Psychotria viridis: Chemical constituents from leaves and biological properties

Abstract

The phytochemical study of hexane, chloroform and methanol extracts from leaves of Psychotria viridis resulted in the identification of: the pentacyclic triterpenes, ursolic and oleanolic acid; the steroids, 24-methylene-cycloartanol, stigmasterol and β-sitosterol; the glycosylated steroids 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol; a polyunsaturated triterpene, squalene; the esters of glycerol, 1-palmitoylglycerol and triacylglycerol; a mixture of long chain hydrocarbons; the aldehyde nonacosanal; the long chain fat acids hentriacontanoic, hexadecanoic and heptadenoic acid; the ester methyl heptadecanoate; the 4-methyl-epi-quinate and two indole alkaloids, N,N-dimethyltryptamine (DMT) and N-methyltryptamine. The chemical structures were determined by means of spectroscopic (IR, 1 H and 13 C NMR, HSQC, HMBC and NOESY) and spectrometric (CG-MS and LCMS-ESI-ITTOF) methods. The study of biologic properties of P. viridis consisted in the evaluation of the acetylcholinesterase inhibition and cytotoxic activities. The hexane, chloroform, ethyl acetate and methanol extracts, the substances 24-methylene-cycloartanol, DMT and a mixture of 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol showed cholinesterase inhibiting activity. This activity induced by chloroform and ethyl acetate extracts was higher than 90%. The methanol and ethyl acetate extracts inhibit the growth and/or induce the death of the tumor cells strains B16F10 and 4T1, without damaging the integrity of the normal cells BHK and CHO. DMT also demonstrated a marked activity against tumor cell strains B16F10 and 4T1.

Risk assessment of ayahuasca use in a religious context: self-reported risk factors and adverse effects

“… 1 , 4 The main component of ayahuasca is the alkaloid N , N ‐dimethyltryptamine (DMT), a tryptamine present in the leaves of Psychotria viridis . 5 This tryptamine acts predominantly as a 5-HT 2A receptor agonist, 6 with effects comparable to those of lysergic acid diethylamide, psilocybin, or mescaline. 7 …”

Influence of environment on the leaf morpho-anatomy and histochemical of the ayahuasca leaf: Populations cultivated in extra-Amazonian regions

“…Psychotria viridis Ruiz & Pav occurs in Mexico, the Antilles, Bolivia, Argentina (Taylor, 2007) and the North (Amazonas) and Southeast (Minas Gerais and São Paulo) regions of Brazil (Pic-Taylor et al, 2015). P. viridis stands out among the genus as an important widespread tropical understory tree providing important bioactive alkaloids (Soares et al, 2017). Leaves of P. viridis are used in the composition of Ayahuasca tea, an entheogenic beverage known as Daime, Caapi, Yajé, Hoasca or Vegetal Hamill, Hallak, Dursun, & Baker, 2019), remarkably used in religious rituals and indigenous pharmacopoeia (Domínguez-Clavé et al, 2016).…”

A Systematic Literature Review of the Potential Therapeutic Effects of Ayahuasca Tea Prepared From the Use of Banisteriopsis Caapi and Psychotria Viridis

“…3-O-β-D-glucosyl-β-sitosterol, 3-O-β-D-glucosyl-stigmasterol, 4-methyl-4-epi-quinate and methyl tetradecanoatotamine; N-methiltriptamine; N,N-dimethyltriptamine (DMT), with DMT standing out as an acetylcholinesterase inhibitor, showing itself as a promising complementary treatment for Alzheimer. Further, the DMT inhibition of tumor cells B16F10 and 4T1 was evidenced in a study (Soares et al, 2017). DMT also inhibits MAO, if administered via parenteral, since it is metabolized in the gastrointestinal tract if not ingested together with β-carbolins, such as harmine, harmaline or tetrahydoharmaline (Tupper, 2008).…”