Two new cytotoxic furoquinoline alkaloids isolated from Aegle marmelos (Linn.) Correa

Abstract

Two new cytotoxic furoquinoline alkaloids were isolated from the leaves of Aegle marmelos (Linn.) Correa; one from the total alkaloidal fraction (acid/base shake-out method) of the CHCl extract and identified as 7,8-dihydroxy-4-hydrofuroquinoline and named trivially as Aegelbine-A. The other new alkaloid isolated from the pet. ether extract and identified as 4-hydro-7-hydroxy-8-prenyloxyfuroquinoline and named trivially as Aegelbine-B, together with a known alkaloid; aegeline and a known phenolic acid; ρ-hydroxybenzoic acid. The structures of all the isolated compounds were established based on 1D and 2D NMR spectroscopy and HR-ESI/MS. The cytotoxic activity of the isolated compounds was evaluated in vitro against HepG-2, PC3, A549 and MCF-7 cell lines. The obtained results revealed promising activity with structure-based relationship which is discussed briefly.

Biologically active quinoline and quinazoline alkaloids part II

“…The former compound also displayed weak cytotoxic activity against THP‐1 and HCT116 (colon cancer) cell lines . Other furoquinoline alkaloids, such as 5‐methoxyrobustine ( 42 ), dictamnine, robustine, isopteleine ( 43 ) (Figure ), and γ‐fagarine also presented weak cytotoxic activity against MCF‐7 cells, and two new furoquinoline alkaloids, aegelbines A ( 44 ) and B ( 45 ) (Figure ) from Aegle marmelos were weakly active against MCF‐7 as well as HepG2 and PC‐3 cell lines …”

“…22,34 Other furoquinoline alkaloids, such as 5-methoxyrobustine (42), dictamnine, robustine, isopteleine (43) ( Figure 5), and -fagarine also presented weak cytotoxic activity against MCF-7 cells, 35,36 and two new furoquinoline alkaloids, aegelbines A (44) and B (45) ( Figure 5) from Aegle marmelos were weakly active against MCF-7 as well as HepG2 and PC-3 cell lines. 37 A new -fagarine derivative, 7-isopentenyloxy--fagarine (46) ( Figure 6), exhibited significant cytotoxicity against Raji (lymphoma) and Jurkat (leukemia) cell lines with IC 50 values of 1.5 and 3.6 g/mL, respectively, compared with 14.5 and 9.3 g/mL for atanine and 15.6 and 11.5 g/mL for skimmianine. 38 Compound 46 was also more cytotoxic against the MCF-7 cell line (IC 50 = 15.5 g/mL), than atanine, skimmianine, and perfamine (47) ( Figure 6).…”

Chemical constituents of Clausena lenis

“…Within Aurantioideae, furoquinoline derivatives are reported only for Aegle marmelos (Linn.) Correa (Mohammed et al 2016). They are also known to occur in Vepris (Kouam et al 2018) and Melicope species (Chen et al 2003;Rasamison et al 2016), which both belong to the subfamily Toddalioideae.…”

Silver(I)‐Catalyzed Regioselective Synthesis of Dihydrofuro[3,4‐b]quinolines from o‐Alkynylquinoline‐MBH Adducts and Evaluation of their Photophysical Properties

“…Recently, tetrahydrofuran-fused quinolines [4] have been reported as inhibitors of methionyl amino peptidase and glucocorticoid receptor modulator, used for the medication of liver disorders and obesity. In the year of 2016, Mohmmed et al [5] isolated two furoquinoline alkaloids (aegelbine-A and aegelbine-B) from the leaves of Aegle marmelos, which exhibited cytotoxic properties against HepG-2, MCF-7, PC3 and A549 cell lines. Hence, the efficient synthesis of furoquinolines has become increasingly important, however, only limited reports are available in the literature for the construction of furoquinoline derivatives.…”

“…Recently, tetrahydrofuran‐fused quinolines have been reported as inhibitors of methionyl amino peptidase and glucocorticoid receptor modulator, used for the medication of liver disorders and obesity. In the year of 2016, Mohmmed et al . isolated two furoquinoline alkaloids (aegelbine‐A and aegelbine‐B) from the leaves of Aegle marmelos , which exhibited cytotoxic properties against HepG‐2, MCF‐7, PC3 and A549 cell lines.…”