Daphnepedunins G and H, Anti-HIV Macrocyclic 3,4-seco-daphnane Orthoesters from Daphne Pedunculata

Overview

Journal J Nat Med

Publisher Springer

Date 2023 Sep 15

PMID 37713094

Authors

Lingjian Tan

Kouharu Otsuki

Mi Zhang

Takashi Kikuchi

Di Zhou

Ning Li

Li Huang

Chin-Ho Chen

Wei Li

Affiliations

Soon will be listed here.

Abstract

Daphnepedunins G (1) and H (2) with unusual macrocyclic 3,4-seco-daphnane orthoester structure were isolated from Daphne pedunculata. Their structures were determined by physicochemical and spectroscopic analyses combined with synthetic methods, including methyl esterification, derivatization reaction using a chiral anisotropic agent, and biomimetic conversion. Compounds 1 and 2 along with their methyl esters 1a and 2a were evaluated for anti-HIV activity, among which 1a and 2a exhibited potent activity with IC values of 1.08 and 1.17 μM, respectively.

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.

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.

References

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

Huang L, Ho P, Yu J, Zhu L, Lee K, Chen C . Picomolar dichotomous activity of gnidimacrin against HIV-1. PLoS One. 2011; 6(10):e26677. PMC: 3200356. DOI: 10.1371/journal.pone.0026677. View

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

Wong G, Gavva N . Therapeutic potential of vanilloid receptor TRPV1 agonists and antagonists as analgesics: Recent advances and setbacks. Brain Res Rev. 2009; 60(1):267-77. DOI: 10.1016/j.brainresrev.2008.12.006. View

Yoshida M, Yokokura H, Hidaka H, Ikekawa T, Saijo N . Mechanism of antitumor action of PKC activator, gnidimacrin. Int J Cancer. 1998; 77(2):243-50. DOI: 10.1002/(sici)1097-0215(19980717)77:2<243::aid-ijc13>3.0.co;2-c. View

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

Asada Y, Sukemori A, Watanabe T, Malla K, Yoshikawa T, Li W . Stelleralides A-C, novel potent anti-HIV daphnane-type diterpenoids from Stellera chamaejasme L. Org Lett. 2011; 13(11):2904-7. PMC: 3109985. DOI: 10.1021/ol200889s. View

Lai W, Huang L, Zhu L, Ferrari G, Chan C, Li W . Gnidimacrin, a Potent Anti-HIV Diterpene, Can Eliminate Latent HIV-1 Ex Vivo by Activation of Protein Kinase C β. J Med Chem. 2015; 58(21):8638-46. PMC: 4767159. DOI: 10.1021/acs.jmedchem.5b01233. View

10.

Sakai K, Fukuda Y, Matsunaga S, Tanaka R, Yamori T . New cytotoxic oleanane-type triterpenoids from the cones of Liquidamber styraciflua. J Nat Prod. 2004; 67(7):1088-93. DOI: 10.1021/np0305369. View

11.

Otsuki K, Li W . Tigliane and daphnane diterpenoids from Thymelaeaceae family: chemistry, biological activity, and potential in drug discovery. J Nat Med. 2023; 77(4):625-643. PMC: 10465420. DOI: 10.1007/s11418-023-01713-x. View

12.

Huang J, Yan X, Li W, Fan R, Li S, Chen J . Discovery of Highly Potent Daphnane Diterpenoids Uncovers Importin-β1 as a Druggable Vulnerability in Castration-Resistant Prostate Cancer. J Am Chem Soc. 2022; 144(38):17522-17532. DOI: 10.1021/jacs.2c06449. View

13.

George J . Biomimetic Dearomatization Strategies in the Total Synthesis of Meroterpenoid Natural Products. Acc Chem Res. 2021; 54(8):1843-1855. DOI: 10.1021/acs.accounts.1c00019. View

14.

ten Brink G, Arends I, Sheldon R . The Baeyer-Villiger reaction: new developments toward greener procedures. Chem Rev. 2004; 104(9):4105-24. DOI: 10.1021/cr030011l. View

15.

Otsuki K, Li W, Asada Y, Chen C, Lee K, Koike K . Daphneodorins A-C, Anti-HIV Gnidimacrin Related Macrocyclic Daphnane Orthoesters from . Org Lett. 2019; 22(1):11-15. PMC: 7437546. DOI: 10.1021/acs.orglett.9b03539. View

16.

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