Flavonoids Isolated from <i>Vitex grandifolia</i>, an Underutilized Vegetable, Exert Monoamine A & B Inhibitory and Anti-inflammatory Effects and Their Structure-activity Relationship

Abstract

Vitex grandifolia, Lamiaceae familyasına aittir; çiçekli bitkilerden oluşur ve aynı zamanda nane ailesi olarak da bilinir. Güneybatı Nijerya'daki Yoruba halkı bitkiyi "Oriri" veya "Efo oriri" olarak adlandırmaktadır. Bu bitki az kullanılan bir bitki olarak sınıflandırılır ve fitokimyası veya biyolojik etkileri hakkında çok az bilgi bulunmaktadır. Gereç ve Yöntemler: Kurutulmuş yaprak ve gövdelerden hazırlanan metanol ekstreleri üzerinde, vakum ve açık kolon kromatografısi metotları kullanılarak fraksiyonlama ve izolasyon çalışmaları yapılmıştır. Bileşiklerin yapıları, IR, 1D-ve 2D-NMR teknikleri kullanılarak ve literatürdeki verilerle ÖZ Objectives: Vitex grandifolia belongs to family Lamiaceae; it consists of flowering plants and it is also called the mint family. The Yoruba people of southwest Nigeria called it "Oriri" or "Efo oriri". This plant is classified as an underutilized vegetable and little is known about its phytochemistry or its biological evaluations. Materials and Methods: Methanol extracts of the dried leaves and stem of the plant were subjected to fractionation and isolation using vacuum layer and column chromatography methods. The structures of the compounds were elucidated using spectroscopic techniques including IR, 1D-, and 2D-NMR and by comparison with the data reported in the literature. They were evaluated in vitro for the inhibition of monoamine recombinant human MAO-A and-B and anti-inflammatory activities. Results: Three known flavonoids were isolated from the methanolic extract of the leaves of V. grandifolia for the first time to the best of our knowledge, i.e. isoorientin (1), orientin (2), and isovitexin (3). Most of the isolated compounds showed selective inhibition of monoamine oxidase B, inhibition of MAO-B by isoorientin (1) and orientin (2) were 9-fold more potent (IC 50 (µg/mL) of 11.08 and 11.04) compared to the inhibition of MAO-A (IC 50 (µg/mL) of ˃100), while clorgyline and deprenyl were used as positive standards. The isolated flavonoids displayed good activity against the NF-κb assay with IC 50 (µg/mL) of 8.9, 12, and 18. This study establishes a link between the structure and the biological activities on the basis of the different patterns of substitution, particularly the C2=C3 double bond and the position of glucose moiety. Conclusion: This study is the first to establish the phytochemistry of the polar part of V. grandifolia and the anti-inflammatory and neuroprotective role of these isolated compounds.

[Retracted] Natural Antioxidants Improve the Vulnerability of Cardiomyocytes and Vascular Endothelial Cells under Stress Conditions: A Focus on Mitochondrial Quality Control

“…Bauhinia championii flavone scavenges free radicals and has an antiarrhythmic effect [ 89 , 90 ]. It improves mitochondrial dysfunction, alleviates H9C2 cardiomyocyte apoptosis induced by H/R, significantly inhibits ROS production, increases ATP synthesis, and inhibits abnormal mPTP opening.…”

A review on Borreria verticillata: A potential bionematicide, channeling its significant antimicrobial activity against root-knot nematodes

“…Over the years, people could notice the adverse effects of these pesticides made from chemicals, they are dangerous on plants, ecosystem, animals and humans. They are very toxic, non-biodegradable and posed hazards to farmers and non-target groups ( Chitwood, 2002 ; Oka et al., 2014 ; Bello et al., 2019a ).…”

In Vivo Antidepressant Effect of Passiflora edulis f. flavicarpa into Cationic Nanoparticles: Improving Bioactivity and Safety

“…Phytochemical constituents of leaves include flavonoids, saponins, cyanogenic glycosides, and terpenoids [10,14]. Recently, behavioral studies in mice have shown that the leaf extract of P. edulis f. flavicarpa displayed antidepressant-like activity, suggesting that this effect was correlated with the presence of C-glycosyl flavones [3,11,[15][16][17].…”

“…Molecules of flavonoid O-glycosides need to be hydrolyzed in the stomach's acidic pH in order to be absorbed in the gastrointestinal tract. The C-glycosyl flavonoids, such as the antidepressant bioactive compounds from P. edulis [3,[15][16][17], are poorly absorbed in the gastrointestinal tract [7,12,13] because they need to be previously metabolized by the intestinal microbiota [7]. This fact, associated with the low aqueous solubility of aglycones, short elimination half-life, and rapid in vivo elimination of flavonoid glycosides, limits their clinical application [7,24,28].…”

“…To date, the majority of flavonoid glycosides are extracted from plant material, whose low yield requires multiple laborious steps [13,16,31]. In fact, the synthesis of C-glycosyl flavonoids is an exhaustive, expensive, and unsustainable process [32].…”