title: Styryllactones and acetogenins from the fruits of Goniothalamus macrocalyx.
abstract: Two new styryllactones, macrocalactone (1) and 3-deoxycardiobutanolide (2), were isolated from the fruits of Goniothalamus macrocalyx Ban (Annonaceae), together with seven known compounds including four acetogenins, annonacin (3), solamin (4), isoannonacin (5), trans-murisolinone (6), and three other compounds, 7-acetylaltholactone (7), beta-caryophyllene-8R,9R-oxide (8) and 2-(2'-hydroxytetracosanoylamino)-octadecane-1,3,4-triol (9). Their structures were determined by spectroscopic and MS analysis. The absolute configuration of 1 was determined by X-ray crystallographic analysis. The structures of the acetogenins were confirmed by liquid chromatography coupled to a hybrid quadrupole-time of flight mass spectrometer, using post-column lithium infusion. The results were compared with the fragmentation obtained with a hybrid linear trap-orbitrap mass spectrometer. Compound 7 had cytotoxicity against KB, HepG2, Lu, and MCF7 cell lines with IC50 values of 13.1, 23.7, 26.3 and 60.2 microM, respectively, whereas annonacin (3) was selectively active against KB cells (IC50 value of 6.5 microM). The discovery of 3-deoxycardiobutanolide (2) from the fruits of this plant revealed that G. macrocalyx could be a valuable natural resource to obtain this compound as it has been previously reported to have a significant cytotoxicity against different cancer cell lines, especially HL-60 cells.
authors.forename: Quy Hung
authors.initials: QH
authors.lastname: Trieu
authors.forename: Huong Doan Thi
authors.initials: HD
authors.lastname: Mai
authors.forename: Van Cuong
authors.initials: VC
authors.lastname: Pham
authors.forename: Marc
authors.initials: M
authors.lastname: Litaudon
authors.forename: Françoise
authors.initials: F
authors.lastname: Gueritte
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Isabelle
authors.initials: I
authors.lastname: Schmitz-Afonso
authors.forename: Olinda
authors.initials: O
authors.lastname: Gimello
authors.forename: Van Hung
authors.initials: VH
authors.lastname: Nguyen
authors.forename: Van Minh
authors.initials: VM
authors.lastname: Chau
mesh_terms: D054378:Acetogenins / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry*; D054335:Goniothalamus / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D054378:Acetogenins; D007783:Lactones