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Distribution and Possible Function of the Marine Alkaloid, Norzoanthamine, in the Zoanthid Zoanthus sp. Using MALDI Imaging Mass Spectrometry

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Abstract

The role of the marine alkaloid, norzoanthamine, in the colonial zoanthid Zoanthus sp. was previously unknown. High concentrations of norzoanthamine are present in the epidermal tissue of Zoanthus sp., as determined using protonated molecular ion peak mapping of norzoanthamine by matrix-assisted laser desorption/ionization mass spectrometry and high-performance liquid chromatography quantification. Sodium dodecylsulfate polyacrylamide gel electrophoresis experiments indicate that norzoanthamine increases the resistance of collagen to damage from UV light, probably not via UV light absorption, but by strengthening collagen itself, thus suggesting that collagen strengthening may be the function of norzoanthamine in Zoanthus sp.

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References

  • Adams E (1978) Invertebrate collagens. Science 202:591–598

    Article  CAS  PubMed  Google Scholar 

  • Bann JG, Peyton DH, Bächinger HP (2000) Sweet is stable: glycosylation stabilizes collagen. FEBS Lett 473:237–240

    Article  CAS  PubMed  Google Scholar 

  • Behenna DC, Stockdill JL, Stoltz BM (2008) The biology and chemistry of the zoanthamine alkaloids. Angew Chem Int Ed 47:2365–2386

    Article  CAS  Google Scholar 

  • Blunt JW, Copp BR, Hu WP, Munro MHG, Northcote PT, Prinsep MR (2009) Marine natural products. Nat Prod Rep 26:170–244

    Article  CAS  PubMed  Google Scholar 

  • Caprioli RM, Farmer TB, Gile J (1997) Molecular imaging of biological samples: localization of peptides and proteins using MALDI-TOF MS. Anal Chem 69:4751–4760

    Article  CAS  PubMed  Google Scholar 

  • Chaurand P, Schwartz SA, Caprioli RM (2004) Assessing protein patterns in disease using imaging mass spectrometry. J Proteome Res 3:245–252

    Article  CAS  PubMed  Google Scholar 

  • Dunlap WC, Chalker BE (1986) Identification and quantitation of near-UV absorbing compounds (S-320) in a hermatypic scleractinian. Coral Reefs 5:155–159

    Article  CAS  Google Scholar 

  • Fukuzawa S, Hayashi Y, Uemura D, Nagatsu A, Yamada K, Ijuin Y (1995) The isolation and structures of five new alkaloids, norzoanthamine, oxyzoanthamine, norzoanthaminone, cyclozoanthamine and epinorzoanthamine. Heterocycl Commun 1:207–214

    CAS  Google Scholar 

  • Haefner B (2003) Drugs from the deep: marine natural products as drug candidates. Drug Discov Today 8:536–544

    Article  CAS  PubMed  Google Scholar 

  • Jang J, Yotsu-Yamashita M (2006) Distribution of tetrodotoxin, saxitoxin, and their analogs among tissues of the puffer fish Fugu pardalis. Toxicon 48:980–987

    Article  CAS  PubMed  Google Scholar 

  • Johnstone IL (1994) The cuticle of the nematode Caenorhabditis elegans: a complex collagen structure. BioEssays 16:171–178

    Article  CAS  PubMed  Google Scholar 

  • Kimura S, Tanzer ML (1977) Nereis cuticle collagen. J Biol Chem 252:8018–8022

    CAS  PubMed  Google Scholar 

  • Kinugawa M, Fukuzawa S, Tachibana K (2009) Skeletal protein protection: the mode of action of an anti-osteoporotic marine alkaloid, norzoanthamine. J Bone Miner Metab 27:303–314

    Article  CAS  PubMed  Google Scholar 

  • Kita M, Uemura D (2005) Iminium alkaloids from marine invertebrates: structure, biological activity, and biogenesis. Chem Lett 34:454–459

    Article  CAS  Google Scholar 

  • Kramer JM (1994) Structures and functions of collagens in Caenorhabditis elegans. FASEB J 8:329–336

    CAS  PubMed  Google Scholar 

  • Kuramoto M, Hayashi K, Yamaguchi K, Yada M, Tsuji T, Uemura D (1998) Structure–activity relationship of norzoanthamine exhibiting significant inhibition of osteoporosis. Bull Chem Soc Jpn 71:771–779

    Article  CAS  Google Scholar 

  • Lee YC, Lang D (1968) D-Galactose di- and trisaccharides from the earthworm cuticle collagen. J Biol Chem 243:677–680

    CAS  PubMed  Google Scholar 

  • Mann K, Mechling DE, Bächinger HP, Eckerskorn C, Gaill F, Timpl R (1996) Glycosylated threonine but not 4-hydroxyproline dominates the triple helix stabilizing positions in the sequence of a hydrothermal vent worm cuticle collagen. J Mol Biol 261:255–266

    Article  CAS  PubMed  Google Scholar 

  • McClintock JB, Raker BL (2001) Marine chemical ecology. CRC, Boca Raton

    Google Scholar 

  • Nakamura H, Kawase Y, Maruyama K, Murai A (1998) Studies on polyketide metabolites of a symbiotic dinoflagellate, Symbiodinium sp.: a new C30 marine alkaloid, zooxanthellamine, a plausible precursor for zoanthid alkaloids. Bull Chem Soc Jpn 71:781–787

    Article  CAS  Google Scholar 

  • Newman DJ, Cragg GM (2004) Marine natural products and related compounds in clinical and advanced preclinical trials. J Nat Prod 67:1216–1238

    Article  CAS  PubMed  Google Scholar 

  • Paul VJ, Ritson-Williams R (2008) Marine chemical ecology. Nat Prod Rep 25:662–695

    Article  CAS  PubMed  Google Scholar 

  • Piel J, Butzke D, Fusetani N, Hui D, Platzer M, Wen G, Matsunaga S (2005) Exploring the chemistry of uncultivated bacterial symbionts: antitumor polyketides of the pederin family. J Nat Prod 68:472–479

    Article  CAS  PubMed  Google Scholar 

  • Puolitaival SM, Burnum KE, Cornett DS, Caprioli RM (2008) Solvent-free matrix dry-coating for MALDI imaging of phospholipids. J Am Mass Spectrom 19:882–886

    Article  CAS  Google Scholar 

  • Rao CB, Anjaneyula ASR, Sarma NS, Venkatateswarlu Y, Rosser RM, Faulkner DJ, Chen MHM, Clardy J (1984) Zoanthamine: a novel alkaloid from a marine zoanthid. J Am Chem Soc 106:7983–7984

    Article  Google Scholar 

  • Reyzer ML, Caprioli RM (2007) MALDI-MS-based imaging of small molecules and proteins in tissues. Cur Opin Chem Biol 11:29–35

    Article  CAS  Google Scholar 

  • Sakai R, Minato S, Koike K, Koike K, Jimbo M, Kamiya H (2005) Cellular and subcellular localization of kainic acid in the marine red alga Digenea simplex. Cell Tissue Res 322:491–502

    Article  CAS  PubMed  Google Scholar 

  • Sakai R, Yoshida K, Kimura A, Koike K, Jimbo M, Koike K, Kobiyama A, Kamiya H (2008) Cellular origin of dysiherbaine, an excitatory amino acid derived from a marine sponge. ChemBioChem 9:543–551

    Article  CAS  PubMed  Google Scholar 

  • Simmons TL, Coates RC, Clark BR, Engene N, Gonzalez D, Esquenazi E, Dorrestein PC, Gerwick WH (2008) Biosynthetic origin of natural products isolated from marine microorganism–invertebrate assemblages. Proc Natl Acad Sci USA 105:4587–4594

    Article  CAS  PubMed  Google Scholar 

  • Walker JM (2002) SDS polyacrylamide gel electrophoresis of proteins. In: Walker JM (ed) The protein protocols handbook. Humana, Totowa, pp 61–67

    Chapter  Google Scholar 

  • Yakovleva I, Bhagooloi R, Takemura A, Hidaka M (2004) Differential susceptibility to oxidative stress of two scleractinian corals: antioxidant functioning of mycosporine-glycine. Comp Biochem Physiol B 139:721–730

    Article  CAS  PubMed  Google Scholar 

  • Yamaguchi K, Yada M, Tsuji T, Kuramoto M, Uemura D (1999) Suppressive effect of norzoanthamine hydrochloride on experimental osteoporosis in ovariectomized mice. Biol Pharm Bull 22:920–924

    CAS  PubMed  Google Scholar 

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Acknowledgments

We are grateful to Prof. Hiroshi Nishihara and Dr. Shoko Kume of the University of Tokyo, for help in measuring MALDI mass spectra. This work was supported by a Grant-in-Aid for Scientific Research on Priority Areas; Targeted Pursuit of Challenging Bioactive Molecules (13024227) and Creation of Biologically Functional Molecules (17035021 and 18032025) from the Ministry of Education, Culture, Sports, Science and Technology of Japan and SEKISUI CHEMICAL CO., LTD. One of the authors (T.G.) was supported by a Grant-in-Aid for The 21st Century COE Program for Frontiers in Fundamental Chemistry and The Global COE Program for Chemistry Innovation through Cooperation of Science and Engineering from the Ministry of Education, Culture, Sports, Science, and Technology of Japan.

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  1. Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan

    Takahisa Genji, Seketsu Fukuzawa & Kazuo Tachibana

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  1. Takahisa Genji
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  2. Seketsu Fukuzawa
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  3. Kazuo Tachibana
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Correspondence to Seketsu Fukuzawa or Kazuo Tachibana.

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Genji, T., Fukuzawa, S. & Tachibana, K. Distribution and Possible Function of the Marine Alkaloid, Norzoanthamine, in the Zoanthid Zoanthus sp. Using MALDI Imaging Mass Spectrometry. Mar Biotechnol 12, 81–87 (2010). https://doi.org/10.1007/s10126-009-9202-5

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