Natural Diterpene and Triterpene Quinone Methides: Structures, Synthesis, and Biological Potentials

Zhou, Qibing

doi:10.1002/9780470452882.ch8

Cited by 11 publications

(10 citation statements)

References 110 publications

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“…The low SI might justify the high toxicity in vivo, and the low bioavailability explains the lack of activity. In fact, quinone methides triterpenoids such as compounds (65 and 66) have been studied for their antitumoral activities [101,102]. It was found their quinone methide moiety was responsible for this effect, namely through the induction of apoptotic pathways, be it with mitochondrial targeting, formation of Michael adducts with chaperones, among other interactions [101][102][103][104].…”

Section: Quinones Anthrones and Derivativesmentioning

confidence: 99%

Natural Phenolic Compounds and Derivatives as Potential Antimalarial Agents

et al. 2020

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Malaria is a parasitic disease endemic to tropical and subtropical regions responsible for hundreds of millions of clinical cases and hundreds of thousands of deaths yearly. Its agent, the Plasmodium sp., has a highly variable antigenicity, which accounts for the emergence and spread of resistance to all available treatments. In light of this rising problem, scientists have turned to naturally occurring compounds obtained from plants recurrently used in traditional medicine in endemic areas. Ethnopharmacological approaches seem to be helpful in selecting the most interesting plants for the search of new antiplasmodial and antimalarial molecules. However, this search for new antimalarials is complex and time-consuming and ultimately leads to a great number of interesting compounds with a lack of discussion of their characteristics. This review aims to examine the most promising antiplasmodial phenolic compounds (phenolic acids, flavonoids, xanthones, coumarins, lignans, among others) and derivatives isolated over the course of the last 28 y (1990 – 2018) and discuss their structure-activity relationships, mechanisms of action, toxicity, new perspectives they could add to the fight against malaria, and finally, the difficulties of transforming these potential compounds into new antimalarials.

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Section: Quinones Anthrones and Derivativesmentioning

confidence: 99%

Natural Phenolic Compounds and Derivatives as Potential Antimalarial Agents

et al. 2020

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“…In addition, OHCT and its precursor exhibit no cytotoxicity at concentrations of 10–60 μM in either human liver cells [ 8 , 9 ] or human lung cells (unpublished data). Both compounds are able to protect human liver cells against aflatoxin B 1 -induced toxicity [ 7 - 9 ]. Therefore, it is conceivable that the nanomolar anti-malarial activity of OHCT may due to a unique mechanism yet to be identified, which is currently under investigation.…”

Section: Discussionmentioning

confidence: 99%

“…It has been shown that a number of terpenes and terpene derivatives isolated from a variety of sources ranging from plants to marine fungi kill P. falciparum parasites [ 3 - 6 ]. Synthetic cis -terpenones, including the oxidized derivative of hydroxy- cis terpenone (OHCT), are synthetic analogues of natural terpene quinone methides that have a broad spectrum of biological activities [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

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Antimalarial activity of a cis-terpenone

Mayer

Bruce

Kochurova

et al. 2009

Malar J

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Background: Malaria is the third most prevalent cause of infectious disease in the world. Resistance of the parasite to classical drugs makes the discovery of new and effective drugs more urgent. The oxidized derivative of hydroxy-cis terpenone (OHCT) is a synthetic molecule that is not toxic to cultured human liver cells at concentrations as high as 60 μM and inhibits activity of cytochrome P450s that metabolize many drugs.

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“…Triterpenoid quinonemethides constitute a relatively small group of unsaturated and oxygenated D:A-friedo-nor-oleananes with interesting structures and a variety of biological activities [1,2,3]. These natural products are restricted to species of the Celastraceae family and, for this reason, the triterpenoid quinonemethides and related compounds (phenolic triterpenoids and triterpene dimers) are called celastroloids [4].…”

Section: Introductionmentioning

confidence: 99%

Biogenesis of Triterpene Dimers from Orthoquinones Related to Quinonemethides: Theoretical Study on the Reaction Mechanism

et al. 2016

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Abstract:The biogenetic origin of triterpene dimers from the Celastraceae family has been proposed as assisted hetero-Diels-Alder reaction (HDA). In this work, computational calculation of HDA between natural quinonemethides (tingenone and isopristimerol) and hypothetical orthoquinones has been performed at the M06-2X/6-31G(d) level of theory. We have located all the HDA transition states supporting the biogenetic route via HDA cycloadditions. We found that all reactions take place through a concerted inverse electron demand and asynchronous mechanism. The enzymatic assistance for dimer formation was analyzed in terms of the calculated transition state energy barrier.

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Natural Diterpene and Triterpene Quinone Methides: Structures, Synthesis, and Biological Potentials

Cited by 11 publications

References 110 publications

Natural Phenolic Compounds and Derivatives as Potential Antimalarial Agents

Natural Phenolic Compounds and Derivatives as Potential Antimalarial Agents

Antimalarial activity of a cis-terpenone

Biogenesis of Triterpene Dimers from Orthoquinones Related to Quinonemethides: Theoretical Study on the Reaction Mechanism

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