Five New Prenylated Stilbenes from the Root Bark of Lonchocarpus chiricanus

Abstract

Besides the known compounds longistylines C (1), D (2), and 3,5-dimethoxystilbene (5), five new prenylated stilbenes, named chiricanines A--E (3, 4, 6--8), have been isolated from the root bark of Lonchocarpus chiricanus. Their structures were resolved on the basis of spectrometric methods including (1)H, (13)C, and 2D NMR experiments and mass spectrometry. Compound 3 was the only prenylated stilbene to demonstrate antifungal effects against Cladosporium cucumerinum. Four of the isolated compounds showed toxic properties against larvae of the yellow fever-transmitting mosquito Aedes aegypti. Compound 5 was found to be as potent as rotenone in larvicidal dilution tests.

Prenylation of Flavonoids by Biotransformation of Yeast Expressing Plant Membrane-Bound Prenyltransferase SfN8DT-1

“…1,2) In addition, prenylated flavonoids have been identified as active components of various medicinal plants, showing a variety of biological activities, such as antimicrobial, antitumor, anti-androgen, anti-leishmania, and anti-NO production. [3][4][5][6] Due to these beneficial effects on human health, prenylated flavonoids draw the substantial interest of many researchers as lead compounds for new drugs and for applications in functional foods.…”

A Stilbenoid-Specific Prenyltransferase Utilizes Dimethylallyl Pyrophosphate from the Plastidic Terpenoid Pathway

“…Interestingly, oxyresveratrol and prenylated oxyresveratrol reported in the bark of Artocarpus dadah (Su et al, 2002) along with pinosylvin isolated from pine (Pinus spp.) hardwood have not been identified in any peanut tissue, while the prenylated product of pinosylvin, chiricanine A, that was first described in the roots of Lonchocarpus chiricanus (Ioset et al, 2001), has been described in peanut seeds after infection with the fungus A. flavus (Sobolev et al, 2009).…”

“…This is the most common type of prenylation found in prenylated stilbenoids from various plant families. For instance, longistylines C, longistylines D, and chiricanine A found in L. chiricanus (Leguminosae; Ioset et al, 2001) also have the same dimethylallyl moiety. Artoindonesianin N with one dimethylallyl moiety and 4-dimethylallyloxystilbene were reported in Artocarpus integer (Moraceae; Boonlaksiri et al, 2000) and Artocarpus gomezianus (Moraceae; Hakim et al, 2002), respectively.…”

Synthesis and Characterization of Novel Stilbene Derivatives with 1,3,4‐Oxadiazole Unit

“…[1][2][3][4][5] In addition, they are also one of the important organic two-photon absorption materials which possess potential application in photochemical therapeutics, micro-and nano-manufacture, twophoton laser scanning fluorescence microscopy. [6][7][8][9][10] Moreover, stilbenyl two-photon materials which demonstrate distinctive blue emission properties become the current research focus.…”