Cladodionen, a Cytotoxic Hybrid Polyketide from the Marine-Derived Cladosporium sp. OUCMDZ-1635

doi:10.3390/md16020071

. 2018 Feb 22;16(2):71.

doi: 10.3390/md16020071.

Cladodionen, a Cytotoxic Hybrid Polyketide from the Marine-Derived Cladosporium sp. OUCMDZ-1635

Guoliang Zhu¹, Fandong Kong^{2

3}, Yi Wang⁴, Peng Fu⁵, Weiming Zhu^{6

7}

Affiliations

¹ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. guoliangzhu2015@hotmail.com.
² Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. kongfandong501@126.com.
³ Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China. kongfandong501@126.com.
⁴ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. wangyi0213@ouc.edu.cn.
⁵ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. fupeng@ouc.edu.cn.
⁶ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. weimingzhu@ouc.edu.cn.
⁷ Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, China. weimingzhu@ouc.edu.cn.

PMID: 29470403
PMCID: PMC5852499
DOI: 10.3390/md16020071

Free PMC article

Cladodionen, a Cytotoxic Hybrid Polyketide from the Marine-Derived Cladosporium sp. OUCMDZ-1635

Guoliang Zhu et al. Mar Drugs. 2018.

Free PMC article

. 2018 Feb 22;16(2):71.

doi: 10.3390/md16020071.

Authors

Guoliang Zhu¹, Fandong Kong^{2

3}, Yi Wang⁴, Peng Fu⁵, Weiming Zhu^{6

7}

Affiliations

¹ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. guoliangzhu2015@hotmail.com.
² Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. kongfandong501@126.com.
³ Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China. kongfandong501@126.com.
⁴ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. wangyi0213@ouc.edu.cn.
⁵ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. fupeng@ouc.edu.cn.
⁶ Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China. weimingzhu@ouc.edu.cn.
⁷ Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology, Qingdao 266003, China. weimingzhu@ouc.edu.cn.

PMID: 29470403
PMCID: PMC5852499
DOI: 10.3390/md16020071

Abstract

A new hybrid polyketide, cladodionen (1), together with a new abscisic acid analogue, cladosacid (2), were isolated from the marine-derived fungus, Cladosporium sp. OUCMDZ-1635. Their structures, including the absolute configurations, were fully elucidated on the basis of spectroscopic analysis, ECD spectra, quantum chemical calculations, and chemical methods. Cladodionen (1) showed cytotoxic activities against MCF-7, HeLa, HCT-116, and HL-60 human cancer cell lines with IC₅₀ values of 18.7, 19.1, 17.9, and 9.1 µM.

Keywords: Cladosporium sp. OUCMDZ-1635; cladodionen; cladosacid; cytotoxicities; marine-derived fungus; polyketide.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

**Figure 1**
Chemical structures of compounds 1–3.

**Scheme 1**
Methylation of cladodionen (1).

**Figure 2**
Key 2D NMR correlations for the structural assignment of 1–3.

**Figure 3**
Measured and calculated ECD spectra for 1.

**Figure 4**
Measured and calculated ECD spectra and ECD exciton chirality model for 2.

See this image and copyright information in PMC

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References

1. Bernan V.S., Greenstein M., Maiese W.M. Marine microorganisms as a source of new natural products. Adv. Appl. Microbiol. 1997;43:57–90. - PubMed
1. Newman D.J., Hill R.T. New drugs from marine microbes: The tide is turning. J. Ind. Microbiol. Biotechnol. 2006;33:539–544. doi: 10.1007/s10295-006-0115-2. - DOI - PubMed
1. Baharum S.N., Beng E.K., Mokhtar M.A.A. Marine microorganisms: Potential application and challenges. J. Biol. Sci. 2010;10:555–564. doi: 10.3923/jbs.2010.555.564. - DOI
1. Corinaldesi C., Barone G., Marcellini F., Dell’Anno A., Danovaro R. Marine microbial-derived molecules and their potential use in cosmeceutical and cosmetic products. Mar. Drugs. 2017;15:118. doi: 10.3390/md15040118. - DOI - PMC - PubMed
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[1] Bernan V.S., Greenstein M., Maiese W.M. Marine microorganisms as a source of new natural products. Adv. Appl. Microbiol. 1997;43:57–90. - PubMed

[2] Bernan V.S., Greenstein M., Maiese W.M. Marine microorganisms as a source of new natural products. Adv. Appl. Microbiol. 1997;43:57–90. - PubMed

[3] Newman D.J., Hill R.T. New drugs from marine microbes: The tide is turning. J. Ind. Microbiol. Biotechnol. 2006;33:539–544. doi: 10.1007/s10295-006-0115-2. - DOI - PubMed

[4] Newman D.J., Hill R.T. New drugs from marine microbes: The tide is turning. J. Ind. Microbiol. Biotechnol. 2006;33:539–544. doi: 10.1007/s10295-006-0115-2. - DOI - PubMed

[5] Baharum S.N., Beng E.K., Mokhtar M.A.A. Marine microorganisms: Potential application and challenges. J. Biol. Sci. 2010;10:555–564. doi: 10.3923/jbs.2010.555.564. - DOI

[6] Baharum S.N., Beng E.K., Mokhtar M.A.A. Marine microorganisms: Potential application and challenges. J. Biol. Sci. 2010;10:555–564. doi: 10.3923/jbs.2010.555.564. - DOI

[7] Corinaldesi C., Barone G., Marcellini F., Dell’Anno A., Danovaro R. Marine microbial-derived molecules and their potential use in cosmeceutical and cosmetic products. Mar. Drugs. 2017;15:118. doi: 10.3390/md15040118. - DOI - PMC - PubMed

[8] Corinaldesi C., Barone G., Marcellini F., Dell’Anno A., Danovaro R. Marine microbial-derived molecules and their potential use in cosmeceutical and cosmetic products. Mar. Drugs. 2017;15:118. doi: 10.3390/md15040118. - DOI - PMC - PubMed

[9] Bugni T.S., Ireland C.M. Marine-derived fungi: A chemically and biologically diverse group of microorganisms. Nat. Prod. Rep. 2004;21:143–163. doi: 10.1039/b301926h. - DOI - PubMed

[10] Bugni T.S., Ireland C.M. Marine-derived fungi: A chemically and biologically diverse group of microorganisms. Nat. Prod. Rep. 2004;21:143–163. doi: 10.1039/b301926h. - DOI - PubMed

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Cladodionen, a Cytotoxic Hybrid Polyketide from the Marine-Derived Cladosporium sp. OUCMDZ-1635

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Cladodionen, a Cytotoxic Hybrid Polyketide from the Marine-Derived Cladosporium sp. OUCMDZ-1635

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