Diterpenoids from Liverworts and their Biological Activities

Liu, Na; Wu, Cong; Wang, Peng; Lou, Hongxiang

doi:10.2174/1385272822666180905112616

Cited by 5 publications

(2 citation statements)

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“…ent -Kauranes are complex tetracyclic diterpenoids, mainly distributed in Jungermannia species of liverworts [ [1] , [2] , [3] ] and Isodon species of higher plants [ 4 ]. Numerous studies reported the α , β -unsaturated ketone was the active center for cytotoxic activity.…”

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confidence: 99%

ent-Kaurane diterpenoids induce apoptosis and ferroptosis through targeting redox resetting to overcome cisplatin resistance

et al. 2021

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Reactive oxygen species (ROS) induction is an effective mechanism to kill cancer cells for many chemotherapeutics, while resettled redox homeostasis induced by the anticancer drugs will promote cancer chemoresistance. Natural ent -kaurane diterpenoids have been found to bind glutathione (GSH) and sulfhydryl group in antioxidant enzymes covalently, which leads to the destruction of intracellular redox homeostasis. Therefore, redox resetting destruction by ent -kaurane diterpenoids may emerge as a viable strategy for cancer therapy. In this study, we isolated 30 ent -kaurane diterpenoids including 20 new samples from Chinese liverworts Jungermannia tetragona Lindenb and studied their specific targets and possible application in cancer drug resistance through redox resetting destruction. 11 β -hydroxy- ent -16-kaurene-15-one ( 23 ) possessed strong inhibitory activity against several cancer cell lines. Moreover, compound 23 induced both apoptosis and ferroptosis through increasing cellular ROS levels in HepG2 cells. ROS accumulation induced by compound 23 was caused by inhibition of antioxidant systems through targeting peroxiredoxin I/II (Prdx I/II) and depletion of GSH. Furthermore, compound 23 sensitized cisplatin (CDDP)-resistant A549/CDDP cancer cells in vitro and in vivo by inducing apoptosis and ferroptosis. Thus, the ent -kaurane derivative showed potential application for sensitizing CDDP resistance by redox resetting destruction through dual inhibition of Prdx I/II and GSH in cancer chemotherapy.

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Section: Introductionmentioning

confidence: 99%

ent-Kaurane diterpenoids induce apoptosis and ferroptosis through targeting redox resetting to overcome cisplatin resistance

et al. 2021

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“…Liverworts, as one of the three phyla of bryophytes, are rich in lipophilic terpenoids. , Terpenoids constitute the most abundant and structurally diverse group of natural products, of which labdane-type entities are widely distributed and abundantly diversified via enzymatic or nonenzymatic pathways, , leading to various structurally different carbon skeletons. In recent years, a total of eight types of new labdane skeletons (pallavicinin, pallavicinolide, pallambins A–D, , hapmnioides A–C, and haplomintrins A–G) have been found among more than 100 different labdane diterpenoids reported from liverworts, which has led to several studies of their total synthesis due to their intriguing structures …”

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Probing the Interconversion of Labdane Lactones from the Chinese Liverwort Pallavicinia ambigua

Zhu

et al. 2019

Org. Lett.

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We report on the spontaneous, reversible intramolecular transesterification of natural labdane lactones. Through extensive spectroscopic analysis, the interconversion between the two tautomers was investigated, which could be retarded when the free hydroxy group was acetylated or the exocyclic double bond of the lactone ring was mutated. Besides, a conversion mechanism was postulated, and the energy barriers were calculated by density functional theory calculations. Furthermore, the tautomers were found to inhibit the virulence of the efflux pump-deficient Candida albicans DSY654.

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