Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1...

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Published inMarine drugs Vol. 18; no. 2; p. 100
Main Authors Ran, Yan-Qin, Lan, Wen-Jian, Qiu, Yi, Guo, Qi, Feng, Gong-Kan, Deng, Rong, Zhu, Xiao-Feng, Li, Hou-Jin, Dong, Jun
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 03.02.2020
MDPI
Subjects
Cancer
Cell lines
Cytotoxicity
Fungi
Hepatocellular carcinoma
hepatoma
humans
Hydrocarbons
isocoumarins
Liver cancer
marine fungus
Marine molluscs
marine shellfish
Metabolites
Microorganisms
monarubin
Monascus ruber
Nasopharyngeal carcinoma
neoplasm cells
Neoplasms
NMR
Nuclear magnetic resonance
Polyketides
Shellfish
Throat cancer
Tumor cell lines
China
monarubin
marine shellfish
Monascus ruber
marine fungus
cytotoxicity
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Abstract Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.
AbstractList Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.
Three new compounds, monarubins A–C ( 1 , 6 and 13 ), together with ten known compounds, including four alkaloids ( 2 – 5 ), two isocoumarins ( 7 and 8 ) and four polyketides ( 9 – 12 ), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3 , 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid ( 3 ) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3- sec -buthylpyrazine ( 4 ) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B ( 6 ) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC 50 values of 1.72 and 0.71 μΜ, respectively; lunatinin ( 7 ) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC 50 values of 9.60, 7.12 and 28.12 μΜ, respectively.
Three new compounds, monarubins A-C ( , and ), together with ten known compounds, including four alkaloids ( - ), two isocoumarins ( and ) and four polyketides ( - ), were isolated from marine shellfish-associated fungus BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds , and were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid ( ) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3- -buthylpyrazine ( ) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B ( ) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC values of 1.72 and 0.71 μΜ, respectively; lunatinin ( ) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC values of 9.60, 7.12 and 28.12 μΜ, respectively.
Three new compounds, monarubins A-C (1, 6 and 13), together with ten known compounds, including four alkaloids (2-5), two isocoumarins (7 and 8) and four polyketides (9-12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.Three new compounds, monarubins A-C (1, 6 and 13), together with ten known compounds, including four alkaloids (2-5), two isocoumarins (7 and 8) and four polyketides (9-12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.
Three new compounds, monarubins A–C ( 1, 6 and 13), together with ten known compounds, including four alkaloids ( 2– 5), two isocoumarins ( 7 and 8) and four polyketides ( 9– 12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid ( 3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3- sec-buthylpyrazine ( 4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B ( 6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC 50 values of 1.72 and 0.71 μΜ, respectively; lunatinin ( 7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC 50 values of 9.60, 7.12 and 28.12 μΜ, respectively.
Three new compounds, monarubins A−C (1, 6 and 13), together with ten known compounds, including four alkaloids (2−5), two isocoumarins (7 and 8) and four polyketides (9−12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.
Author Deng, Rong
Li, Hou-Jin
Feng, Gong-Kan
Lan, Wen-Jian
Ran, Yan-Qin
Dong, Jun
Qiu, Yi
Guo, Qi
Zhu, Xiao-Feng
AuthorAffiliation 3 School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China; qiuyi0771@163.com (Y.Q.); guoqi1228@126.com (Q.G.)
4 State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Cancer Center, Sun Yat-sen University, Guangzhou 510060, China; fenggk@sysucc.org.cn (G.-K.F.); dengrong@sysucc.org.cn (R.D.); zhuxfeng@mail.sysu.edu.cn (X.-F.Z.)
2 School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China; lanwj@mail.sysu.edu.cn
1 School of Traditional Chinese Medicine, Guangdong Pharmaceutical University, Guangzhou 510006, China; ranyq03@163.com
AuthorAffiliation_xml – name: 4 State Key Laboratory of Oncology in South China, Collaborative Innovation Center for Cancer Medicine, Cancer Center, Sun Yat-sen University, Guangzhou 510060, China; fenggk@sysucc.org.cn (G.-K.F.); dengrong@sysucc.org.cn (R.D.); zhuxfeng@mail.sysu.edu.cn (X.-F.Z.)
– name: 2 School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China; lanwj@mail.sysu.edu.cn
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/32028626$$D View this record in MEDLINE/PubMed
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Keywords monarubin
marine shellfish
Monascus ruber
marine fungus
cytotoxicity
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Snippet Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four...
Three new compounds, monarubins A-C ( , and ), together with ten known compounds, including four alkaloids ( - ), two isocoumarins ( and ) and four polyketides...
Three new compounds, monarubins A-C (1, 6 and 13), together with ten known compounds, including four alkaloids (2-5), two isocoumarins (7 and 8) and four...
Three new compounds, monarubins A–C ( 1, 6 and 13), together with ten known compounds, including four alkaloids ( 2– 5), two isocoumarins ( 7 and 8) and four...
Three new compounds, monarubins A–C ( 1 , 6 and 13 ), together with ten known compounds, including four alkaloids ( 2 – 5 ), two isocoumarins ( 7 and 8 ) and...
Three new compounds, monarubins A−C (1, 6 and 13), together with ten known compounds, including four alkaloids (2−5), two isocoumarins (7 and 8) and four...
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StartPage 100
SubjectTerms Cancer
Cell lines
Cytotoxicity
Fungi
Hepatocellular carcinoma
hepatoma
humans
Hydrocarbons
isocoumarins
Liver cancer
marine fungus
Marine molluscs
marine shellfish
Metabolites
Microorganisms
monarubin
Monascus ruber
Nasopharyngeal carcinoma
neoplasm cells
Neoplasms
NMR
Nuclear magnetic resonance
Polyketides
Shellfish
Throat cancer
Tumor cell lines
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Title Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5
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