Gloria Cardona

Musanolones : four 9-phenylphenalenones from rhizomes of Musa acuminata

Abstract Four new phenalenone-type phytoalexins, named musanolones C-F, have been isolated from infected rhizomes of banana plants (Musa acuminata; AAA cultivar Grand Nain). These phytoalexins were biosynthesized de novo by the plants upon infection by Fusarium oxysporum f. sp. cubense race 4, Panamas disease causal agent. The structures of the new phytoalexins were elucidated using spectroscopic data and chemical correlations. Hydroxyanigorufone has been previously described as a constitutive natural product, from Anigozanthos rufus, but it was never described as a phytoalexin. The chemical shift for all of the hydrogen and carbon atoms in the musanolones C-F were unambiguously established by mono- and bi-dimensional, homo- and hetero-nuclear NMR experiments (1H NMR, 13C NMR, COSY, HMQC and HMBC). Preliminary in vitro assays of all the musanolones tested until now show a strong inhibitory activity on the growth of the germination tube of F. oxysporum f. sp. cubense race 4.

ERMANIN : AN INSECT DETERRENT FLAVONOID FROM PASSIFLORA FOETIDA RESIN

Abstract Ten flavonoids were isolated from Passiflora foetida L. resin. One of them, ermanin, has a high deterrent activity at 40 ppm against Dione juno larvae.

Synthesis and Antifungal Activity of Musa Phytoalexins and Structural Analogs

Winston Quinones, Gustavo Escobar, Fernando Echeverri *, Fernando Torres, Yoni Rosero,Vi ctor Arango, Gloria Cardona and Adriana GallegoDepartment of Chemistry, Universidad de Antioquia, P. O. Box 1226, Medellin, ColombiaTel.: (57+4)2105658, Fax: (57+4)2330120, E-mail: echeveri@catios.udea.edu.coReceived : 18 January 2000 ; revised form 14 July 2000 / Accepted : 14 July 2000 / Published : 26 July 2000Abstract: Several perinaphthenone/phenylphenalenone compounds were synthesized to es-tablish a relationship between structure and antifungal activity against Mycosphaerella fijie n-sis. Substitutions on the unsaturated carbonyl system or addition of a phenyl group reducedantibiotic activity.Keywords: phenylphenalenones, synthesis, antifungal activity, Mycosphaerella fijiensis .IntroductionPhytoalexins are natural antibiotic compounds proposed as fungicides or templates for production ofnew pesticides [1]. Recently, the search for novel antifungal compounds has received special attentionas a result of an enhanced microbial resistance to current pesticides.Banana plants are affected by the pathogenic fungi Fusarium oxysporum var. cubensis type 4 andMycosphaerella fijiensis , causal agents of the diseases named Black Sigatoka and Panama Disease, r e-spectively. These diseases can drastically reduce banana production by as much as ca. 20% [2]. Undercolonization by these microorganisms or treatment of the leaves with kanamycin, banana plants producetwo types of phytoalexins, 9-phenylphenalenones (also known as musanolones [3]) and 4-phenylphenalenones [4], The main aim of the present work was to synthesize several structurally-relatedcompounds and to determine the relationship between phytoalexin structure and their antifungal effectsagainst M. fijiensis .Results and DiscussionThe planned synthetic approach involved a 1,4-addition of a Grignard reagent to a perinaphthenone,followed by reduction with DDQ, epoxidation with

Withajardins, withanolides with a new type of skeleton structure of withajardins A, B, C and D absolute configuration of withajardin C

Abstract Withajardins A, B, C and D are withanolides with a new skeleton isolated from the leaves of Deprea orinocensis . Their structure and the absolute configuration of withajardin C were established by spectral analysis, including 2D-NMR and X-ray diffraction. The 13 C NMR assignments of withajardins and acnistins were compared and biogenetic pathways to these compounds were formulated.

Danilol, A New Drimane Sesquiterpene from Polygonum Punctatum Leaves

Abstract A new sesquiterpene related to the insecticide polygodial was obtained from P. punctatum leaves. Its structure was established as a tricyclic hemiacetal by means of 2D NMR spectroscopy. The compound was inactive against tick (Boophiilus microplus).

Unambiguous 13C NMR assignment of acnistins and absolute configuration of acnistin A

Carbon and proton atoms were fully assigned in this new type of withanolide by HMQC and HMBC experiments. The absolute configuration of acnistin A was determined by X-ray diffraction. Proton and 13C NMR measurements are particularly useful in identifying members of this group of natural products.