title: New seco-limonoids from Cipadessa baccifera: Isolation, structure determination, synthesis and their antiproliferative activities.
abstract: A comprehensive reinvestigation of chemical constituents from CHCl3-soluble extract of Cipadessa baccifera led to the isolation of two new limonoids 1, 2 together with six known compounds 3-8. Their structures were established on the basis of extensive analysis of spectroscopic (IR, MS, 2D NMR) data. Further, a series of cipaferen G (3) derivatives were efficiently synthesized utilizing Yamaguchi esterification (2, 4, 6-trichlorobenzoyl chloride, Et3N, THF, DMAP, toluene) at the C-3 position of the limonoids core, which is being reported for the first time. The anti-proliferative activity of the isolates and the synthetic analogues were studied against HeLa, PANC 1, HepG2, SKNSH, MDA-MB-231 and IMR32 cancer cells using the sulphorodamine B assay. Among the tested compounds, 13d and 13h manifested potent activity against IMR32, HepG2 cell lines with GI500.013 and 0.01μM, respectively.
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Bandi
authors.initials: B
authors.lastname: Siva
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Arramshetti
authors.initials: A
authors.lastname: Venkanna
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Borra
authors.initials: B
authors.lastname: Poornima
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Solipeta
authors.initials: S
authors.lastname: Divya Reddy
authors.affiliation: UMR CNRS 6226 ISCR PNSCM, Université de Rennes 1, 2 Avenue du Professeur Léon Bernard, 35043 Rennes, France.
authors.forename: Joel
authors.initials: J
authors.lastname: Boustie
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India; UMR CNRS 6226 ISCR PNSCM, Université de Rennes 1, 2 Avenue du Professeur Léon Bernard, 35043 Rennes, France.
authors.forename: Schnell
authors.initials: S
authors.lastname: Bastien
authors.affiliation: Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Nishant
authors.initials: N
authors.lastname: Jain
authors.affiliation: Biology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: Pathipati
authors.initials: P
authors.lastname: Usha Rani
authors.affiliation: Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. Electronic address: suresh@iict.res.in.
authors.forename: Katragadda
authors.initials: K
authors.lastname: Suresh Babu
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification; D045744:Cell Line, Tumor; D006801:Humans; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification; D036701:Limonins / Q000737:chemistry* / Q000302:isolation & purification; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D012639:Seeds / Q000737:chemistry; D018411:Spodoptera
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D007306:Insecticides; D036701:Limonins; D010936:Plant Extracts
keywords: Cipadessa baccifera; Ester derivatives and anti-proliferative activity; Limonoids; Yamaguchi esterification