Amantamide C, an Antitrypanosomal Linear Lipopeptide from a Marine Okeania sp. Cyanobacterium

doi:10.1021/acsomega.4c05909

. 2024 Aug 15;9(34):36795-36801.

doi: 10.1021/acsomega.4c05909. eCollection 2024 Aug 27.

Amantamide C, an Antitrypanosomal Linear Lipopeptide from a Marine Okeania sp. Cyanobacterium

Natsumi Watanabe¹, Ghulam Jeelani², Tomoyoshi Nozaki², Arihiro Iwasaki¹

Affiliations

¹ Department of Applied Chemistry, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
² Department of Biomedical Chemistry, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8654, Japan.

PMID: 39220484
PMCID: PMC11359621
DOI: 10.1021/acsomega.4c05909

Amantamide C, an Antitrypanosomal Linear Lipopeptide from a Marine Okeania sp. Cyanobacterium

Natsumi Watanabe et al. ACS Omega. 2024.

. 2024 Aug 15;9(34):36795-36801.

doi: 10.1021/acsomega.4c05909. eCollection 2024 Aug 27.

Authors

Natsumi Watanabe¹, Ghulam Jeelani², Tomoyoshi Nozaki², Arihiro Iwasaki¹

Affiliations

¹ Department of Applied Chemistry, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
² Department of Biomedical Chemistry, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8654, Japan.

PMID: 39220484
PMCID: PMC11359621
DOI: 10.1021/acsomega.4c05909

Abstract

Amantamides are lipopeptides that act as selective CXC chemokine receptor 7 agonists and modulate spontaneous calcium oscillations in primary cultured neocortical neurons. We isolated a new analog of amantamides, amantamide C, from marine Okeania sp. cyanobacterium collected in Japan and established its structure based on NMR and MS/MS analyses, and degradation reactions. In addition, we evaluated the biological activity of amantamide C and revealed novel biological features of amantamide-type compounds.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

**Figure 1**
Key correlations from the 2D NMR spectra and the planar structure of amantamide C (1).

**Figure 2**
Selected MS/MS fragmentation patterns of amantamide C (1).

**Figure 3**
Evaluation of induction of apoptosis by amantamide C (1).

See this image and copyright information in PMC

References

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5. Mevers E.; Haeckl F. P.; Boudreau P. D.; Byrum T.; Dorrestein P. C.; Valeriote F. A.; Gerwick W. H. Lipopeptides from the tropical marine cyanobacterium Symploca sp. J. Nat. Prod. 2014, 77, 969–975. 10.1021/np401051z. - DOI - PMC - PubMed
1. Kwan J. C.; Eksioglu E. A.; Liu C.; Paul V. J.; Luesch H. Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation. J. Med. Chem. 2009, 52, 5732–5747. 10.1021/jm9009394. - DOI - PMC - PubMed
2. Al-Awadhi F. H.; Law B. K.; Paul V. J.; Luesch H. Grassystatins D-F, Potent Aspartic Protease Inhibitors from Marine Cyanobacteria as Potential Antimetastatic Agents Targeting Invasive Breast Cancer. J. Nat. Prod. 2017, 80, 2969–2986. 10.1021/acs.jnatprod.7b00551. - DOI - PMC - PubMed
1. Kanamori Y.; Iwasaki A.; Sumimoto S.; Matsubara T.; Sato T.; Suenaga K. Izenamides A and B, Statine-Containing Depsipeptides, and an Analogue from a Marine Cyanobacterium. J. Nat. Prod. 2018, 81, 1673–1681. 10.1021/acs.jnatprod.8b00417. - DOI - PubMed
1. Iwasaki A.; Ohno O.; Sumimoto S.; Suda S.; Suenaga K. Maedamide, a novel chymotrypsin inhibitor from a marine cyanobacterial assemblage of Lyngbya sp. Tetrahedron Lett. 2014, 55, 4126–4128. 10.1016/j.tetlet.2014.05.099. - DOI
2. Takayanagi A.; Iwasaki A.; Suenaga K. Total synthesis and stereochemical reassignment of maedamide. Tetrahedron Lett. 2015, 56, 4947–4949. 10.1016/j.tetlet.2015.06.090. - DOI
1. Al-Awadhi F. H.; Gao B.; Rezaei M. A.; Kwan J. C.; Li C.; Ye T.; Paul V. J.; Luesch H. Discovery, Synthesis, Pharmacological Profiling, and Biological Characterization of Brintonamides A-E, Novel Dual Protease and GPCR Modulators from a Marine Cyanobacterium. J. Med. Chem. 2018, 61, 6364–6378. 10.1021/acs.jmedchem.8b00885. - DOI - PMC - PubMed

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[1] Williams P. G.; Yoshida W. Y.; Moore R. E.; Paul V. J. Tasiamide, a cytotoxic peptide from the marine cyanobacterium Symploca sp. J. Nat. Prod. 2002, 65, 1336–1339. 10.1021/np020184q. - DOI - PubMed

Ma Z.; Song N.; Li C.; Zhang W.; Wang P.; Li Y. Total synthesis and stereochemical reassignment of tasiamide. J. Pept. Sci. 2008, 14, 1139–1147. 10.1002/psc.1051. - DOI - PubMed

Williams P. G.; Yoshida W. Y.; Moore R. E.; Paul V. J. The isolation and structure elucidation of Tasiamide B, a 4-amino-3-hydroxy-5-phenylpentanoic acid containing peptide from the marine Cyanobacterium Symploca sp. J. Nat. Prod. 2003, 66, 1006–1009. 10.1021/np030114z. - DOI - PubMed

Sun T.; Zhang W.; Zong C.; Wang P.; Li Y. Total synthesis and stereochemical reassignment of tasiamide B. J. Pept. Sci. 2010, 16, 364–374. 10.1002/psc.1254. - DOI - PubMed

Mevers E.; Haeckl F. P.; Boudreau P. D.; Byrum T.; Dorrestein P. C.; Valeriote F. A.; Gerwick W. H. Lipopeptides from the tropical marine cyanobacterium Symploca sp. J. Nat. Prod. 2014, 77, 969–975. 10.1021/np401051z. - DOI - PMC - PubMed

[2] Williams P. G.; Yoshida W. Y.; Moore R. E.; Paul V. J. Tasiamide, a cytotoxic peptide from the marine cyanobacterium Symploca sp. J. Nat. Prod. 2002, 65, 1336–1339. 10.1021/np020184q. - DOI - PubMed

[3] Ma Z.; Song N.; Li C.; Zhang W.; Wang P.; Li Y. Total synthesis and stereochemical reassignment of tasiamide. J. Pept. Sci. 2008, 14, 1139–1147. 10.1002/psc.1051. - DOI - PubMed

[4] Williams P. G.; Yoshida W. Y.; Moore R. E.; Paul V. J. The isolation and structure elucidation of Tasiamide B, a 4-amino-3-hydroxy-5-phenylpentanoic acid containing peptide from the marine Cyanobacterium Symploca sp. J. Nat. Prod. 2003, 66, 1006–1009. 10.1021/np030114z. - DOI - PubMed

[5] Sun T.; Zhang W.; Zong C.; Wang P.; Li Y. Total synthesis and stereochemical reassignment of tasiamide B. J. Pept. Sci. 2010, 16, 364–374. 10.1002/psc.1254. - DOI - PubMed

[6] Mevers E.; Haeckl F. P.; Boudreau P. D.; Byrum T.; Dorrestein P. C.; Valeriote F. A.; Gerwick W. H. Lipopeptides from the tropical marine cyanobacterium Symploca sp. J. Nat. Prod. 2014, 77, 969–975. 10.1021/np401051z. - DOI - PMC - PubMed

[7] Kwan J. C.; Eksioglu E. A.; Liu C.; Paul V. J.; Luesch H. Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation. J. Med. Chem. 2009, 52, 5732–5747. 10.1021/jm9009394. - DOI - PMC - PubMed

Al-Awadhi F. H.; Law B. K.; Paul V. J.; Luesch H. Grassystatins D-F, Potent Aspartic Protease Inhibitors from Marine Cyanobacteria as Potential Antimetastatic Agents Targeting Invasive Breast Cancer. J. Nat. Prod. 2017, 80, 2969–2986. 10.1021/acs.jnatprod.7b00551. - DOI - PMC - PubMed

[8] Kwan J. C.; Eksioglu E. A.; Liu C.; Paul V. J.; Luesch H. Grassystatins A-C from marine cyanobacteria, potent cathepsin E inhibitors that reduce antigen presentation. J. Med. Chem. 2009, 52, 5732–5747. 10.1021/jm9009394. - DOI - PMC - PubMed

[9] Al-Awadhi F. H.; Law B. K.; Paul V. J.; Luesch H. Grassystatins D-F, Potent Aspartic Protease Inhibitors from Marine Cyanobacteria as Potential Antimetastatic Agents Targeting Invasive Breast Cancer. J. Nat. Prod. 2017, 80, 2969–2986. 10.1021/acs.jnatprod.7b00551. - DOI - PMC - PubMed

[10] Kanamori Y.; Iwasaki A.; Sumimoto S.; Matsubara T.; Sato T.; Suenaga K. Izenamides A and B, Statine-Containing Depsipeptides, and an Analogue from a Marine Cyanobacterium. J. Nat. Prod. 2018, 81, 1673–1681. 10.1021/acs.jnatprod.8b00417. - DOI - PubMed

[11] Kanamori Y.; Iwasaki A.; Sumimoto S.; Matsubara T.; Sato T.; Suenaga K. Izenamides A and B, Statine-Containing Depsipeptides, and an Analogue from a Marine Cyanobacterium. J. Nat. Prod. 2018, 81, 1673–1681. 10.1021/acs.jnatprod.8b00417. - DOI - PubMed

[12] Iwasaki A.; Ohno O.; Sumimoto S.; Suda S.; Suenaga K. Maedamide, a novel chymotrypsin inhibitor from a marine cyanobacterial assemblage of Lyngbya sp. Tetrahedron Lett. 2014, 55, 4126–4128. 10.1016/j.tetlet.2014.05.099. - DOI

Takayanagi A.; Iwasaki A.; Suenaga K. Total synthesis and stereochemical reassignment of maedamide. Tetrahedron Lett. 2015, 56, 4947–4949. 10.1016/j.tetlet.2015.06.090. - DOI

[13] Iwasaki A.; Ohno O.; Sumimoto S.; Suda S.; Suenaga K. Maedamide, a novel chymotrypsin inhibitor from a marine cyanobacterial assemblage of Lyngbya sp. Tetrahedron Lett. 2014, 55, 4126–4128. 10.1016/j.tetlet.2014.05.099. - DOI

[14] Takayanagi A.; Iwasaki A.; Suenaga K. Total synthesis and stereochemical reassignment of maedamide. Tetrahedron Lett. 2015, 56, 4947–4949. 10.1016/j.tetlet.2015.06.090. - DOI

[15] Al-Awadhi F. H.; Gao B.; Rezaei M. A.; Kwan J. C.; Li C.; Ye T.; Paul V. J.; Luesch H. Discovery, Synthesis, Pharmacological Profiling, and Biological Characterization of Brintonamides A-E, Novel Dual Protease and GPCR Modulators from a Marine Cyanobacterium. J. Med. Chem. 2018, 61, 6364–6378. 10.1021/acs.jmedchem.8b00885. - DOI - PMC - PubMed

[16] Al-Awadhi F. H.; Gao B.; Rezaei M. A.; Kwan J. C.; Li C.; Ye T.; Paul V. J.; Luesch H. Discovery, Synthesis, Pharmacological Profiling, and Biological Characterization of Brintonamides A-E, Novel Dual Protease and GPCR Modulators from a Marine Cyanobacterium. J. Med. Chem. 2018, 61, 6364–6378. 10.1021/acs.jmedchem.8b00885. - DOI - PMC - PubMed

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Amantamide C, an Antitrypanosomal Linear Lipopeptide from a Marine Okeania sp. Cyanobacterium

Affiliations

Amantamide C, an Antitrypanosomal Linear Lipopeptide from a Marine Okeania sp. Cyanobacterium

Authors

Affiliations

Abstract

Conflict of interest statement

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