Tigliane and Daphnane Diterpenoids from Thymelaeaceae Family: Chemistry, Biological Activity, and Potential in Drug Discovery

Overview

Journal J Nat Med

Publisher Springer

Date 2023 Jun 9

PMID 37294498

Authors

Kouharu Otsuki

Wei Li

Affiliations

Soon will be listed here.

Abstract

Tigliane and daphnane diterpenoids are characteristically distributed in plants of the Thymelaeaceae family as well as the Euphorbiaceae family and are structurally diverse due to the presence of polyoxygenated functionalities in the polycyclic skeleton. These diterpenoids are known as toxic components, while they have been shown to exhibit a wide variety of biological activities, such as anti-cancer, anti-HIV, and analgesic activity, and are attracting attention in the field of natural product drug discovery. This review focuses on naturally occurring tigliane and daphnane diterpenoids from plants of the Thymelaeaceae family and provides an overview of their chemical structure, distribution, isolation, structure determination, chemical synthesis, and biological activities, with a prime focus on the recent findings.

Citing Articles

Anti-HIV diterpenoids from Daphne pseudomezereum.

Otsuki K, Hosoya C, Takamiya R, Kimura M, Kikuchi T, Huang L Phytochemistry. 2024; 232():114366.

PMID: 39694394 PMC: 11748344. DOI: 10.1016/j.phytochem.2024.114366.

Diterpenes: An Updated Review Concerning Their Structural Diversity, Therapeutic Performance, and Future Pharmaceutical Applications.

Souza T, Pereira L, Alves A, Dourado D, Lins J, Scotti M Pharmaceuticals (Basel). 2024; 17(10).

PMID: 39459038 PMC: 11510188. DOI: 10.3390/ph17101399.

Topological Heterogeneity of Protein Kinase C Modulators in Human T-Cells Resolved with In-Cell Dynamic Nuclear Polarization NMR Spectroscopy.

Overall S, Hartmann S, Luu-Nguyen Q, Judge P, Pinotsi D, Marti L J Am Chem Soc. 2024; 146(40):27362-27372.

PMID: 39322225 PMC: 11468733. DOI: 10.1021/jacs.4c05704.

Daphnane diterpenoid orthoesters with an odd-numbered aliphatic side chain from Daphne pedunculata.

Tan L, Otsuki K, Kikuchi T, Zhou D, Li N, Huang L J Nat Med. 2024; 78(4):901-907.

PMID: 38780746 PMC: 11365762. DOI: 10.1007/s11418-024-01826-x.

Unveiling the pharmacological potential of plant triterpenoids in breast cancer management: an updated review.

Aly S, Elbadry A, Doghish A, El-Nashar H Naunyn Schmiedebergs Arch Pharmacol. 2024; 397(8):5571-5596.

PMID: 38563878 PMC: 11329582. DOI: 10.1007/s00210-024-03054-2.

References

Li W, Chen H, Wang H, Mei W, Dai H . Natural products in agarwood and Aquilaria plants: chemistry, biological activities and biosynthesis. Nat Prod Rep. 2020; 38(3):528-565. DOI: 10.1039/d0np00042f. View

Diamond L, OBrien T, Baird W . Tumor promoters and the mechanism of tumor promotion. Adv Cancer Res. 1980; 32:1-74. DOI: 10.1016/s0065-230x(08)60360-7. View

Liao S, Chen H, Yue J . Plant orthoesters. Chem Rev. 2009; 109(3):1092-140. DOI: 10.1021/cr0782832. View

Wang H, Wang X, Liu L, Qin G, Kang T . Tigliane diterpenoids from the Euphorbiaceae and Thymelaeaceae families. Chem Rev. 2015; 115(9):2975-3011. DOI: 10.1021/cr200397n. View

Moesta P, West C . Casbene synthetase: regulation of phytoalexin biosynthesis in Ricinus communis L. seedlings. Purification of casbene synthetase and regulation of its biosynthesis during elicitation. Arch Biochem Biophys. 1985; 238(1):325-33. DOI: 10.1016/0003-9861(85)90171-7. View

Adolf W, Seip E, Hecker E, Dossaji S . Irritant principles of the mezereon family (Thymelaeaceae), V. New skin irritants and tumor promoters of the daphnane and 1 alpha-alkyldaphnane type from Synaptolepis kirkii and Synaptolepis retusa. J Nat Prod. 1988; 51(4):662-74. DOI: 10.1021/np50058a003. View

He W, Cik M, Van Puyvelde L, van Dun J, Appendino G, Lesage A . Neurotrophic and antileukemic daphnane diterpenoids from Synaptolepis kirkii. Bioorg Med Chem. 2002; 10(10):3245-55. DOI: 10.1016/s0968-0896(02)00163-3. View

Asada Y, Otsuki K, Morooka M, Huang L, Chen C, Koike K . Anti-HIV Macrocyclic Daphnane Orthoesters with an Unusual Macrocyclic Ring from . J Nat Prod. 2022; 85(10):2399-2405. PMC: 10114293. DOI: 10.1021/acs.jnatprod.2c00618. View

Hayes P, Chow S, Somerville M, Fletcher M, De Voss J . Daphnane- and tigliane-type diterpenoid esters and orthoesters from Pimelea elongata. J Nat Prod. 2010; 73(11):1907-13. DOI: 10.1021/np1005746. View

10.

Guo J, Tian J, Yao G, Zhu H, Xue Y, Luo Z . Three new 1α-alkyldaphnane-type diterpenoids from the flower buds of Wikstroemia chamaedaphne. Fitoterapia. 2015; 106:242-6. DOI: 10.1016/j.fitote.2015.09.017. View

11.

Otsuki K, Zhang M, Kikuchi T, Tsuji M, Tejima M, Bai Z . Identification of anti-HIV macrocyclic daphnane orthoesters from Wikstroemia ligustrina by LC-MS analysis and phytochemical investigation. J Nat Med. 2021; 75(4):1058-1066. DOI: 10.1007/s11418-021-01551-9. View

12.

Schmidt R, Hecker E . Autoxidation of phorbol esters under normal storage conditions. Cancer Res. 1975; 35(5):1375-7. View

13.

Powell R, Weisleder D, Smith Jr C . Daphnane diterpenes from Diarthron vesiculosum: vesiculosin and isovesiculosin. J Nat Prod. 1985; 48(1):102-7. DOI: 10.1021/np50037a018. View

14.

Nyborg J, la Cour T . X-ray diffraction study of molecular structure and conformation of mezerein. Nature. 1975; 257(5529):824-5. DOI: 10.1038/257824a0. View

15.

Kupchan S, Shizuri Y, Murae T, Swenny J, Haynes H, Shen M . Letter: Gnidimacrin and gnidimacrin 20-palmitate, novel macrocyclic antileukemic diterpenoid esters from Gnidia subcordata1,2. J Am Chem Soc. 1976; 98(18):5719-20. DOI: 10.1021/ja00434a063. View

16.

Du Q, Zhao Y, Liu H, Tang C, Zhang M, Ke C . Isolation and Structure Characterization of Cytotoxic Phorbol Esters from the Seeds of Croton tiglium. Planta Med. 2017; 83(17):1361-1367. DOI: 10.1055/s-0043-110227. View

17.

Klausen T, Pagani A, Minassi A, Ech-Chahad A, Prenen J, Owsianik G . Modulation of the transient receptor potential vanilloid channel TRPV4 by 4alpha-phorbol esters: a structure-activity study. J Med Chem. 2009; 52(9):2933-9. DOI: 10.1021/jm9001007. View

18.

Otsuki K, Zhang M, Yamamoto A, Tsuji M, Tejima M, Bai Z . Anti-HIV Tigliane Diterpenoids from . J Nat Prod. 2020; 83(12):3584-3590. PMC: 8176626. DOI: 10.1021/acs.jnatprod.0c00700. View

19.

Otsuki K, Li W, Miura K, Asada Y, Huang L, Chen C . Isolation, Structural Elucidation, and Anti-HIV Activity of Daphnane Diterpenoids from . J Nat Prod. 2020; 83(11):3270-3277. PMC: 8176625. DOI: 10.1021/acs.jnatprod.0c00540. View

20.

Tan L, Otsuki K, Zhang M, Kikuchi T, Okayasu M, Azumaya I . Daphnepedunins A-F, Anti-HIV Macrocyclic Daphnane Orthoester Diterpenoids from . J Nat Prod. 2022; 85(12):2856-2864. PMC: 10131280. DOI: 10.1021/acs.jnatprod.2c00894. View