Antileishmanial Activity of Lignans, Neolignans, and Other Plant Phenols.

Secondary metabolites (SM) from organisms have served medicinal chemists over the past two centuries as an almost inexhaustible pool of new drugs, drug-like skeletons, and chemical probes that have been used in the "hunt" for new biologically active molecules with a "beneficial effect on human mind and body." Several secondary metabolites, or their derivatives, have been found to be the answer in the quest to search for new approaches to treat or even eradicate many types of diseases that oppress humanity. A special place among SM is occupied by lignans and neolignans. These phenolic compounds are generated biosynthetically via radical coupling of two phenylpropanoid monomers, and are known for their multitarget activity and low toxicity. The disadvantage of the relatively low specificity of phenylpropanoid-based SM turns into an advantage when structural modifications of these skeletons are made. Indeed, phenylpropanoid-based SM previously have proven to offer great potential as a starting point in drug development. Compounds such as Warfarin® (a coumarin-based anticoagulant) as well as etoposide and teniposide (podophyllotoxin-based anticancer drugs) are just a few examples. At the beginning of the third decade of the twenty-first century, the call for the treatment of more than a dozen rare or previously "neglected" diseases remains for various reasons unanswered. Leishmaniasis, a neglected disease that desperately needs new ways of treatment, is just one of these. This disease is caused by more than 20 leishmanial parasites that are pathogenic to humans and are spread by as many as 800 sandfly species across subtropical areas of the world. With continuing climate changes, the presence of Leishmania parasites and therefore leishmaniasis, the disease caused by these parasites, is spreading from previous locations to new areas. Thus, leishmaniasis is affecting each year a larger proportion of the world's population. The choice of appropriate leishmaniasis treatment depends on the severity of the disease and its form of manifestation. The success of current drug therapy is often limited, due in most cases to requiring long hospitalization periods (weeks to months) and the toxicity (side effects) of administered drugs, in addition to the increasing resistance of the parasites to treatment. It is thus important to develop new drugs and treatments that are less toxic, can overcome drug resistance, and require shorter periods of treatment. These aspects are especially important for the populations of developing countries. It was reported that several phenylpropanoid-based secondary metabolites manifest interesting antileishmanial activities and are used by various indigenous people to treat leishmaniasis. In this chapter, the authors shed some light on the various biological activities of phenylpropanoid natural products, with the main focus being on their possible applications in the context of antileishmanial treatment.

Different drought resistance mechanisms between two buckwheat species Fagopyrum esculentum and Fagopyrum tataricum.

Water availability is one of the main factors affecting crop production and the occurrence of drought periods is expected to increase in the context of ongoing climate change. We investigated the impact of water stress on two pseudocereal species, common buckwheat (Fagopyrum esculentum) and Tartary buckwheat (Fagopyrum tataricum). Plants were grown under greenhouse conditions under two water regimes: control (40-50% soil humidity) and water stress (<20% soil humidity). Although closely related, both species differed by their resistance to water stress. The vegetative growth was affected in F. esculentum but not in F. tataricum as water stress decreased leaf production, leaf fresh, and dry weight, stomatal conductance, transpiration rate, and photosynthesis rate in the former but not in the latter. However, chlorophyll fluorescence parameters were not affected by water stress, whatever the species, and the chlorophyll content increased in water-stressed plants in both species. Oxidative stress was observed in both species in response to water stress, and antioxidant content was increased in F. tataricum. The reproductive phase was affected by water stress in both species: the number of inflorescences and pollen production decreased, mainly in F. esculentum. Seed set was maintained in F. tataricum while this parameter was not investigated in F. esculentum due to its self-incompatibility. Our results suggested that F. tataricum was more resistant to water stress than F. esculentum and that F. esculentum had characteristics of drought avoidance, while F. tataricum exhibited traits of drought tolerance.

Comparison of high temperature resistance in two buckwheat species Fagopyrum esculentum and Fagopyrum tataricum.

In the context of ongoing climate change, expected temperature rise may significantly limit plant growth and productivity of crop species. In this study, we investigated the effects of a sub-optimal temperature on buckwheat, a pseudocereal known for its nutraceutical advantages. Two buckwheat species differing by their reproduction method, namely Fagopyrum esculentum and Fagopyrum tataricum were grown at 21 °C and 27 °C in growth chambers. High temperature increased leaf production mainly in F. tataricum but decreased leaf area in both species. Water and photosynthesis-related parameters were affected by high temperature but our results suggested that although transpiration rate was increased, adaptive mechanisms were developed to limit the negative impact on photosynthesis. High temperature mainly affected the reproductive stage. It delayed flowering time but boosted inflorescence and flower production. Nevertheless, flower and seed abortions were observed in both species at 27 °C. Regarding flower fertility, heat affected more the female stage than the male stage and reduced the stigma receptivity. Pollen production increased with temperature in F. esculentum while it decreased in F. tataricum. Such discrepancy could be related to the self-incompatibility of F. esculentum. Both species increased their antioxidant production under high temperature to limit oxidative stress and antioxidant capacity was higher in the inflorescences than in the leaves. Total flavonoid content was particularly increased in the leaves of F. esculentum and in the inflorescences of F. tataricum. Altogether, our results showed that even if high temperature may negatively affect reproduction in buckwheat, it improves its antioxidant content.

1-(Phenylsulfonyl)-3-oxabicyclo[3.1.0]hexan-2-one as a Building Block in Organic Synthesis.

The transformation of the readily available phenylsulfonyl lactone building block to structurally diverse molecular scaffolds is described. Depicted structures are accessed in one to three steps, and their overall yields are high. The rigidity of the starting building block greatly directs the stereoselectivity of the transformations, and newly generated stereogenic centers including the quaternary carbon centers are formed with high stereoselectivity generally superior to dr > 95:1.