A New Neolignan, and the Cytotoxic and Anti-HIV-1 Activities of Constituents from the Roots of Dasymaschalon sootepense

Abstract

Bioassay-guided isolation from the ethyl acetate extract of Dasymaschalon sootepense roots led to the isolation of twelve compounds including a new dihydrobenzo-furan neolignan, (+)-(2S,3S)-2,3-dihydro-2-(3,4-dimethoxyphenyl)-3-methylbenzofuran-5-carbaldehyde (5), and eleven known compounds (1-4, and 6-12). The chemical structures and stereochemistry of all the isolated compounds were established by spectroscopic techniques. The known compounds 4 and 6 have been fully characterized spectroscopically, including their absolute configurations. Cytotoxic and anti-HIV-1 reverse transcriptase (RT) activities of compounds 1-3, 5 and 8-12 were determined. Among compounds screened, compounds 2, 3 and 10 displayed weak cytotoxic activity with ED 50 values ranging from 9.6-47.5 µM and only compound 2 was found weakly active against HIV-1 RT with an IC 50 value of 323.2 µM.

Lignans: Quantitative Analysis of the Research Literature

“…Within the bioactive compounds realm Santini and Novellino, 2018;Daliu et al, 2019;Durazzo et al, 2019), the class of lignans is of interest for their potential biological activities, i.e., estrogenic and antiestrogenic, antioxidant, antiinflammatory, metabolism-modulating, anti-proliferative, and anticancerogenic properties (Baumgartner et al, 2011;Teponno et al, 2016;Wang et al, 2016;Linder et al, 2019;Zálešák et al, 2019). Moreover, it is worth mentioning that the spectrum of biological activities attributed to lignans is being enlarged, i.e., related to newly discovered compounds belonged to this group (Zhang et al, 2014;Gnabre et al, 2015;Su and Wink, 2015;Hongthong et al, 2016;Azam et al, 2019;Zhuang et al, 2019).…”

Anti-HIV Activity of Alkaloids from Dasymaschalon echinatum

“…To the best of our knowledge, the chemical and biological studies of D. echinatum have not been previously reported. Our research group has been systematically investigating bioactive consituents of plants in the Dasymaschalon genus [18,21,25,26]. In the present work, we reported the bioassay-guided fractionation, structure elucidation and anti-HIV 1-RT effects of compounds isolated from D. echinatum.…”

“…Twelve species of the Dasymaschalon genus were found in Thailand [16]. Phytochemical investigation of plants in this genus led to the isolation of several biologically active compounds including essential oils [17], acetogenins [18], cycloartanes [19], alkaloids [19][20][21][22][23], flavonoids [18,24], cyclohexene oxide derivatives [19,25], neolignans [26] and a novel anti-tumor caged xanthone [27].…”

Dasymaschalolactams A–E, Aristolactams from a Twig Extract of Dasymaschalon dasymaschalum

“…In Thailand, only 12 species are recognized . Previous phytochemical investigations on this genus have resulted in the isolation of various classes of compounds including flavonoids, triterpenoids, alkaloids, , neolignans, benzyl benzoate derivatives, , phenylpropanoids, acetogenins, and oxygenated cyclohexene derivatives. , Some of these compounds have shown interesting biological properties including cytotoxicity, − , antimalarial, anti-inflammatory, and anti-HIV effects. , Dasymaschalon dasymaschalum (Blume) I.M. Turner has many synonym names, including D. blumei Finet & Gagnep., D. coelophloeum (Scheff.)…”