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El-Sawy, E.R.; Kirsch, G. Chemical Structures and Biological Activities of of Aplysinopsins. Encyclopedia. Available online: https://encyclopedia.pub/entry/43992 (accessed on 09 October 2024).
El-Sawy ER, Kirsch G. Chemical Structures and Biological Activities of of Aplysinopsins. Encyclopedia. Available at: https://encyclopedia.pub/entry/43992. Accessed October 09, 2024.
El-Sawy, Eslam R., Gilbert Kirsch. "Chemical Structures and Biological Activities of of Aplysinopsins" Encyclopedia, https://encyclopedia.pub/entry/43992 (accessed October 09, 2024).
El-Sawy, E.R., & Kirsch, G. (2023, May 08). Chemical Structures and Biological Activities of of Aplysinopsins. In Encyclopedia. https://encyclopedia.pub/entry/43992
El-Sawy, Eslam R. and Gilbert Kirsch. "Chemical Structures and Biological Activities of of Aplysinopsins." Encyclopedia. Web. 08 May, 2023.
Chemical Structures and Biological Activities of of Aplysinopsins
Edit

Marine products are among the most promising sources of biologically active molecules. Aplysinopsins, tryptophan-derived marine natural products, were isolated from different natural marine sources including sponges, stony corals (hard corals) especially genus scleractinian, as well as sea anemone, in addition to one nudibranch. Aplysinopsins were reported to be isolated from different marine organisms related to various geographic areas such as Pacific, Indonesia, Caribbean, and Mediterranean regions.

aplysinopsin sources synthesis bioactivity

1. Different Sources and Chemical Structures of Aplysinopsins

The chemical backbone of the natural aplysinopsins include a simple configuration of monomeric aplysinopsin-type structures and their brominated derivatives at the A ring, variation in the structure of the C ring, the presence and configuration of the C-8-C-1′ double bond, the oxidation state of the 2-aminoimidazoline fragment and N-alkylated at the B ring (Figure 1), in addition to the aplysinopsin dimers form.
Figure 1. The chemical configuration of monomeric aplysinopsin-type structures shows detailed segmentation of the rings, carbon numbering, and type of bonds.
Aplysinopsin, (E)-5-((1H-indol-3-yl)methylene)-2-imino-1,3-dimethylimidazo-li-din-4-one (1), was first isolated from the sponge genus Thorecta of the Australian Great Barrier Reef by Kazlauskas et al. [1]. Sequentially, aplysinopsin and its derivatives have been reported in many other marine organisms from various geographic areas (Table 1, Table 2, Table 3 and Table 4) [2].
Table 1. Monomeric aplysinopsin-type structures and their brominated derivatives.
Table 2. Aplysinopsins substituted at the nitrogen atom.
Table 3. Aplysinopsins with a single C-8-C-1′ bond.
Marinedrugs 21 00268 i003
Aplysinopsin Derivatives R X Sources [Ref.]
1′,8-Dihydroaplysinopsin (19) H H Tubastrea coccinea coral Hawaii [16], Radianthus kuekenthali sea anemone Japan [9], and Thorectandra sp. sponge Indo-Pacific reefs [13].
6-Bromo-1′,8-dihydroaplysinopsin (20) Br H
6-Bromo-1-hydroxy-1′,8-dihydroaplysinopsin (21) Br OH Thorectandra sp. sponge Indo-Pacific reefs [13].
6-Bromo-1-methoxy-1′,8-dihydroaplysinopsin (22) Br OCH3
6-Bromo-1-ethoxy-1′,8-dihydroaplysinopsin (23) Br OCH2CH3

References

  1. Kazlauskas, R.; Murphy, P.T.; Quinn, R.J.; Wells, R.J. Aplysinopsin, a new tryptophan derivative from a sponge. Tetrahedron Lett. 1977, 18, 61–64.
  2. Bialonska, D.; Zjawiony, J.K. Aplysinopsins—Marine Indole Alkaloids: Chemistry, Bioactivity and Ecological Significance. Mar. Drugs 2009, 7, 166.
  3. Kh, H.; Fj, S. Aplysinopsin: Antineoplastic Tryptophan Derivative from the Marine Sponge Verongia Spengelii. Lloydia 1977, 40, 479–481.
  4. Djura, P.; Faulkner, D.J. Metabolites of the marine sponge Dercitus species. J. Org. Chem. 1980, 45, 735–737.
  5. Tymiak, A.A.; Rinehart, K.L.; Bakus, G.J. Constituents of morphologically similar sponges: Aplysina and Smenospongia Species. Tetrahedron 1985, 41, 1039–1047.
  6. Fattorusso, E.; Lanzotti, V.; Magno, S.; Novellino, E. Tryptophan Derivatives from a Mediterranean Anthozoan, Astroides calycularis. J. Nat. Prod. 1985, 48, 924–927.
  7. Fusetani, N.; Asano, M.; Matsunaga, S.; Hashimoto, K. Bioactive marine metabolites—XV. Isolation of aplysinopsin from the Scleractinian coral Tubastrea aurea as an inhibitor of development of fertilized sea urchin eggs. Comp. Biochem. Physiol. Part B Comp. Biochem. 1986, 85, 845–846.
  8. Guella, G.; Mancini, I.; Zibrowius, H.; Pietra, F. Novel Aplysinopsin-Type Alkaloids from Scleractinian Corals of the Family Dendrophylliidae of the Mediterranean and the Philippines. Configurational-assignment criteria, stereospecific synthesis, and photoisomerization. Helvetica Chim. Acta 1988, 71, 773–782.
  9. Murata, M.; Miyagawa-Kohshima, K.; Nakanishi, K.; Naya, Y. Characterization of Compounds That Induce Symbiosis Between Sea Anemone and Anemone Fish. Science 1986, 234, 585–587.
  10. Kondo, K.; Nishi, J.; Ishibashi, M.; Kobayashi, J. Two New Tryptophan-Derived Alkaloids from the Okinawan Marine Sponge Aplysina sp. J. Nat. Prod. 1994, 57, 1008–1011.
  11. Koh, E.G.; Sweatman, H. Chemical warfare among scleractinians: Bioactive natural products from Tubastraea faulkneri Wells kill larvae of potential competitors. J. Exp. Mar. Biol. Ecol. 2000, 251, 141–160.
  12. Iwagawa, T.; Miyazaki, M.; Okamura, H.; Nakatani, M.; Doe, M.; Takemura, K. Three novel bis(indole) alkaloids from a stony coral, Tubastraea sp. Tetrahedron Lett. 2003, 44, 2533–2535.
  13. Segraves, N.L.; Crews, P. Investigation of Brominated Tryptophan Alkaloids from Two Thorectidae Sponges: Thorectandra and Smenospongia. J. Nat. Prod. 2005, 68, 1484–1488.
  14. Kochanowska, A.J.; Rao, K.V.; Childress, S.; El-Alfy, A.; Matsumoto, R.R.; Kelly, M.; Stewart, G.S.; Sufka, K.J.; Hamann, M.T. Secondary Metabolites from Three Florida Sponges with Antidepressant Activity. J. Nat. Prod. 2008, 71, 186–189.
  15. Hu, J.-F.; Schetz, J.A.; Kelly, M.; Peng, J.-N.; Ang, K.K.H.; Flotow, H.; Leong, C.Y.; Ng, S.B.; Buss, A.D.; Wilkins, S.P.; et al. New Antiinfective and Human 5-HT2 Receptor Binding Natural and Semisynthetic Compounds from the Jamaican Sponge Smenospongia aurea. J. Nat. Prod. 2002, 65, 476–480.
  16. Okuda, R.K.; Klein, D.; Kinnel, R.B.; Li, M.; Scheuer, P.J. Marine natural products: The past twenty years and beyond. Pure Appl. Chem. 1982, 54, 1907–1914.
  17. Aoki, S.; Ye, Y.; Higuchi, K.; Takashima, A.; Tanaka, Y.; Kitagawa, I.; Kobayashi, M. Novel Neuronal Nitric Oxide Synthase (nNOS) Selective Inhibitor, Aplysinopsin-Type Indole Alkaloid, from Marine Sponge Hyrtios erecta. Chem. Pharm. Bull. 2001, 49, 1372–1374.
  18. Djura, P.; Stierle, D.B.; Sullivan, B.; Faulkner, D.J.; Arnold, E.V.; Clardy, J. Some metabolites of the marine sponges Smenospongia aurea and Smenospongia (Ident.Polyfibrospongia) echina. J. Org. Chem. 1980, 45, 1435–1441.
  19. Mancini, I.; Guella, G.; Zibrowius, H.; Pietra, F. On the origin of quasi-racemic aplysinopsin cycloadducts, (bis)indole alkaloids isolated from scleractinian corals of the family Dendrophylliidae. Involvement of enantiodefective Diels–Alderases or asymmetric induction in artifact processes involving adventitious catalysts? Tetrahedron 2003, 59, 8757–8762.
  20. Meyer, M.; Delberghe, F.; Liron, F.; Guillaume, M.; Valentin, A.; Guyot, M. An antiplasmodial new (bis)indole alkaloid from the hard coral Tubastraea sp. Nat. Prod. Res. 2009, 23, 178–182.
  21. Balansa, W.; Islam, R.; Gilbert, D.F.; Fontaine, F.; Xiao, X.; Zhang, H.; Piggott, A.M.; Lynch, J.W.; Capon, R.J. Australian marine sponge alkaloids as a new class of glycine-gated chloride channel receptor modulator. Bioorganic Med. Chem. 2013, 21, 4420–4425.
  22. Iwagawa, T.; Miyazaki, M.; Yokogawa, Y.; Okamura, H.; Nakatani, M.; Doe, M.; Morimoto, Y.; Takemura, K. Aplysinopsin Dimers from a Stony Coral. Tubastraea aurea. Heterocycles 2008, 75, 2023.
  23. Dai, J.; Jiménez, J.I.; Kelly, M.; Barnes, S.; Lorenzo, P.; Williams, P. Dictazolines A and B, Bisspiroimidazolidinones from the Marine Sponge Smenospongia cerebriformis. J. Nat. Prod. 2008, 71, 1287–1290.
  24. Dai, J.; Jiménez, J.I.; Kelly, M.; Williams, P.G. Dictazoles: Potential Vinyl Cyclobutane Biosynthetic Precursors to the Dictazolines. J. Org. Chem. 2010, 75, 2399–2402.
  25. Nuthakki, V.K.; Yadav Bheemanaboina, R.R.; Bharate, S.B. Identification of aplysinopsin as a blood-brain barrier permeable scaffold for anti-cholinesterase and anti-BACE-1 activity. Bioorganic Chem. 2021, 107, 104568.
  26. Nuthakki, V.K.; Sharma, A.; Kumar, A.; Bharate, S.B. Identification of embelin, a 3-undecyl-1,4-benzoquinone from Embelia ribes as a multitargeted anti-Alzheimer agent. Drug Dev. Res. 2019, 80, 655–665.
  27. Lewellyn, K.; Bialonska, D.; Loria, M.J.; White, S.W.; Sufka, K.J.; Zjawiony, J.K. In vitro structure–activity relationships of aplysinopsin analogs and their in vivo evaluation in the chick anxiety–depression model. Bioorganic Med. Chem. 2013, 21, 7083–7090.
  28. Passemar, C.; Saléry, M.; Soh, P.N.; Linas, M.-D.; Ahond, A.; Poupat, C.; Benoit-Vical, F. Indole and aminoimidazole moieties appear as key structural units in antiplasmodial molecules. Phytomedicine 2011, 18, 1118–1125.
  29. Wells, R.J.; Murphy, P.T. 5-(Indol-3-Ylmethylene)-1,3-Dimethyl-2-Methylamino-4-Imidazolidinone. U.S. Patent US4195179A, 25 March 1980.
  30. Baird-Lambert, J.; Davis, P.A.; Taylor, K.M. Methylaplysinopsin: A natural product of marine origin with effects on serotonergic neurotransmission. Clin. Exp. Pharmacol. Physiol. 1982, 9, 203–212.
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