Demethylacrovestone from Achronychia pedunculata fruits

Silva, Leslie B. De; Herath, Wimal M.; Liyanage, Chandrani; Kumar, Vijaya; Ahmad, Viqar Uddin; Sultana, Azra

doi:10.1016/0031-9422(91)84240-s

Cited by 13 publications

(6 citation statements)

References 3 publications

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“…214 Another compound with an isopropyl chain at methylene bridge, helinudifolin (523), was isolated from Helichrysum nudifolium. 214 Phloroglucinol dimers from other species include two prenylated dimers with cytotoxic and insecticidal activity, acrovestone (524) 344 and demethylacrovestone (525), 345 isolated from the bark of Acronychia pedunculata and Acronychia laurifolia. 344,345 The structure of acrovestone has been established by X-ray crystallographic studies.…”

Section: Dimers Formed By a Methylene Linkagementioning

confidence: 99%

“…214 Phloroglucinol dimers from other species include two prenylated dimers with cytotoxic and insecticidal activity, acrovestone (524) 344 and demethylacrovestone (525), 345 isolated from the bark of Acronychia pedunculata and Acronychia laurifolia. 344,345 The structure of acrovestone has been established by X-ray crystallographic studies. 346 Acrovestone showed potent cytotoxicity (100% inhibition at 0.5 lg mL −1 ) in a KB tissue culture assay.…”

Section: Dimers Formed By a Methylene Linkagementioning

confidence: 99%

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Phloroglucinol compounds of natural origin

2006

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Section: Dimers Formed By a Methylene Linkagementioning

confidence: 99%

Section: Dimers Formed By a Methylene Linkagementioning

confidence: 99%

Phloroglucinol compounds of natural origin

2006

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“…The naturally occurring Acronychia-type acetophenone dimers can be further subdivided into homo-and heterodimers, with the latter far exceeding the former in number. 19,20,26 The only homodimer isolated so far is demethylacrovestone (14), which lacks a methoxy group compared to the model compound acrovestone (1), constituting a totally symmetrical dimer. 26 Having no SAR data concerning the biological activity of compound 14 and with this being the only representative of a homodimer produced by A. pedunculata, the chemical development of such molecules was considered challenging.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…19,20,26 The only homodimer isolated so far is demethylacrovestone (14), which lacks a methoxy group compared to the model compound acrovestone (1), constituting a totally symmetrical dimer. 26 Having no SAR data concerning the biological activity of compound 14 and with this being the only representative of a homodimer produced by A. pedunculata, the chemical development of such molecules was considered challenging. In addition, guided by the goal to generate a library of Acronychia-type acetophenones analogues, the synthesis of demethylacrovestone along with a new type of homodimers was undertaken.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Evaluation of Dual 5-Lipoxygenase/Microsomal Prostaglandin E2 Synthase-1 Inhibitory Effect of Natural and Synthetic Acronychia-Type Isoprenylated Acetophenones

et al. 2017

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Among the pathways responsible for the development of inflammatory responses, the cyclooxygenase and lipoxygenase pathways are among the most important ones. Two key enzymes, namely, 5-LO and mPGES-1, are involved in the biosynthesis of leukotrienes and prostaglandins, respectively, which are considered attractive therapeutic targets, so their dual inhibition might be an effective strategy to control inflammatory deregulation. Several natural products have been identified as 5-LO inhibitors, with some also being dual 5-LO/mPGES-1 inhibitors. Here, some prenylated acetophenone dimers from Acronychia pedunculata have been identified for their dual inhibitory potency toward 5-LO and mPGES-1. To gain insight into the SAR of this family of natural products, the synthesis and biological evaluation of analogues are presented. The results show the ability of the natural and synthetic molecules to potently inhibit 5-LO and mPEGS-1 in vitro. The potency of the most active compound (10) has been evaluated in vivo in an acute inflammatory mouse model and displayed potent anti-inflammatory activity comparable in potency to the drug zileuton used as a positive control.

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“…Prenylated acetophenones − are characteristic secondary metabolites of the family Rutaceae. Especially, the genus Acronychia is known to biosynthesize dimeric compounds, in which two prenylated acetophenones are connected by a methylene with a pendant isobutyl group.…”

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confidence: 99%

Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis

et al. 2019

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The isolation of 12 secondary metabolites, including seven new acetophenone monomers, from the 50% CH 3 OH/CH 2 Cl 2 extract (N089419-L/6) of Acronychia trifoliolata was reported previously. In the present work, three new prenylated acetophenone dimers (1-3) and five known dimers (4-8) were isolated, and their structures were elucidated by using various NMR spectroscopic techniques and HRMS. Among the new dimers, an unprecedented 4-isobutyl-3 isopropyltetrahydro-2H-pyran ring was observed in the structure of 1. This study is the first to report the formation of a 2H-pyran ring between two prenylated acetophloroglucinols. Only four related dimers have been reported before, and they were formylated phloroglucinol dimers from the family Eucalypteae. Compounds 2 and 3 are acrovestone-like dimers, and the structure of 3 was confirmed by total synthesis. The evaluation of the antiproliferative activity of isolated and synthesized acrovestone-like dimers indicated that a double bond in the prenyl-like moiety as *

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Demethylacrovestone from Achronychia pedunculata fruits

Cited by 13 publications

References 3 publications

Phloroglucinol compounds of natural origin

Phloroglucinol compounds of natural origin

Evaluation of Dual 5-Lipoxygenase/Microsomal Prostaglandin E2 Synthase-1 Inhibitory Effect of Natural and Synthetic Acronychia-Type Isoprenylated Acetophenones

Prenylated Acetophloroglucinol Dimers from Acronychia trifoliolata: Structure Elucidation and Total Synthesis

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