Indole Alkaloids and Quassinoids from the Stems of Brucea mollis

Abstract

Seven new indole alkaloids, bruceollines H-N (1-7), three new quassinoids, yadanziolides T-V (10-12), and four known analogues, bruceolline E (8), bruceolline F (9), bruceine D (13), and yadanziolide B (14), were isolated from an ethanol extract of the stems of Brucea mollis. The absolute configurations of compounds 2 and 5 were determined by comparison of their experimental and calculated ECD spectra. The absolute configuration of the known compound 9 was determined by using Mo2(OAc)4-induced CD analysis for the first time. Compounds 10, 13, and 14 exhibited cytotoxic activities with IC50 values of 3.00-5.81 μM.

Chemical Composition and Cytotoxic Activities of Petroleum Ether Fruit Extract of Fruits of <i>Brucea javanica</i> (Simarubaceae)

“…Recently, much attention has been paid to the Brucea genus and its chemical constituents because of its manysided activities. Many chemical constituents have been isolated from Brucea genus, including quassinoids, alkaloids, triterpenoids, and flavonoids [2][3][4][5]. Its core components are quassinoids, which possess various biological activities including anti-tumor [4], anti-malarial and anti-babesial [6,7], anti-viral [8], anti-bacterial [9,10] and hyperglycemic [11] activities.…”

Chemical components, pharmacological properties, and nanoparticulate delivery systems of Brucea javanica

“…Researchers have now isolated several natural components from Brucea javanica. These include the tetracyclic triterpene quassinoids, 7 anthraquinone, olein, oleic acid, linoleic acid, 8 pregnane glucosides, 9,10 and sesquiterpenes. 11 In particular, tetracyclic triterpene quassinoids are the main active ingredients of Brucea javanica with remarkable antitumor activity.…”

Bruceolline D: 3,3-dimethyl-1H,4H-cyclopenta[b]indol-2(3H)-one

“…For the palladium-catalysed synthesis of related fused indole structures, see: Nazare et al (2004). For the isolation of related bruceollines, see : Chen et al (2011). For the total synthesis and crystal structure of bruceolline E, see : Jordan et al (2011: Jordan et al ( , 2012.…”

“…The reaction of phenylhydrazine with 2-methylcyclopentane-1,3-dione (Fischer indole synthesis) under thermal and acidic conditions has been investigated (Dashkevich, 1978). Other structurally similar bruceollines have been isolated more recently (Chen et al, 2011). Bruceolline E has been synthesized by a sequential Nazarov cyclization/selenium dioxide oxidation (Jordan et al, 2011) and the crystal structure determined (Jordan et al, 2012).…”