Anti-Inflammatory Prenylated Phenylpropenols and Coumarin Derivatives from <i>Murraya exotica</i>

Liu, Bingyu; Zhang, Chen; Zeng, Ke‐Wu; Li, Jun; Guo, Xiaoyu; Zhao, Ming; Tu, Peng‐Fei; Jiang, Yong

doi:10.1021/acs.jnatprod.7b00518

Cited by 42 publications

(29 citation statements)

References 57 publications

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“…A further investigation on the 95% aqueous EtOH extract of the roots allowed the obtainment of new coumarins, together with other bioactive molecules. The compounds were tested for their inhibitory effect on NO production and compound 103 ( Figure 36 In 2018, Liu et al identified ten new coumarin derivatives (3 monomers and 7 dimers) isolated in a phytochemical study on Murraya exotica, a dwarf tree that is native of the tropical and subtropical areas of Asia and traditionally used in the treatment of inflammatory-related diseases [147]. Previous studies had shown that the main active components in M. exotica were coumarins; also bis-coumarins were isolated from the plant.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

“…In 2018, Liu et al identified ten new coumarin derivatives (3 monomers and 7 dimers) isolated in a phytochemical study on Murraya exotica , a dwarf tree that is native of the tropical and subtropical areas of Asia and traditionally used in the treatment of inflammatory-related diseases [ 147 ]. Previous studies had shown that the main active components in M. exotica were coumarins; also bis-coumarins were isolated from the plant.…”

Section: Biological Activitiesmentioning

confidence: 99%

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An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

283

156

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Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

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Section: Anti-inflammatory Activitymentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

283

156

View full text Add to dashboard Cite

show abstract

“…Although 24 could not be isolated in a pure form, a sample of pure (±)-exotine A ( 1 ) was obtained via reverse-phase HPLC, eluting with MeCN:H 2 O (35:65 → 50:50, 90 min) and recrystallized (MeOH–CHCl 3 ) to afford pure (±)-exotine A as pale yellow needles. MP 246–247 °C (lit . mp 249–250 °C).…”

Section: Methodsmentioning

confidence: 99%

“…In particular, 1 and 2 possess a coumarin-substituted cyclohepta[ b ]indole skeleton, a substructure that was previously unknown among natural products; however, the cyclohepta[ b ]indole ring is a common motif found in both natural products and other biologically active molecules . A plausible proposal for the biosynthesis of 1 and 2 was advanced by the Jiang group that posited that 1 and 2 arise from a Diels–Alder reaction between the β-deydroprenylindole 6 and either trans -dehydroosthol ( 3 ) or gleinadiene ( 4 ), each of which is a natural product identified in M. exotica extracts, to give the respective cycloadducts 7 and 8 (Scheme ). Subsequent ring expansion via a 1,2-alkyl migration, which is well-precedented for 3,3-disubstituted and 3,3-spiroindolinenes, then leads to 1 and 2 .…”

Section: Introductionmentioning

confidence: 99%

Biomimetically Inspired, One-Step Synthesis of Exotine A and Exotine B

Lepovitz

Martin

2020

J. Org. Chem.

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The one-step syntheses of exotine A and exotine B, which comprise the unusual coumarin-cyclohepta[b]indole ring system, have been achieved via the biomimetically inspired combination of indole, prenal, and either trans-dehydroosthol or gleinadiene. This facile threecomponent reaction delivered a mixture (17:1) of exotine A and 11′-epiexotine A in a 43% yield from trans-dehydroosthol and a mixture (4:1) of exotine B and 11′-epi-exotine B in a 50% yield from gleinadiene. Some mechanistic aspects of this process were explored, and spectral evidence for 3,3′-spiroindolenine intermediates was obtained. Moreover, a skeletal isomer of exotine A that likely originates from a 1,2-alkyl rearrangement of a protonated 3,3′-spiroindolenine was isolated and characterized by Xray crystallography. These findings not only provide experimental support for Jiang's proposed biosynthesis of exotine A and exotine B but also foreshadow the existence of other exotine-derived natural products having isomeric frameworks. Exploratory attempts to induce an enantioselective 3CR using a chiral phosphoric acid were unsuccessful.

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“…Moreover, in vivo studies revealed that compound (4m) could inhibit AA-induced rat ankle joints. Yong Jiang et al [68] isolated three new prenylated phenylpropenols, exotiacetals A-C (1-3), 10 new coumarin derivatives, exotimarins A-I (4-13), and 35 known analogs (14-48) from the roots of Murraya exotica. The absolute configurations of the new compounds were characterized through comparison of their specific rotations, single-crystal X-ray diffraction data, Mosher's method, the ECD exciton coupling method, comparison of experimental and calculated ECD data, and the ECD data of the in situ formed transition metal complexes.…”

Section: Anti-inflammatory Activitymentioning

confidence: 99%

Coumarins: A Unique Scaffold With Versatile Biological Behavior

Gupta¹,

Kumar²,

Chaudhary³

2019

Asian J Pharm Clin Res

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Benzopyrones are the club of compounds that can be coumarins or flavonoids. The hydroxyl derivatives of coumarins such as 4-hydroxycoumarins and 7-hydroxycoumarins have extensive biological activities which have employed for the synthesis of miscellaneous coumarin derivatives. These derivatives have exhibited impressive pharmacological and physiological activities such as anticoagulant, antibacterial, antiviral, antitumor, bactericidal, fungicidal, anti-inflammatory agents, and anti-HIV activity. This review comprised pharmacokinetic studies, including absorption, distribution, and metabolism of coumarin analogs along with toxicological studies. The studies of coumarins and their derivatives exhibiting immense pharmacological activity are also summarized in the current study.

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Anti-Inflammatory Prenylated Phenylpropenols and Coumarin Derivatives from Murraya exotica

Cited by 42 publications

References 57 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Biomimetically Inspired, One-Step Synthesis of Exotine A and Exotine B

Coumarins: A Unique Scaffold With Versatile Biological Behavior

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