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Journal of Natural Medicines

, Volume 72, Issue 1, pp 364–368 | Cite as

Agelamasines A and B, diterpene alkaloids from an Okinawan marine sponge Agelas sp.

  • Sanghoon Lee
  • Naonobu TanakaEmail author
  • Jun’ichi Kobayashi
  • Yoshiki KashiwadaEmail author
Note

Abstract

Two new diterpene alkaloids having an N-methyladenine moiety, agelamasines A (1) and B (2), were isolated from an Okinawan marine sponge Agelas sp. The structures of 1 and 2 were elucidated on the basis of spectroscopic analyses. Agelamasine A (1) is the first diterpene alkaloid with a rearranged (4 → 2)-abeo-clerodane skeleton from a marine source, while agelamasine B (2) is a clerodane diterpene alkaloid.

Keywords

Marine sponge Agelas sp. Diterpene alkaloid Rearranged clerodane Agelamasines A and B 

Notes

Acknowledgements

We thank Mr. Z. Nagahama for his help with the sponge collection. This work was partly supported by JSPS KAKENHI Grant number JP17K08337.

References

  1. 1.
    Mehbub MF, Lei J, Franco C, Zhang W (2014) Marine sponge derived natural products between 2001 and 2010: trends and opportunities for discovery of bioactives. Mar Drugs 12:4539–4577CrossRefGoogle Scholar
  2. 2.
    Fathi-Afshar R, Allen TM (1988) Biologically active metabolites from Agelas mauritiana. Can J Chem 66:46–50CrossRefGoogle Scholar
  3. 3.
    Kinnel RB, Gehrken HP, Swali R, Skoropowski G, Scheuer PJ (1998) Palau’amine and its congners: a family of bioactive bisguanidines from the marine sponge Stylotella aurantium. J Org Chem 63:3281–3286CrossRefGoogle Scholar
  4. 4.
    Pettit GR, Tang Y, Zhang Q, Bourne GT, Arm CA, Leet JE, Knight JC, Pettie RK, Chapuis J, Doubek DL, Ward FJ, Weber C, Hooper JNA (2013) Isolation and structures of axistatins 1–3 from the republic of Palau marine sponge Agelas axifera Hentschel. J Nat Prod 76:420–424CrossRefGoogle Scholar
  5. 5.
    Abdjul DB, Yamazaki H, Kano S, Takahashi O, Kirikoshi R, Ukai K, Namikoshi M (2015) Structures and biological evaluations of agelasines isolated from the Okinawan marine sponge Agelas nakamurai. J Nat Prod 78:1428–1433CrossRefGoogle Scholar
  6. 6.
    Kubota T, Iwai T, Takahashi-Nakaguchi A, Fromont J, Gonoi T, Kobayashi J (2012) Agelasines O–U, new diterpene alkaloids with a 9-N-methyladenine unit from a marine sponge Agelas sp. Tetrahedron 68:9738–9744CrossRefGoogle Scholar
  7. 7.
    Kusama T, Tanaka N, Sakai K, Gonoi T, Fromont J, Kashiwada Y, Kobayashi J (2014) Agelamadins A and B, dimeric bromopyrrole alkaloids from a marine sponge Agelas sp. Org Lett 16:3916–3918CrossRefGoogle Scholar
  8. 8.
    Kusama T, Tanaka N, Sakai K, Gonoi T, Fromont J, Kashiwada Y, Kobayashi J (2014) Agelamadins C–E, bromopyrrole alkaloids comprising oroidin and 3-hydroxykynurenine from a marine sponge Agelas sp. Org Lett 16:5176–5179CrossRefGoogle Scholar
  9. 9.
    Tanaka N, Kusama T, Takahashi-Nakaguchi A, Gonoi T, Fromont J, Kobayashi J (2013) Nagelamides X–Z, dimeric bromopyrrole alkaloids from a marine sponge Agelas sp. Org Lett 15:3262–3265CrossRefGoogle Scholar
  10. 10.
    Calcul L, Tenney K, Ratnam J, McKerrow JH, Crews P (2011) Structural variations to the 9-N-methyladeninium diterpenoid hybrid commonly isolated from Agelas sponges. Aust J Chem 63:915–921CrossRefGoogle Scholar
  11. 11.
    Wu H, Nakamura H, Kobayashi J, Kobayashi M, Ohizumi Y, Hirata Y (1986) Structures of agelasines, diterpenes having a 9-methyladeninium chromophore isolated from the Okinawan marine sponge Agelas nakamurai Hoshino. Bull Chem Soc Jpn 59:2495–2504CrossRefGoogle Scholar
  12. 12.
    Li T, Wang B, de Voogd NJ, Tang X, Wang Q, Chu M, Li P, Li G (2016) Two new diterpene alkaloids from the South China sea sponge Agelas aff. nemoechinata. Chin Chem Lett 27:1048–1051CrossRefGoogle Scholar
  13. 13.
    Tori M, Katto A, Sono M (1999) Nine new clerodane diterpenoids from rhizomes of Solidago alttissima. Phytochemistry 52:487–493CrossRefGoogle Scholar
  14. 14.
    Wu TH, Cheng YY, Chen CJ, Ng LT, Chou LC, Huang LJ, Chen YH, Kuo SC, El-Shazly M, Wu YC, Chang FR, Liaw CC (2014) Three new clerodane diterpenes from Polyalthia longifolia var. pendula. Molecules 19:2049–2060CrossRefGoogle Scholar
  15. 15.
    Bomm MD, Zukerman-Schpector J, Lopes LMX (1999) Rearranged (4 → 2)-abeo-clerodane and clerodane diterpenes from Aristolochia chamissonis. Phytochemistry 50:455–461CrossRefGoogle Scholar
  16. 16.
    Bohlmann F, Singh P, Singh RK, Joshi KC, Jakupovic J (1985) A diterpene with a new carbon skeleton from Solidago altissima. Phytochemistry 24:1114–1115CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK, part of Springer Nature 2017

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesTokushima UniversityTokushimaJapan
  2. 2.Graduate School of Bioscience and BioindustryTokushima UniversityTokushimaJapan
  3. 3.Graduate School of Pharmaceutical SciencesHokkaido UniversitySapporoJapan

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