The Oxepane Motif in Marine Drugs

Overview

Journal Mar Drugs

Publisher MDPI

Specialties Biology
Pharmacology

Date 2017 Nov 16

PMID 29140270

Citations 14

Authors

Hector Barbero

Carlos Diez-Poza

Asuncion Barbero

Affiliations

Soon will be listed here.

Abstract

Oceans have shown to be a remarkable source of natural products. The biological properties of many of these compounds have helped to produce great advances in medicinal chemistry. Within them, marine natural products containing an oxepanyl ring are present in a great variety of algae, sponges, fungus and corals and show very important biological activities, many of them possessing remarkable cytotoxic properties against a wide range of cancer cell lines. Their rich chemical structures have attracted the attention of many researchers who have reported interesting synthetic approaches to these targets. This review covers the most prominent examples of these types of compounds, focusing the discussion on the isolation, structure determination, medicinal properties and total synthesis of these products.

Citing Articles

Construction of Seven-Membered Oxacycles Using a Rh(I)-Catalyzed Cascade C-C Formation/Cleavage of Cyclobutenol Derivatives.

Ham J, Son M, Na C, Park B, Baik M, Sarpong R J Org Chem. 2024; 89(7):4647-4656.

PMID: 38497619 PMC: 11646678. DOI: 10.1021/acs.joc.3c02914.

Cooperative Bifurcated Chalcogen Bonding and Hydrogen Bonding as Stereocontrolling Elements for Selective Strain-Release Septanosylation.

Ma W, Kirchhoff J, Strohmann C, Grabe B, Loh C J Am Chem Soc. 2023; 145(49):26611-26622.

PMID: 38032866 PMC: 10722516. DOI: 10.1021/jacs.3c06984.

Naturally Occurring Organohalogen Compounds-A Comprehensive Review.

Gribble G Prog Chem Org Nat Prod. 2023; 121:1-546.

PMID: 37488466 DOI: 10.1007/978-3-031-26629-4_1.

Changing the Reaction Pathway of Silyl-Prins Cyclization by Switching the Lewis Acid: Application to the Synthesis of an Antinociceptive Compound.

Diez-Poza C, Fernandez-Pena L, Gonzalez-Andres P, Barbero A J Org Chem. 2023; 88(11):6776-6783.

PMID: 37220201 PMC: 10242753. DOI: 10.1021/acs.joc.3c00050.

The Tetrahydrofuran Motif in Marine Lipids and Terpenes.

Gonzalez-Andres P, Fernandez-Pena L, Diez-Poza C, Barbero A Mar Drugs. 2022; 20(10).

PMID: 36286465 PMC: 9605582. DOI: 10.3390/md20100642.

References

Fernandez J, Souto M, Norte M . Marine polyether triterpenes. Nat Prod Rep. 2000; 17(3):235-46. DOI: 10.1039/a909496b. View

Edrada R, Proksch P, Wray V, Witte L, van Ofwegen L . Four new bioactive lobane diterpenes of the soft coral Lobophytum pauciflorum from Mindoro, Philippines. J Nat Prod. 1998; 61(3):358-61. DOI: 10.1021/np970276t. View

Vilotijevic I, Jamison T . Synthesis of marine polycyclic polyethers via endo-selective epoxide-opening cascades. Mar Drugs. 2010; 8(3):763-809. PMC: 2857356. DOI: 10.3390/md8030763. View

Belofsky G, Anguera M, Jensen P, Fenical W, Kock M . Oxepinamides A-C and fumiquinazolines H--I: bioactive metabolites from a marine isolate of a fungus of the genus Acremonium. Chemistry. 2000; 6(8):1355-60. DOI: 10.1002/(sici)1521-3765(20000417)6:8<1355::aid-chem1355>3.0.co;2-s. View

Berlinck R, Burtoloso A, Kossuga M . The chemistry and biology of organic guanidine derivatives. Nat Prod Rep. 2008; 25(5):919-54. DOI: 10.1039/b507874c. View

Kawahara N, Nozawa K, Yamazaki M, Nakajima S, Kawai K . Structures of novel epipolythiodioxopiperazines, emethallicins B, C, and D, potent inhibitors of histamine release, from Emericella heterothallica. Chem Pharm Bull (Tokyo). 1990; 38(1):73-8. DOI: 10.1248/cpb.38.73. View

Gonzalez-Jarti N J, Alfonso A, Sainz M, Vieytes M, Botana L . UPLC-MS-IT-TOF Identification of Circumdatins Produced by Aspergillus ochraceus. J Agric Food Chem. 2017; 65(23):4843-4852. DOI: 10.1021/acs.jafc.7b01845. View

Welch T, Williams R . Epidithiodioxopiperazines. occurrence, synthesis and biogenesis. Nat Prod Rep. 2014; 31(10):1376-404. PMC: 4162872. DOI: 10.1039/c3np70097f. View

Pettit G, Herald C, Allen M, Von Dreele R, Vanell L, Kao J . The isolation and structure of aplysistatin. J Am Chem Soc. 1977; 99(1):262-3. DOI: 10.1021/ja00443a055. View

10.

Aron Z, Pietraszkiewicz H, Overman L, Valeriote F, Cuevas C . Synthesis and anticancer activity of side chain analogs of the crambescidin alkaloids. Bioorg Med Chem Lett. 2004; 14(13):3445-9. DOI: 10.1016/j.bmcl.2004.04.071. View

11.

Choi E, Park J, Kim Y, Jung J, Lee J, Kwon H . Apoptosis-inducing effect of diketopiperazine disulfides produced by Aspergillus sp. KMD 901 isolated from marine sediment on HCT116 colon cancer cell lines. J Appl Microbiol. 2010; 110(1):304-13. DOI: 10.1111/j.1365-2672.2010.04885.x. View

12.

Gomes N, Lefranc F, Kijjoa A, Kiss R . Can Some Marine-Derived Fungal Metabolites Become Actual Anticancer Agents?. Mar Drugs. 2015; 13(6):3950-91. PMC: 4483665. DOI: 10.3390/md13063950. View

13.

Onodera H, Hasegawa A, Tsumagari N, Nakai R, Ogawa T, Kanda Y . MPC1001 and its analogues: new antitumor agents from the fungus Cladorrhinum species. Org Lett. 2004; 6(22):4101-4. DOI: 10.1021/ol048202d. View

14.

Ohizumi Y, Sasaki S, Kusumi T, Ohtani I . Ptilomycalin A, a novel Na+, K(+)- or Ca2(+)-ATPase inhibitor, competitively interacts with ATP at its binding site. Eur J Pharmacol. 1996; 310(1):95-8. DOI: 10.1016/0014-2999(96)00482-7. View

15.

Couladouros E, Vidali V . Novel stereocontrolled approach to syn- and anti-oxepene-cyclogeranyl trans-fused polycyclic systems: asymmetric total synthesis of (-)-Aplysistatin, (+)-Palisadin A, (+)-Palisadin B, (+)-12-hydroxy-palisadin B, and the AB ring system of.... Chemistry. 2004; 10(15):3822-35. DOI: 10.1002/chem.200400407. View

16.

Su H, Shi D, Li J, Guo S, Li L, Yuan Z . Sesquiterpenes from Laurencia similis. Molecules. 2009; 14(5):1889-97. PMC: 6254443. DOI: 10.3390/molecules14051889. View

17.

Kuniyoshi M, Marma M, Higa T, Bernardinelli G, Jefford C . New bromoterpenes from the red alga Laurencia luzonensis. J Nat Prod. 2001; 64(6):696-700. DOI: 10.1021/np000638o. View

18.

Bonnard I, Jhaumeer-Laulloo S, Bontemps N, Banaigs B, Aknin M . New lobane and cembrane diterpenes from two comorian soft corals. Mar Drugs. 2010; 8(2):359-72. PMC: 2852843. DOI: 10.3390/md8020359. View

19.

Makarieva T, Tabakmaher K, Guzii A, Denisenko V, Dmitrenok P, Shubina L . Monanchocidins B-E: polycyclic guanidine alkaloids with potent antileukemic activities from the sponge Monanchora pulchra. J Nat Prod. 2011; 74(9):1952-8. DOI: 10.1021/np200452m. View

20.

Schuber Jr P, Williams R . Synthetic Studies Towards MPC1001: Preparation of a β-hydroxyl-Tyrosine Derivative. Tetrahedron Lett. 2012; 53(4):380-382. PMC: 3265114. DOI: 10.1016/j.tetlet.2011.11.069. View