Tuaimenals B-H, Merosesquiterpenes from the Irish Deep-Sea Soft Coral with Bioactivity Against Cervical Cancer Cell Lines

Overview

Journal J Nat Prod

Date 2022 Dec 29

PMID 36580354

Authors

Joshua T Welsch

Tracess B Smalley

Jenet K Matlack

Nicole E Avalon

Jennifer M Binning

Mark P Johnson

A Louise Allcock

Bill J Baker

Affiliations

Soon will be listed here.

Abstract

Previous chemical investigation of the Irish deep-sea soft coral led to the identification of tuaimenal A (), a new merosesquiterpene containing a highly substituted chromene core and modest cytotoxicity against cervical cancer. Further MS/MS and NMR-guided investigation of this octocoral has resulted in the isolation and characterization of seven additional tuaimenal analogs, B-H (-), as well as two known A-ring aromatized steroids (, ), and additional tuaimenal A (). Tuaimenals B, F, and G (, , ), bearing an oxygen at the C position, as well as monocyclic tuaimenal H (), show increased cervical cancer inhibition profiles in comparison to that of . Tuaimenal G further displayed potent, selective cytotoxicity with an EC value of 0.04 μM against the C33A cell line compared to the CaSki cell line (EC 20 μM). These data reveal the anticancer properties of tuaimenal analogs and suggest unique antiproliferation mechanisms across these secondary metabolites.

Citing Articles

Marine natural products as a source of novel anticancer drugs: an updated review (2019-2023).

El-Seedi H, Refaey M, Elias N, El-Mallah M, Albaqami F, Dergaa I Nat Prod Bioprospect. 2025; 15(1):13.

PMID: 39853457 PMC: 11759743. DOI: 10.1007/s13659-024-00493-5.

An Overview of Secondary Metabolites from Soft Corals of the Genus over the Five Decades: Chemical Structures, Pharmacological Activities, NMR Data, and Chemical Synthesis.

Liu C, Yang Q, Zhang L, Liang L Mar Drugs. 2024; 22(9).

PMID: 39330283 PMC: 11433205. DOI: 10.3390/md22090402.

Anti-SARS-CoV-2 Activity and Cytotoxicity of Amaryllidaceae Alkaloids from .

Le N, De Jonghe S, Erven K, Vermeyen T, Balde A, Herrebout W Molecules. 2023; 28(7).

PMID: 37049986 PMC: 10096449. DOI: 10.3390/molecules28073222.

References

Birringer M, Siems K, Maxones A, Frank J, Lorkowski S . Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications. RSC Adv. 2022; 8(9):4803-4841. PMC: 9078042. DOI: 10.1039/c7ra11819h. View

Skropeta D, Wei L . Recent advances in deep-sea natural products. Nat Prod Rep. 2014; 31(8):999-1025. DOI: 10.1039/c3np70118b. View

Bedell S, Goldstein L, Goldstein A, Goldstein A . Cervical Cancer Screening: Past, Present, and Future. Sex Med Rev. 2019; 8(1):28-37. DOI: 10.1016/j.sxmr.2019.09.005. View

Travis J . Probing the unsolved mysteries of the deep. Science. 1993; 259(5098):1123-4. DOI: 10.1126/science.259.5098.1123. View

Merza J, Aumond M, Rondeau D, Dumontet V, Le Ray A, Seraphin D . Prenylated xanthones and tocotrienols from Garcinia virgata. Phytochemistry. 2004; 65(21):2915-20. DOI: 10.1016/j.phytochem.2004.06.037. View

Lu Z, Wagoner R, Harper M, Hooper J, Ireland C . Two ring-A-aromatized bile acids from the marine sponge Sollasella moretonensis. Nat Prod Commun. 2010; 5(10):1571-4. PMC: 3050653. View

Canfell K . Towards the global elimination of cervical cancer. Papillomavirus Res. 2019; 8:100170. PMC: 6722296. DOI: 10.1016/j.pvr.2019.100170. View

Skropeta D . Deep-sea natural products. Nat Prod Rep. 2008; 25(6):1131-66. DOI: 10.1039/b808743a. View

Burd E . Human papillomavirus and cervical cancer. Clin Microbiol Rev. 2003; 16(1):1-17. PMC: 145302. DOI: 10.1128/CMR.16.1.1-17.2003. View

10.

Avalon N, Nafie J, De Marco Verissimo C, Warrensford L, Dietrick S, Pittman A . Tuaimenal A, a Meroterpene from the Irish Deep-Sea Soft Coral , Displays Inhibition of the SARS-CoV-2 3CLpro Enzyme. J Nat Prod. 2022; 85(5):1315-1323. PMC: 9127705. DOI: 10.1021/acs.jnatprod.2c00054. View

11.

Newman D, Cragg G . Natural Products as Sources of New Drugs over the Nearly Four Decades from 01/1981 to 09/2019. J Nat Prod. 2020; 83(3):770-803. DOI: 10.1021/acs.jnatprod.9b01285. View

12.

Reher R, Kim H, Zhang C, Mao H, Wang M, Nothias L . A Convolutional Neural Network-Based Approach for the Rapid Annotation of Molecularly Diverse Natural Products. J Am Chem Soc. 2020; 142(9):4114-4120. PMC: 7210566. DOI: 10.1021/jacs.9b13786. View

13.

Arbyn M, Weiderpass E, Bruni L, de Sanjose S, Saraiya M, Ferlay J . Estimates of incidence and mortality of cervical cancer in 2018: a worldwide analysis. Lancet Glob Health. 2019; 8(2):e191-e203. PMC: 7025157. DOI: 10.1016/S2214-109X(19)30482-6. View