Cytotoxic Prenylated Polyphenolic Compounds from <i>Maackia amurensis</i> Root Bark

Веселова, М. В.; Fedoreyev, S. A.; Tarbeeva, Darya V.; Кулеш, Н. И.; Kalinovskiy, Anatoliy I.; Kuzmich, Alexandra S.; Kim, Natalia Y.; Grigorchuk, Valeria P.

doi:10.1177/1934578x1701200709

Cited by 4 publications

(4 citation statements)

References 13 publications

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“…The active compounds of this complex were isoflavones, pterocarpans, flavanones, isoflavans, isoflavanones, chalcones, lignans, and monomeric and dimeric stilbenes [ 1 ]. In contrast to M. amurensis heartwood, the main polyphenolic metabolites of M. amurensis root bark were shown to be glycosides of isoflavones and pterocarpans as well as prenylated flavanones [ 2 , 3 ].…”

Section: Introductionmentioning

confidence: 99%

Neuroprotective and Antiherpetic Properties of Polyphenolic Compounds from Maackia amurensis Heartwood

et al. 2023

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In this study, we isolated a new isoflavanostilbene maackiapicevestitol (1) as a mixture of two stable conformers 1a and 1b as well as five previously known dimeric and monomeric stilbens: piceatannol (2), maackin (3), scirpusin A (4), maackiasine (5), and maackolin (6) from M. amurensis heartwood, using column chromatography on polyamide, silicagel, and C-18. The structures of these compounds were elucidated by NMR, HR-MS, and CD techniques. Maksar® obtained from M. amurensis heartwood and polyphenolics 1–6 possessed moderate anti-HSV-1 activity in cytopathic effect (CPE) inhibition and RT-PCR assays. A model of PQ-induced neurotoxicity was used to study the neuroprotective potential of polyphenolic compounds from M. amurensis. Maksar® showed the highest neuroprotective activity and increased cell viability by 18% at a concentration of 10 μg/mL. Maackolin (6) also effectively increased the viability of PQ-treated Neuro-2a cells and the value of mitochondrial membrane potential at concentrations up to 10 μΜ. Maksar® and compounds 1–6 possessed higher FRAP and DPPH-scavenging effects than quercetin. However, only compounds 1 and 4 at concentrations of 10 μM as well as Maksar® (10 μg/mL) statistically significantly reduced the level of intracellular ROS in PQ-treated Neuro-2a cells.

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Section: Introductionmentioning

confidence: 99%

Neuroprotective and Antiherpetic Properties of Polyphenolic Compounds from Maackia amurensis Heartwood

et al. 2023

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“…We isolated 14 previously known compounds from M. amurensis heartwood: isoflavonoids genistein (2), retusin (3), maackiain (4), tectorigenin (5), medicarpin (7), formononetin (8), (±)-3-hydroxyvestitone (12), flavonoid liquiritigenin (6), monomeric stilbenes resveratrol (1), piceatannol (11), dimeric stilbens maackin (9), scirpusin A (13), isoflavonostilbenes maackiazin (10), and maackiapicevestitol (14) (Figure 1). We used 1 (10) and Scirpusin A (13) We also determined the absolute configurations for scirpusin A (13) and maackiazin (10).…”

Section: Polyphenolic Compounds From M Amurensis Heartwoodmentioning

confidence: 99%

“…These polyphenols constitute the polyphenolic complex of M. amurensis heartwood. In contrast to the heartwood, the roots of this plant produce isoflavone glycosides and prenylated flavanones [2,3].…”

Section: Introductionmentioning

confidence: 99%

Polyphenols from Maackia amurensis Heartwood Protect Neuronal Cells from Oxidative Stress and Prevent Herpetic Infection

Tarbeeva,

Pislyagin,

Menchinskaya

et al. 2024

IJMS

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Here, we continued the investigation of anti-HSV-1 activity and neuroprotective potential of 14 polyphenolic compounds isolated from Maackia amurensis heartwood. We determined the absolute configurations of asymmetric centers in scirpusin A (13) and maackiazin (10) as 7R,8R and 1″S,2″S, respectively. We showed that dimeric stilbens maackin (9) and scirpusin A (13) possessed the highest anti-HSV-1 activity among polyphenols 1–14. We also studied the effect of polyphenols 9 and 13 on the early stages of HSV-1 infection. Direct interaction with the virus (virucidal activity) was the main mechanism of the antiviral activity of these compounds. The neuroprotective potential of polyphenolic compounds from M. amurensis was studied using models of 6-hydroxydopamine (6-OHDA)-and paraquat (PQ)-induced neurotoxicity. A dimeric stilbene scirpusin A (13) and a flavonoid liquiritigenin (6) were shown to be the most active compounds among the tested polyphenols. These compounds significantly increased the viability of 6-OHDA-and PQ-treated Neuro-2a cells, elevated mitochondrial membrane potential and reduced the intracellular ROS level. We also found that scirpusin A (13), liquiritigenin (6) and retusin (3) considerably increased the percentage of live Neuro-2a cells and decreased the number of early apoptotic cells. Scirpusin A (13) was the most promising compound possessing both anti-HSV-1 activity and neuroprotective potential.

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“…The IC 50 values of 463 were 8.2 and 6.5 µ M, whereas the IC 50 values of 482 were 12 and 7.7 µ M, respectively. However, the structurally similar analogues, isomaackiaflavanone A ( 465 ), isomaackiaflavanone B ( 473 ), and abyssinone V ( 479 ), exhibit weak cytotoxicity against HeLa and SK-MEL-5 cells with IC 50 value range of 16–36 µ M suggesting that 8-prenyl side chain promotes the cytotoxicity, and methoxy at C-2′ on the B ring decreased the cytotoxicity (Veselova et al 2017 ). Sanggenol Q ( 480 ), isolated from the root bark of Morus alba , showed cytotoxicity against HepG2 cells with an EC 50 value of 6.94 µ M (Jung et al 2015 ).…”

Section: Biosynthesis Of Prenylated Flavonoidsmentioning

confidence: 99%

Phytochemistry and pharmacology of natural prenylated flavonoids

Wang

Luo

et al. 2023

Arch. Pharm. Res.

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Prenylated flavonoids are a special kind of flavonoid derivative possessing one or more prenyl groups in the parent nucleus of the flavonoid. The presence of the prenyl side chain enriched the structural diversity of flavonoids and increased their bioactivity and bioavailability. Prenylated flavonoids show a wide range of biological activities, such as anti-cancer, anti-inflammatory, neuroprotective, anti-diabetic, anti-obesity, cardioprotective effects, and anti-osteoclastogenic activities. In recent years, many compounds with significant activity have been discovered with the continuous excavation of the medicinal value of prenylated flavonoids, and have attracted the extensive attention of pharmacologists. This review summarizes recent progress on research into natural active prenylated flavonoids to promote new discoveries of their medicinal value. Supplementary Information The online version contains supplementary material available at 10.1007/s12272-023-01443-4.

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Cytotoxic Prenylated Polyphenolic Compounds from Maackia amurensis Root Bark

Cited by 4 publications

References 13 publications

Neuroprotective and Antiherpetic Properties of Polyphenolic Compounds from Maackia amurensis Heartwood

Neuroprotective and Antiherpetic Properties of Polyphenolic Compounds from Maackia amurensis Heartwood

Polyphenols from Maackia amurensis Heartwood Protect Neuronal Cells from Oxidative Stress and Prevent Herpetic Infection

Phytochemistry and pharmacology of natural prenylated flavonoids

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