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Article ; Online: Design, Synthesis, and Anticancer Activity of Novel 3,6-Diunsaturated 2,5-Diketopiperazines

Xiaolin Li / Tianrong Xun / Huayan Xu / Xiaoyan Pang / Bin Yang / Junfeng Wang / Xuefeng Zhou / Xiuping Lin / Suiyi Tan / Yonghong Liu / Shengrong Liao

Marine Drugs, Vol 21, Iss 325, p

2023 Volume 325

Abstract: Based on the marine natural products piperafizine B, XR334, and our previously reported compound 4m , fourteen novel 3,6-diunsaturated 2,5-diketopiperazine (2,5-DKP) derivatives ( 1 , 2 , 4 – 6 , 8 – 16 ), together with two known ones ( 3 and 7 ), were ... ...

Abstract	Based on the marine natural products piperafizine B, XR334, and our previously reported compound 4m , fourteen novel 3,6-diunsaturated 2,5-diketopiperazine (2,5-DKP) derivatives ( 1 , 2 , 4 – 6 , 8 – 16 ), together with two known ones ( 3 and 7 ), were designed and synthesized as anticancer agents against the A549 and Hela cell lines. The MTT assay results showed that the derivatives 6 , 8 – 12, and 14 had moderate to good anticancer capacities, with IC 50 values ranging from 0.7 to 8.9 μM. Among them, compound 11, with naphthalen-1-ylmethylene and 2-methoxybenzylidene functions at the 3 and 6 positions of 2,5-DKP ring, respectively, displayed good inhibitory activities toward both A549 (IC 50 = 1.2 μM) and Hela (IC 50 = 0.7 μM) cancer cells. It could also induce apoptosis and obviously block cell cycle progression in the G2/M phases in both cells at 1.0 μM. The electron-withdrawing functions might not be favorable for the derivatives with high anticancer activities. Additionally, compared to piperafizine B and XR334, these semi- N -alkylated derivatives have high liposolubilities (>1.0 mg mL −1 ). Compound 11 can be further developed, aiming at the discovery of a novel anticancer candidate.
Keywords	2,5-diketopiperazine derivative ; intermolecular hydrogen bond ; liposolubility ; electron property ; anticancer activity ; Biology (General) ; QH301-705.5
Subject code	540
Language	English
Publishing date	2023-05-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Discovery of a Dimeric Zinc Complex and Five Cyclopentenone Derivatives from the Sponge-Associated Fungus Aspergillus ochraceopetaliformis

Cui Guo / Pei Wang / Xiaoyan Pang / Xiuping Lin / Shengrong Liao / Bin Yang / Xuefeng Zhou / Junfeng Wang / Yonghong Liu

ACS Omega, Vol 6, Iss 13, Pp 8942-

2021 Volume 8949

Keywords	Chemistry ; QD1-999
Language	English
Publishing date	2021-03-01T00:00:00Z
Publisher	American Chemical Society
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Bioactive Novel Indole Alkaloids and Steroids from Deep Sea-Derived Fungus Aspergillus fumigatus SCSIO 41012

Salendra Limbadri / Xiaowei Luo / Xiuping Lin / Shengrong Liao / Junfeng Wang / Xuefeng Zhou / Bin Yang / Yonghong Liu

Molecules, Vol 23, Iss 9, p

2018 Volume 2379

Abstract: Two new alkaloids, fumigatosides E (1) and F (2), and a new natural product, 3, 7-diketo-cephalosporin P1 (6) along with five known compounds (3–5, 7, 8) were isolated from deep-sea derived fungal Aspergillus fumigatus SCSIO 41012. Their structures were ... ...

Abstract	Two new alkaloids, fumigatosides E (1) and F (2), and a new natural product, 3, 7-diketo-cephalosporin P1 (6) along with five known compounds (3–5, 7, 8) were isolated from deep-sea derived fungal Aspergillus fumigatus SCSIO 41012. Their structures were determined by extensive spectroscopic data analysis, including 1D, 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS), and comparison between the calculated and experimental electronic circular dichroism (ECD) spectra. In addition, all compounds were tested for antibacterial and antifungal inhibitory activities. Compound 1 showed significant antifungal activity against Fusarium oxysporum f. sp. momordicae with MIC at 1.56 µg/mL. Compound 4 exhibited significant higher activity against S. aureus (16,339 and 29,213) with MIC values of 1.56 and 0.78 µg/mL, respectively, and compound 2 exhibited significant activity against A. baumanii ATCC 19606 with a MIC value of 6.25 µg/mL.
Keywords	deep sea-derived fungus ; Aspergillus fumigatus SCSIO 41012 ; indole alkaloids ; steroids ; antibacterial activity ; antifungal activity ; Organic chemistry ; QD241-441
Subject code	540
Language	English
Publishing date	2018-09-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Lipopeptide Epimers and a Phthalide Glycerol Ether with AChE Inhibitory Activities from the Marine-Derived Fungus Cochliobolus Lunatus SCSIO41401

Yu Dai / Kunlong Li / Jianglian She / Yanbo Zeng / Hao Wang / Shengrong Liao / Xiuping Lin / Bin Yang / Junfeng Wang / Huaming Tao / Haofu Dai / Xuefeng Zhou / Yonghong Liu

Marine Drugs, Vol 18, Iss 547, p

2020 Volume 547

Abstract: A pair of novel lipopeptide epimers, sinulariapeptides A ( 1 ) and B ( 2 ), and a new phthalide glycerol ether ( 3 ) were isolated from the marine algal-associated fungus Cochliobolus lunatus SCSIO41401, together with three known chromanone derivates ( 4 ...

Abstract	A pair of novel lipopeptide epimers, sinulariapeptides A ( 1 ) and B ( 2 ), and a new phthalide glycerol ether ( 3 ) were isolated from the marine algal-associated fungus Cochliobolus lunatus SCSIO41401, together with three known chromanone derivates ( 4 – 6 ). The structures of the new compounds, including the absolute configurations, were determined by comprehensive spectroscopic methods, experimental and calculated electronic circular dichroism (ECD), and Mo 2 (OAc) 4 -induced ECD methods. The new compounds 1 – 3 showed moderate inhibitory activity against acetylcholinesterase (AChE), with IC 50 values of 1.3–2.5 μM, and an in silico molecular docking study was also performed.
Keywords	lipopeptides ; phthalide ; Cochliobolus lunatus ; absolute configurations ; AChE inhibitory ; Biology (General) ; QH301-705.5
Subject code	540
Language	English
Publishing date	2020-10-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article: Transition-metal-free insertion of benzyl bromides into 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde: One-pot switchable syntheses of benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base

Xu, Huayan / Liang Xu / Xiaowei Luo / Junfeng Wang / Xuefeng Zhou / Bin Yang / Ding Li / Zaigang Luo / Yonghong Liu / Shengrong Liao

Tetrahedron. 2019 May 10, v. 75, no. 19

2019

Abstract: A transition-metal-free insertion of benzyl group between aldehyde and imidazole of 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde was achieved for the first time. Two diverse sets of quinolin-4-one derivatives: benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones (2) ... ...

Abstract	A transition-metal-free insertion of benzyl group between aldehyde and imidazole of 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde was achieved for the first time. Two diverse sets of quinolin-4-one derivatives: benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones (2) and 3-arylquinolin-4-ones (3) were synthesized based on identical starting materials 2-(1H-benzo[d]imidazol-1-yl)benzaldehydes (1) and benzyl bromides. In the preparations, two key intermediates I and II were involved and might be synthesized in situ through the reaction of an intra-Breslow intermediate with benzyl bromide via an enol attack in the presence of base or a NHC-based enamine attack in the absence of base, respectively, in which the intra-Breslow intermediate might function as a nucleophilic reagent by following two novel different pathways.
Keywords	Lewis bases ; benzaldehyde ; chemical reactions ; enamines ; enols ; imidazoles ; moieties ; organobromine compounds
Language	English
Dates of publication	2019-0510
Size	p. 2785-2796.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	204285-x
ISSN	1464-5416 ; 0040-4020 ; 0563-2064
ISSN (online)	1464-5416
ISSN	0040-4020 ; 0563-2064
DOI	10.1016/j.tet.2019.03.058
Database	NAL-Catalogue (AGRICOLA)

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Article: Prenylated indole alkaloids and chromone derivatives from the fungus Penicillium sp. SCSIO041218

Yang, Bin / Huaming Tao / Xiuping Lin / Junfeng Wang / Shengrong Liao / Junde Dong / Xuefeng Zhou / Yonghong Liu

Tetrahedron. 2017,

2017

Abstract: Four new prenylated indole alkaloids (1â4), and four new chromone derivatives (7â10), together with six known compounds (5, 6, and 11â14), have been isolated from the mangrove sediment derived fungus Penicillium sp. SCSIO041218, cultured in the 1% ... ...

Abstract	Four new prenylated indole alkaloids (1â4), and four new chromone derivatives (7â10), together with six known compounds (5, 6, and 11â14), have been isolated from the mangrove sediment derived fungus Penicillium sp. SCSIO041218, cultured in the 1% NaCl PDB substrate. The structures of new compounds were determined by analysis of the NMR and MS spectroscopic data. The absolute configuration of the prenylated indole alkaloids were elucidated based on the comparison of ECDs with known analogues. The absolute configurations of the chromone derivatives were determined by time-dependent density functional theory calculations of the ECD spectra. In all of these isolated compounds, penixanthones A and B (12 and 13) exhibited antiallergic activities inÂ vitro.
Keywords	Penicillium ; anti-allergic agents ; chemical reactions ; chemical structure ; fungi ; indole alkaloids ; nuclear magnetic resonance spectroscopy ; sediments ; sodium chloride ; spectral analysis
Language	English
Size	p. .
Publishing place	Elsevier Ltd
Document type	Article
Note	Pre-press version
ZDB-ID	204285-x
ISSN	1464-5416 ; 0040-4020 ; 0563-2064
ISSN (online)	1464-5416
ISSN	0040-4020 ; 0563-2064
DOI	10.1016/j.tet.2017.11.038
Database	NAL-Catalogue (AGRICOLA)

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Article: Antifungal New Oxepine-Containing Alkaloids and Xanthones from the Deep-Sea-Derived Fungus Aspergillus versicolor SCSIO 05879

Wang, Junfeng / Weijun He / Xiaolong Huang / Xinpeng Tian / Shengrong Liao / Bin Yang / Fazuo Wang / Xiaojiang Zhou / Yonghong Liu

Journal of agricultural and food chemistry. 2016 Apr. 13, v. 64, no. 14

2016

Abstract: Phytopathogenic fungi remain a continuous and huge threat in the agricultural fields. The agrochemical industry has made great development of the use of microbial natural products, which has been regarded as an effective strategy against phytopathogenic ... ...

Abstract	Phytopathogenic fungi remain a continuous and huge threat in the agricultural fields. The agrochemical industry has made great development of the use of microbial natural products, which has been regarded as an effective strategy against phytopathogenic fungi. Antifungal bioassay-directed fractionation was used to isolate two new oxepine-containing alkaloids (1 and 2), two new 4-aryl-quinolin-2-one alkaloids (3 and 4), and four new prenylated xanthones (5â8) from the deep-sea-derived fungus Aspergillus versicolor SCSIO 05879. Extensive NMR spectroscopic analysis, quantum mechanical calculations, and X-ray single-crystal diffraction were used to elucidate their structures, including their absolute configurations. Versicoloids A and B, versicone A, and cottoquinazoline A showed antifungal activities against three phytopathogenic fungi. The antifungal activities of these bioactive compounds strongly depend on the fungal species. Especially versicoloids A and B showed strong fungicidal effect (MIC of 1.6 Î¼g/mL) against Colletotrichum acutatum, compared with that of the positive control cycloheximide (MIC of 6.4 Î¼g/mL). The results of antifungal experiments indicated that versicoloids A and B may be regarded as candidate agents of antifungal agrochemicals.
Keywords	Aspergillus versicolor ; Colletotrichum acutatum ; X-radiation ; agrochemicals ; alkaloids ; antifungal properties ; bioactive compounds ; cycloheximide ; fractionation ; industry ; nuclear magnetic resonance spectroscopy ; plant pathogenic fungi ; xanthones
Language	English
Dates of publication	2016-0413
Size	p. 2910-2916.
Publishing place	American Chemical Society, Books and Journals Division
Document type	Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.6b00527
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Cytomorphological Characterization of the Backcross Progeny of Synthetic Amphiploid Rice (AABB) and Tetraploid Oryza sativa (AAAA)

Xianhua Zhang / Wei Wang / Junjie Jin / Shengrong Liao / Xiaonan Liu / Zhaojian Song / Detian Cai

Journal of Agricultural Science, Vol 5, Iss

2013 Volume 12

Abstract: DCW008, a synthetic allopolyploid rice (2n = 4X = 48, AABB), was obtained from chromosome doubling of interspecific hybrids between Oryza sativa (2n = 24, AA) and O. punctata (2n = 24, BB). The F 1 and backcross (BC 1 ) hybrids were produced by crossing ... ...

Abstract	DCW008, a synthetic allopolyploid rice (2n = 4X = 48, AABB), was obtained from chromosome doubling of interspecific hybrids between Oryza sativa (2n = 24, AA) and O. punctata (2n = 24, BB). The F 1 and backcross (BC 1 ) hybrids were produced by crossing DCW008 as a female parent with a high seed set tetraploid rice Sg99012 - 4X (2n = 4X = 48, AAAA). BC 1 F 1 and BC 1 F 2 overcame many of the wild-type traits of DCW008; they had yellow-hulled grains, seed set ranged from 0% to 71.31% and the grain morphology was similar to that of cultivated rice. Variable numbers of chromosomes were observed in pollen mother cells (PMCs) from the BC 1 plant. Genomic in situ hybridization (GISH) revealed that the majority of somatic cells and PMCs contained six chromosomes of O. punctata with fragment recombination observed in two of them. The backcross selection method employed in this study to generate allopolyploid progeny provides a reliable way of transferring useful genes from wild species into cultivated rice.
Keywords	Agriculture (General) ; S1-972 ; Agriculture ; S
Subject code	580
Language	English
Publishing date	2013-11-01T00:00:00Z
Publisher	Canadian Center of Science and Education
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Sinulolides A–H, New Cyclopentenone and Butenolide Derivatives from Soft Coral Sinularia sp.

Bin Yang / Xiaoyi Wei / Jingxia Huang / Xiuping Lin / Juan Liu / Shengrong Liao / Junfeng Wang / Xuefeng Zhou / Lishu Wang / Yonghong Liu

Marine Drugs, Vol 12, Iss 10, Pp 5316-

2014 Volume 5327

Abstract: Eight new compounds, sinulolides A–H (1–8), along with two known compounds, α-methoxy-2,3-dimethyl-butenolide (9) and sinularone D (10), were isolated from the soft coral Sinularia sp. The structures of these compounds were elucidated on the basis of ... ...

Abstract	Eight new compounds, sinulolides A–H (1–8), along with two known compounds, α-methoxy-2,3-dimethyl-butenolide (9) and sinularone D (10), were isolated from the soft coral Sinularia sp. The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis. The absolute configurations were determined on the basis of electronic circular dichroism (ECD) data analysis. Compounds 5 and 10 exhibited moderate effects for the inhibition of NF-κB activation.
Keywords	soft coral ; Sinularia sp ; sinulolide ; NF-κB ; Biology (General) ; QH301-705.5
Language	English
Publishing date	2014-10-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: New Sinularianin Sesquiterpenes from Soft Coral Sinularia sp.

Bin Yang / Shengrong Liao / Xiuping Lin / Junfeng Wang / Juan Liu / Xuefeng Zhou / Xianwen Yang / Yonghong Liu

Marine Drugs, Vol 11, Iss 12, Pp 4741-

2013 Volume 4750

Abstract: Four new sesquiterpenes, sinularianins C–F (3–6), together with known sinularianins A (1) and B (2) were identified from a South China Sea soft coral Sinularia sp. Compounds 1–6 were evaluated for inhibition of NF-κB activation using the cell-based ... ...

Abstract	Four new sesquiterpenes, sinularianins C–F (3–6), together with known sinularianins A (1) and B (2) were identified from a South China Sea soft coral Sinularia sp. Compounds 1–6 were evaluated for inhibition of NF-κB activation using the cell-based HEK293 NF-κB luciferase reporter gene assay. Compounds 1 and 4 were exhibited a potent effect with inhibitory rates of 41.3% and 43.0% at the concentration of 10 µg/mL, respectively.
Keywords	soft coral ; Sinularia sp ; sesquiterpenes ; sinularianins ; NF-κB ; Biology (General) ; QH301-705.5
Language	English
Publishing date	2013-12-01T00:00:00Z
Publisher	MDPI AG
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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