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Prof. Ligang Zhou
Department of Plant Pathology, College of Plant Protection, China Agricultural University

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0 mycotoxin
0 Biosynthesis
0 biological activities
0 phytotoxic activity
0 Plant biotechnology

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Review
Published: 06 April 2021 in Toxins
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Fungal phytotoxic secondary metabolites are poisonous substances to plants produced by fungi through naturally occurring biochemical reactions. These metabolites exhibit a high level of diversity in their properties, such as structures, phytotoxic activities, and modes of toxicity. They are mainly isolated from phytopathogenic fungal species in the genera of Alternaria, Botrytis, Colletotrichum, Fusarium, Helminthosporium, and Phoma. Phytotoxins are either host specific or non-host specific phytotoxins. Up to now, at least 545 fungal phytotoxic secondary metabolites, including 207 polyketides, 46 phenols and phenolic acids, 135 terpenoids, 146 nitrogen-containing metabolites, and 11 others, have been reported. Among them, aromatic polyketides and sesquiterpenoids are the main phytotoxic compounds. This review summarizes their chemical structures, sources, and phytotoxic activities. We also discuss their phytotoxic mechanisms and structure–activity relationships to lay the foundation for the future development and application of these promising metabolites as herbicides.

ACS Style

Dan Xu; Mengyao Xue; Zhen Shen; Xiaowei Jia; Xuwen Hou; Daowan Lai; Ligang Zhou. Phytotoxic Secondary Metabolites from Fungi. Toxins 2021, 13, 261 .

AMA Style

Dan Xu, Mengyao Xue, Zhen Shen, Xiaowei Jia, Xuwen Hou, Daowan Lai, Ligang Zhou. Phytotoxic Secondary Metabolites from Fungi. Toxins. 2021; 13 (4):261.

Chicago/Turabian Style

Dan Xu; Mengyao Xue; Zhen Shen; Xiaowei Jia; Xuwen Hou; Daowan Lai; Ligang Zhou. 2021. "Phytotoxic Secondary Metabolites from Fungi." Toxins 13, no. 4: 261.

Review
Published: 16 October 2020 in Journal of Fungi
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Clonostachys (teleomorph: Bionectria) fungi are well known to produce a variety of secondary metabolites with various biological activities to show their pharmaceutical and agrochemical applications. Up to now, at least 229 secondary metabolites, mainly including 84 nitrogen-containing metabolites, 85 polyketides, 40 terpenoids, and 20 other metabolites, have been reported. Many of these compounds exhibit biological activities, such as cytotoxic, antimicrobial, antileishmanial, antimalarial activities. This mini-review aims to summarize the diversity of the secondary metabolites as well as their occurrences in Clonostachys fungi and biological activities.

ACS Style

Peipei Han; Xuping Zhang; Dan Xu; Bowen Zhang; Daowan Lai; Ligang Zhou. Metabolites from Clonostachys Fungi and Their Biological Activities. Journal of Fungi 2020, 6, 229 .

AMA Style

Peipei Han, Xuping Zhang, Dan Xu, Bowen Zhang, Daowan Lai, Ligang Zhou. Metabolites from Clonostachys Fungi and Their Biological Activities. Journal of Fungi. 2020; 6 (4):229.

Chicago/Turabian Style

Peipei Han; Xuping Zhang; Dan Xu; Bowen Zhang; Daowan Lai; Ligang Zhou. 2020. "Metabolites from Clonostachys Fungi and Their Biological Activities." Journal of Fungi 6, no. 4: 229.

Paper
Published: 27 July 2020 in RSC Advances
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Rhizovagine A (1), a dibenzo-α-pyrone alkaloid with a 5/5/6/6/6 fused pentacyclic skeleton and acetylcholinesterase inhibitory activity, was isolated from the endophytic fungus Rhizopycnis vagum Nitaf22.

ACS Style

Ali Wang; Siji Zhao; Gan Gu; Dan Xu; Xuping Zhang; Daowan Lai; Ligang Zhou. Rhizovagine A, an unusual dibenzo-α-pyrone alkaloid from the endophytic fungus Rhizopycnis vagum Nitaf22. RSC Advances 2020, 10, 27894 -27898.

AMA Style

Ali Wang, Siji Zhao, Gan Gu, Dan Xu, Xuping Zhang, Daowan Lai, Ligang Zhou. Rhizovagine A, an unusual dibenzo-α-pyrone alkaloid from the endophytic fungus Rhizopycnis vagum Nitaf22. RSC Advances. 2020; 10 (47):27894-27898.

Chicago/Turabian Style

Ali Wang; Siji Zhao; Gan Gu; Dan Xu; Xuping Zhang; Daowan Lai; Ligang Zhou. 2020. "Rhizovagine A, an unusual dibenzo-α-pyrone alkaloid from the endophytic fungus Rhizopycnis vagum Nitaf22." RSC Advances 10, no. 47: 27894-27898.

Article
Published: 11 June 2020 in Current Microbiology
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Ustiloxin is a kind of 13-membered cyclic peptides found in mature rice false smut generated by Ustilaginoidea virens infecting rice spikelet. So far, six kinds of ustiloxins have been identified from false smut balls (FSBs) in which ustiloxin A is the main component. The toxins can not only inhibit the growth of rice, wheat, and corn, but also poison people and animals. However, so far, there have been few studies of the content of ustiloxin except that in mature FSB. The effect of ustiloxins on the process of infection has not been clarified. In this study, the technique of artificial inoculation coupled with UPLC-ESI–MS was introduced to investigate the content of ustiloxins in the course of infection. The initial formation time of ustiloxin A, B, C, D, F, and G was no later than 5, 5, 9, 7, 7, and 9 days post inoculation (dpi) prior to FSB’s formation, respectively. The content of ustiloxin A per spikelet was increased rapidly from 6.0 ng at 5 dpi to 14,157.1 ng at 25 dpi. Meanwhile, the content of ustiloxin A per dry weight (DW) of the FSBs also peaked at 1321.2 μg/g at 25 dpi. Interestingly, both the contents of ustiloxin A per dry weight and per spikelet were significantly reduced from 25 to 30 dpi. Transcriptome sequencing revealed that a total of 146 transcripts (103 upregulated and 43 downregulated) were significantly changed in rice spikelets after 3-h acute exposure to 100 ng ustiloxin A. In addition, several of the significantly altered genes were validated by RT-qPCR.

ACS Style

Zheng Hu; Lu Zheng; Junbin Huang; Ligang Zhou; Chunsheng Liu; Hao Liu. Ustiloxin A is Produced Early in Experimental Ustilaginoidea virens Infection and Affects Transcription in Rice. Current Microbiology 2020, 77, 2766 -2774.

AMA Style

Zheng Hu, Lu Zheng, Junbin Huang, Ligang Zhou, Chunsheng Liu, Hao Liu. Ustiloxin A is Produced Early in Experimental Ustilaginoidea virens Infection and Affects Transcription in Rice. Current Microbiology. 2020; 77 (10):2766-2774.

Chicago/Turabian Style

Zheng Hu; Lu Zheng; Junbin Huang; Ligang Zhou; Chunsheng Liu; Hao Liu. 2020. "Ustiloxin A is Produced Early in Experimental Ustilaginoidea virens Infection and Affects Transcription in Rice." Current Microbiology 77, no. 10: 2766-2774.

Journal article
Published: 18 May 2020 in Scientific Reports
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Five new chlamydosporol derivatives, named pleospyrones A-E (1–5), together with one known congener (6), were isolated from the culture of the endophytic fungus Pleosporales sp. Sigrf05, obtained from the medicinal plant Siraitia grosvenorii. The structures of the new compounds were elucidated mainly by analysis of the HRESIMS, and (1D, 2D) NMR data, while ECD and optical rotation calculations were used to assign the absolute configurations. The plausible biosynthetic pathway of these compounds were proposed. The isolated compounds were evaluated for their cytotoxicity, antifungal and antibacterial activities. Compounds 1, and 4–6 were cytotoxic against the tested cancer cells with IC50 values of 1.26~47.5 μM. Compounds 1–3 showed moderate antifungal activities against Magnaporthe oryzae, while compound 5 displayed weak antibacterial activity.

ACS Style

Daowan Lai; Ziling Mao; Zhiyao Zhou; Siji Zhao; Mengyao Xue; Jungui Dai; Ligang Zhou; Dianpeng Li. New chlamydosporol derivatives from the endophytic fungus Pleosporales sp. Sigrf05 and their cytotoxic and antimicrobial activities. Scientific Reports 2020, 10, 8193 .

AMA Style

Daowan Lai, Ziling Mao, Zhiyao Zhou, Siji Zhao, Mengyao Xue, Jungui Dai, Ligang Zhou, Dianpeng Li. New chlamydosporol derivatives from the endophytic fungus Pleosporales sp. Sigrf05 and their cytotoxic and antimicrobial activities. Scientific Reports. 2020; 10 (1):8193.

Chicago/Turabian Style

Daowan Lai; Ziling Mao; Zhiyao Zhou; Siji Zhao; Mengyao Xue; Jungui Dai; Ligang Zhou; Dianpeng Li. 2020. "New chlamydosporol derivatives from the endophytic fungus Pleosporales sp. Sigrf05 and their cytotoxic and antimicrobial activities." Scientific Reports 10, no. 1: 8193.

Journal article
Published: 14 February 2020 in RSC Advances
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Four new 3,4-dihydroisocoumarin congeners, named lophiostomin A–D (1–4), together with two known α-pyridones (5 and 6) were isolated from cultures of the endophytic fungus Lophiostoma sp. Sigrf10 obtained from Siraitia grosvenorii.

ACS Style

Ziling Mao; Mengyao Xue; Gan Gu; Weixuan Wang; Dianpeng Li; Daowan Lai; Ligang Zhou. Lophiostomin A–D: new 3,4-dihydroisocoumarin derivatives from the endophytic fungus Lophiostoma sp. Sigrf10. RSC Advances 2020, 10, 6985 -6991.

AMA Style

Ziling Mao, Mengyao Xue, Gan Gu, Weixuan Wang, Dianpeng Li, Daowan Lai, Ligang Zhou. Lophiostomin A–D: new 3,4-dihydroisocoumarin derivatives from the endophytic fungus Lophiostoma sp. Sigrf10. RSC Advances. 2020; 10 (12):6985-6991.

Chicago/Turabian Style

Ziling Mao; Mengyao Xue; Gan Gu; Weixuan Wang; Dianpeng Li; Daowan Lai; Ligang Zhou. 2020. "Lophiostomin A–D: new 3,4-dihydroisocoumarin derivatives from the endophytic fungus Lophiostoma sp. Sigrf10." RSC Advances 10, no. 12: 6985-6991.

Review
Published: 14 February 2020 in Toxins
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Mycotoxins are toxic fungal secondary metabolites that pose a major threat to the safety of food and feed. Mycotoxins are usually converted into less toxic or non-toxic metabolites through biotransformation that are often made by living organisms as well as the isolated enzymes. The conversions mainly include hydroxylation, oxidation, hydrogenation, de-epoxidation, methylation, glycosylation and glucuronidation, esterification, hydrolysis, sulfation, demethylation and deamination. Biotransformations of some notorious mycotoxins such as alfatoxins, alternariol, citrinin, fomannoxin, ochratoxins, patulin, trichothecenes and zearalenone analogues are reviewed in detail. The recent development and applications of mycotoxins detoxification through biotransformation are also discussed.

ACS Style

Peng Li; Ruixue Su; Ruya Yin; Daowan Lai; Mingan Wang; Yang Liu; Ligang Zhou. Detoxification of Mycotoxins through Biotransformation. Toxins 2020, 12, 121 .

AMA Style

Peng Li, Ruixue Su, Ruya Yin, Daowan Lai, Mingan Wang, Yang Liu, Ligang Zhou. Detoxification of Mycotoxins through Biotransformation. Toxins. 2020; 12 (2):121.

Chicago/Turabian Style

Peng Li; Ruixue Su; Ruya Yin; Daowan Lai; Mingan Wang; Yang Liu; Ligang Zhou. 2020. "Detoxification of Mycotoxins through Biotransformation." Toxins 12, no. 2: 121.

Journal article
Published: 27 December 2019 in Molecules
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Two new decalin/tetramic acid hybrid metabolites, hyalodendrins A (1) and B (2) were isolated from plant endophytic fungus Hyalodendriella sp. Ponipodef12. The structures of the new compounds were elucidated by analysis of the spectroscopic data, including NMR, HRMS and ECD, and by chemical conversion. Compounds 1 and 2 were phomasetin analogues, and both showed potent larvicidal activity against the fourth-instar larvae of Aedes aegypti with the median lethal dose (LC50) values of 10.31 and 5.93 μg/mL, respectively.

ACS Style

Ziling Mao; Weixuan Wang; Ruixue Su; Gan Gu; Zhi Long Liu; Daowan Lai; Ligang Zhou. Hyalodendrins A and B, New Decalin-Type Tetramic Acid Larvicides from the Endophytic Fungus Hyalodendriella sp. Ponipodef12. Molecules 2019, 25, 114 .

AMA Style

Ziling Mao, Weixuan Wang, Ruixue Su, Gan Gu, Zhi Long Liu, Daowan Lai, Ligang Zhou. Hyalodendrins A and B, New Decalin-Type Tetramic Acid Larvicides from the Endophytic Fungus Hyalodendriella sp. Ponipodef12. Molecules. 2019; 25 (1):114.

Chicago/Turabian Style

Ziling Mao; Weixuan Wang; Ruixue Su; Gan Gu; Zhi Long Liu; Daowan Lai; Ligang Zhou. 2019. "Hyalodendrins A and B, New Decalin-Type Tetramic Acid Larvicides from the Endophytic Fungus Hyalodendriella sp. Ponipodef12." Molecules 25, no. 1: 114.

Short communication
Published: 29 November 2019 in Natural Product Research
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Five chromone derivatives, including 2,6-dimethyl-5-methoxyl-7-hydroxylchromone (1), 6-hydroxymethyleugenin (2), 6-methoxymethyleugenin (3), chaetoquadrin D (4), and isoeugenitol (5), and three isocoumarin congeners, namely diaporthin (6), 8-hydroxy-6-methoxy-3-methylisocoumarin (7), and 6-methoxymellein (8), were isolated from the culture of the endophytic fungus Xylomelasma sp. Samif07 derived from the medicinal plant Salvia miltiorrhiza Bunge. Among them, compound 1 was a new natural product. Their structures were determined by spectroscopic methods and comparison with the literature. The isolated compounds were evaluated for their antibacterial and antioxidant activities. Compound 5 showed notable antitubercular activity against Mycobacterium tuberculosis with MIC value of 10.31 µg/mL, while compounds 1–3, and 5–7 displayed inhibitory activities against the other bacteria with MIC range of 25 ∼ 100 µg/mL. Meanwhile, compound 6 showed potent hydroxyl radical-scavenging activity with EC50 value of 15.1 µg/mL, while compounds 5–7 showed certain ferric reducing ability.

ACS Style

Daowan Lai; Jing Li; Siji Zhao; Gan Gu; Xiao Gong; Peter Proksch; Ligang Zhou. Chromone and isocoumarin derivatives from the endophytic fungus Xylomelasma sp. Samif07, and their antibacterial and antioxidant activities. Natural Product Research 2019, 1 -5.

AMA Style

Daowan Lai, Jing Li, Siji Zhao, Gan Gu, Xiao Gong, Peter Proksch, Ligang Zhou. Chromone and isocoumarin derivatives from the endophytic fungus Xylomelasma sp. Samif07, and their antibacterial and antioxidant activities. Natural Product Research. 2019; ():1-5.

Chicago/Turabian Style

Daowan Lai; Jing Li; Siji Zhao; Gan Gu; Xiao Gong; Peter Proksch; Ligang Zhou. 2019. "Chromone and isocoumarin derivatives from the endophytic fungus Xylomelasma sp. Samif07, and their antibacterial and antioxidant activities." Natural Product Research , no. : 1-5.

Journal article
Published: 12 August 2019 in Natural Product Research
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Ustilaginoidin M1 (1), a novel bis-naphtho-γ-pyrone, was isolated from the cultures of the fungus Villosiclava virens which was the pathogen of rice false smut disease. Its structure was elucidated by spectroscopic analysis and by comparison of its physical and spectroscopic data with the literature. Compound 1 was tested for its cytotoxicity against five human cancer cell lines.

ACS Style

Jiajia Meng; Siji Zhao; Pengqin Dang; Zhiyao Zhou; Daowan Lai; Ligang Zhou. Ustilaginoidin M1, a new bis-naphtho-γ-pyrone from the fungus Villosiclava virens. Natural Product Research 2019, 35, 1555 -1560.

AMA Style

Jiajia Meng, Siji Zhao, Pengqin Dang, Zhiyao Zhou, Daowan Lai, Ligang Zhou. Ustilaginoidin M1, a new bis-naphtho-γ-pyrone from the fungus Villosiclava virens. Natural Product Research. 2019; 35 (9):1555-1560.

Chicago/Turabian Style

Jiajia Meng; Siji Zhao; Pengqin Dang; Zhiyao Zhou; Daowan Lai; Ligang Zhou. 2019. "Ustilaginoidin M1, a new bis-naphtho-γ-pyrone from the fungus Villosiclava virens." Natural Product Research 35, no. 9: 1555-1560.

Review
Published: 09 July 2019 in Molecules
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Quinoa (Chenopodium quinoa Willd.) was known as the “golden grain” by the native Andean people in South America, and has been a source of valuable food over thousands of years. It can produce a variety of secondary metabolites with broad spectra of bioactivities. At least 193 secondary metabolites from quinoa have been identified in the past 40 years. They mainly include phenolic acids, flavonoids, terpenoids, steroids, and nitrogen-containing compounds. These metabolites exhibit many physiological functions, such as insecticidal, molluscicidal and antimicrobial activities, as well as various kinds of biological activities such as antioxidant, cytotoxic, anti-diabetic and anti-inflammatory properties. This review focuses on our knowledge of the structures, biological activities and functions of quinoa secondary metabolites. Biosynthesis, development and utilization of the secondary metabolites especially from quinoa bran were prospected.

ACS Style

Minyi Lin; Peipei Han; Yuying Li; Weixuan Wang; Daowan Lai; Ligang Zhou. Quinoa Secondary Metabolites and Their Biological Activities or Functions. Molecules 2019, 24, 2512 .

AMA Style

Minyi Lin, Peipei Han, Yuying Li, Weixuan Wang, Daowan Lai, Ligang Zhou. Quinoa Secondary Metabolites and Their Biological Activities or Functions. Molecules. 2019; 24 (13):2512.

Chicago/Turabian Style

Minyi Lin; Peipei Han; Yuying Li; Weixuan Wang; Daowan Lai; Ligang Zhou. 2019. "Quinoa Secondary Metabolites and Their Biological Activities or Functions." Molecules 24, no. 13: 2512.

Research article
Published: 10 June 2019 in Natural Product Research
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Two new nitrogen-containing metabolites methyl N-acetyl-O-(4-acetylphenyl)-L-homoserinate (1), dimethyl (1H-indole-3-carbonyl)-D-glutamate (2), and two new natural products, 1,2-O-isopropylidene-D-mannitol (3), N-acetyl-β-methyl-L-phenylalanine (4), along with five known compounds (5–9) were isolated from the rice false smut pathogen Villosiclava virens UV-8b cultured in the solid rice medium. The structures were elucidated by spectroscopic analysis and by comparison of their physical and spectroscopic data with the literature. These metabolites were evaluated for their antibacterial and phytotoxic activities. Compounds 5–7 showed weak inhibition against the tested bacteria, while compounds 4–6 and 9 displayed inhibitory activity against the radicle elongation of rice seeds.

ACS Style

Ali Wang; Peng Li; Peipei Han; Gan Gu; Tijiang Shan; Daowan Lai; Ligang Zhou. New nitrogen-containing metabolites from cultures of rice false smut pathogen Villosiclava virens. Natural Product Research 2019, 35, 272 -281.

AMA Style

Ali Wang, Peng Li, Peipei Han, Gan Gu, Tijiang Shan, Daowan Lai, Ligang Zhou. New nitrogen-containing metabolites from cultures of rice false smut pathogen Villosiclava virens. Natural Product Research. 2019; 35 (2):272-281.

Chicago/Turabian Style

Ali Wang; Peng Li; Peipei Han; Gan Gu; Tijiang Shan; Daowan Lai; Ligang Zhou. 2019. "New nitrogen-containing metabolites from cultures of rice false smut pathogen Villosiclava virens." Natural Product Research 35, no. 2: 272-281.

Rapid communication
Published: 20 February 2019 in Organic Letters
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Ustilobisorbicillinol A (1), which is a novel bisorbicillinoid featuring a unique cage structure that incorporates one sorbicillinol and one sorbyl-containing phenanthrenone unit, was isolated from the culture of Ustilaginoidea virens. Three biogenetically related new metabolites (2–4) were also isolated. Their structures were elucidated by extensive spectroscopic analyses, including the 13C NMR and electronic circular dichroism (ECD) calculations for the configurational assignment. The biosynthetic pathway for these sorbyl-containing polyketides was proposed. Compound 1 showed pronounced cytotoxicity, and it induced significant cell cycle arrest and apoptosis.

ACS Style

Daowan Lai; Jiajia Meng; Xuping Zhang; Dan Xu; Jungui Dai; Ligang Zhou. Ustilobisorbicillinol A, a Cytotoxic Sorbyl-Containing Aromatic Polyketide from Ustilaginoidea virens. Organic Letters 2019, 21, 1311 -1314.

AMA Style

Daowan Lai, Jiajia Meng, Xuping Zhang, Dan Xu, Jungui Dai, Ligang Zhou. Ustilobisorbicillinol A, a Cytotoxic Sorbyl-Containing Aromatic Polyketide from Ustilaginoidea virens. Organic Letters. 2019; 21 (5):1311-1314.

Chicago/Turabian Style

Daowan Lai; Jiajia Meng; Xuping Zhang; Dan Xu; Jungui Dai; Ligang Zhou. 2019. "Ustilobisorbicillinol A, a Cytotoxic Sorbyl-Containing Aromatic Polyketide from Ustilaginoidea virens." Organic Letters 21, no. 5: 1311-1314.

Journal article
Published: 12 February 2019 in Scientific Reports
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Ustilaginoidins are a kind of mycotoxins with 9,9′-linked bis-naphtho-γ-pyrones structures produced by the rice false smut pathogen Villosiclava virens. These metabolites displayed a wide range of bioactivities, such as teratogenic, cytotoxic, phytotoxic, and antibacterial activities. So far 26 ustilaginoidins have been isolated from V. virens, among which 18 compounds contained stereogenic center(s), however, most of them were unknown for the absolute configurations, except that of ustilaginoidin D. In this study, the absolute structures of these ustilaginoidins were constructed for the first time by analysis of the biosynthetic monomers obtained from a gene knockout mutant (ΔUV_2091) of V. virens. The gene UV_2091 was predicted to encode an enzyme that dimerized the monomeric naphtho-γ-pyrones in V. virens. Knockout of this gene led to the accumulation of three monomers, namely hemiustilaginoidin F (1), epihemiustilaginoidin D (2), and hemiustilaginoidin D (3), but the production of ustilaginoidins was completely blocked. The structures of the monomers were deduced by spectroscopic analysis, in combination with TDDFT ECD calculations for determining the absolute configurations. These compounds were tested for their phytotoxic, cytotoxic, antibacterial, and antifungal activities. Compounds 1 and 3 showed inhibition against the radicle and plumule elongation of rice and lettuce seeds at the tested concentrations. Compound 1 was active against the tested five human cancer cells, with half maximal inhibitory concentrations (IC50s) of 13.2~37.3 μM. Compounds 1~3 inhibited the growth of the tested pathogenic bacteria with minimum inhibitory concentrations of 8~32 µg/mL, while compound 3 exhibited antifungal activity against Magnaporthe oryzae (IC50, 5.21 µg/mL). A comparison of these data with those of the ustilaginoidins provided insights into the structure-bioactivity relationships.

ACS Style

Daowan Lai; Jiajia Meng; Dan Xu; Xuping Zhang; Yafeng Liang; Yu Han; Cong Jiang; Huiquan Liu; Chenfang Wang; Ligang Zhou; Jin-Rong Xu. Determination of the absolute configurations of the stereogenic centers of ustilaginoidins by studying the biosynthetic monomers from a gene knockout mutant of Villosiclava virens. Scientific Reports 2019, 9, 1 -10.

AMA Style

Daowan Lai, Jiajia Meng, Dan Xu, Xuping Zhang, Yafeng Liang, Yu Han, Cong Jiang, Huiquan Liu, Chenfang Wang, Ligang Zhou, Jin-Rong Xu. Determination of the absolute configurations of the stereogenic centers of ustilaginoidins by studying the biosynthetic monomers from a gene knockout mutant of Villosiclava virens. Scientific Reports. 2019; 9 (1):1-10.

Chicago/Turabian Style

Daowan Lai; Jiajia Meng; Dan Xu; Xuping Zhang; Yafeng Liang; Yu Han; Cong Jiang; Huiquan Liu; Chenfang Wang; Ligang Zhou; Jin-Rong Xu. 2019. "Determination of the absolute configurations of the stereogenic centers of ustilaginoidins by studying the biosynthetic monomers from a gene knockout mutant of Villosiclava virens." Scientific Reports 9, no. 1: 1-10.

Review
Published: 27 November 2018 in Molecules
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Rice (Oryza sativa L.) is an important food crop providing energy and nutrients for more than half of the world population. It produces vast amounts of secondary metabolites. At least 276 secondary metabolites from rice have been identified in the past 50 years. They mainly include phenolic acids, flavonoids, terpenoids, steroids, alkaloids, and their derivatives. These metabolites exhibit many physiological functions, such as regulatory effects on rice growth and development, disease-resistance promotion, anti-insect activity, and allelopathic effects, as well as various kinds of biological activities such as antimicrobial, antioxidant, cytotoxic, and anti-inflammatory properties. This review focuses on our knowledge of the structures, biological functions and activities, biosynthesis, and metabolic regulation of rice secondary metabolites. Some considerations about cheminformatics, metabolomics, genetic transformation, production, and applications related to the secondary metabolites from rice are also discussed.

ACS Style

Weixuan Wang; Yuying Li; Pengqin Dang; Siji Zhao; Daowan Lai; Ligang Zhou. Rice Secondary Metabolites: Structures, Roles, Biosynthesis, and Metabolic Regulation. Molecules 2018, 23, 3098 .

AMA Style

Weixuan Wang, Yuying Li, Pengqin Dang, Siji Zhao, Daowan Lai, Ligang Zhou. Rice Secondary Metabolites: Structures, Roles, Biosynthesis, and Metabolic Regulation. Molecules. 2018; 23 (12):3098.

Chicago/Turabian Style

Weixuan Wang; Yuying Li; Pengqin Dang; Siji Zhao; Daowan Lai; Ligang Zhou. 2018. "Rice Secondary Metabolites: Structures, Roles, Biosynthesis, and Metabolic Regulation." Molecules 23, no. 12: 3098.

Journal article
Published: 01 October 2018 in Food Control
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Rice false smut (RFS) is one of the most destructive diseases in majority of rice growing areas around the world. Ustiloxins A (UA) and B (UB) are the main cyclopeptide mycotoxins (>90%) among all characterized ustiloxins which are produced by the RFS pathogen Villosiclava virens. Rapid diagnosis of ustiloxins is essential to assess the safety of rice food and feed contaminated with the pathogen. In this study, a monoclonal antibody (mAb) with equal reactivity to UA and UB, which was named as mAb 4C4F11, was successfully screened. After optimization, the sensitivity, selectivity and accuracy of the direct competitive enzyme-linked immunosorbent assay (dc-ELISA) for simultaneous detection of the total content of UA and UB in rice samples was explicated. The concentration causing 50% of inhibition (IC50) was 13.0 ng/mL for UA or UB, the limit of detection (LOD) was 0.7 ng/mL, and the calibration range was from 2 to 76 ng/mL. The LOD and limit of quantification (LOQ) of UA plus UB in rice were 35 and 100 ng/g, respectively. Average recoveries of UA or UB from the spiked RFS balls and grains were between 84.1% and 102.5% with coefficient of variation less than 15%. The developed immunoassay can be employed as a rapid, effective and accurate method for detection of main ustiloxins in RFS balls as well as rice food and feed samples.

ACS Style

Xiaoxiang Fu; Weixuan Wang; Yuying Li; Xiaohan Wang; Guiyu Tan; Daowan Lai; Mingan Wang; Ligang Zhou; Baomin Wang. Development of a monoclonal antibody with equal reactivity to ustiloxins A and B for quantification of main cyclopeptide mycotoxins in rice samples. Food Control 2018, 92, 201 -207.

AMA Style

Xiaoxiang Fu, Weixuan Wang, Yuying Li, Xiaohan Wang, Guiyu Tan, Daowan Lai, Mingan Wang, Ligang Zhou, Baomin Wang. Development of a monoclonal antibody with equal reactivity to ustiloxins A and B for quantification of main cyclopeptide mycotoxins in rice samples. Food Control. 2018; 92 ():201-207.

Chicago/Turabian Style

Xiaoxiang Fu; Weixuan Wang; Yuying Li; Xiaohan Wang; Guiyu Tan; Daowan Lai; Mingan Wang; Ligang Zhou; Baomin Wang. 2018. "Development of a monoclonal antibody with equal reactivity to ustiloxins A and B for quantification of main cyclopeptide mycotoxins in rice samples." Food Control 92, no. : 201-207.

Review article
Published: 13 August 2018 in Journal of Natural Products
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Palmarumycin B6 and its regioisomer were synthesized via 7- and 13-step routes using 2-chlorophenol and 4-chlorophenyl methyl ether as the starting materials in overall yields of 2.7% and 12%, respectively. Their structures were characterized by 1H and 13C NMR, HRESIMS, and X-ray diffraction data. The structure of palmarumycin B6 was revised as 6-chloropalmarumycin CP17. The bioassay results showed that the larvicidal activity of palmarumycin B6 with an LC50 value of 32.7 μM was significantly higher than that of its 8-chloro isomer, with an LC50 value of 227.3 μM.

ACS Style

Xinlei Liu; Weiwei Wang; Yu Zhao; Daowan Lai; Ligang Zhou; Zhilong Liu; Mingan Wang. Total Synthesis and Structure Revision of Palmarumycin B6. Journal of Natural Products 2018, 81, 1803 -1809.

AMA Style

Xinlei Liu, Weiwei Wang, Yu Zhao, Daowan Lai, Ligang Zhou, Zhilong Liu, Mingan Wang. Total Synthesis and Structure Revision of Palmarumycin B6. Journal of Natural Products. 2018; 81 (8):1803-1809.

Chicago/Turabian Style

Xinlei Liu; Weiwei Wang; Yu Zhao; Daowan Lai; Ligang Zhou; Zhilong Liu; Mingan Wang. 2018. "Total Synthesis and Structure Revision of Palmarumycin B6." Journal of Natural Products 81, no. 8: 1803-1809.

Communication
Published: 06 March 2018 in Molecules
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Rhizopycnis acids A (1) and B (2), two new anisic acid derivatives, were obtained from the ethyl acetate extract of the fermentation cultures of Rhizopycnis vagum, an endophytic fungus isolated from the healthy tissues of Nicotiana tabacum. The structures of the two compounds were determined through a series of 1D and 2D NMR and HRMS spectral analyses. Both compounds were the first anisic acid derivatives containing methylbutanoic/methylbutenoic acid group found in fungi. 1 and 2 displayed antibacterial activity against six tested bacteria with IC50 values in the range 16.1~81.3 μg/mL.

ACS Style

Ali Wang; Peng Li; Xuping Zhang; Peipei Han; Daowan Lai; Ligang Zhou. Two New Anisic Acid Derivatives from Endophytic Fungus Rhizopycnis vagum Nitaf22 and Their Antibacterial Activity. Molecules 2018, 23, 591 .

AMA Style

Ali Wang, Peng Li, Xuping Zhang, Peipei Han, Daowan Lai, Ligang Zhou. Two New Anisic Acid Derivatives from Endophytic Fungus Rhizopycnis vagum Nitaf22 and Their Antibacterial Activity. Molecules. 2018; 23 (3):591.

Chicago/Turabian Style

Ali Wang; Peng Li; Xuping Zhang; Peipei Han; Daowan Lai; Ligang Zhou. 2018. "Two New Anisic Acid Derivatives from Endophytic Fungus Rhizopycnis vagum Nitaf22 and Their Antibacterial Activity." Molecules 23, no. 3: 591.

Review
Published: 15 January 2018 in Molecules
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Cyclic depsipeptides (CDPs) are cyclopeptides in which amide groups are replaced by corresponding lactone bonds due to the presence of a hydroxylated carboxylic acid in the peptide structure. These peptides sometimes display additional chemical modifications, including unusual amino acid residues in their structures. This review highlights the occurrence, structures and biological activities of the fungal CDPs reported until October 2017. About 352 fungal CDPs belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, and tridecadepsipeptides have been isolated from fungi. These metabolites are mainly reported from the genera Acremonium, Alternaria, Aspergillus, Beauveria, Fusarium, Isaria, Metarhizium, Penicillium, and Rosellina. They are known to exhibit various biological activities such as cytotoxic, phytotoxic, antimicrobial, antiviral, anthelmintic, insecticidal, antimalarial, antitumoral and enzyme-inhibitory activities. Some CDPs (i.e., PF1022A, enniatins and destruxins) have been applied as pharmaceuticals and agrochemicals.

ACS Style

Xiaohan Wang; Xiao Gong; Peng Li; Daowan Lai; Ligang Zhou. Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi. Molecules 2018, 23, 169 .

AMA Style

Xiaohan Wang, Xiao Gong, Peng Li, Daowan Lai, Ligang Zhou. Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi. Molecules. 2018; 23 (1):169.

Chicago/Turabian Style

Xiaohan Wang; Xiao Gong; Peng Li; Daowan Lai; Ligang Zhou. 2018. "Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi." Molecules 23, no. 1: 169.

Review
Published: 27 November 2017 in Molecules
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Cyclic peptides are cyclic compounds formed mainly by the amide bonds between either proteinogenic or non-proteinogenic amino acids. This review highlights the occurrence, structures and biological activities of fungal cyclic peptides (excluding cyclodipeptides, and peptides containing ester bonds in the core ring) reported until August 2017. About 293 cyclic peptides belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, dodeca-, tetradeca-, and octadecapeptides as well as cyclic peptides containing ether bonds in the core ring have been isolated from fungi. They were mainly isolated from the genera Aspergillus, Penicillium, Fusarium, Acremonium and Amanita. Some of them were screened to have antimicrobial, antiviral, cytotoxic, phytotoxic, insecticidal, nematicidal, immunosuppressive and enzyme-inhibitory activities to show their potential applications. Some fungal cyclic peptides such as the echinocandins, pneumocandins and cyclosporin A have been developed as pharmaceuticals.

ACS Style

Xiaohan Wang; Minyi Lin; Dan Xu; Daowan Lai; Ligang Zhou. Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides. Molecules 2017, 22, 2069 .

AMA Style

Xiaohan Wang, Minyi Lin, Dan Xu, Daowan Lai, Ligang Zhou. Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides. Molecules. 2017; 22 (12):2069.

Chicago/Turabian Style

Xiaohan Wang; Minyi Lin; Dan Xu; Daowan Lai; Ligang Zhou. 2017. "Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides." Molecules 22, no. 12: 2069.