Aglaia

Abstract: Of all plant families the Meliaceae is among the more useful to man, chiefly for its high quality timbers and for the ease with which some species can be grown in plantations. Almost confined to the tropics, its species nevertheless pervade them, and occur, often conspicuously, in a variety of habitats from rain forest to mangrove swamp and semidesert. For its size, the family probably contains a wider range of floral and fruit structures than any comparable group. In what other family is there such a diversity of primitive ‘arillate’5 seeds, side-by-side with such an array of derived fruits and seeds, and still connected by intermediates? Or, to take the flower, where else can be found such a diversity of forms, from the minute, but structurally complex, flowers of Aglaia, often no larger than a pin-head, to the moth-pollinated flowers of some Turraea, with their slender staminal tubes reaching a length of 12 cm or more?

Abstract: Two cytotoxic rocaglate derivatives possessing an unusual dioxanyloxy unit, silvestrol (1) and episilvestrol (2), were isolated from the fruits and twigs of Aglaia silvestris by bioassay-guided fractionation monitored with a human oral epidermoid carcinoma (KB) cell line. Additionally, two new baccharane-type triterpenoids, 17,24-epoxy-25-hydroxybaccharan-3-one (3) and 17,24-epoxy-25-hydroxy-3-oxobaccharan-21-oic acid (4), as well as eleven known compounds, 1β,6α-dihydroxy-4(15)-eudesmene (5), ferulic acid (6), grasshopper ketone (7), apigenin, cabraleone, chrysoeriol, 1β,4β-dihydroxy-6α,15α-epoxyeudesmane, 4-hydroxy-3-methoxyacetophenone, 4-hydroxyphenethyl alcohol, ocotillone, and β-sitosterol 3-O-β-d-glucopyranoside, were also isolated and characterized. The structures of compounds 1−4 were elucidated by spectroscopic studies and by chemical transformation. The absolute stereochemistry of silvestrol (1) was established by a X-ray diffraction study of its di-p-bromobenzoate derivative, and the structure...

Abstract: The structures and relative stereochemistries of recaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran isolated from Aglaia elliptifolia, and dehydrorocaglamide, derived from rocaglamide, have been established from spectral and single-crystal X-ray analysis.

Abstract: The genus Aglaia is the source of a unique group of natural products featuring a cyclopenta(b)tetrahydrobenzofuran skeleton. Commonly these compounds, which until now include more than 50 naturally occurring derivatives, are named after the parent compound, rocaglamide, which was described for the first time almost twenty years ago. This review highlights the chemical diversity of rocaglamide derivatives and of biogenetically similar compounds from the genus Aglaia and their remarkable biological activity in the fields of insecticides and cytostatic agents. With a few exceptions, all naturally occurring rocaglamide derivatives exhibit striking insecticidal activity against various pest insects. In addition, they display pronounced cytostatic activity against human cancer cell lines in vitro. Furthermore, it was shown recently that rocaglamide and several of its congeners inhibit NF-κB induced gene activation in human T cells and are able to elicit apoptosis in resistant tumor cells. Taken together, these data make rocaglamide derivatives interesting candidates for possible therapeutic agents primarily in the field of cancer chemotherapy. In some Aglaia species, rocaglamide derivatives co-occur with biogenetically similar natural products of the aglain, aglaforbesin or forbaglin type. These latter compounds differ from rocaglamide and its congeners mainly by the nature of their heterocycle. Furthermore, they seem to be devoid of significant biological activity at least in the areas mentioned above, thereby pointing to the cyclopenta(b)tetrahydrobenzofuran core of the rocaglamide skeleton as one essential structural requirement for the pronounced biological activity of the rocaglamides.