Antiviral Triketone‐Phloroglucinol‐Monoterpene Adducts from <i>Callistemon rigidus</i>

Cao, Jiaqing; Wu, Yan; Zhong, Yuan‐Lin; Li, Ni-Ping; Mu, Chunlai; Li, Man‐Mei; Ye, Wen‐Cai; Wang, Lei

doi:10.1002/cbdv.201800172

Cited by 16 publications

(16 citation statements)

References 19 publications

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“…Callistemon species are used traditionally for treating hemorrhoids and gastrointestinal and respiratory disorders. , Callistemon extracts have exerted antidiabetic, anti-inflammatory, antimicrobial, cytotoxic, , cardioprotective, and hepatoprotective effects . Recently, a series of triketone-phloroglucinol-monoterpene hybrids named “callistrilone” has been reported from C. rigidus . − In our present study, C. citrinus active extract was subjected to phytochemical investigation, which resulted in the isolation of three new structurally challenging meroterpenoids each existing in a distinct equilibrium mixture of two conformational isomers, named callistrilones L–N ( 1 – 3 ), together with 14 known compounds ( 4 – 17 ). The known compounds were identified as callistrilone E ( 4 ), , callistiviminene N ( 5 ), callistiviminen M ( 6 ), callistiviminene F ( 7 ), myrtucommulone L ( 8 ), calliviminone A ( 9 ), myrtucommulone K ( 10 ), callistiviminene I ( 11 ), callistenone D ( 12 ), endoperoxide G3 ( 13 ), 8-demethyleucalyptin ( 14 ), eucalyptin ( 15 ), catechin ( 16 ), and isoguaiacin ( 17 ) …”

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confidence: 88%

Highly Potent Antiausterity Agents from Callistemon citrinus and Their Mechanism of Action against the PANC-1 Human Pancreatic Cancer Cell Line

et al. 2020

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Human pancreatic cancer cells display remarkable tolerance to nutrition starvation that help them to survive in a hypovascular tumor microenvironment, a phenomenon known as "austerity". The elucidation of agents countering this tolerance is an established antiausterity strategy in anticancer drug discovery. In this study, a Callistemon citrinus leaf extract inhibited the viability of PANC-1 human pancreatic cancer cells preferentially under nutrient-deprived medium (NDM) with a PC 50 value of 7.4 μg/mL. Workup of this extract resulted in the isolation of three new meroterpenoids, callistrilones L−N (1−3), together with 14 known compounds (4−17). The structure elucidation of the new compounds was achieved by HRFABMS and by NMR and ECD spectroscopic analysis. The new compounds showed highly potent preferential cytotoxicity against PANC-1 cells with PC 50 values ranging from 10 to 65 nM in NDM. Of these, callistrilone L (1) inhibited PANC-1 cell migration and colony formation in a normal nutrient-rich condition. Callistrilone L (1) also strongly suppressed the migration of PANC-1 cells in real time. Mechanistically, 1 was found to inhibit the Akt/mTOR and autophagy activation pathway. Callistrilone L (1) and related meroterpenoids are promising leads for anticancer drug development based on the antiausterity strategy used in this work.

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confidence: 88%

Highly Potent Antiausterity Agents from Callistemon citrinus and Their Mechanism of Action against the PANC-1 Human Pancreatic Cancer Cell Line

et al. 2020

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“…Further intramolecular reactions could involve the phenolic or ketonic group to form, respectively, pyranic or furanic rings. Prenylation has also been reported for compounds from this class [25,27,45,49,52].…”

Section: Structures and Chemical Propertiesmentioning

confidence: 99%

“…Antiviral effects were displayed in vitro by the mixture of compounds 3 – 4 , so far only extracted from two Kunzea species, based on the inhibition of the cytopathic effects of Herpes simplex type 1 (HSV-1) and Polio type 1 viruses [26]. Moderate effects in similar assays against HSV-1 have been also reported for callistrilones H–I ( 38 – 39 ) [49].…”

Section: Biological Activitiesmentioning

confidence: 99%

Structures and Bioactive Properties of Myrtucommulones and Related Acylphloroglucinols from Myrtaceae

et al. 2018

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Myrtaceae are a group of plants that include a number of renowned species used in ethnomedicine in many areas worldwide. Their valuable therapeutic properties have stimulated a fruitful research activity addressed to the identification of the bioactive components of their extracts yielding a great diversity of terpenes; polyphenols; and other exclusive products. Among the latter, starting with the discovery of myrtucommulone A from myrtle (Myrtus communis), a series of structurally-related acylphloroglucinol compounds have been characterized from several species that represent the basic active principles to be considered in view of possible drug development. Aspects concerning chemical and biological properties of these products are reviewed in the present paper.

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“…Previous investigations has resulted in the identification of some phloroglucinol derivatives with antibacterial activities from this plant [4,11–13] . Over the course of our ongoing effort to obtain bioactive and structure unique constituents from Myrtaceae plants, [14–19] three pairs of new triketone‐phloroglucinol‐triketone adducts with an rare polycyclic ketal skeleton, myrtucyclitones A–C ((+)‐ and (−)‐ 1 – 3 ), ( Figure 1) were obtained from the title plant. Their structures and absolute configurations were determined by NMR analysis and chemical calculations.…”

Section: Introductionmentioning

confidence: 99%