans-fused 5/7/6 ring system in an angular shape was important to the activity. A mechanistic study indicated that 1 and 1a could inhibit the glucocorticoid receptor α-Dexras1 axis in adipocyte, leading to the retardation of cell differentiation at the early stage. These findings may provide a new type of lipid-lowering agents for future antiobesity drug development.
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http://dx.doi.org/10.1021/acs.jmedchem.8b01693DOI Listing
February 2019

Geospallins A⁻C: New Thiodiketopiperazines with Inhibitory Activity against Angiotensin-Converting Enzyme from a Deep-Sea-Derived Fungus FS140.

Mar Drugs 2018 Nov 23;16(12). Epub 2018 Nov 23.

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.

Three new thiodiketopiperazines, geospallins A⁻C (⁻), together with nine known analogues (⁻), were isolated from the culture of the deep-sea sediment-derived fungus FS140. Among them, geospallins A and B ( and ) represent rare examples of thiodiketopiperazines featuring an S-methyl group at C-10 and a tertiary hydroxyl group at C-11. Their structures were determined by high-resolution electrospray mass spectrometry (HRESIMS), spectroscopic analyses, and electronic circular dichroism (ECD) calculations. Their angiotensin-converting enzyme (ACE) inhibitory activity was reported, and geospallins A⁻C (⁻) showed inhibitory activity with IC values of 29⁻35 µM.
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http://dx.doi.org/10.3390/md16120464DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6315564PMC
November 2018

Tetrahydrocurcumin and octahydrocurcumin, the primary and final hydrogenated metabolites of curcumin, possess superior hepatic-protective effect against acetaminophen-induced liver injury: Role of CYP2E1 and Keap1-Nrf2 pathway.

Food Chem Toxicol 2019 Jan 10;123:349-362. Epub 2018 Nov 10.

Guangdong Provincial Key Laboratory of New Drug Development and Research of Chinese Medicine, Mathematical Engineering Academy of Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou, 510006, PR China. Electronic address:

Acetaminophen (APAP) overdose-induced hepatotoxicity is tightly associated with oxidative stress. Tetrahydrocurcumin (THC) and octahydrocurcumin (OHC), the primary and final hydrogenated metabolites of curcumin (CUR), possess stronger antioxidant activity in vitro. The present study was performed to investigate the potential and mechanism of OHC and THC against APAP-induced hepatotoxicity in parallel to CUR. Our results showed that OHC and THC dose-dependently enhanced liver function (ALT and AST levels) and alleviated histopathological deterioration. Besides, OHC and THC significantly restored the hepatic antioxidant status by miring level of MDA and ROS, and elevated levels of GSH, SOD, CAT and T-AOC. In addition, OHC and THC markedly suppressed the activity and expressions of CYP2E1, and bound to the active sites of CYP2E1. Moreover, OHC and THC activated the Keap1-Nrf2 pathway and enormously enhanced the translational activation of Nrf2-targeted gene (GCLC, GCLM, NQO1 and HO-1) against oxidative stress, via inhibiting the expression of Keap1 and blocking the interaction between Keap1 and Nrf2. Particularly, OHC and THC exerted superior hepato-protective and antioxidant activities to CUR. In conclusion, OHC and THC possess favorable hepato-protective effect through restoring antioxidant status, inhibiting CYP2E1 and activating Keap1-Nrf2 pathway, which might represent promising antioxidants for the treatment of APAP-induced hepatotoxicity.
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http://dx.doi.org/10.1016/j.fct.2018.11.012DOI Listing
January 2019

[Sesquiterpenoids of endophytic fungus Cerrena sp. from Pogostemon cablin and their cytotoxic activities].

Zhongguo Zhong Yao Za Zhi 2017 May;42(9):1693-1698

Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, State Key Laboratory of Applied Microbiology Southern China, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.

The secondary metabolites of endophytic fungus Cerrena sp.A593 from Pogostemon cablin and their cytotoxic activities were investigated. Eight sesquiterpenoids were isolated from the fermentation broth of the strain A593 by silica gel, reverse phase silica gel, Sephadex LH-20, HPLC and so on. Their structures were identified as chloriolin B(1), chloriolin C(2), pleurocybellone A(3), dihydrohypnophilin(4), cucumin F(5), antrodin A(6), 10α-hydroxyamorphan-4-en-3-one(7), and connatusin A(8). Compounds 1- 8 were firstly found from the genus Cerrena. All isolated sesquiterpenoids were evaluated for in vitro cytotoxic activities against HepG-2, SF-268, MCF-7 and NCI-H460 tumor cell lines. Compounds 1-3 showed inhibitory activities against the four tumor cell lines with IC₅₀ values ranging from 20.33 to 63.13 μmol•L⁻¹.
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http://dx.doi.org/10.19540/j.cnki.cjcmm.20170224.009DOI Listing
May 2017

Two New Metabolites from the Endophytic Fungus Alternaria sp. A744 Derived from Morinda officinalis.

Molecules 2017 May 8;22(5). Epub 2017 May 8.

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.

Two new compounds isobenzofuranone A () and indandione B (), together with eleven known compounds (-) were isolated from liquid cultures of an endophytic fungus sp., which was obtained from the medicinal plant . Among them, the indandione () showed a rarely occurring indanone skeleton in natural products. Their structures were elucidated mainly on the basis of extensive spectroscopic data analysis. All of the compounds were evaluated with cytotoxic and α-glucosidase inhibitory activity assays. Compounds and showed significant inhibitory activities against four tumor cell lines; MCF-7, HepG-2, NCI-H460 and SF-268, with IC values in the range of 1.91-9.67 μM, and compounds , , , , and showed excellent inhibitory activities against α-glucosidase with IC values in the range of 12.05-166.13 μM.
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http://dx.doi.org/10.3390/molecules22050765DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154570PMC
May 2017

Three new highly-oxygenated metabolites from the endophytic fungus Cytospora rhizophorae A761.

Fitoterapia 2017 Mar 13;117:1-5. Epub 2016 Dec 13.

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China. Electronic address:

Cytosporaphenones A-C, one new polyhydric benzophenone and two new naphtopyrone derivatives, along with eight known ones, were isolated from Cytospora rhizophorae, an endophytic fungus from Morinda officinalis. Their structures were fully characterized by means of detailed spectroscopic analysis and X-ray single crystal diffraction. To our knowledge, the three new compounds were the most highly oxygenated metabolites of their families discovered in nature. Moreover, all of the compounds were evaluated for in vitro cytotoxic activities against MCF-7, NCI-H460, HepG-2 and SF-268 tumor cell lines, and the new compound 1 exhibited weak growth inhibitory activity against the tumor cell lines MCF-7 and HepG-2 with IC values of 70 and 60μM, respectively.
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http://dx.doi.org/10.1016/j.fitote.2016.12.005DOI Listing
March 2017

Dichotocejpins A-C: New Diketopiperazines from a Deep-Sea-Derived Fungus Dichotomomyces cejpii FS110.

Mar Drugs 2016 Sep 9;14(9). Epub 2016 Sep 9.

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.

Three new diketopiperazines, dichotocejpins A-C (1-3), together with eight known analogues (4-11), were isolated from the culture of the deep-sea sediment derived fungus Dichotomomyces cejpii FS110. Their structures, including absolute configurations, were elucidated by a combination of HRESIMS, NMR, X-ray crystallography, and ECD calculations. Compounds 4-6, 10-11 showed significant cytotoxic activities against MCF-7, NCI-H460, HepG-2, and SF-268 tumor cell lines. Compound 1 exhibited excellent inhibitory activity against α-glucosidase with an IC50 of 138 μM.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5039535PMC
http://dx.doi.org/10.3390/md14090164DOI Listing
September 2016

Two New Secondary Metabolites from the Endophytic Fungus Endomelanconiopsis endophytica.

Molecules 2016 Jul 20;21(7). Epub 2016 Jul 20.

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.

Two new secondary metabolites, endomeketals A-B (1-2), a new natural product (3), and a known compound (4) were isolated from the ethyl acetate extract of the endophytic fungus Endomelanconiopsis endophytica A326 derived from Ficus hirta. Their structures were determined on the basis of extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. However, no compound showed cytotoxic activity against these human tumor cell lines.
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http://dx.doi.org/10.3390/molecules21070943DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274285PMC
July 2016

A new serratene triterpenoid from Lycopodium japonicum.

J Asian Nat Prod Res 2017 Mar 14;19(3):299-303. Epub 2016 Jul 14.

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

Phytochemical investigation on the herbs of Lycopodium japonicum led to the isolation of a new serratene triterpenoid, 3α,21α-dihydroxy-16-oxoserrat-14-en-24-yl p-coumarate (1), together with two known ones, lycernuic ketone C (2) and tohogenol (3). Their structures were elucidated by extensive spectroscopic methods, including 1D- and 2D-NMR and HR-ESI-MS. The C NMR data of tohogenol was first reported.
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http://dx.doi.org/10.1080/10286020.2016.1208182DOI Listing
March 2017

Monoterpenes and sesquiterpenes from the marine sediment-derived fungus Eutypella scoparia FS46.

J Asian Nat Prod Res 2017 Feb 3;19(2):145-151. Epub 2016 Jun 3.

a State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology , Guangdong Institute of Microbiology , Guangzhou 510070 , China.

Eutypellol A (1), the first norsesquiterpenoid of sequicarene family, as well as eutypellol B (2), a rare 7-methyl oxidized 2-carene derivative, and one new natural product 2-(2-hydroxy-4-methylcyclohex-3-enyl)propanoic acid (3), along with eight known terpenoids, were isolated from the marine sediment-derived fungus Eutypella scoparia FS46 collected from the South China Sea. Their structures were established on the basis of extensive spectroscopic analysis. Compounds 1-3 were evaluated for their antibacterial activities against Staphylococcus aureus and cytotoxic activities against MCF-7, NCI-H460, and SF-268 tumor cell lines.
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http://dx.doi.org/10.1080/10286020.2016.1189906DOI Listing
February 2017

Two new xyloketals from the endophytic fungus Endomelanconiopsis endophytica derived from medicinal plant Ficus hirta.

J Asian Nat Prod Res 2016 Nov 31;18(11):1036-41. Epub 2016 May 31.

a State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology , Guangdong Institute of Microbiology , Guangzhou 510070 , China.

Chemical examination of the liquid culture of Endomelanconiopsis endophytica A326 isolated from the Chinese folk medicine Ficus hirta resulted in the isolation of two new xyloketals named xyloketals K and L (1-2) and three known analogs (3-5) including a new natural product (5). Their structures were determined on the basis of extensive spectroscopic analysis. All compounds were evaluated for their cytotoxic activities against the SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. Nonetheless, no significant activity was observed.
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http://dx.doi.org/10.1080/10286020.2016.1188084DOI Listing
November 2016

[Study on cytotoxic secondary metabolites of endophytic fungus Diaporthe longicolla A616 from Pogostemon cablin].

Zhongguo Zhong Yao Za Zhi 2016 Jun;41(11):2112-2117

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.

To study active secondary metabolites of endophytic fungus Diaporthe longicolla A616 isolated from Pogostemon cablin. Ten compounds were isolated from fermentation product of the strain 616 by silica gel, reverse phase silica gel, Sephadex-LH20, HPLC and so on. Their structures were identified as 1,3-diamino-1,3-dimethylurea(1),(7R,9R)-7-hydroxy-9-propyl-5-nonen-9-olide(2), Ergosta-5,7,22-trien-3β-ol(3),(22E,24R)-ergosta-4,6,8(14)-22-tetraen-3-one(4),(22E,24R)-3β,5α-dihydroxy-6β-ergosta-7,22-diene(5), citreoisocoumarin(6), glycerol monolinoleate(7), 1-(2-hydroxyethoxy)ethyl(E)-octadec-9-enoate(8), cyclo-(L-Pro-L-Ala)(9), cyclo(L)-Pro-(L)-Val(10), respectively, based on extensive spectroscopic analysis and literature comparisons. Compounds 6-10 were isolated from the genus Diaporthe for the first time. All isolated compounds were evaluated for in vitro cytotoxic activities against SF-268, MCF-7, NCI-H460 and HepG-2 tumor cell lines. Compounds 4 and 5 showed potent growth inhibitory activities against the four cell lines with IC₅₀ values of 5.3, 6.5, 12.2, 6.1μmol•L⁻¹ and 8.2, 5.2, 6.1, 9.4μmol•L⁻¹, respectively.
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http://dx.doi.org/10.4268/cjcmm20161122DOI Listing
June 2016

Perangustols A and B, a pair of new azaphilone epimers from a marine sediment-derived fungus Cladosporium perangustm FS62.

J Asian Nat Prod Res 2016 Nov 30;18(11):1024-9. Epub 2016 May 30.

a State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology , Guangdong Institute of Microbiology , Guangzhou 510070 , China.

A pair of new azaphilone epimers, perangustols A-B (1-2), and two new natural products (3-4), together with two known metabolites (5-6) were isolated from the culture of the marine sediment-derived fungus Cladosporium perangustum FS62. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The isolated compounds (1-6) were evaluated for their cytotoxic activities against the SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. Nonetheless, no significant activity was observed.
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http://dx.doi.org/10.1080/10286020.2016.1181623DOI Listing
November 2016

New Cembrane-Type Diterpenoids from the South China Sea Soft Coral Sarcophyton ehrenbergi.

Molecules 2016 May 4;21(5). Epub 2016 May 4.

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

Chemical investigation on the soft coral Sarcophyton ehrenbergi collected from the Xisha Islands of the South China Sea have led to the isolation of eight cembranoids including five new ones, sarcophytonoxides A-E (1-5). The structures of new cembranoids (1-5) were determined by spectroscopic analysis and comparison of the NMR data with those of related analogues. The cytotoxicities of compounds 1-8 against human ovarian cancer cell line A2780 were also evaluated.
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http://dx.doi.org/10.3390/molecules21050587DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273003PMC
May 2016

Two New Cinnamyl Isovalerate Derivatives from Sabina gaussenii.

Molecules 2016 Apr 29;21(5). Epub 2016 Apr 29.

Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Kunming 650223, China.

Chemical investigation of the 90% acetone extract of the branches and leaves of Sabina gaussenii led to the isolation of two new cinnamyl isovalerate derivatives (1-2) and eighteen known compounds (3-20). Their structures were determined mainly by means of MS, 1D- and 2D-NMR data, and this is the first time these compounds have been reported from this plant. The biological activity test results indicated that the 90% acetone extract showed cytotoxicity against the human lung adenocarcinoma (A549) cell line (IC50 = 0.98 ± 0.1 μg/mL), compound 6 showed cytotoxicities against human cervical carcinoma (HeLa) (IC50 = 0.4 ± 0.1 μM ) and human gastric carcinoma (BGC-823) (IC50 = 0.9 ± 0.2 μM) cancer cell lines, and compound 19 showed cytotoxicities against HeLa (IC50 = 1.5 ± 0.4 μM), BGC-823 (IC50 = 7.0 ± 0.8 μM ), and A549 (IC50 = 10.6 ± 1.5 μM ) cancer cell lines.
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http://dx.doi.org/10.3390/molecules21050571DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273497PMC
April 2016

Cytotoxic cochlioquinone derivatives from the endophytic fungus Bipolaris sorokiniana derived from Pogostemon cablin.

Fitoterapia 2016 Apr 11;110:77-82. Epub 2016 Feb 11.

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Xianlie Road 100, Guangzhou 510070, China.

Chemical investigation of the liquid culture of the endophytic fungus Bipolaris sorokiniana A606, which was isolated from the medicinal plant Pogostemon cablin resulted in the isolation of four new cytotoxic compounds, named isocochlioquinones D-E (1-2) and cochlioquinones G-H (3-4), along with five known cochlioquinone analogues (5-9). Their structures were determined on the basis of extensive spectroscopic analysis. Isocochlioquinone D (1) possessed a rare benzothiazin-3-one moiety and cochlioquinone G (3) was the first example of cochlioquinones bearing an indole-4,7-dione fragment. All of the isolates (1-9) were evaluated for their cytotoxic activities against MCF-7, NCI-H460, SF-268 and HepG-2 tumor cell lines by the sulforhodamine B (SRB) assay. Compounds 4 and 6-9, featuring a cochlioquinone core, exhibited potent cytotoxicities in vitro against the four tumor cell lines, and a preliminary structure-activity relationship of these compounds was also discussed.
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http://dx.doi.org/10.1016/j.fitote.2016.02.005DOI Listing
April 2016

Cytotoxic trichothecene macrolides from the endophyte fungus Myrothecium roridum.

J Asian Nat Prod Res 2016 Jul 21;18(7):684-9. Epub 2016 Jan 21.

a State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology , Guangdong Institute of Microbiology , Guangzhou , China.

A new cytotoxic roridin-type trichothecene macrolide named epiroridin acid (1) and two known compounds epiroridin E (2) and mytoxin B (3) were isolated from the liquid culture of Myrothecium roridum A553, which was isolated from the medicinal plant Pogostemon cablin. The structure of the new macrolide (1) was elucidated by extensive spectroscopic measurements (UV, IR, MS, and 1D and 2D NMR) analyses. All isolated compounds (1-3) were evaluated for their cytotoxic activities against SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. The new compound (1) exhibited well cytotoxicity against the four selected tumor cell lines.
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http://dx.doi.org/10.1080/10286020.2015.1134505DOI Listing
July 2016

Guignardones P-S, New Meroterpenoids from the Endophytic Fungus Guignardia mangiferae A348 Derived from the Medicinal Plant Smilax glabra.

Molecules 2015 Dec 21;20(12):22900-7. Epub 2015 Dec 21.

State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Guangdong Open Laboratory of Applied Microbiology, Guangdong Institute of Microbiology, Guangzhou 510070, China.

Four new meroterpenoids, guignardones P-S (1-4), and three known analogues (5-7) were isolated from the endophytic fungal strain Guignardia mangiferae A348. Their structures were elucidated on the basis of spectroscopic analysis and single crystal X-ray diffraction. All the isolated compounds were evaluated for their inhibitory effects on SF-268, MCF-7, and NCI-H460 human cancer cell lines. Compounds 2 and 4 exhibited weak inhibitions of cell proliferation against MCF-7 cell line.
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http://dx.doi.org/10.3390/molecules201219890DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6332344PMC
December 2015

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

Isolation and cytotoxicity evaluation of taxanes from the barks of Taxus wallichiana var. mairei.

Bioorg Med Chem Lett 2015 Mar 30;25(6):1240-3. Epub 2015 Jan 30.

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

Fifteen taxanes (1-15) including a new taxane glucoside, 7β,9α,10β-triacetoxy-13α-hydroxy-5α-O-(β-d-glucopyranosyl)taxa-4(20),11-diene (1), were isolated from the barks of Taxus wallichiana var. mairei. Compounds 1-15 representing three sub-types of 6/8/6-taxane were evaluated in vitro for anti-proliferative activity against a panel of parental and drug-resistant cancer cells. Potent compounds were found while several exhibited selective cytotoxicity. Especially, 3, 8, and 10 showed selective inhibition to breast carcinoma cell line MCF-7, while 13 selectively inhibited taxol resistant human ovarian carcinoma cell line A2780/TAX (IC50=0.19μM), being more potent than the clinical drugs taxol (IC50=4.4μM) and docetaxol (IC50=0.42μM), and less cytotoxic to mouse embryonic fibroblast cell line NIH-3T3, a cell line close to normal cell line. The possible P-glycoprotein evasion mechanism of 13 against A2780/TAX and the preliminary structure-activity relationships (SARs) of this group of compounds were also discussed.
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http://dx.doi.org/10.1016/j.bmcl.2015.01.056DOI Listing
March 2015

A new lignan glycoside from Chamaecyparis obtusa var. breviramea f. crippsii.

Nat Prod Commun 2014 Feb;9(2):215-6

A new lignan glycoside, (-)-(8S, 8'R)-thujastandin-4-O-beta-D-glucopyranoside (1), together with fourteen known lignanoids (2-15) and one coumarin (16) were isolated from the branches and leaves of Chamaecyparis obtusa var. breviramea f. crippsii. Their structures were elucidated by extensive spectroscopic and spectrometric analysis. Compound 16 exhibited cytotoxicity against A549, BGC-823 and Hela cell lines with IC50 values of 25.9, 20.9 and 18.5 microM, respectively.
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February 2014

Six new tetraprenylated alkaloids from the South China Sea gorgonian Echinogorgia pseudossapo.

Mar Drugs 2014 Jan 27;12(2):672-81. Epub 2014 Jan 27.

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

Six new tetraprenylated alkaloids, designated as malonganenones L-Q (1-6), were isolated from the gorgonian Echinogorgia pseudossapo, collected in Daya Bay of Guangdong Province, China. The structures of 1-6 featuring a methyl group at N-3 and a tetraprenyl chain at N-7 in the hypoxanthine core were established by extensive spectroscopic analyses. Compounds 1-6 were tested for their inhibitory activity against the phosphodiesterases (PDEs)-4D, 5A, and 9A, and compounds 1 and 6 exhibited moderate inhibitory activity against PDE4D with IC₅₀ values of 8.5 and 20.3 µM, respectively.
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http://dx.doi.org/10.3390/md12020672DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3944508PMC
January 2014

Neuroprotective polyhydroxypregnane glycosides from Cynanchum otophyllum.

Steroids 2013 Oct 4;78(10):1015-20. Epub 2013 Jul 4.

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

Five new polyhydroxypregnane glycosides, namely cynanotosides A-E (1-5), together with two known analogues, deacetylmetaplexigenin (6) and cynotophylloside H (7), were isolated from the roots of Cynanchum otophyllum. Their structures were established by spectroscopic methods and acid hydrolysis. The neuroprotective effects of compounds 1-7 against glutamate-, hydrogen peroxide-, and homocysteic acid (HCA)-induced cell death were tested by MTT assay in a hippocampal neuronal cell line HT22. Compounds 1, 2, and 7 exhibited protective activity against HCA-induced cell death in a dose-dependent manner ranging from 1 to 30μM, which may explain the Traditional Chinese Medicine (TCM) use of this plant for the treatment of epilepsy.
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http://dx.doi.org/10.1016/j.steroids.2013.06.007DOI Listing
October 2013

A new phenolic glycoside from Chamaecyparis obtusa var. breviramea f. crippsii.

Molecules 2013 Jan 18;18(1):1255-61. Epub 2013 Jan 18.

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Heilongtan, Kunming 650201, China.

A new phenolic glycoside, 3-methoxyphenol 1-O-α-L-rhamnopyranosyl-(1→6)- O-β-D-glucopyranoside (1), was isolated from the 90% acetone extract of the branches and leaves of Chamaecyparis obtusa var. breviramea f. crippsii along with another 10 known phenolics 2-11. Their structures were determined mainly by means of MS, 1D- and 2D-NMR data. Cytotoxicities of compounds 3 and 5-11 were tested on BGC-823, Hela and A549 cancer cell lines, the results showed that compound 8 was bioactive and its IC(50) values were 6.9, 29.7 and 52.9 μM, respectively.
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http://dx.doi.org/10.3390/molecules18011255DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270199PMC
January 2013