Japonicone A and related dimeric sesquiterpene lactones: molecular targets and mechanisms of anticancer activity

Bailly, Christian; Vergoten, Gérard

doi:10.1007/s00011-021-01538-y

Cited by 8 publications

(4 citation statements)

References 61 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sintenin is a non-cytotoxic lactone, with no effect on the proliferation of different types of cancer cells [53,54]. Sesquiterpene lactones often present marked antitumor properties, such as those isolated from the Inula species for example [63,64], but it is not the case for sintenin and cladantholide, both non-cytotoxic compounds. They deserve further studies as anti-inflammatory and antidiabetic agents.…”

Section: Phytochemical Analysismentioning

confidence: 99%

The Medicinal Moroccan Plant Cladanthus arabicus as a Prominent Source of Sesquiterpenes Cladantholide and Sintenin

Bouissane,

Bailly

2024

AppliedChem

Self Cite

View full text Add to dashboard Cite

The yellow-flowering plant Cladanthus arabicus (L.) Cass., commonly called Arabian Cladanthus or palm springs daisy, is typical of the West Mediterranean region and is particularly abundant in Morocco. The plant is used in traditional Moroccan medicine for the treatment of diabetes and other ailments. Over the past 20 years, this abundant wild plant has been neglected from a phytochemical viewpoint. For the first time, the present review provides a survey of the pharmacological properties reported from extracts of C. arabicus and from essential oils derived from the aerial parts, mainly antimicrobial, antioxidant, and anti-inflammatory properties. The main bioactive natural products are discussed, with a focus on two rare sesquiterpenes of major interest, which are abundant in the stems and leaves: the 6,12-guaianolide cladantholide and the germacranolide sintenin. These sesquiterpene lactones and their analogues are presented to highlight their properties, extraction or total synthesis, and their therapeutic benefits. They both represent convenient biosourced precursors for the synthesis of derivatives. Sintenin may be used as a starting material for the design of hemi-synthetic germacradienolide-type costunolide or parthenolide derivatives. The 6,12-guaianolide scaffold of cladantholide offers opportunities to design novel arglabin derivatives. The therapeutic potential of the neglected and under-utilized plant Cladanthus arabicus and its original phytochemicals shall be explored further.

show abstract

Section: Phytochemical Analysismentioning

confidence: 99%

The Medicinal Moroccan Plant Cladanthus arabicus as a Prominent Source of Sesquiterpenes Cladantholide and Sintenin

Bouissane,

Bailly

2024

AppliedChem

Self Cite

View full text Add to dashboard Cite

show abstract

“…In addition, Bailly et al constructed a molecular model of the compound/target interaction. Molecular docking showed that the compound can be used as an interfacial ligand, which fits well at the junction between two TNF-α subunits and binds to proteins through a series of molecular interactions such as hydrogen bonding and van der Waals contacts [ 89 ].…”

Section: Molecular Targets Of Inula Sesquiterpene ...mentioning

confidence: 99%

“…The ability of JapA to bind MDM2 protein was higher than that of p53 residue [ 95 ]. Bailly et al further showed that the compound may fit between two α-helices and interaction with the protein via H-bonds with residues Lysine 51 and Glutamine 24, and via several other molecular contacts [ 89 ].…”

Section: Molecular Targets Of Inula Sesquiterpene ...mentioning

confidence: 99%

Research progress on antitumor mechanisms and molecular targets of Inula sesquiterpene lactones

Cao,

Chu,

Qin

et al. 2023

Chin Med

View full text Add to dashboard Cite

The pharmacological effects of natural product therapy have received sigificant attention, among which terpenoids such as sesquiterpene lactones stand out due to their biological activity and pharmacological potential as anti-tumor drugs. Inula sesquiterpene lactones are a kind of sesquiterpene lactones extracted from Inula species. They have many pharmacological activities such as anti-inflammation, anti-asthma, anti-tumor, neuroprotective and anti-allergic. In recent years, more and more studies have proved that they are important candidate drugs for the treatment of a variety of cancers because of its good anti-tumor activity. In this paper, the structure, structure–activity relationship, antitumor activities, mechanisms and targets of Inula sesquiterpene lactones reported in recent years were reviewed in order to provide clues for the development of novel anticancer drugs. Graphical abstract

show abstract

“…The Asteraceae family comprises more than 1,600 genera, of which the genus Inula is characterized by their composite flower heads traditionally used as herbal medicines . In recent years, an increasingly large number of dimerized [4 + 2] sesquiterpenoids with diverse skeletons and activities were isolated from the genus Inula . − The first [4 + 2] trimer was found with anticancer activities in nature in 2008 . For decades, only nine members of those complex natural products have been isolated with different types [4 + 2] trimers, including endo - endo and endo - exo spiro-polycyclic skeleton. − Inulajaponicolide A, an endo - exo sesquiterpenoid [4 + 2] trimer, was isolated from the genus Inula for the first time in 2018 .…”

Section: Introductionmentioning

confidence: 99%

Inubritantrimers A–D: Trimerized Sesquiterpenoid [4 + 2] Adducts Featuring a Distinctive Spiro-Polycyclic Scaffold from Inula britannica

Guo,

Qi,

Ren

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

Inubritantrimer A (1), a trace trimerized sesquiterpenoid [4 + 2] adduct featuring an unusual exo-exo type spiro-polycyclic scaffold, together with three new endo-exo [4 + 2] adducts, inubritantrimers B–D (2–4), were discovered from the flowers of Inula britannica. Their structures were elucidated using 1D/2D NMR, X-ray diffraction, and ECD approaches. 1 is characterized as a novel exo-exo trimer, synthesized biogenetically from three sesquiterpenoid monomers, featuring a unique linkage of C-11/C-1′, C-13/C-3′ and C-13′/C-3″, C-11′/C-1″ through a two-step exo [4 + 2] cycloaddition process. Compounds 1–4 exhibited modest cytotoxicity against breast cancer cells with IC50 values in the range of 5.84–12.01 μM.

show abstract

Japonicone A and related dimeric sesquiterpene lactones: molecular targets and mechanisms of anticancer activity

Cited by 8 publications

References 61 publications

The Medicinal Moroccan Plant Cladanthus arabicus as a Prominent Source of Sesquiterpenes Cladantholide and Sintenin

The Medicinal Moroccan Plant Cladanthus arabicus as a Prominent Source of Sesquiterpenes Cladantholide and Sintenin

Research progress on antitumor mechanisms and molecular targets of Inula sesquiterpene lactones

Inubritantrimers A–D: Trimerized Sesquiterpenoid [4 + 2] Adducts Featuring a Distinctive Spiro-Polycyclic Scaffold from Inula britannica

Contact Info

Product

Resources

About