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Hua-jie Zhu - One of the best experts on this subject based on the ideXlab platform.
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a novel Azaphilone muyophilone a from the endophytic fungus muyocopron laterale 0307 2
Frontiers in Chemistry, 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) calculations, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
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a new epimer of Azaphilone derivative pinophilin b from the gorgonian derived fungus aspergillus fumigatus 14 27
Natural Product Research, 2021Co-Authors: Yahui Zhang, Fei Cao, Hua-jie Zhu, Xiaoyue Peng, Lixi Feng, Chang-yun WangAbstract:A new epimer of Azaphilone derivative pinophilin B, epi-pinophilin B (1), and three known analogues (2–4) were obtained from the culture of the gorgonian-derived fungus Aspergillus fumigatus 14–27....
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a novel Azaphilone muyophilone a from the endophytic fungus muyocopron laterale 0307 2
Frontiers in Chemistry, 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
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DataSheet1_A Novel Azaphilone Muyophilone A From the Endophytic Fungus Muyocopron laterale 0307-2.PDF
'Frontiers Media SA', 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
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DataSheet2_A Novel Azaphilone Muyophilone A From the Endophytic Fungus Muyocopron laterale 0307-2.ZIP
'Frontiers Media SA', 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
Chao Yuan - One of the best experts on this subject based on the ideXlab platform.
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a novel Azaphilone muyophilone a from the endophytic fungus muyocopron laterale 0307 2
Frontiers in Chemistry, 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) calculations, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
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a novel Azaphilone muyophilone a from the endophytic fungus muyocopron laterale 0307 2
Frontiers in Chemistry, 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
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DataSheet1_A Novel Azaphilone Muyophilone A From the Endophytic Fungus Muyocopron laterale 0307-2.PDF
'Frontiers Media SA', 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
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DataSheet2_A Novel Azaphilone Muyophilone A From the Endophytic Fungus Muyocopron laterale 0307-2.ZIP
'Frontiers Media SA', 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
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Table1_A Novel Azaphilone Muyophilone A From the Endophytic Fungus Muyocopron laterale 0307-2.DOCX
'Frontiers Media SA', 2021Co-Authors: Chao Yuan, Yuhua Guo, Ke Wang, Zhunian Wang, Hua-jie ZhuAbstract:Two known Azaphilone derivatives, 4,6-dimethylcurvulinic acid (1) and austdiol (2), and their novel heterotrimer, muyophilone A (3), were isolated and identified from an endophytic fungus, Muyocopron laterale 0307-2. Their structures and stereochemistry were established by extensive spectroscopic analyses including HRMS, NMR spectroscopy, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopic methods, as well as single crystal X-ray diffraction. In the structure of 3, two compound 2-derived Azaphilone units were connected through an unprecedented five-membered carbon bridge which was proposed to be originated from compound 1. Compound 3 represents the first example of Azaphilone heterotrimers.
Chang-yun Wang - One of the best experts on this subject based on the ideXlab platform.
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a new epimer of Azaphilone derivative pinophilin b from the gorgonian derived fungus aspergillus fumigatus 14 27
Natural Product Research, 2021Co-Authors: Yahui Zhang, Fei Cao, Hua-jie Zhu, Xiaoyue Peng, Lixi Feng, Chang-yun WangAbstract:A new epimer of Azaphilone derivative pinophilin B, epi-pinophilin B (1), and three known analogues (2–4) were obtained from the culture of the gorgonian-derived fungus Aspergillus fumigatus 14–27....
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nabr induced production of brominated Azaphilones and related tricyclic polyketides by the marine derived fungus penicillium janthinellum hk1 6
Journal of Natural Products, 2019Co-Authors: Li Shen, Yao-yao Zheng, Nan-xing Shen, Min Chen, Zhiqi Chen, Fengmin Zhang, Xiaojian Zhou, Chang-yun WangAbstract:Cultivation of the mangrove rhizosphere soil-derived fungus Penicillium janthinellum HK1-6 with NaBr led to the isolation of two new brominated Azaphilones, penicilones G and H (5, 6), two new tricyclic polyketides, penijanthinones A and B (7, 8), and two known Azaphilones, penicilones A and B (1, 2). The planar structures and relative configurations of the new compounds were elucidated using comprehensive spectroscopic methods including 1D and 2D NOE spectra. Their absolute configurations were determined by chemical conversions, TDDFT ECD calculations, and comparisons of their ECD spectra. Interestingly, the NaBr-induced brominated Azaphilones (5, 6) had the opposite configuration at C-7 compared to the chloro analogues (3, 4) produced by this fungus cultivated with sea salt. Ester hydrolysis of penicilone B (2) afforded the carboxylic acid side chain 2,4-dimethyldec-2-enoic acid (9), with a 4 S configuration assigned by its specific rotation. Penicilone H (6) showed antibacterial activity with MIC values ranging from 3.13 to 12.5 μg/mL.
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NaBr-Induced Production of Brominated Azaphilones and Related Tricyclic Polyketides by the Marine-Derived Fungus Penicillium janthinellum HK1‑6
2019Co-Authors: Min Chen, Yao-yao Zheng, Nan-xing Shen, Li Shen, Zhiqi Chen, Fengmin Zhang, Xiaojian Zhou, Chang-yun WangAbstract:Cultivation of the mangrove rhizosphere soil-derived fungus Penicillium janthinellum HK1-6 with NaBr led to the isolation of two new brominated Azaphilones, penicilones G and H (5, 6), two new tricyclic polyketides, penijanthinones A and B (7, 8), and two known Azaphilones, penicilones A and B (1, 2). The planar structures and relative configurations of the new compounds were elucidated using comprehensive spectroscopic methods including 1D and 2D NOE spectra. Their absolute configurations were determined by chemical conversions, TDDFT ECD calculations, and comparisons of their ECD spectra. Interestingly, the NaBr-induced brominated Azaphilones (5, 6) had the opposite configuration at C-7 compared to the chloro analogues (3, 4) produced by this fungus cultivated with sea salt. Ester hydrolysis of penicilone B (2) afforded the carboxylic acid side chain 2,4-dimethyldec-2-enoic acid (9), with a 4S configuration assigned by its specific rotation. Penicilone H (6) showed antibacterial activity with MIC values ranging from 3.13 to 12.5 μg/mL
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Pleosporalone A, the first Azaphilone characterized with aromatic A-ring from a marine-derived Pleosporales sp. fungus
Natural product research, 2016Co-Authors: Fei Cao, Jian-kun Yang, Yun-feng Liu, Hua-jie Zhu, Chang-yun WangAbstract:A fungal strain, Pleosporales sp. CF09-1, was isolated from marine sediment collected from the Bohai Sea. A novel Azaphilone derivative, named pleosporalone A (1), along with two known analogues, cohaerins A and B (2 and 3), were obtained and identified from the culture extract of Pleosporales sp. CF09-1. Their planar structures were elucidated by detailed analysis of spectroscopic data and by comparison with related known compounds. Pleosporalone A (1) represents the first Azaphilone derivative characterised with A-ring aromatisation. Compound 1 showed strong antifungal activity against three plant pathogenic fungi Botrytis cinerea, Rhizopus oryzae and Phytophthora capsici with the MIC values of 0.39, 0.78 and 0.78 μM, respectively.
Soulard Marine - One of the best experts on this subject based on the ideXlab platform.
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Synthetic approach toward the total synthesis of epicocconone, studies of oxydative dearomatization mediated by I(III) or I(V)
2014Co-Authors: Soulard MarineAbstract:L'epicocconone est un produit naturel tricyclique, de la famille des Azaphilones, isolé en 2003 d'un champignon Epicoccum nigrum. Ce composé se lie de façon covalente aux amines, conduisant à la formation d'une énamine fluorescente. Cette réaction, réversible en fonction du pH, fait de ce composé un excellent marqueur de protéines pour la détection sur gels d'électrophorèse compatible avec une analyse de spectrométrie de masse. La synthèse de ce produit naturel a été débutée au sein de notre laboratoire en s'appuyant sur les travaux réalisés précédemment et mettant en jeu une étape clé de désaromatisation oxydante à l'aide d'iode hypervalent. Une étude méthodologique de réaction clé a permis de comparer l'efficacité et la diastéréosélectivité de l'oxydation effectuée par l'iode (III) ou l'iode (V).Epicocconone is a tricyclic natural product of the Azaphilone family, isolated from the fungus Epicoccum nigrum. This compound covalently binds to primary amines, leading to a protein conjugate which is highly fluorescent. This reaction, reversible according to the pH, make this compound an excellent protein stain compatible with mass spectrometry analysis. The synthesis of this natural product has been started in our laboratory based on the previous work in involves a key oxidative dearomatization using hypervalent iodine. Methodological studies of this key reaction allowed us to compare the efficiency and diastereoselectivity of iodine (III) and iodine (V) mediated oxidations
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Approche synthétique vers la synthèse totale de l’epicocconone, étude de la réaction de désaromatisation oxydante à l’aide d’iode hypervalent (III) ou (V)
HAL CCSD, 2014Co-Authors: Soulard MarineAbstract:Epicocconone is a tricyclic natural product of the Azaphilone family, isolated from the fungus Epicoccum nigrum. This compound covalently binds to primary amines, leading to a protein conjugate which is highly fluorescent. This reaction, reversible according to the pH, make this compound an excellent protein stain compatible with mass spectrometry analysis. The synthesis of this natural product has been started in our laboratory based on the previous work in involves a key oxidative dearomatization using hypervalent iodine. Methodological studies of this key reaction allowed us to compare the efficiency and diastereoselectivity of iodine (III) and iodine (V) mediated oxidations.L'epicocconone est un produit naturel tricyclique, de la famille des Azaphilones, isolé en 2003 d'un champignon Epicoccum nigrum. Ce composé se lie de façon covalente aux amines, conduisant à la formation d'une énamine fluorescente. Cette réaction, réversible en fonction du pH, fait de ce composé un excellent marqueur de protéines pour la détection sur gels d'électrophorèse compatible avec une analyse de spectrométrie de masse. La synthèse de ce produit naturel a été débutée au sein de notre laboratoire en s'appuyant sur les travaux réalisés précédemment et mettant en jeu une étape clé de désaromatisation oxydante à l'aide d'iode hypervalent. Une étude méthodologique de réaction clé a permis de comparer l'efficacité et la diastéréosélectivité de l'oxydation effectuée par l'iode (III) ou l'iode (V)
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Approche synthétique vers la synthèse totale de l'epicocconone, étude de la réaction de désaromatisation oxydante à l'aide d'iode hypervalent (III) ou (V)
2014Co-Authors: Soulard Marine, Franck Xavier, Witulski BernhardAbstract:L'epicocconone est un produit naturel tricyclique, de la famille des Azaphilones, isolé en 2003 d'un champignon Epicoccum nigrum. Ce composé se lie de façon covalente aux amines, conduisant à la formation d'une énamine fluorescente. Cette réaction, réversible en fonction du pH, fait de ce composé un excellent marqueur de protéines pour la détection sur gels d'électrophorèse compatible avec une analyse de spectrométrie de masse. La synthèse de ce produit naturel a été débutée au sein de notre laboratoire en s'appuyant sur les travaux réalisés précédemment et mettant en jeu une étape clé de désaromatisation oxydante à l'aide d'iode hypervalent. Une étude méthodologique de réaction clé a permis de comparer l'efficacité et la diastéréosélectivité de l'oxydation effectuée par l'iode (III) ou l'iode (V).Epicocconone is a tricyclic natural product of the Azaphilone family, isolated from the fungus Epicoccum nigrum. This compound covalently binds to primary amines, leading to a protein conjugate which is highly fluorescent. This reaction, reversible according to the pH, make this compound an excellent protein stain compatible with mass spectrometry analysis. The synthesis of this natural product has been started in our laboratory based on the previous work in involves a key oxidative dearomatization using hypervalent iodine. Methodological studies of this key reaction allowed us to compare the efficiency and diastereoselectivity of iodine (III) and iodine (V) mediated oxidations.ROUEN-INSA Madrillet (765752301) / SudocSudocFranceF
Tzuming Pan - One of the best experts on this subject based on the ideXlab platform.
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mpp7 controls regioselective knoevenagel condensation during the biosynthesis of monascus Azaphilone pigments
Tetrahedron Letters, 2014Co-Authors: Bijinu Balakrishnan, Tzuming Pan, Chien-chi Chen, Hyung-jin KwonAbstract:Targeted inactivation of the mpp7 gene in the Monascus Azaphilone pigment (MAzP) biosynthetic gene cluster resulted in the accumulation of monasfluol A (7) and B (8), of which the latter was a novel compound, and the abolition of the main MAzPs. It is thus proposed that 7 and 8 are the products of non-enzymatic Knoevenagel condensation followed by a reduction and that Mpp7 assists in regioselective Knoevenagel aldol condensation during MAzP biosynthesis.
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anti inflammatory properties of yellow and orange pigments from monascus purpureus ntu 568
Journal of Agricultural and Food Chemistry, 2013Co-Authors: Lichuan Hsu, Yawen Hsu, Yuhan Liang, Yaohaur Kuo, Tzuming PanAbstract:The Monascus species has been used in foods for thousands of years in China. In this study, 10 Azaphilone pigments, including four yellow and six orange pigments, were isolated from the fermented r...
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monaphilones a c three new antiproliferative Azaphilone derivatives from monascus purpureus ntu 568
Journal of Agricultural and Food Chemistry, 2010Co-Authors: Yawen Hsu, Lichuan Hsu, Yuhan Liang, Yaohaur Kuo, Tzuming PanAbstract:Monascus purpureus NTU 568 was a mutant strain from M. purpureus HM105. The methanol extract of red mold rice fermented by this strain exhibited four major yellow pigment signals on HPLC profile. By repeated chemical chromatography methods, three new Azaphilone derivatives, namely, monaphilone A (1), B (2) and C (3), along with the known pigments ankaflavin (4) and monascin (5), were isolated and characterized. Based on spectroscopic analyses, mainly 1D and 2D NMR data, the structures of compounds 1-3 were completely elucidated; in addition, 1-3 were determined to be new Azaphilone structures, due to the decrease of carbon monoxide for producing a gamma-lactone ring, compared with other Azaphilone derivatives. Biological evaluations showed that monaphilone A (1) and B (2) exhibited an antiproliferative effect against HEp-2 (human laryngeal carcinoma cell line) and WiDr (human colon adenocarcinoma cell line), and none of the five compounds had toxicity to normal human lung cell lines (WI-38 and MRC-5) at 70 muM.
