New Alkaloids and Cytotoxic Principles from Sinomenium acutum

Abstract

Two new alkaloids, 2-demethyl-oxypalmatine (1) and 5-ethoxycarbonylsinoracutine (2), were isolated from the rhizomes of Sinomenium acutum, along with thirty-four known compounds. Cytotoxicity of the isolated compounds was examined for the MCF-7, H460, HT-29, and CEM human cancer cell lines. Dauriporphine (16), 6-O-demethylmenisporphine (17), bianfugecine (18), menisporphine (19), and 6-O-demethyldauriporphine (20) showed differential effects in their cytotoxic activity on the target cancer cell lines. Significant angiogenesis inhibitions of 16 and 19 were also observed.

Oxoisoaporphine Alkaloids: Prospective Anti‐Alzheimer's Disease, Anticancer, and Antidepressant Agents

“…In an experiment by Cheng et al., three natural oxoisoaporphine alkaloids exhibited excellent cytotoxic activities. Compounds 3 , 4 , and 6 were cytotoxic to CEM cells with IC 50 values ranging from 0.22 to 0.46 μ m .…”

“…Cheng et al. evaluated the antiangiogenesis effects of oxoisoaporphine alkaloids isolated from S. acutum . The results indicated that 3 and 6 showed significant inhibitory effects with IC 50 values of (3.3±0.7) and (2.4±0.3) μ m , respectively.…”

“…[11][12][13] It hasb een claimed that these compounds could be phytoalexins generated by plants against pathogen infections. [14] With increasing attention being paid to the source of these alkaloids, oxoisoaporphines have been isolated from not only M. dauricum DC., but also Stephania hernandifolia Walp, [15] Sinomenium acutum, [16] and Sciadotenia toxifera. [17] Currently,1 5o xoisoquinoline alkaloids have been isolated and identified from natural sources( Figure 1): bianfugcine (2), bianfugenine/dauriporphine (3), [11,18] 6-O-demethylmenisporphine (4), dauriporphinoline (5), menisporphine (6), daurioxoisoporphine B( 7), daurioxoisoporphine C( 8), [19] daurioxoisoporphine D( 9), tyraminoporphine( 10), [20] daurioxoisoporphine A( 11), [19] 2,3-dihydrodauriporphine (12), [20] bianfugedine (13), [11,18] 2,3-dihydromenisporphine (14), [12] 9-O-demethylbianfugenine (15), [15] and lakshminine (16).…”

Rapid determination of eight oxoisoaporphine alkaloids in Rhizoma Menispermi by the optimal homogenate extraction followed by UPLC-MS/MS

“…In particular, the natural occurrence of oxoisoaporphine alkaloids is apparently restricted to this plant species (family Menispermaceae), with the exception of lakshminine found in Sciadoternia toxifera [1]. Pharmacological studies have suggested that characteristic alkaloids are the main bioactive constituents of Rhizoma Menispermi, a series of oxoisoaporphine alkaloids from the herbs have been reported to be responsible for anti-tumor [2,3], anti-angiogenic activity [3], and differential P-gp MDR inhibition activity in MES-SA/DX5 and HCT 15 cells [4]. Hence, exploring the content of these alkaloids in Rhizoma Menispermi would be helpful for understanding the pharmacological basis of their activity as well as enhancing the product quality control of Rhizoma Menispermi.…”

Microwave‐assisted extraction in combination with HPLC‐UV for quantitative analysis of six bioactive oxoisoaporphine alkaloids in Menispermum dauricum DC

“…In the past few decades, systematic phytochemical studies of MDD have revealed that it mainly contains a variety of alkaloids classified as bisbenzylisoquinolines, aporphines, isoquinolines, isoindoles, isoquinolones, protoberberines and oxoisoaporphines (Tan et al, 1990;Pan et al, 1999;Sugimoto et al, 1999;Yu et al, 2001Yu et al, , 2002Zhang et al, 2004;. Of these, the natural occurrence of oxoisoaporphine alkaloids (OA) is apparently restricted to this plant species (family Menispermaceae; Sugimoto et al, 1999;Yu et al, 2001;Cheng et al, 2012), with the exception of lakshminine found in Sciadoternia toxifera (Killmer et al, 2003). Modern pharmacological studies demonstrated that OA exhibited a wide spectrum of biological and pharmacological activities such as cytotoxic activities against a number of cancer cell lines (Yu et al, 2001), antiangiogenic activity (Cheng et al, 2012) and differential P-gp MDR inhibition in MES-SA/DX5 and HCT 15 cells (Min et al, 2006).…”