Marine Terpenic Endoperoxides

Overview

Journal Mar Drugs

Publisher MDPI

Specialties Biology
Pharmacology

Date 2021 Dec 23

PMID 34940660

Citations 2

Authors

Irene Torres-Garcia

Josefa L Lopez-Martinez

Manuel Munoz-Dorado

Ignacio Rodriguez-Garcia

Miriam Alvarez-Corral

Affiliations

Soon will be listed here.

Abstract

Organic extracts of marine invertebrates, mainly sponges, from seas all over the world are well known for their high in vitro anticancer and antibiotic activities which make them promising sources of compounds with potential use as pharmaceutical leads. Most of the structures discovered so far have a peculiar structural feature in common: a 1,2-dioxane ring. This is a highly reactive heterocycle that can be considered as an endoperoxide function. Together with other structural features, this group could be responsible for the strong biological activities of the substances present in the extracts. Numerous research programs have focused on their structural elucidation and total synthesis since the seventies. As a consequence, the number of established chiral centres and the similarity between different naturally occurring substances is increasingly higher. Most of these compounds have a terpenoid nature, mainly diterpene and sesterterpene, with several peculiar structural features, such as the loss of one carbon atom. Although there are many reviews dealing with the occurrence of marine peroxides, their activities, or potential pharmaceutical uses, no one has focused on those having a terpene origin and the endoperoxide function. We present here a comprehensive review of these compounds paying special attention to their structural features and their biological activity.

Citing Articles

Cheminformatics-Based Study Identifies Potential Ebola VP40 Inhibitors.

Broni E, Ashley C, Adams J, Manu H, Aikins E, Okom M Int J Mol Sci. 2023; 24(7).

PMID: 37047270 PMC: 10094735. DOI: 10.3390/ijms24076298.

Advocacy for the Medicinal Plant (Yingzhao) and Antimalarial Yingzhaosu Endoperoxides.

Bailly C, Henichart J Molecules. 2022; 27(19).

PMID: 36234725 PMC: 9573098. DOI: 10.3390/molecules27196192.

References

Lefranc F, Nuzzo G, Hamdy N, Fakhr I, Moreno Y Banuls L, Van Goietsenoven G . In vitro pharmacological and toxicological effects of norterpene peroxides isolated from the Red Sea sponge Diacarnus erythraeanus on normal and cancer cells. J Nat Prod. 2013; 76(9):1541-7. DOI: 10.1021/np400107t. View

Miyazato H, Taira J, Ueda K . Hydrogen peroxide derived from marine peroxy sesquiterpenoids induces apoptosis in HCT116 human colon cancer cells. Bioorg Med Chem Lett. 2016; 26(19):4641-4644. DOI: 10.1016/j.bmcl.2016.08.057. View

Dai J, Liu Y, Zhou Y, Nagle D . Hypoxia-selective antitumor agents: norsesterterpene peroxides from the marine sponge Diacarnus levii preferentially suppress the growth of tumor cells under hypoxic conditions. J Nat Prod. 2007; 70(1):130-3. PMC: 2910712. DOI: 10.1021/np0604883. View

Erickson K, Beutler J, Gray G, Cardellina 2nd J, Boyd M . Majapolene A, a cytotoxic peroxide, and related sesquiterpenes from the red alga Laurencia majuscula. J Nat Prod. 1995; 58(12):1848-60. DOI: 10.1021/np50126a007. View

DAniello E, Iannotti F, Falkenberg L, Martella A, Gentile A, De Maio F . In Silico Identification and Experimental Validation of (-)-Muqubilin A, a Marine Norterpene Peroxide, as PPARα/γ-RXRα Agonist and RARα Positive Allosteric Modulator. Mar Drugs. 2019; 17(2). PMC: 6410278. DOI: 10.3390/md17020110. View

Sperry S, Valeriote F, Corbett T, Crews P . Isolation and cytotoxic evaluation of marine sponge-derived norterpene peroxides. J Nat Prod. 1998; 61(2):241-7. DOI: 10.1021/np970467w. View

Cheenpracha S, Park E, Rostama B, Pezzuto J, Chang L . Inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophage RAW 264.7 cells by the norsesterterpene peroxide, epimuqubilin A. Mar Drugs. 2010; 8(3):429-37. PMC: 2857364. DOI: 10.3390/md8030429. View

Yang F, Wang R, Xu B, Yu H, Ma G, Wang G . New antimalarial norterpene cyclic peroxides from Xisha Islands sponge Diacarnus megaspinorhabdosa. Bioorg Med Chem Lett. 2016; 26(8):2084-7. DOI: 10.1016/j.bmcl.2016.02.070. View

Rubio B, Tenney K, Ang K, Abdulla M, Arkin M, McKerrow J . The marine sponge Diacarnus bismarckensis as a source of peroxiterpene inhibitors of Trypanosoma brucei, the causative agent of sleeping sickness. J Nat Prod. 2009; 72(2):218-22. PMC: 2880650. DOI: 10.1021/np800711a. View

10.

Ovenden , Capon . Nuapapuin A and sigmosceptrellins D and E: new norterpene cyclic peroxides from a southern australian marine sponge, sigmosceptrella sp . J Nat Prod. 1999; 62(2):214-8. DOI: 10.1021/np980223r. View

11.

Chao C, Wen Z, Wu Y, Yeh H, Sheu J . Cytotoxic and anti-inflammatory cembranoids from the soft coral Lobophytum crassum. J Nat Prod. 2008; 71(11):1819-24. DOI: 10.1021/np8004584. View

12.

Jiang M, Wu Z, Guo H, Liu L, Chen S . A Review of Terpenes from Marine-Derived Fungi: 2015-2019. Mar Drugs. 2020; 18(6). PMC: 7345631. DOI: 10.3390/md18060321. View

13.

Wu Q, Ye F, Li X, Liang L, Sun J, Sun H . Uncommon Polyoxygenated Sesquiterpenoids from South China Sea Soft Coral Lemnalia flava. J Org Chem. 2019; 84(6):3083-3092. DOI: 10.1021/acs.joc.8b02912. View

14.

Vairappan C, Suzuki M, Ishii T, Okino T, Abe T, Masuda M . Antibacterial activity of halogenated sesquiterpenes from Malaysian Laurencia spp. Phytochemistry. 2008; 69(13):2490-4. DOI: 10.1016/j.phytochem.2008.06.015. View

15.

Mason R, Kalyanaraman B, Tainer B, Eling T . A carbon-centered free radical intermediate in the prostaglandin synthetase oxidation of arachidonic acid. Spin trapping and oxygen uptake studies. J Biol Chem. 1980; 255(11):5019-22. View

16.

Roethle P, Trauner D . The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products. Nat Prod Rep. 2008; 25(2):298-317. DOI: 10.1039/b705660p. View

17.

Duh C, Wang S, Chung S, Chou G, Dai C . Cytotoxic cembrenolides and steroids from the formosan soft coral Sarcophyton crassocaule. J Nat Prod. 2001; 63(12):1634-7. DOI: 10.1021/np0002381. View

18.

Peng J, Shen X, El Sayed K, Dunbar D, Perry T, Wilkins S . Marine natural products as prototype agrochemical agents. J Agric Food Chem. 2003; 51(8):2246-52. PMC: 4969014. DOI: 10.1021/jf0207880. View

19.

Li G, Zhang Y, Deng Z, van Ofwegen L, Proksch P, Lin W . Cytotoxic cembranoid diterpenes from a soft coral Sinularia gibberosa. J Nat Prod. 2005; 68(5):649-52. DOI: 10.1021/np040197z. View

20.

Chao C, Chou K, Wang G, Wu Y, Wang L, Chen J . Norterpenoids and related peroxides from the formosan marine sponge Negombata corticata. J Nat Prod. 2010; 73(9):1538-43. DOI: 10.1021/np100353x. View