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Flavonoids with Preclinical Antidepressant-Like Effects
Published in Scott Mendelson, Herbal Treatment of Major Depression, 2019
Orientin is a flavone glycoside from cecropia, mimosa pudica, passionflower, acai berries, olives, buckwheat, and millet. Chronic oral administration of orientin decreased immobility and restored appetite for sucrose in mice that had been subjected to chronic unpredictable stress. Orientin treatment also reduced levels of oxidative stress markers, and increased the concentrations of serotonin and norepinephrine in the hippocampus and prefrontal cortex. Levels of BDNF and synapse‐associated proteins in those areas of the brain were increased.68
Cannabis Flavonoids—Antioxidant & Anti-Inflammatory Benefits
Published in Betty Wedman-St Louis, Cannabis as Medicine, 2019
Flavonoids are important in both human and animal nutrition [8] and more than 20 have been reported in cannabis [9]. Diets rich in phenolic compounds have been linked to a reduced incidence of chronic diseases—cancer, cardiovascular disease, and neurodegenerative conditions [10]. The flavones and flavonols in cannabis exert a wide range of biological effects along with terpenes and cannabinoids. The anti-inflammatory, anti-cancer, and neuroprotective properties are reviewed by Andre et al. in Current Nutrition Food Science [11] with flavones and flavonols being the primary ones [12]. A brief review of the flavonoids in cannabis has been provided as follows: Cannflavin A,B,C are methylated isoprenoid flavones with anti-inflammatory activity that inhibits the prostaglandins inflammatory pathway and enhance synergy with terpenoids [13,14].Vitexin and Isovitexin are used therapeutically for gout and inhibiting thyroid peroxidase [15].Kaempferol has been reported to have an antidepressant effect [15].Apigenin has been shown to be capable of stimulating the monoamine transporter, which alters neurotransmitter levels and acts as an anxiolytic and sedative on the GABA receptors along with cannabinoids [16].Quercetin inhibits viral enzymes and can have antiviral effects along with inhibiting prostaglandin production as an anti-inflammatory agent. It has synergistic benefits with cannabinoids to increase anti-inflammatory effects. Quercetin has also been shown to inhibit MAO (monoamine oxidase enzyme), so it can create possible interactions with some pharmaceuticals [17].Luteolin and Orientin have been shown to have pharmacological properties of antioxidants, anti-inflammatories, antibiotics, and anti-cancer [16].Liganamides/Lignans have been found in cannabis fruits and roots [18]. These phenolic amides and liganamides have health-promoting properties such as antioxidants, antivirals, antidiabetic, antitumorigenic and anti-obesity, but human studies are scarce [19]. Sun et al. [20] have shown anti-inflammatory properties in vitro while Cui-Ying et al. [21] have demonstrated cytotoxic activities of lignans that may be confirmed in cannabis.
Nardostachys jatamansi (Spikenard) and Ocimum tenuiflorum (Holy Basil)
Published in Azamal Husen, Herbs, Shrubs, and Trees of Potential Medicinal Benefits, 2022
Mani Iyer Prasanth, Premrutai Thitilertdecha, Dicson Sheeja Malar, Tewin Tencomnao, Anchalee Prasansuklab, James Michael Brimson
Concerning O. tenuiflorum, the stems and leaves contain several naturally occurring compounds comprising volatile oils, saponins, flavonoids, triterpenoids, sesquiterpenes, and tannins. Rosmarinic acid (Kelm et al., 2000; Pattanayak et al., 2010), propanoic acid (Pattanayak et al., 2010), ursolic acid (Anandjiwala et al., 2006; Batra and Sastry, 2014; Vetal et al., 2012), oleanolic acid (Anandjiwala et al., 2006), gallic acid (Hussain et al., 2017), chlorogenic acid (Hussain et al., 2017), p-hydroxy benzoic acid (Hussain et al., 2017), caffeic acid (Hussain et al., 2017), vanillic acid (Hussain et al., 2017), p-coumaric acid (Hussain et al., 2017), sinapic acid (Hussain et al., 2017), ferulic acid (Hussain et al., 2017), quercetin (Hussain et al., 2017), myricetin (Hussain et al., 2017), apigenin (Kelm et al., 2000; Pattanayak et al., 2010), luetolin (Anandjiwala et al., 2006), cirsimaritin (Kelm et al., 2000; Pattanayak et al., 2010), isothymusin (Kelm et al., 2000; Pattanayak et al., 2010), isothymonin (Kelm et al., 2000; Pattanayak et al., 2010), orientin (Pattanayak et al., 2010), vicenin (Pattanayak et al., 2010), eugenol (Anandjiwala et al., 2006; Hussain et al., 2017; Kelm et al., 2000), carvacrol (Pattanayak et al., 2010), linalool (Ijaz et al., 2017), β-elemene (Hussain et al., 2017), β-caryophyllene (Hussain et al., 2017), germacrene D (Hussain et al., 2017), and cirsilineol (Kelm et al., 2000) are characterized. Some studies have explored the anti-oxidative and anti-inflammatory properties of O. tenuiflorum through its active components, especially polyphenolic compounds, which are the majority within (Figure 9.3). Chlorogenic acid was a prominent phenolic acid in ethanol, methanol, and hexane extracts of this plant and showed significant inhibition of linoleic acid oxidation and free radical scavenging (Hussain et al., 2017). Ursolic acid and its derivatives also possessed anti-oxidative activity (Batra and Sastry, 2014). Furthermore, rosmarinic acid was a key component for anti-oxidation with mechanisms in free radical scavenging and chelation in ferrous ions and ferric ions and anti-inflammation via COX-2 inhibition (Hakkim et al., 2007; Kelm et al., 2000). Eugenol, cirsilineol, isothymusin, and isothymonin illustrated good antioxidant properties at the concentration of 10 μM, and eugenol exhibited excellent anti-inflammation with over 97% inhibition of COX-1 and -2 activities. In contrast, irsimaritin and apigenin specifically suppressed the COX-2 mechanism (Kelm et al., 2000). Orientin and vicenin also inhibited free radical formation through scavenging at the equivalent efficiency (Uma Devi et al., 2000) and were reported to act as modulators of radiation injury and enhancers for DNA repair (Satyamitra et al., 2014).Structures of compounds found in O. tenuiflorum.
Application of the Mannich reaction in the structural modification of natural products
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2023
Miao-Xia Pu, Hong-Yan Guo, Zhe-Shan Quan, Xiaoting Li, Qing-Kun Shen
Orientins, isoorientins, and luteolins are flavonoids. Lv et al.71 evaluated antibacterial activity against Gibberella sanbinetti. Orientin (inhibition rate of 77.23%) and isoorientin (inhibition rate of 82.2%) at 20 mg/L showed excellent antifungal activity against G. sanbinetti (Table 3). However, luteolin (inhibition rate of 0.00%) was barely active. Their structural differences are reflected in the 8th or 6th position of the A ring. It has been reported that the 8th position substitution of flavonoid derivatives is better than the 6th position substitution; therefore, drawing on the structure of orientin and isoorientin, flavonoids can be substituted at the 8th position. A series of 19 compounds was synthesised and evaluated for their antifungal activity against G. sanbinetti and Gaeumannomyces graminis. However, in vitro, antifungal activity experiments showed that the antifungal activity of these compounds did not reach the expected levels. The inhibition rate range was 0.00–47.5%. They were then evaluated for their antibacterial activity against two gram-positive bacteria (S. aureus and Listeria monocytogenes) and two gram-negative bacteria (E. coli and Salmonella gallinarum). Compound 56 (Figure 4) exhibited broad-spectrum antibacterial activity against all four bacteria (MIC = 1, 0.5, 2, and 0.05 mg/L). Compound 55 (Figure 4) (MIC = 2, 0.125 mg/L) showed significant inhibitory activity against S. aureus and S. gallinarum compared to novobiocin (MIC = 2, 0.25 mg/L).
Açaí (Euterpe oleracea Mart.) presents anti-neuroinflammatory capacity in LPS-activated microglia cells
Published in Nutritional Neuroscience, 2022
Diulie Valente de Souza, Lauren Pappis, Thuany Teixeira Bandeira, Gabriela Geraldo Sangoi, Tuyla Fontana, Vitor Braga Rissi, Michele Rorato Sagrillo, Marta Maria Duarte, Thiago Duarte, David Frederick Bodenstein, Ana Cristina Andreazza, Ivana Beatrice Mânica da Cruz, Euler Esteves Ribeiro, Alfredo Antoniazzi, Aline Ferreira Ourique, Alencar Kolinski Machado
Freeze-dried hydroalcoholic açaí extract was made and characterized by HPLC, which found 10 different bioactive molecules. The most abundant molecules were orientin, p-coumaric acid, and luteolin, respectively. These results replicated the characterization of a previously prepared açaí extract using the complete fruit by Machado et al. [21]. It is already known that these molecules present several bioactive properties, such as the ability to modulate different cellular responses. Specifically, orientin has neuroprotective [35,36] and anti-inflammatory effects [37,38]. In a study using in vivo and in vitro experimental models, it was shown that p-coumaric acid has anti-inflammatory effects by attenuating LPS activation [39]. Additionally, studies demonstrated that luteolin is capable of reducing inflammatory response via modulation of NF-κB expression [40]. In an in vivo study, it was shown that an açaí-enriched diet could modulate oxidative stress and the inflammatory response [22]. These authors suggested a correlation between oxidative imbalance, inflammatory activation, and autophagy, where açaí could act as a positive enhancing agent.
Recent advances towards natural plants as potential inhibitors of SARS-Cov-2 targets
Published in Pharmaceutical Biology, 2023
Zhouman He, Jia Yuan, Yuanwen Zhang, Runfeng Li, Meilan Mo, Yutao Wang, Huihui Ti
Naringenin, naringin, and hesperetin are flavonoids in Citrus compounds, all of which have the potential to anti-SARS-CoV-2 through binding to the ACE2 enzyme (Liu et al. 2022b). Conducted by MD, naringenin is also a potential inhibitor of 3CLpro (Khaerunnisa et al. 2020). Naringin could inhibit the expression of the proinflammatory cytokines (cyclooxygenase-2, nitric oxide synthase, IL-1β and IL-6) in vitro induced by lipopolysaccharide (LPS), and has a strong binding affinity with the ACE2 by simulating MD (Liu et al. 2022b). Kaempferol, luteolin-7-glucoside, and apigenin-7-glucoside are potential main Protease (Mpro) inhibitors and have similar pharmacophores to nelfinavir, which was used to treat patients with new coronavirus-induced pneumonia (Khaerunnisa et al. 2020). Rutin is a natural antioxidant widely found in tea, apples, grapes, oranges, cherries and other plants (Rahman F et al. 2021). Rutin has antiviral activity on SARS-CoV-2 3CLPro and RNA-dependent RNA polymerase (RdRp) by docking analysis (da Silva et al. 2020). The residues of the SARS-CoV-2 protein substrate binding pocket and rutin are closely interactive, which helps to lock rutin in the substrate binding pocket and effectively inhibits the SARS-CoV-2 protein (Jain et al. 2021). Alagu Lakshmi et al. (2021) screened the active ligands of medicinal plants and found that orientin and vitexin have high binding affinities for the 3CLpro, the S protein of SARS-CoV-2 and human (h)ACE2. In their study, the binding energy of orientin with 3CLpro, S protein and hACE2 ranged from −90.2 to −70.6 kcal/mol. Vitexin is an apigenin flavonoid glycoside, and its docking scores for 3CLpro, S protein, and hACE2 ranged from −98.34 to −95.24 kcal/mol.