Cytotoxic and Antimalarial Alkaloids from the Twigs of Dasymaschalon obtusipetalum

Abstract

One new p-quinonoid aporphine alkaloid, obtusipetadione (1), and eleven known compounds (2-12) were isolated from the acetone extract of the twigs of Dasymaschalon obtusipetalum. Their structures were elucidated by spectroscopic methods. The cytotoxic and antimalarial activities of the isolated compounds were evaluated. Compound 1 showed significant in vitro antiplasmodial activity against the P. falciparum strains TM4 and K1 (multidrug resistant strain) with IC 50 values of 2.460.12 and 1.380.99 µg/mL, respectively with no cytotoxicity. Compound 9 had more modest antiplasmodial activity, but significant cytotoxicity.

Alkaloids from Plants with Antimalarial Activity: A Review of Recent Studies

“…Further, from the twigs of Dasymaschalon obtusipetalum, one new p-quinonoid aporphine alkaloid, obtusipetadione (52), and eleven known compounds were isolated. Compound 52 shows significant in vitro antiplasmodial activity against the P. falciparum strains TM4 and K1 (multidrug-resistant strain) with IC 50 values of 2.46 ± 0.12 and 1.38 ± 0.99 μg/mL, respectively, with no cytotoxicity [43]. In another report, six alkaloids were isolated from the bark of Dehaasia longipedicellata.…”

“…Also, six alkaloids were isolated from Alseodaphne corneri. ese include (+)-laurotetanine (43) and (+)-norstephasubine (44), both of which exhibit strong antiplasmodial activity with IC 50 values of 0.189 and 0.116 μM, respectively [38]. are dimeric.…”

“…Evidence-Based Complementary and Alternative Medicine [36] ree new alkaloids, (-)-pseudocurine (40), (-)-pseudoisocurine (41), and (-)-10-oxoaknadinine (42) Bisbenzylisoquinoline alkaloids (40 and 41) and one hasubanane alkaloid (42) Leaf of Stephania abyssinica ey show strong-to-mild activity with IC 50 values ranging from 0.29 ± 0.00 to 1.65 ± 0.03 μg/mL against both chloroquinesusceptible D6 and chloroquine-resistant strains [37] Six known alkaloids including (+)-laurotetanine (43) and (+)-norstephasubine (44)…”

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

“…To date, twelve species of Dasymaschalon have been reported in Thailand [1]. They possess various biological activities and comprise various types of chemical structures including acetogenins [2], cycloartane [3], alkaloids [3][4][5][6][7][8], flavonoids [2], cyclohexene oxide derivatives [3,9], and a novel anti-tumor caged xanthone [10].…”

“…The bioactive compounds from the ethyl acetate extract of D. sootepense roots were separated and purified using chromatographic and crystallization techniques to yield one new dihydrobenzofuran neolignan (5) and eleven known compounds (1-4, and 6-12). The 1 H and 13 C NMR spectral data of the known compounds, including (2S,3S)-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-methyl-5-(E)-propenyl-benzofuran (1) [11,12], (+)-conocarpan (2) [13,14], (2S,3S)-2,3-dihydro-2-(3,4-dimethoxyphenyl)-3-methyl-5-(E)propenylbenzofu-ran (3) [15], benzyl benzoate (7) [16], dasytrichone (8) [5], 3,5,7,3,5-pentahydroxyflavane (9) [17], dicentrinone (10) [18], ()-sinactine (11) [19] and discretine (12) [20] were directly compared with those reported in the literature. Compounds 4 [21,22] and 6 [23] were only partially characterized in the previous reports.…”