El-Demerdash A et al. (2018), Batzella, Crambe and Monanchora: Highly Prolifi...

ECB-ART-45996

Nutrients 2018 Jan 02;101:. doi: 10.3390/nu10010033.

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Batzella, Crambe and Monanchora: Highly Prolific Marine Sponge Genera Yielding Compounds with Potential Applications for Cancer and Other Therapeutic Areas.

El-Demerdash A , Atanasov AG , Bishayee A , Abdel-Mogib M , Hooper JNA , Al-Mourabit A .

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Pyrroloquinoline and guanidine-derived alkaloids present distinct groups of marine secondary metabolites with structural diversity that displayed potentialities in biological research. A considerable number of these molecular architectures had been recorded from marine sponges belonging to different marine genera, including Batzella, Crambe, Monanchora, Clathria, Ptilocaulis and New Caledonian starfishes Fromia monilis and Celerina heffernani. In this review, we aim to comprehensively cover the chemodiversity and the bioactivities landmarks centered around the chemical constituents exclusively isolated from these three marine genera including Batzella, Crambe and Monanchora over the period 1981-2017, paying a special attention to the polycyclic guanidinic compounds and their proposed biomimetic landmarks. It is concluded that these marine sponge genera represent a rich source of novel compounds with potential applications for cancer and other therapeutic areas.

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Genes referenced: irak1bp1

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	Figure 1. Isolated iminosugars 1–3 from Batzella sp.
	Figure 2. Isolated bicyclic guanidine alkaloids 4–27.
	Figure 3. Isolated tricyclic guanidine alkaloids 28–37.
	Figure 4. Isolated pyrroloquinoline alkaloids 38–50 from Batzella sp.
	Figure 5. Isolated batzelladine alkaloids 51–64.
	Figure 6. Isolated batzelladine alkaloids 65–77.
	Figure 7. Isolated pentacyclic crambescidin alkaloids 78–89.
	Figure 8. Isolated pentacyclic crambescidin alkaloids 90–117.
	Figure 9. Isolated acyclic guanidine alkaloids 118–125.
	Figure 10. Isolated terpenoid and steroidal metabolites 126–147 isolated from Monanchora sp.
	Figure 11. Structural analysis of different polycyclic guanidine alkaloids.
	Figure 12. Proposed retrosynthetic analysis of the bicyclic alkaloids.
	Figure 13. a: 2 equiv. O-methylisourea and 7 equiv. NaHCO3 in DMF for 12 h at 60 °C, 79%; b: hydrolysis, TBAF, THF, 12 h, rt, 90%; c: NH4OAc (1.5 equiv.), MeOH saturated with NH3 at 60 °C for 2 days, 61%; d: MsCl, Et3N in DCM for 30 min, 0 °C, 6 h, rt; e: Et3N in CHCl3, reflux, 12 h, 90%; f: Et3N in CHCl3, Δ, 12 h.
	Figure 14. a: Guanidine hydrochloride, t-BuOK, CF3CH2OH, 30 min, then 154, rt, 48 h, 25%; b: Ph3P, imidazole, I2, CH2Cl2, −18 °C, 6 h, 67%.
	Figure 15. a: Guanidine, PH, reflux 25 h, then HNO3 (1% aq), 35%.
	Figure 16. a: Guanidine, DMF, 0 °C, then 25 °C, 5 h b: 0 °C, MeOH-H2O (2:1), NaBH4 (6 equiv.), 25 °C, 16 h, 25%.
	Figure 17. a: O-methylisourea, i-Pr2EtN, DMSO, 80 °C, 1.5 h (52%, 4:l, H10, H13 trans: H10, H13 cis); b: NH3, NH4OAc, t-BuOH, 60 °C, 40 h (72%, 1:1, H10, H13 cis β: H10, H13 cis α); c: 3:7 HF-CH3CN, −30 °C, 3d; d: Et3N, MeOH, 60 °C, 20 h (78%).
	Figure 18. Proposed conversions (a–e) and hypothetical biogenesis of different pentacyclic guanidine alkaloids.
	Figure 19. Pulchranin A (118), as a biosynthetic precursor for pentacyclic compounds (103–104).