Review on canthin-6-one alkaloids: Distribution, chemical aspects and biological activities

Analysis of canthin-6-one alkaloids derived from Eurycoma spp. by micellar liquid chromatography and conventional high-performance liquid chromatography: a comparative evaluation

“…1 Given the broad safety profile of EL root extracts and the abundance of bioactive species (mainly quassinoids, canthin-6-one alkaloids, and β-carboline alkaloids), 1–3 these extracts are utilized in numerous medicinal applications: they are used for improving male sexual performance 4 and treating sexual dysfunction, malaria, cancer, diabetes, constipation, inflammation, fever, fatigue, leukemia, and infectious and bone diseases. 3,5,6…”

“…1 Given the broad safety prole of EL root extracts and the abundance of bioactive species (mainly quassinoids, canthin-6-one alkaloids, and b-carboline alkaloids), [1][2][3] these extracts are utilized in numerous medicinal applications: they are used for improving male sexual performance 4 and treating sexual dysfunction, malaria, cancer, diabetes, constipation, inammation, fever, fatigue, leukemia, and infectious and bone diseases. 3,5,6 The aphrodisiac activities of EL are attributed to canthin-6one alkaloids, such as canthin-6-one-9-O-b-D-glucopyranoside (C6OG), 9-methoxycanthin-6-one (MCO), canthin-6-one (C6O), and 9-hydroxycanthin-6-one (HCO), which exert their effects by inhibiting phosphodiesterase type 5 (IC 50 = 2.86 ± 0.23, 3.30 ± 1.03, 4.31 ± 0.52, and 4.66 ± 1.13 mM, respectively). 7 In addition, HCO may be associated with penile erection and delayed ejaculation in rats, by interfering with Ca 2+ mobilization and, thus, antagonistically toning the smooth muscles of the corpus cavernosum and seminal vesicle.…”

Structures and Biological Activities of Alkaloids Produced by Mushrooms, a Fungal Subgroup

“…Canthin-6-one alkaloids 5 – 8 ( Figure 2 ) were the first discovered β-carboline alkaloids in the review period and were isolated from the fruiting bodies of Boletus curtisii [ 25 ]. Canthin-6-one (or canthinone, 9 , Figure 2 ) alkaloids are a subclass of β-carboline alkaloids that contain an additional D-ring [ 86 ]. Alkaloids 5 – 8 are characterized by the presence of a sulfur atom in their structure.…”

“…The same authors also reported the first isolation of canthin-6-one ( 9 ) outside of higher plants. Compound 9 has anti-fungal, anti-parasite, and cytotoxic properties [ 86 , 87 ]. As no activities were reported for thiomethylated alkaloids 5 – 8 , extensive studies on their pharmacological activities would be of interest.…”

“…Other authors have also reported the potential cholinesterase inhibitory activity of β-carbolines, and it was found that the quaternary ones are about one-sixth as potent as the reference alkaloid physostigmine [ 26 ]. A recent review on a wider overview on the bioactivities of β-carbolines and canthinones was recently published by Farouil et al (2022) [ 86 ].…”