Melicodenine I, a new quinolinone alkaloid from Melicope denhamii leaves

Abstract

A new quinolinone alkaloid, Melicodenine I (1), along with five known compounds, bergapten (2), isoevodionol methyl ether (3), isoevodionol (4), ternatin (5), β-sitosteryl-3-O-β-D-glucopyranoside (6) and a mixture of β-sitosterol and stigmasterol were isolated from Melicope denhamii leaves, and their structures were elucidated using H NMR,C NMR, 2D NMR and UPLC-qToF-MS.

Three novel quinolinone alkaloids from the leaves of Melicope denhamii

“…Compound 2 indicated that 27 carbon signals were utterly separated in the 13 C NMR spectra, including five methyl carbons, two methylene carbons, nine methine carbons, one carbonyl carbon, and ten quaternary carbons. From the NMR ( 1 H, 13 C) NMR spectrum exhibited that the structure of 2 is a Diels-Alder adduct moiety and was confirmed by HMBC spectrum (Nakashima et al, 2012;George et al 2016). The HMBC correlation, an N-methyl at d H 3.80, and an aromatic at d (H-4)], indicating the structure of 2 are Diels-Alder adduct.…”

“…Many alkaloids from Melicope show biological activities as cytotoxic agents (Chen et al 2003;Nakashima et al 2012), and antimalaria (Rasamison et al 2016). Recently studies on Melicope resulted in the hybrid compound by [2 þ 2] cycloaddition and a Diels-Alder adduct from incorporated phenylpropanoid-phenylpropanoid, alkaloid-alkaloid, alkaloid-benzopyran, and alkaloid-phenylpropanoid derivatives (Nakashima et al 2011(Nakashima et al , 2012George et al 2016;Saputri et al 2021). Three new compounds, melicodenine J (1) is a [2 þ 2] cycloaddition, melicodenines K (2), and L (3) are Diels-Alder adduct derivatives were isolated from M. denhamii leaves.…”

High-Value Plant Species Used for the Treatment of “Fever” by the Karen Hill Tribe People

“…Unlike Elephanthopus scaber and Mimosa pudica, there is no detailed knowledge of the chemistry of Melicope glomerata. Other species of Melicope quinoline alkaloids (the same group as quinine/chloroquine) have been identified [47,48], but with a similar cyclobutane moiety as the δ-truxinate (melicodenine D: (Figure 3c), so it is reasonable to expect related structures in Melicope glomerata. With the prevalence of resistance to quinine across the world [49] and predicted resistance development to artemisinin [38], Melicope glomerata may be a valuable research option in the search for alternatives.…”

Synthesis of 2‐Quinolones based on Visible Light‐Catalyzed Annulation of Diazo compounds

“…2-Quinolones are important synthetic scaffolds found in many natural products [1][2][3] and biologically active compounds. [4][5][6][7][8][9][10] The preparation of the 2-quinolone cores has been recognized with interest in medicinal chemistry and drug discovery.…”