Worldwide, there are plants known as psychoactive plants that naturally contain psychedelic active components. They have a high concentration of neuroprotective substances that can interact with the nervous system to produce psychedelic effects. Despite these plants' hazardous potential, recreational use of them is on the rise because of their psychoactive properties. Early neuroscience studies relied heavily on psychoactive plants and plant natural products (NPs), and both recreational and hazardous NPs have contributed significantly to the understanding of almost all neurotransmitter systems. Worldwide, there are many plants that contain psychoactive properties, and people have been using them for ages. Psychoactive plant compounds may significantly alter how people perceive the world.
1. Zhongguo Zhong Yao Za Zhi. 2017 Jul;42(13):2510-2517. doi: 10.19540/j.cnki.cjcmm.2017.0116. [Studies on chemical constituents of Clinopodium chinense]. [Article in Chinese] Wang LT(1)(2), Sun ZH(3), Zhong ML(3), Wu HF(3), Zhang HJ(3), Zhu NL(3), Sun GB(3), Ye XX(1), Xu XD(3), Zhu YD(1), Yang JS(3). Author information: (1)School of Pharmacy, Wenzhou Medical University, Wenzhou 325035, China. (2)School of Medicine, Shandong University, Ji'nan 250012, China. (3)Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Science & Peking Union Medical College, Beijing 100193, China. Twenty-eight compounds were isolated and purified from Clinopodium chinense by Sephedax LH-20, ODS, MCI and preparative HPLC. Their structures were identified as apigenin (1), apigenin-7-O-β-D-glucopyranoside (2), apigenin-7-O-β-D-glucuronopyranoside (3), thellungianol (4), apigenin-7-O-β-D-rutinoside (5), luteolin (6), luteolin-4'-O-β-D-glucopyranoside (7), apigenin-7-O-β-D-pyranglycuronate butyl ester (8), luteolin-7-O-β-D-rutinoside (9), luteolin-7-O-β-D-noehesperidoside (10), acacetin (11), acacetin-7-O-β-D-glucuronopyranoside (12), buddleoside (13), naringenin (14), pruning (15), nairutin (16), isosakuranetin (17), isosakuranin (18), didymin (19), hesperidin (20), kaempferol (21), quercetin (22), kaempferol-3-O-α-L-rahmnoside (23), p-hydroxycinnamic acid (24), caffeic acid (25), cis-3-[2-[1-(3,4-dihydroxy-phenyl)-1 -hydroxymethyl]-1,3-ben-zodioxol-5-yl]-(E)-2-propenoic acid (26), mesaconic acid (27), gentisic acid 5-O-β-D-(6'-salicylyl)-glucopyranoside (28). Among them, compounds 7, 9-10, 12, 23, 26-28 were isolated from the Clinopodium for the first time. The protective effects of compounds 1-6, 8-17 and 19 against H2O2-induced H9c2 cardiomyocyte injury were tested, compounds 15 exhibited significantly protective effects. Compared with the cell viability of (62.12±6.18)% in the model, pruning exhibited viabilities of (84.25±7.36)% at 25.0 mg•L⁻¹, respectively, using quercetin as a positive control [cell viability of (84.55±8.26)%, 20 mg•L⁻¹]. Copyright© by the Chinese Pharmaceutical Association. DOI: 10.19540/j.cnki.cjcmm.2017.0116 PMID: 28840692 [Indexed for MEDLINE] Conflict of interest statement: The authors of this article and the planning committee members and staff have no relevant financial relationships with commercial interests to disclose. 2. Molecules. 2015 Aug 14;20(8):14970-84. doi: 10.3390/molecules200814970. Fast Identification of Radical Scavengers from Securigera varia by Combining 13C-NMR-Based Dereplication to Bioactivity-Guided Fractionation. Sientzoff P(1), Hubert J(2), Janin C(3), Voutquenne-Nazabadioko L(4), Renault JH(5), Nuzillard JM(6), Harakat D(7), Magid AA(8). Author information: (1)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. Pacome.sientzoff@etudiant.univ-reims.fr. (2)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. jane.hubert@univ-reims.fr. (3)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. coralie.janin@etudiant.univ-reims.fr. (4)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. (5)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. jh.renault@univ-reims.fr. (6)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. jm.nuzillard@univ-reims.fr. (7)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. dominique.harakat@univ-reims.fr. (8)ICMR, UMR CNRS 7312, Campus Moulin de la Housse BP 1039, Reims 51687, France. abdulmagid.alabdulmagid@univ-reims.fr. Securigera varia (Fabaceae) is a common herbaceous perennial plant widely growing in Europe and Asia and purposely established for erosion control, roadside planting, and soil rehabilitation. The aim of this study was to determine the radical scavenging activity of a crude methanol extract of S. varia aerial parts by using the free radical DPPH (1,1-diphenyl-2-picrylhydrazyl) and to rapidly identify the compounds involved in this activity. The crude extract was initially separated in five fractions on Diaion HP20 resin and the most active part was fractionated by Centrifugal Partition Extraction (CPE). Known compounds were directly identified by a (13)C-NMR-based dereplication method. Semi-preparative high performance liquid chromatography purification experiments were further performed to identify unknown or minor active compounds. As a result, one new (13) and twelve known flavonoid glycosides together with three nitropropanoylglucopyranoses were isolated, including astragalin (1), kaempferol-3-O-(6-O-acetyl)-β-D-glucopyranoside (2), kaempferol-3,4'-di-O-β-D-glucopyranoside (3), trifolin (4), isoquercitrin (5), hyperoside (6), isovitexin (7), isoorientin (8), isovitexin 4'-O-β-D-glucopyranoside (9), apigenin 7-O-β-D-glucuronopyranoside (10), luteolin 7-O-β-D-glucuronopyranoside (11), apigenin 7-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucuronopyranoside (12), apigenin 7-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucuronopyranoside (13), 6-O-(3-nitropropanoyl)-β-D-glucopyranoside (14), coronillin (16) and coronarian (15). 120 mg of the most active compound isoorientin against the free radical DPPH was recovered by CPE with an HPLC purity of 99%. DOI: 10.3390/molecules200814970 PMCID: PMC6331992 PMID: 26287151 [Indexed for MEDLINE] Conflict of interest statement: The authors declare no conflict of interest. 3. Carbohydr Res. 2010 Nov 22;345(17):2529-33. doi: 10.1016/j.carres.2010.09.002. Epub 2010 Sep 7. Phenolic Glycosides with antiproteasomal activity from Centaurea urvillei DC. subsp. urvillei. Gülcemal D(1), Alankuş-Çalışkan O, Karaalp C, Ors AU, Ballar P, Bedir E. Author information: (1)Department of Chemistry, Faculty of Science, Ege University, Bornova, 35100 Izmir, Turkey. A new flavanone glycoside, naringenin-7-O-β-D-glucuronopyranoside, and a new flavonol glycoside, 6-hydroxykaempferol-7-O-β-D-glucuronopyranoside were isolated together with 12 known compounds, 5 flavone glycoside; hispidulin-7-O-β-D-glucuronopyranoside, apigenin-7-O-β-D-methylglucuronopyranoside, hispidulin-7-O-β-D-methylglucuronopyranoside, hispidulin-7-O-β-D-glucopyranoside, apigenin-7-O-β-D-glucopyranoside, a flavonol; kaempferol, two flavone; apigenin, and luteolin, a flavanone glycoside; eriodictyol-7-O-β-D-glucuronopyranoside, and three phenol glycoside; arbutin, salidroside, and 3,5-dihydroxyphenethyl alcohol-3-O-β-D-glucopyranoside from Centaurea urvillei subsp. urvillei. The structure elucidation of the new compounds was achieved by a combination of one- ((1)H and (13)C) and two-dimensional NMR techniques (G-COSY, G-HMQC, and G-HMBC) and LC-ESI-MS. The isolated compounds were tested for their antiproteasomal activity. The results indicated that kaempferol, a well known and widely distributed flavonoid in the plant kingdom, was the most active antiproteasomal agent, followed by apigenin, eriodictyol-7-O-β-D-glucuronopyranoside, 3,5-dihydroxyphenethyl alcohol-3-O-β-D-glucopyranoside, and salidroside, respectively. Copyright © 2010 Elsevier Ltd. All rights reserved. DOI: 10.1016/j.carres.2010.09.002 PMID: 20937505 [Indexed for MEDLINE] 4. Nat Prod Res. 2008;22(17):1487-97. doi: 10.1080/14786410802038556. Fructose-amino acid conjugate and other constituents from Cyperus rotundus L. Sayed HM(1), Mohamed MH, Farag SF, Mohamed GA, Omobuwajo OR, Proksch P. Author information: (1)Faculty of Pharmacy, Pharmacognosy Department, Assiut University, Assiut, Egypt. Further phytochemical study on the aerial parts of Cyperus rotundus L. led to the isolation of a fructose-amino acid conjugate, N-(1-deoxy-alpha-D-fructos-1-yl)-L-tryptophan (16) and its tautomers, in addition to n-butyl-beta-D-fructopyranoside (1), ethyl-alpha-D-glucopyranoside (2), adenosine (3), (-)-(E)-caffeoylmalic acid (4), vitexin (5), isovitexin (6), orientin (7), epiorientin (8), myricetin 3-O-beta-D-galactopyranoside (9), luteolin 7-O-beta-D-glucuronopyranoside-6''-methyl ester (10), chlorogenic acid (11), luteolin 4'-O-beta-D-glucuronopyranoside (12), luteolin 7-O-beta-D-glucuronopyranoside (13), uridine (14) and ellagic acid (15). Their structures were elucidated on the basis of spectroscopic methods. Additionally, antioxidant and alpha-amylase inhibitory activities of some of the isolated phenolic compounds were carried out. DOI: 10.1080/14786410802038556 PMID: 19023813 [Indexed for MEDLINE] 5. J Agric Food Chem. 2007 Apr 4;55(7):2645-52. doi: 10.1021/jf063635b. Epub 2007 Mar 10. Flavonoids from barrel medic (Medicago truncatula) aerial parts. Kowalska I(1), Stochmal A, Kapusta I, Janda B, Pizza C, Piacente S, Oleszek W. Author information: (1)Department of Biochemistry, Institute of Soil Science and Plant Cultivation, ul. Czartoryskich 8, 24-100 Pulawy, Poland. Twenty-three flavonoids have been identified in the aerial parts of barrel medic, and their structures were established by spectrometric and spectroscopic (ESI-MS/MS and NMR) techniques. Eight of the identified compounds, including apigenin 7-O-beta-D-glucuronopyranosyl-(1-->3)-O-beta-D-glucuronopyranosyl-(1-->2)-O-beta-D-glucuronopyranoside, apigenin 7-O-[2'-O-sinapoyl-beta-D-glucuronopyranosyl-(1-->2)-O-beta-D-glucuronopyranoside], apigenin 7-O-{2-O-feruloyl-[beta-D-glucuronopyranosyl-(1-->3)]-O-beta-D-glucuronopyranosyl-(1-->2)-O-beta-D-glucopyranoside}, chrysoeriol 7-O-[beta-D-glucuronopyranosyl-(1-->2)-O-beta-D-glucuronopyranoside, chrysoeriol 7-O-{2'-O-p-coumaroyl-[beta-D-glucuronopyranosyl-(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside}, tricin 7-O-beta-D-glucuronopyranosyl-4'-O-glucopyranoside, tricin 7-O-[2'-O-feruloyl-beta-D-glucuronopyranosyl-(1-->2)-O-beta-D-glucopyranoside], and tricin 7-O-{2'-O-p-coumaroyl-[beta-D-glucuronopyranosyl-(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside}, have not been reported before in the plant kingdom. Additionally, the presence of two luteolin, three apigenin, one chrysoeriol, and six tricin glycosides, previously identified in alfalfa (Medicago sativa), was confirmed in M. truncatula. Moreover, besides the above flavones, the aerial parts of this species contained three flavonols including rutin, laricitrin 3,7,5'-triglucoside, and laricitrin 3,5'-diglucoside. DOI: 10.1021/jf063635b PMID: 17348681 [Indexed for MEDLINE]