Zhi-Gang She

Name: 佘志刚; She, ZhiGang

Organization: Sun Yat-sen (Zhongshan) University , China

Department: School of Chemistry and Chemical Engineering

Title: Professor(PhD)

Chemicals
References

Diaporisoindoles A–C: Three Isoprenylisoindole Alkaloid Derivatives from the Mangrove Endophytic Fungus Diaporthe sp. SYSU-HQ3

Co-reporter:Hui Cui, Yun Lin, Mingchu Luo, Yongjun Lu, Xishan Huang, and Zhigang She

Organic Letters October 20, 2017 Volume 19(Issue 20) pp:5621-5621

Publication Date(Web):September 29, 2017

DOI:10.1021/acs.orglett.7b02748

Diaporisoindoles A (1) and B (2), two novel isoprenylisoindole alkaloids, and an unusual diisoprenylisoindole dimer diaporisoindole C (3), together with a precursor tenellone C (4) were all isolated from the endophytic fungus Diaporthe sp. SYSU-HQ3. The absolute configurations of 1–4 were elucidated by spectroscopic analysis, X-ray diffraction, and quantum chemical calculations. Diaporisoindole A (1) and tenellone C (4) exhibited inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B with IC50 values of 4.2 and 5.2 μM.

Lasiodiplactone A, a novel lactone from the mangrove endophytic fungus Lasiodiplodia theobromae ZJ-HQ1

Co-reporter:Senhua Chen;Zhaoming Liu;Hongju Liu;Yuhua Long;Dongni Chen;Yongjun Lu;Zhigang She

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 30) pp:6338-6341

Publication Date(Web):2017/08/02

DOI:10.1039/C7OB01657C

Lasiodiplactone A (1), an unprecedented lactone, was obtained from the mangrove endophytic fungus Lasiodiplodia theobromae ZJ-HQ1. The structure of 1 was established by analysis of NMR spectroscopic data and electronic circular dichroism (ECD) spectra. Lasiodiplactone A (1) was the first example of lactone that possesses a unique tetracyclic system (12/6/6/5) of RAL12 (12-membered β-resorcylic acid lactone) with a pyran ring and a furan ring. A possible biogenetic pathway for 1 was proposed. Compound 1 showed anti-inflammatory activity by inhibiting nitric oxide (NO) production in lipopolysaccharide activated in RAW264.7 cells with IC50 value of 23.5 μM and exhibited potential α-glucosidase inhibitory activity with IC50 values of 29.4 μM.

Depsidones from Talaromyces stipitatus SK-4, an endophytic fungus of the mangrove plant Acanthus ilicifolius

Co-reporter:Runlin Cai, Senhua Chen, Yuhua Long, Chunyuan Li, ... Zhigang She

Phytochemistry Letters 2017 Volume 20(Volume 20) pp:

Publication Date(Web):1 June 2017

DOI:10.1016/j.phytol.2017.04.023

•Two new depsidones named talaromyones A and B (1 and 2) were isolated from Talaromyces stipitatus.•New compound's absolute configuration was elucidated by modified Mosher's method.•Compound 2 showed antibacterial activity against Bacillus subtilis with an MIC value of 12.5 μg/mL.•Compounds 2, 4 and 5 displayed moderate inhibitory activities against α-glucosidase with IC50 values ranging from 48.4 to 99.8 μM.An endophytic fungus (Talaromyces stipitatus SK-4) was isolated from the leaves of a mangrove plant Acanthus ilicifolius. Its crude extract exhibited significant antibacterial activity and was purified to afford two new depsidones, talaromyones A and B (1 and 2), along with five known depsidone analogs (3–7). Their structures, including absolute configuration, were elucidated through extensive spectroscopic data analysis and modified Mosher's method. Compound 2 showed antibacterial activity against Bacillus subtilis with an MIC value of 12.5 μg/mL. In the inhibitory assay against α-glucosidase, compounds 2, 4 and 5 displayed moderate activities with IC50 values ranging from 48.4 to 99.8 μM.Download high-res image (138KB)Download full-size image

Talaramide A, an unusual alkaloid from the mangrove endophytic fungus Talaromyces sp. (HZ-YX1) as an inhibitor of mycobacterial PknG

Co-reporter:Senhua Chen;Liqing He;Dongni Chen;Runlin Cai;Yuhua Long;Yongjun Lu;Zhigang She

New Journal of Chemistry (1998-Present) 2017 vol. 41(Issue 11) pp:4273-4276

Publication Date(Web):2017/05/30

DOI:10.1039/C7NJ00059F

An unusual alkaloid, talaramide A (1), was obtained from the mangrove endophytic fungus Talaromyces sp. (HZ-YX1). The structure of 1 was established by analysis of NMR spectroscopic data, X-ray diffraction data, and electronic circular dichroism (ECD) spectra. Talaramide A (1) is the second example of an alkaloid that possesses a unique oxidized tricyclic system. A possible biosynthetic pathway for 1 was proposed. Compound 1 showed promising inhibition of mycobacterial PknG activity with an IC50 value of 55 μM.

Chroman-4-one and pyrano[4,3-b]chromenone derivatives from the mangrove endophytic fungus Diaporthe phaseolorum SKS019

Co-reporter:Hui Cui;Meng Ding;Dane Huang;Zhengrui Zhang;Huiting Liu;Hongbo Huang;Zhigang She

RSC Advances (2011-Present) 2017 vol. 7(Issue 33) pp:20128-20134

Publication Date(Web):2017/04/05

DOI:10.1039/C7RA03032K

Seven new compounds: diaporchromanones A–D (1–4), (−)-phomopsichin A (5a), (+)-phomopsichin B (6a), and (±)-diaporchromone A (7), along with the known (+)-phomopsichin A (5b) and (−)-phomopsichin B (6b) were isolated from an endophytic fungus Diaporthe phaseolorum SKS019. The structures of the new compounds, including their absolute configurations, were determined on the basis of HRESIMS and NMR spectroscopic data, and experimental ECD and Rh2(OCOCF3)4-induced CD spectra analyses. Diaporchromanone A (1)/B (2), and C (3)/D (4) are two pairs of 3-epimers, and their structures possessing 3-substituted-chroman-4-one skeleton are rarely found in natural sources. (−)-Phomopsichin A (5a) and (+)-phomopsichin B (6a) are enantiomers of (+)-phomopsichin A (5b) and (−)-phomopsichin B (6b), respectively. All of the isolates were evaluated for their inhibitory effects against osteoclastogenesis in the RAW 264.7 cell line using luciferase reporter gene assays. Compounds 3–6b exhibited moderate inhibitory effects on osteoclastogenesis by suppressing the receptor activator of NF-κB by ligand-induced NF-κB activation.

(+)- and (−)-Ascomlactone A: a pair of novel dimeric polyketides from a mangrove endophytic fungus Ascomycota sp. SK2YWS-L

Co-reporter:Zhaoming Liu;Senhua Chen;Pei Qiu;Chunbing Tan;Yuhua Long;Yongjun Lu;Zhigang She

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 48) pp:10276-10280

Publication Date(Web):2017/12/14

DOI:10.1039/C7OB02707A

A pair of novel enantiomeric polyketide dimers, (+)- and (−)-ascomlactone A (1a and 1b), were obtained from a mangrove endophytic fungus Ascomycota sp. SK2YWS-L. The structures were elucidated based on spectroscopic methods, and the absolute configurations were determined by X-ray diffraction and electronic circular dichroism (ECD) calculations. Ascomlactone A possessed an unprecedented polymerization system, which constructed an unusual nine-membered lactone ring between the monomers. A possible biogenetic pathway was proposed. Both 1a and 1b exhibited significant inhibitory effects against α-glucosidase with IC50 values of 63.7 and 27.9 μM, respectively. A further docking study provided an inside perspective of the action in α-glucosidase.

Aspterpenacids A and B, Two Sesterterpenoids from a Mangrove Endophytic Fungus Aspergillus terreus H010

Co-reporter:Zhaoming Liu, Yan Chen, Senhua Chen, Yayue Liu, Yongjun Lu, Dongni Chen, Yongcheng Lin, Xishan Huang, and Zhigang She

Organic Letters 2016 Volume 18(Issue 6) pp:1406-1409

Publication Date(Web):March 3, 2016

DOI:10.1021/acs.orglett.6b00336

Two new sesterterpenoids, aspterpenacids A (1) and B (2), with an unusual carbon skeleton of a 5/3/7/6/5 ring system were isolated from the mangrove endophytic fungus Aspergillus terreus H010. Their structures were elucidated on the basis of spectroscopic methods, single-crystal X-ray diffraction analysis, and electronic circular dichroism calculations. A biogenetic pathway for 1 and 2 is proposed. Both 1 and 2 showed no significant antibacterial activity or cytotoxicity at 50 μM.

Cytotoxic and Antibacterial Preussomerins from the Mangrove Endophytic Fungus Lasiodiplodia theobromae ZJ-HQ1

Co-reporter:Senhua Chen, Dongni Chen, Runlin Cai, Hui Cui, Yuhua Long, Yongjun Lu, Chunyuan Li, and Zhigang She

Journal of Natural Products 2016 Volume 79(Issue 9) pp:2397-2402

Publication Date(Web):August 25, 2016

DOI:10.1021/acs.jnatprod.6b00639

Two new chlorinated preussomerins, chloropreussomerins A and B (1 and 2), together with nine known preussomerin analogues, 3–11, were obtained from the endophytic fungus Lasiodiplodia theobromae ZJ-HQ1. Their structures were elucidated by a combination of spectroscopic analyses. The absolute configurations of 1 and 2 were both determined by single-crystal X-ray diffraction using Cu Kα radiation. Chloropreussomerins A and B (1 and 2) are the first chlorinated compounds in the preussomerin family, and preussomerin M (3) is reported for the first time as a natural product. Compounds 1 and 2 showed potent in vitro cytotoxicity against A549 and MCF-7 human cancer cell lines, with IC50 values ranging from 5.9 to 8.9 μM, and compounds 4–7 exhibited significant bioactivity against A549, HepG2, and MCF-7 human cancer cell lines, with IC50 values of 2.5–9.4 μM. In the antibacterial assay, compounds 1, 2, 5–7, and 11 exhibited significant activities against Staphylococcus aureus, with MIC values between 1.6 and 13 μg/mL.

Isocoumarins and benzofurans from the mangrove endophytic fungus Talaromyces amestolkiae possess α-glucosidase inhibitory and antibacterial activities

Co-reporter:Senhua Chen, Yayue Liu, Zhaoming Liu, Runlin Cai, Yongjun Lu, Xishan Huang and Zhigang She

RSC Advances 2016 vol. 6(Issue 31) pp:26412-26420

Publication Date(Web):04 Mar 2016

DOI:10.1039/C6RA02566H

Six new isocoumarins, compounds 1–4 and 14–15, two new benzofurans, 16–17, along with nine known isocoumarin analogues, 5–13 were obtained from the mangrove endophytic fungus Talaromyces amestolkiae YX1. Their structures were elucidated by analysis of spectroscopic data. The absolute configuration of compounds 4, 14 and 15 were determined by the modified Mosher's method and comparison of their CD spectra with dihydroisocoumarins described in the literature. The structure of compound 5 was further confirmed by a single-crystal X-ray diffraction experiment using Cu Kα radiation. Compounds 2, 6, 8, and 10 showed α-glucosidase inhibitory activity with IC50 values of 89.4, 17.2, 36.4, and 38.1 μM, respectively. In the antibiotic assay, compounds 16 and 17 exhibited antibacterial activities with MIC values between 25–50 μg mL−1 against the Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, and Bacillus subtilis.

Altenusin derivatives from mangrove endophytic fungus Alternaria sp. SK6YW3L

Co-reporter:Yayue Liu, Yingnan Wu, Rui Zhai, Zhaoming Liu, Xishan Huang and Zhigang She

RSC Advances 2016 vol. 6(Issue 76) pp:72127-72132

Publication Date(Web):22 Jul 2016

DOI:10.1039/C6RA16214B

Five new altenusin derivatives, compounds 1–5, along with six known analogues 6–11, were isolated from a culture of the endophytic fungus Alternaria sp. SK6YW3L, which was isolated from a fresh fruit of the mangrove plant Sonneratia caseolaris, collected from the South China Sea. Their structures were elucidated by analysis of 1D and 2D NMR and high resolution mass spectroscopic data. The absolute configurations of compounds 1–3 and 5 were assigned by quantum chemical calculations of the electronic circular dichroic (ECD) spectra. Structures of compounds 1 and 4 were further confirmed by single-crystal X-ray diffraction experiments using Cu Kα radiation. All isolated compounds were evaluated for α-glucosidase inhibitory activity, and compounds 2, 3 and 9 exhibited moderate inhibitory activity. The plausible biosynthetic pathways for all the compounds were proposed.

Polyketides with α-Glucosidase Inhibitory Activity from a Mangrove Endophytic Fungus, Penicillium sp. HN29-3B1

Co-reporter:Yayue Liu, Qin Yang, Guoping Xia, Hongbo Huang, Hanxiang Li, Lin Ma, Yongjun Lu, Lei He, Xuekui Xia, and Zhigang She

Journal of Natural Products 2015 Volume 78(Issue 8) pp:1816-1822

Publication Date(Web):July 31, 2015

DOI:10.1021/np500885f

Five new compounds, pinazaphilones A and B (1, 2), two phenolic compounds (4, 5), and penicidone D (6), together with the known Sch 1385568 (3), (±)-penifupyrone (7), 3-O-methylfunicone (8), 5-methylbenzene-1,3-diol (9), and 2,4-dihydroxy-6-methylbenzoic acid (10) were obtained from the culture of the endophytic fungus Penicillium sp. HN29-3B1, which was isolated from a fresh branch of the mangrove plant Cerbera manghas collected from the South China Sea. Their structures were determined by analysis of 1D and 2D NMR and mass spectroscopic data. Structures of compounds 4 and 7 were further confirmed by a single-crystal X-ray diffraction experiment using Cu Kα radiation. The absolute configurations of compounds 1–3 were assigned by quantum chemical calculations of the electronic circular dichroic spectra. Compounds 2, 3, 5, and 7 inhibited α-glucosidase with IC50 values of 28.0, 16.6, 2.2, and 14.4 μM, respectively, and are thus more potent than the positive control, acarbose.

β-Resorcylic acid derivatives with α-glucosidase inhibitory activity from Lasiodiplodia sp. ZJ-HQ1, an endophytic fungus in the medicinal plant Acanthus ilicifolius

Co-reporter:Senhua Chen, Zhaoming Liu, Hanxiang Li, Guoping Xia, Yongjun Lu, Lei He, Shaodong Huang, Zhigang She

Phytochemistry Letters 2015 Volume 13() pp:141-146

Publication Date(Web):September 2015

DOI:10.1016/j.phytol.2015.05.019

•Three new resorcylic acid derivatives were isolated from Lasiodiplodia sp. ZJ-HQ1.•The structure of the new compounds were determined by spectroscopic data analysis.•Seven compounds showed better α-glucosidase inhibitory potential than acarbose.Three new β-resorcylic acid derivatives, compounds 1–3, along with six known analogues (4–9) were isolated from an endophytic fungus Lasiodiplodia sp. ZJ-HQ1 derived from medicinal plant Acanthus ilicifolius. Their structures were elucidated by 1D and 2D NMR spectroscopic analysis, high resolution mass spectrometric (HREIMS) data, and X-ray crystallography. The absolute configurations of compounds 1 and 2 were determined by the modified Mosher’s method. Compounds 1–7 showed more potent inhibitory effects against α-glucosidase activity than the clinical α-glucosidase inhibitor acarbose.

Peniphenones A–D from the Mangrove Fungus Penicillium dipodomyicola HN4-3A as Inhibitors of Mycobacterium tuberculosis Phosphatase MptpB

Co-reporter:Hanxiang Li ; Jieyi Jiang ; Zhaoming Liu ; Shaoe Lin ; Guoping Xia ; Xuekui Xia ; Bo Ding ; Lei He ; Yongjun Lu ;Zhigang She

Journal of Natural Products 2014 Volume 77(Issue 4) pp:800-806

Publication Date(Web):March 5, 2014

DOI:10.1021/np400880w

A pair of unusual benzannulated 6,6-spiroketal enantiomers [(−)-1 and (+)-1] and three new biogenetically related compounds (2–4), together with two known related analogues (5 and 6), have been isolated from a mangrove fungus, Penicillium dipodomyicola HN4-3A. Their structures were elucidated on the basis of spectroscopic analysis (1D and 2D NMR data) and X-ray crystallography. The absolute configurations of enantiomers (−)-1 and (+)-1 were determined using quantum chemical calculations of the electronic circular dichroic (ECD) spectra. Compounds 2 and 3 exhibited strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with IC50 values of 0.16 ± 0.02 and 1.37 ± 0.05 μM, respectively.

A New Polyketide from the Mangrove Endophytic Fungus Penicillium sp. sk14JW2P

Co-reporter:Xi-Shan Huang;Bin Yang;Xue-Feng Sun;Guo-Ping Xia;Ya-Yue Liu;Lin Ma

Helvetica Chimica Acta 2014 Volume 97( Issue 5) pp:664-668

Publication Date(Web):

DOI:10.1002/hlca.201300248

Abstract

Two polyketides were isolated from the mangrove endophytic fungus, Penicillium sp. sk14JW2P, and one derivative with a modified structure. The structures were elucidated by spectroscopic analyses, the structure of the compound 1 was further confirmed by single-crystal X-ray diffraction, and its absolute configuration was determined. Compound 1 and 2 showed acetylcholinesterase (AchE) inhibitory activities with IC₅₀ values of 12±0.3 and 79±2 nM, respectively.

Asperterpenols A and B, New Sesterterpenoids Isolated from a Mangrove Endophytic Fungus Aspergillus sp. 085242

Co-reporter:Ze’en Xiao, Huarong Huang, Changlun Shao, Xuekui Xia, Lin Ma, Xishan Huang, Yongjun Lu, Yongcheng Lin, Yuhua Long, and Zhigang She

Organic Letters 2013 Volume 15(Issue 10) pp:2522-2525

Publication Date(Web):May 3, 2013

DOI:10.1021/ol401005j

Asperterpenol A (1) and asperterpenol B (2), two novel sesterterpenoids with an unusual 5/8/6/6 tetracyclic ring skeleton, were isolated from a mangrove endophytic fungus Aspergillus sp. 085242. The structures were elucidated on the basis of spectroscopic methods and the absolute configurations determined by single-crystal X-ray diffraction analysis. Compounds 1 and 2 inhibit acetylcholinesterase with IC50 values of 2.3 and 3.0 μM, respectively.

Asperterpenoid A, a New Sesterterpenoid as an Inhibitor of Mycobacterium tuberculosis Protein Tyrosine Phosphatase B from the Culture of Aspergillus sp. 16-5c

Co-reporter:Xishan Huang, Hongbo Huang, Hanxiang Li, Xuefeng Sun, Huarong Huang, Yongjun Lu, Yongcheng Lin, Yuhua Long, and Zhigang She

Organic Letters 2013 Volume 15(Issue 4) pp:721-723

Publication Date(Web):January 29, 2013

DOI:10.1021/ol303549c

Asperterpenoid A (1), a novel sesterterpenoid with a new carbon skeleton, has been isolated from a mangrove endophytic fungus Aspergillus sp. 16-5c. Its structure was characterized by extensive spectroscopic methods, and the absolute configuration was determined by single crystal X-ray diffraction analysis. Asperterpenoid A (1) exhibited strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (mPTPB) with an IC50 value of 2.2 μM.

Structure and Absolute Configuration of Fumiquinazoline L, an Alkaloid from a Gorgonian-Derived Scopulariopsis sp. Fungus

Co-reporter:Chang-Lun Shao, Ru-Fang Xu, Mei-Yan Wei, Zhi-Gang She, and Chang-Yun Wang

Journal of Natural Products 2013 Volume 76(Issue 4) pp:779-782

Publication Date(Web):April 15, 2013

DOI:10.1021/np4002042

Fumiquinazoline L (1), an alkaloid with a heptacyclic skeleton formed via a bridging hemiaminal linkage, was isolated from a gorgonian-derived Scopulariopsis sp. fungus. The structure and absolute configuration of the new compound were identified by comprehensive spectroscopic data and X-ray diffraction analysis. During acid hydrolysis of 1, the isomerization of the valine residue was observed and also studied in different conditions. Fumiquinazoline L (1) showed no cytotoxic or antibacterial activities.

Bioactive Indole Alkaloids and Phenyl Ether Derivatives from a Marine-Derived Aspergillus sp. Fungus

Co-reporter:Min Chen, Chang-Lun Shao, Xiu-Mei Fu, Ru-Fang Xu, Juan-Juan Zheng, Dong-Lin Zhao, Zhi-Gang She, and Chang-Yun Wang

Journal of Natural Products 2013 Volume 76(Issue 4) pp:547-553

Publication Date(Web):March 25, 2013

DOI:10.1021/np300707x

Two new prenylated indole alkaloids, 17-epi-notoamides Q and M (1 and 2), and two new phenyl ether derivatives, cordyols D and E (9 and 13), together with 10 known compounds (3–8, 10–12, 14) were isolated from a marine-derived Aspergillus sp. fungus. Among them, 1/5 and 2/4 were pairs of epimers. The planar structures and absolute configurations of the new compounds were determined by extensive NMR spectroscopic data as well as CD spectra. The absolute configuration of 3 was confirmed by single-crystal X-ray diffraction analysis for the first time. All isolated metabolites (1–14) and eight synthetic phenyl ether derivatives (12a, 14a–14g) were evaluated for their antibacterial activities in vitro. The polybromide phenyl ether 14g showed pronounced antibacterial activity against Staphylococcus epidermidis with an MIC value of 0.556 μM, stronger than that of the positive control ciprofloxacin (MIC = 3.13 μM).

Bioactive Hydroanthraquinones and Anthraquinone Dimers from a Soft Coral-Derived Alternaria sp. Fungus

Co-reporter:Cai-Juan Zheng, Chang-Lun Shao, Zhi-Yong Guo, Jian-Feng Chen, Dong-Sheng Deng, Kai-Lin Yang, Yi-Yan Chen, Xiu-Mei Fu, Zhi-Gang She, Yong-Cheng Lin, and Chang-Yun Wang

Journal of Natural Products 2012 Volume 75(Issue 2) pp:189-197

Publication Date(Web):January 25, 2012

DOI:10.1021/np200766d

Five new hydroanthraquinone derivatives, tetrahydroaltersolanols C–F (1–4) and dihydroaltersolanol A (5), and five new alterporriol-type anthranoid dimers, alterporriols N–R (12–16), along with seven known analogues (6–11 and 17), were isolated from the culture broth and the mycelia of Alternaria sp. ZJ-2008003, a fungus obtained from a Sarcophyton sp. soft coral collected from the South China Sea. Their structures and the relative configurations were elucidated using comprehensive spectroscopic methods including 1D and 2D NOE spectra as well as single-crystal X-ray crystallography. Compound 13 represents the first isolated alterporriol dimer with a C-4–C-4′ linkage, and the absolute configuration of 4 was determined using the modified Mosher’s method. Compounds 1 and 15 exhibited antiviral activity against the porcine reproductive and respiratory syndrome virus (PRRSV), with IC50 values of 65 and 39 μM, respectively. Compound 14 showed cytotoxic activity against PC-3 and HCT-116 cell lines, with IC50 values of 6.4 and 8.6 μM, respectively.

Antibacterial Anthraquinone Derivatives from a Sea Anemone-Derived Fungus Nigrospora sp.

Co-reporter:Kai-Lin Yang, Mei-Yan Wei, Chang-Lun Shao, Xiu-Mei Fu, Zhi-Yong Guo, Ru-Fang Xu, Cai-Juan Zheng, Zhi-Gang She, Yong-Cheng Lin, and Chang-Yun Wang

Journal of Natural Products 2012 Volume 75(Issue 5) pp:935-941

Publication Date(Web):April 30, 2012

DOI:10.1021/np300103w

Chemical investigation of a marine-derived fungus Nigrospora sp., isolated from an unidentified sea anemone, yielded two new hydroanthraquinone analogues, 4a-epi-9α-methoxydihydrodeoxybostrycin (1) and 10-deoxybostrycin (2), together with seven known anthraquinone derivatives (3–9). The structures of the two new compounds were established through extensive NMR spectroscopy as well as a single-crystal X-ray diffraction analysis using Cu Kα radiation. The antibacterial activities of compounds 1–9 and 10 acetyl derivatives (6a, 7a, 8a–8g, 9a) were evaluated in vitro. Compound 6a, the acetylated derivative of 6, exhibited promising activity against Bacillus cereus with an MIC value of 48.8 nM, which was stronger than that of the positive control ciprofloxacin (MIC = 1250 nM). Analysis of the antibacterial screening data for the metabolites and their acetyl derivatives revealed the key structural features required for this activity.

Pimarane diterpenes from the fungus Epicoccum sp. HS-1 associated with Apostichopus japonicus

Co-reporter:Xuekui Xia, Jianye Zhang, Yonggang Zhang, Fang Wei, Xin Liu, Airong Jia, Changheng Liu, Wei Li, Zhigang She, Yongcheng Lin

Bioorganic & Medicinal Chemistry Letters 2012 Volume 22(Issue 8) pp:3017-3019

Publication Date(Web):15 April 2012

DOI:10.1016/j.bmcl.2012.01.055

Three new pimarane diterpenes (1, 2 and 3) as well as a known compound 4, were isolated from the marine-derived fungus HS-1 from Apostichopus japonicus. Their structures and relative stereochemistry of 1–3 were elucidated using a combination of NMR spectroscopy and CD. In the primary bioassay, compounds 1, 2 and 4 inhibited the growth of KB and KBv200 with IC50 of 3.51, 2.34 μg/mL, 20.74, 14.47 μg/mL, and 3.86, 6.52 μg/mL, respectively.Three new pimarane diterpenes (1, 2 and 3) as well as a known compound 4, were isolated from the marine-derived fungus HS-1 from Apostichopus japonicus. Their cytotoxicity has been tested and showed varying levels against the growth of KB and KBv200, and compound 1 is the most potent with IC50 of 3.51 and 2.34 μg/mL.

Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus

Co-reporter:Chang-Lun Shao, Hui-Xian Wu, Chang-Yun Wang, Qing-Ai Liu, Ying Xu, Mei-Yan Wei, Pei-Yuan Qian, Yu-Cheng Gu, Cai-Juan Zheng, Zhi-Gang She, and Yong-Cheng Lin

Journal of Natural Products 2011 Volume 74(Issue 4) pp:629-633

Publication Date(Web):February 24, 2011

DOI:10.1021/np100641b

Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A−C (1−3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1−3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCl3 slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined.

Cytotoxic Norsesquiterpene Peroxides from the Endophytic Fungus Talaromyces flavus Isolated from the Mangrove Plant Sonneratia apetala

Co-reporter:Hanxiang Li, Hongbo Huang, Changlun Shao, Huarong Huang, Jieyi Jiang, Xun Zhu, Yayue Liu, Lan Liu, Yongjun Lu, Mengfeng Li, Yongcheng Lin, and Zhigang She

Journal of Natural Products 2011 Volume 74(Issue 5) pp:1230-1235

Publication Date(Web):May 5, 2011

DOI:10.1021/np200164k

Four new norsesquiterpene peroxides, named talaperoxides A–D (1–4), as well as one known analogue, steperoxide B (5, or merulin A), have been isolated from a mangrove endophytic fungus, Talaromyces flavus. Their structures were elucidated mainly by 1D and 2D NMR. Structures of 1, 2, and 5 were further confirmed by single-crystal X-ray diffraction, and their absolute configurations were also determined using copper radiation. Cytotoxic activities of compounds 1–5 were evaluated in vitro against human cancer cell lines MCF-7, MDA-MB-435, HepG2, HeLa, and PC-3. Compounds 2 and 4 showed cytotoxicity against the five human cancer cell lines with IC50 values between 0.70 and 2.78 μg/mL.

Azaphilones and p-Terphenyls from the Mangrove Endophytic Fungus Penicillium chermesinum (ZH4-E2) Isolated from the South China Sea

Co-reporter:Hongbo Huang, Xiaojun Feng, Ze’en Xiao, Lan Liu, Hanxiang Li, Lin Ma, Yongjun Lu, Jianhua Ju, Zhigang She, and Yongcheng Lin

Journal of Natural Products 2011 Volume 74(Issue 5) pp:997-1002

Publication Date(Web):April 21, 2011

DOI:10.1021/np100889v

Eight secondary metabolites, including three new azaphilones (chermesinones A–C, 1–3), three new p-terphenyls (6′-O-desmethylterphenyllin, 4; 3-hydroxy-6′-O-desmethylterphenyllin, 5; 3′′-deoxy-6′-O-desmethylcandidusin B, 7), and two known p-terphenyls (6, 8), were isolated from the culture of the mangrove endophytic fungus Penicillium chermesinum (ZH4-E2). Their structures were established by spectroscopic analysis. The absolute configuration of 1 was determined by X-ray crystallography. Terphenyls 4, 5, and 6 exhibited strong inhibitory effects against α-glucosidase with IC50 values of 0.9, 4.9, and 2.5 μM, respectively. Terphenyls 7 and 8 showed inhibitory activity toward acetylcholinesterase with IC50 values of 7.8 and 5.2 μM.

Aspergilones A and B, two benzylazaphilones with an unprecedented carbon skeleton from the gorgonian-derived fungus Aspergillus sp.

Co-reporter:Chang-Lun Shao, Chang-Yun Wang, Mei-Yan Wei, Yu-Cheng Gu, Zhi-Gang She, Pei-Yuan Qian, Yong-Cheng Lin

Bioorganic & Medicinal Chemistry Letters 2011 Volume 21(Issue 2) pp:690-693

Publication Date(Web):15 January 2011

DOI:10.1016/j.bmcl.2010.12.005

Two novel benzylazaphilone derivatives with an unprecedented carbon skeleton, aspergilone A (1), and its symmetrical dimer with a unique methylene bridge, aspergilone B (2), have been isolated from the culture broth of a marine-derived fungus Aspergillus sp. from a gorgonian Dichotella gemmacea. Their structures and relative stereochemistries of 1 and 2 were elucidated using a combination of NMR spectroscopy and X-ray crystallography. Compound 1 not only exhibited in vitro selective cytotoxicity but also showed potent antifouling activity.

Cytotoxic Naphtho--pyrones from the Mangrove Endophytic Fungus Aspergillus tubingensis (GX1-5E)

Co-reporter:Hong-Bo Huang;Ze-En Xiao;Xiao-Jun Feng;Cai-Huan Huang;Xun Zhu;Jian-Hua Ju;Meng-Feng Li;Yong-Cheng Lin;Lan Liu

Helvetica Chimica Acta 2011 Volume 94( Issue 9) pp:1732-1740

Publication Date(Web):

DOI:10.1002/hlca.201100050

Abstract

Four new dimeric naphtho-γ-pyrones, named rubasperone D (1), rubasperone E (2), rubasperone F (3), and its atropisomer rubasperone G (4), together with four known monomeric naphtho-γ-pyrones, TMC 256 A1 (5), rubrofusarin B (6), fonsecin (7), and flavasperone (8), were isolated from the mangrove endophytic fungus Aspergillus tubingensis (GX1-5E) cultivated in solid rice medium. Their structures were elucidated by spectroscopic methods, including IR, 1D- and 2D-NMR, and MS. In the in vitro cytotoxicity assays, 5 displayed inhibitory activities against tumor cell lines of MCF-7, MDA-MB-435, Hep3B, Huh7, SNB19, and U87 MG with IC₅₀ values between 19.92 and 47.98 μM. Compounds 1, 6, and 8 also showed mild cytotoxic activity.

SZ-685C, a marine anthraquinone, is a potent inducer of apoptosis with anticancer activity by suppression of the Akt/FOXO pathway

Co-reporter:Gui'e Xie;Xun Zhu;Qing Li;Minghui Gu;Zhenjian He;Jueheng Wu;Jun Li;Yongcheng Lin;Mengfeng Li;Zhigang She;Jie Yuan

British Journal of Pharmacology 2010 Volume 159( Issue 3) pp:689-697

Publication Date(Web):

DOI:10.1111/j.1476-5381.2009.00577.x

Background and purpose: The aims of this study were to investigate the anti-cancer activity of SZ-685C, an anthracycline analogue isolated from marine-derived mangrove endophytic fungi, and to explore the molecular mechanisms underlying such activity.

Experimental approach: The effect of SZ-685C on the viability of cancer cell lines was investigated using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. SZ-685C-induced apoptosis was assessed by Annexin V-fluorescein isothiocyanate/propidium iodide staining, terminal deoxynucleotidyl transferase-mediated dUTP nick end labelling assay and analysis of caspase activation. The effect of SZ-685C on the Akt/FOXO pathway was studied using Western blotting analysis, and the in vivo anti-tumour efficacy was examined in an MDA-MB-435 breast cancer xenograft model.

Key results: SZ-685C suppressed the proliferation of six cancer cell lines derived from human breast cancer, prostate cancer, glioma and hepatoma (IC₅₀ values ranged from 3.0 to 9.6 µM) and the growth of breast cancer xenografts in mice. SZ-685C had a direct apoptosis-inducing effect through both the extrinsic and intrinsic apoptotic pathways, as shown by activation of caspase-8 and 9 as well as effector caspase-3 and poly (ADP-ribose) polymerase. Phosphorylation of Akt and its downstream effectors, forkhead box protein O1 and forkhead box protein O3a, was down-regulated in SZ-685C-treated cancer cells. Furthermore, the pro-apoptotic protein Bim was up-regulated by SZ-685C treatment consistent with FOXO dephosphorylation.

Conclusions and implications: SZ-685C could induce apoptosis through the Akt/FOXO pathway, which consequently leads to the observed anti-tumour effect both in vitro and in vivo. Our data suggest that SZ-685C may be a potentially promising Akt inhibitor and anti-cancer drug candidate.

Penicinoline, a new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system from an endophytic fungus Penicillium sp.

Co-reporter:Chang-Lun Shao, Chang-Yun Wang, Yu-Cheng Gu, Mei-Yan Wei, Jia-Hui Pan, Dong-Sheng Deng, Zhi-Gang She, Yong-Cheng Lin

Bioorganic & Medicinal Chemistry Letters 2010 Volume 20(Issue 11) pp:3284-3286

Publication Date(Web):1 June 2010

DOI:10.1016/j.bmcl.2010.04.043

A new pyrrolyl 4-quinolinone alkaloid with an unprecedented ring system, named penicinoline (1) was isolated from a mangrove endophytic fungus. The structure of 1 was elucidated by spectroscopic methods and comparison with its derivative, penicinotam (1a), an unexpected lactam that was obtained from 1 by intramolecular dehydration. The structure of 1a was unambiguously confirmed by single-crystal X-ray analysis. Penicinoline (1) showed potent in vitro cytotoxicity toward 95-D and HepG2 cell lines with IC50 values of 0.57 and 6.5 μg/mL, respectively.

Structural elucidation and NMR assignments of four aromatic lactones from a mangrove endophytic fungus (No. GX4-1B)

Co-reporter:Hongbo Huang;Qing Li;Xiaojun Feng;Bin Chen;Jun Wang;Lan Liu;Zhigang She;Yongcheng Lin

Magnetic Resonance in Chemistry 2010 Volume 48( Issue 6) pp:496-499

Publication Date(Web):

DOI:10.1002/mrc.2605

Abstract

Two new aromatic lactones, 6-hydroxy-4-hydroxymethyl-8-methoxy-3- methylisocoumarin (1) and 1,10-dihydroxy-8-methyl-dibenz[b, e]oxepin-6,11-dione (2), together with two known compounds, 1,10-dihydroxy-dibenz[b, e]oxepin-6,11-dione (3) and 3-hydroxymethyl-6,8-dimethoxycoumarin (4), were isolated from a mangrove endophytic fungus (No. GX4-1B) collected from the South China Sea. Their structures were elucidated and the data of ¹H and ¹³C NMR were assigned completely by HREIMS, 1D and 2D NMR experiments including HMQC, HMBC and NOESY. Copyright © 2010 John Wiley & Sons, Ltd.

Structure elucidation and NMR assignments for two amide alkaloids from a Mangrove endophytic Fungus (No. ZZF-22)

Co-reporter:Yiguang Chen;Changlun Shao;Zhongjing Huang;Ying Zhang;Xiaoling Cai;Zhigang She;Shining Zhou;Yongcheng Lin

Magnetic Resonance in Chemistry 2009 Volume 47( Issue 1) pp:92-95

Publication Date(Web):

DOI:10.1002/mrc.2346

Abstract

The structure elucidations and complete ¹H and ¹³C NMR assignments are reported for two new natural products: 3-benzylidene-8,8a-dihydroxy-2-methyl-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione(1) and 4-hydroxy-6-(hydroxy-phenyl-methyl)-N-(3-methyl-butyryl)-nicotinamide (2). Both of these secondary metabolites were isolated from the fermentation medium of a Mangrove endophytic fungus. High resolution electron impact mass spectrometry (HREIMS), FT-IR Spectroscopy and NMR experiments including gCOSY, gHMQC, gHMBC and NOE were used for determination of the structures and assignments of the amide alkaloids. Copyright © 2008 John Wiley & Sons, Ltd.

Structure elucidation and NMR assignments for three anthraquinone derivatives from the marine fungus Fusarium sp. (No. ZH-210)

Co-reporter:Yiguang Chen;Xiaoling Cai;Jiahui Pan;Junping Gao;Jing Li;Jie Yuan;Liwu Fu;Zhigang She;Yongcheng Lin

Magnetic Resonance in Chemistry 2009 Volume 47( Issue 4) pp:362-365

Publication Date(Web):

DOI:10.1002/mrc.2391

Abstract

The structure elucidations and complete ¹H and ¹³C NMR assignments are reported for three new anthraquinone derivatives: Fusaquinon A (1), B (2), and C (3) isolated from the fermentation medium of the marine fungus Fusarium sp. (No. ZH-210). HREIMS, Fourier transform infrared absorption spectrometry (FT-IR), NMR experiments including gCOSY, gHMQC, gHMBC, and NOESY were used for the determination of the structures and NMR spectral assignments. Preliminary pharmacological test showed that they exhibited low cytotoxic activity towards KB, KBv200, and MCF-7 cell lines. Copyright © 2009 John Wiley & Sons, Ltd.

Structure elucidation of three diphenyl ether derivatives from the mangrove endophytic fungus SBE-14 from the South China Sea

Co-reporter:Fan Liu;Qing Li;Hong Yang;Xiao-Ling Cai;Xue-Kui Xia;Sheng-Ping Chen;Meng-Feng Li;Yong-Cheng Lin

Magnetic Resonance in Chemistry 2009 Volume 47( Issue 5) pp:453-455

Publication Date(Web):

DOI:10.1002/mrc.2405

Abstract

Two new natural products, tenelate A (1) and B (2), together with the known compound, tenellic acid C (3), were isolated from the mangrove endophytic fungus Talaromyces sp. (SBE-14), from the South China Sea. Their structures were elucidated by spectroscopic methods, mainly 1D and 2D NMR techniques. Copyright © 2009 John Wiley & Sons, Ltd.

1H and 13C NMR assignments for 6-demethylvermistatin and two penicillide derivatives from the mangrove fungus Guignardia sp. (No. 4382) from the South China Sea

Co-reporter:Xue-kui Xia;Fan liu;Li-guo Yang;Meng-feng Li;L. L. P. Vrijmoed;Yong-cheng Lin

Magnetic Resonance in Chemistry 2008 Volume 46( Issue 7) pp:693-696

Publication Date(Web):

DOI:10.1002/mrc.2216

Abstract

One new compound 6-demethylvermistatin (1), together with two known compounds, the penicillide derivatives (2) and (3) were isolated from the mangrove fungus Guignardia sp. No. 4382 obtained from the South China Sea. Their structures were assigned using high-resolution electron ionization mass spectrometry(HREIMS), ¹H and ¹³C NMR spectra, DEPT, and by 2D COSY, HMQC, and HMBC experiments. The absolute configuration of 1 was established by comparison of its CD with that of vermistatin. Copyright © 2008 John Wiley & Sons, Ltd.

Structural and spectral assignments of six anthraquinone derivatives from the mangrove fungus (ZSUH-36)

Co-reporter:Changlun Shao;Changyun Wang;Meiyan Wei;Shangde Li;Zhigang She;Yucheng Gu;Yongcheng Lin

Magnetic Resonance in Chemistry 2008 Volume 46( Issue 9) pp:886-889

Publication Date(Web):

DOI:10.1002/mrc.2266

Abstract

A new natural product named 6,8,1′-tri-O-methyl averantin(1) has been isolated together with five known anthraquinones 1′-O-methyl averantin(2), 6,8-di-O-methyl averufin (3) averufin (4), versicolorin C (5) and 6,8-di-O-methyl averufanin (6) from a mangrove endophytic fungus ZSUH-36 collected from the South China Sea. NMR techniques including COSY, HMQC, and HMBC were used to elucidate the structures of these compounds. We report the unambiguous assignments of the ¹H and ¹³C NMR spectra of the new compound 6,8,1′-tri-O-methyl averantin(1). Copyright © 2008 John Wiley & Sons, Ltd.

Structure elucidation of two new xanthone derivatives from the marine fungus Penicillium sp. (ZZF 32#) from the South China Sea

Co-reporter:Changlun Shao;Changyun Wang;Meiyan Wei;Yucheng Gu;Xuekui Xia;Zhigang She;Yongcheng Lin

Magnetic Resonance in Chemistry 2008 Volume 46( Issue 11) pp:1066-1069

Publication Date(Web):

DOI:10.1002/mrc.2293

Abstract

Two new xanthones, 8-(methoxycarbonyl)-1-hydroxy-9-oxo-9H-xanthene-3-carboxylic acid (1) and dimethyl 8-methoxy-9-oxo-9H-xanthene-1, 6-dicarboxylate (2) and one known xanthone methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (3) were isolated from the culture broth of the mangrove fungus Penicillium sp. (ZZF 32#) collected from the South China Sea. Their structures were established by comprehensive analysis of one-dimensional (1D) and two-dimensional (2D) NMR data. The structure of compound 3 was confirmed by X-ray crystallography, which led to the suggestion that janthinone (4) might have the same structure as 3. Compounds 1–3 were inactive against KB or KBv200 cells during cytotoxicity evaluations. Copyright © 2008 John Wiley & Sons, Ltd.

Structural and Biological Properties of Vermistatin and Two New Vermistatin Derivatives Isolated from the Marine-Mangrove Endophytic Fungus Guignardia sp. No. 4382

Co-reporter:Xue-Kui Xia;Hua-Rong Huang;Ji-Wen Cai;Liu Lan;Jian-Ye Zhang;Li-Wu Fu;L. L. P. Vrijmoed;Yong-Cheng Lin

Helvetica Chimica Acta 2007 Volume 90(Issue 10) pp:1925-1931

Publication Date(Web):22 OCT 2007

DOI:10.1002/hlca.200790200

Vermistatin (=(3R)-4,6-dimethoxy-3-{4-oxo-6-[(1E)-prop-1-en-1-yl]-4H-pyran-3-yl}-2-benzofuran-1(3H)-one; 1) and two new vermistatin derivatives, compounds 2 and 3, were isolated from the fungal strain Guignardia sp. No. 4382 obtained from the South-China Sea. Their structures were elucidated by various methods, including circular dichroism (CD), 1D- and 2D-NMR, and HR-EI-MS. The structures of 1 and 2 were unequivocally corroborated by X-ray crystallography, and their absolute configurations were derived by CD spectroscopy based on a literature comparison. The in vitro cytotoxic and antifungal activities of 1 and 2 were tested.

1H and 13C NMR assignments for five anthraquinones from the mangrove endophytic fungus Halorosellinia sp. (No. 1403)

Co-reporter:Xue-Kui Xia;Hua-Rong Huang;Chang-Lun Shao;Fan Liu;L. L. P. Vrijmoed;Xiao-Ling Cai;Yong-Cheng Lin

Magnetic Resonance in Chemistry 2007 Volume 45(Issue 11) pp:1006-1009

Publication Date(Web):26 SEP 2007

DOI:10.1002/mrc.2078

We report the unambiguous assignments of the ¹H and ¹³C NMR spectra of two new natural products, namely, 1,4,5,6,7,9-hexahydroxy-2-methoxy-7-methyl-5β,9β,8aβ, 6α,10aα-hexahydroanthracen-10 (10aH)-one (1) and 1,4,6-trihydroxy-2-methoxy-7-methylanthracene-9, 10-dione (2), together with three known anthraquinones. These compounds were all isolated from the marine endophytic fungus No. 1403 collected from the South China Sea. Compounds 3 and 4 were isolated from the marine fungus for the first time. The structures were elucidated by the spectroscopic methods 1D and 2D NMR including COSY, HMQC, HMBC and NOE, and HREIMS. In our cytotoxicity assays, compound 5 showed cytotoxicity toward KB and KBv-200 cells with IC₅₀ of 1.40 and 2.58 µg/ml, respectively. In addition, the plausible biogenic relationship of compounds 1, 2, 3 and 4 is discussed. Copyright © 2007 John Wiley & Sons, Ltd.

Lasiodiplactone A, a novel lactone from the mangrove endophytic fungus Lasiodiplodia theobromae ZJ-HQ1

Co-reporter:Senhua Chen, Zhaoming Liu, Hongju Liu, Yuhua Long, Dongni Chen, Yongjun Lu and Zhigang She

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 30) pp:NaN6341-6341

Publication Date(Web):2017/07/17

DOI:10.1039/C7OB01657C