Polyol monoterpenes isolated from Chenopodium ambrosioides

Abstract

Phytochemical study on the 95% ethyl alcohol extract of stems of Chenopodium ambrosioides resulted in the isolation of two new polyol monoterpenes, 4-hydroxy-4(α or β)-isopropyl-2-methyl-2-cyclohexen-1-one (1) and 1-methyl-4β- isopropyl-1-cyclohexene-4α,5α,6α-triol (2), together with five known compounds, (1S,2S,3R,4S)-1-methyl-4-(propan-2-yl)cyclohexane-1,2,3,4-tetrol (3), (1R,2S,3S,4S)- 1,2,3,4-tetrahydroxy-p-menthane (4), (1R,2S)-3-p-menthen-1,2-diol (5), (1R,4S)-p- menth-2-en-1-ol (6) and 1,4-dihydroxy-p-menth-2-ene (7). The structures of the new compounds were established on the basis of detailed spectroscopic evidence including extensive 1D and 2D NMR techniques. Compounds 1-7 were evaluated for their anti-inflammatory activity, and compound 1 showed moderate ability to inhibit NO production of LPS-stimulated RAW 264.7 macrophages with an IC value of 16.83 μM.

Ethnomedical uses, chemical constituents, and evidence-based pharmacological properties of Chenopodium ambrosioides L.: extensive overview

“…Inhibition of NO production of LPS-stimulated Raw macrophages [183] α-Terpinene Antimicrobial Reduction of efflux pump in Staphylococcus aureus [244,245] Myorelaxant Inhibition of contraction induced by potassium, acetylcholine, or serotonin in rats. [197] Ascaridole Antimalarial Inhibition of the growth and development of Plasmodium falciparum [246] Analgesic Prolongation of anesthesia effect and protection against writhings induced by using acetic acid in mice [187] Sedative Reduction of locomotor activity in mice [187] Antifungal Inhibition of the growth of Sclerotium rolf [186] Cytotoxic Inhibition of human lymphoblastic leukemia T, promyelocytic leukemia, and breast cancer cells.…”

Antimicrobial Effect of Silk and Catgut Suture Threads Coated with Biogenic Silver Nanoparticles

“…We have studied that there is huge potential of Mexican medicinal plants [36], among them, Chenopodium ambrosioides (Mexican Epazote) has been utilized in traditional cuisine and folk medicine since ancient times [18], it has demonstrated diverse pharmacological applications, it is also useful for healing of skin ulceration, and shows anti-inflammatory and antitumor properties [19,37]. It is difficult to assign a single component of being responsible for the bioreduction; however, it is considered that the main chemical constituents involved in this process are mainly monoterpenoids, sesquiterpenoids, and flavonoids, among others [38].…”

Avaliação pré-clínica do extrato hidroalcoólico de Chenopodium retusum: ênfase ao efeito antinociceptivo

“…-isopropil-2-metil-2-ciclo-hexen-1-ona (1) e 1-metil-4β-isopropil-1-ciclohexeno-4α, 5α, 6αtriol (2), juntamente com cinco compostos conhecidos, (1S, 2S, 3R, 4S) -1-metil-4-(propan-2il) ciclo-hexano-1,2,3,4-tetrol (3), (1R, 2S, 3S, 4S) -1,2,3,4-tetra-hidroxi-p-mentano (4), (1R, 2S ) -3-p-menten-1,2-diol ( 5), (1R, 4S) -p-ment-2-en1-ol (6) e 1,4-di-hidroxi-p-menth-2-ene (7) (Hou et al, 2017). Também foram isolados da planta vários alcaloides (Shoaib et al, 2016), flavonoides como quercetina, luteolina, e outros compostos com atividade antinociceptiva comprovada cientificamente (Liu et al, 2022, Ntalouka , Tsirivakou, 2023, Estudos fitoquímicos com C. retusum estão sendo conduzidos por Farias (resultados não publicados) e evidenciaram 65% de semelhança fitoquímica com C. ambrosioides.…”