This thesis describes phytochemical studies on Buxus macowanii, a medicinal plant collected from South Africa and the fungal transformation of glycyrrhetinic acid (71), a triterpenoid found in Glycyrrhiza plants. The crude methanolic extract of B. macowanii was active in the acetylcholinesterase inhibition assay (IC50 = 30 μg/mL). Chemical investigation of its alkaline dichloromethane extract afforded five novel triterpenoidal alkaloids, 31-hydroxybuxatrienone (56), macowanioxazine (57), 16α-hydroxyma- cowanitriene (58), macowanitriene (59), and macowamine (60), along with two known Buxus bases, Nb-demethylpapillotrienine (61) and moenjodaramine (62). Compounds 56, 57, and 61 exhibited different level of AChE inhibitory activities with compound 56 being significantly active (IC50 = 8.0 μM). Glycyrrhetinic acid (71) was incubated with Curvularia lunata (ATCC 12017) for ten days to afford one metabolite which was characterized by NMR spectral data as known biotransformed product, 3-oxo-glycyrrhetinic acid (85). This metabolite was previously obtained through biotransformation of 71 by using other fungi.

This thesis describes phytochemical studies on Buxus macowanii, a medicinal plant collected from South Africa and the fungal transformation of glycyrrhetinic acid (71), a triterpenoid found in Glycyrrhiza plants. The crude methanolic extract of B. macowanii was active in the acetylcholinesterase inhibition assay (IC50 = 30 μg/mL). Chemical investigation of its alkaline dichloromethane extract afforded five novel triterpenoidal alkaloids, 31-hydroxybuxatrienone (56), macowanioxazine (57), 16α-hydroxyma- cowanitriene (58), macowanitriene (59), and macowamine (60), along with two known Buxus bases, Nb-demethylpapillotrienine (61) and moenjodaramine (62). Compounds 56, 57, and 61 exhibited different level of AChE inhibitory activities with compound 56 being significantly active (IC50 = 8.0 μM). Glycyrrhetinic acid (71) was incubated with Curvularia lunata (ATCC 12017) for ten days to afford one metabolite which was characterized by NMR spectral data as known biotransformed product, 3-oxo-glycyrrhetinic acid (85). This metabolite was previously obtained through biotransformation of 71 by using other fungi.

Depuis les années 1990, on observe une accélération de la vitesse de propagation après établissementd’une grande partie des insectes introduits accidentellement en Europe. L’invasion fulgurante de lapyrale du buis, Cydalima perspectalis, est un exemple de ce phénomène. Observée pour la premièrefois en 2007 en Allemagne, elle s’est ensuite propagée jusqu’au Caucase en une décennie. Il a étérapidement supposé que le commerce de buis d’ornement entre les pays européens et la Chine auraitpermis son introduction tandis que l‘intensification des échanges commerciaux entre pays européensaurait facilité sa propagation à travers le continent. Cependant, certains traits biologiques de l’insecteont également pu favoriser son invasion. Pour mieux comprendre les facteurs impliqués dans soninvasion fulgurante, une approche pluridisciplinaire a été utilisée au cours de cette thèse. Tout d’abord,les routes d’invasion ont été appréhendées avec deux types de marqueurs génétiques. Puis, deux traitsbiologiques ayant pu favoriser son établissement et son expansion ont été étudiés : ses capacités devol et la diapause. Les résultats génétiques ont permis de cibler la partie côtière de la Chine commezone source probable, et suggèrent au moins deux introductions indépendantes depuis la Chine suivipar un phénomène tête de pont probablement lié au commerce d’ornement. Les capacités de volestimées sont élevées et expliqueraient la dispersion de l’insecte à l’échelle locale. De plus, la sortie dediapause influencée par la température a pu permettre l’adaptation du nombre de générations enfonction du climat annuel. Ces deux traits biologiques ont par conséquent dû favoriser son invasion àl’échelle locale mais il apparaît que les activités humaines, en particulier le commerce des plantesornementales, ont joué un rôle majeur dans son invasion fulgurante à large échelle en Europe et auCaucase. / Since 1990, recently established non-native insect species appear to be spreading across Europesignificantly faster than before. The box tree moth, Cydalima perspectalis, is a representative of such arapid spread. First observed in 2007, it spread across Europe to Asia Minor in a decade, damaging onBuxus plants in urban areas as well as in forests. The trade of ornamental box plants between Europeand China has been hypothesized as the invasion pathway of the insect while the trade betweenEuropean countries could explain its fast expansion. The biological traits of the moth may also havefavored its spread. To understand the factors involved in both its invasion and fast expansion, we useda multidisciplinary approach. First, the invasion routes were tentatively assessed using two geneticmarkers. Then, two biological traits, flight capacities and diapause, were studied because they may havepromote its spread. The genetic analyses clearly suggest an origin from Eastern China origin but alsocomplex invasion pathways. Two independent introduction events probably happened directly fromChina followed by bridgehead effects due to ornamental plant trade. The moth flight capacities areimportant but can only explain dispersal at local scale. Moreover, diapause termination was influencedby temperature, which may lead to an adapted number of generation depending on local climate. Thesebiological traits may have favored local invasions. However, our study suggests that human-mediateddispersal played a key role in the fast expansion of C. perspectalis across Europe and Asia Minor.