Detalolactone: A novel pyranocoumarin from the root bark of Zanthoxylum dipetalum

Cytotoxic coumarins and lignans from extracts of the northern prickly ash (Zanthoxylum americanum)

“…IR UV l nm(MeOH): 206, 237, 287. IR cm À1 : 2929, 2849, 1500, 1444, 1365, 1250, 1195, 1096, 1058, 1036 All of the above data are consistent with values reported in the literature (Fish et al, 1975;1976;Robert andSubramanin, 1937 Gustafson et al, 1994;Greger and Horfer, 1980) with the exception of compound 2, for which spectral data have not been published previously. were cultivated in the 1.62% RPMI 1640 medium, supplemented with 10% fetal calf serum and 1% penicillin-streptomycin.…”

“…Earlier phytochemical work on the bark and berries resulted in the identification of some coumarins and alkaloids (Fish et al, 1975;Saqib et al, 1990;Robert and Sabramanin, 1937). Coumarins constitute a major class of O-heterocyclic natural products with widespread distribution and broad pharmacological profile (Fish et al, 1976;Murray, 1991;Murray and Forbes, 1967), including anticancer, carcinogenic and antiviral (HIV) activities (Gustatson et al, 1994). Lignans have also been shown to have cytotoxic and antimitotic properties.…”

One‐pot Synthesis of Fused Dipyranocoumarins from Dihydroxycoumarins and Propargyl Chlorides under Microwave Irradiation

“…Dipetalolactone (Fig. ), isolated from the tree Zanthoxylum dipetalum [4a], examined for cytotoxic activity [4b]. (+)‐Calanolide A is a nonnucleoside HIV‐1 specific reverse transcriptase inhibitor .…”

“…Dipyranocoumarins and almost exclusively dipetalolactone have been synthesized from 5,7‐dihydroxycoumarin and 3‐methylbut‐2‐enal [3e, 15a] in low yields or 4,4‐dimethoxy‐2‐methylbutan‐2‐ol[4, 15b] in moderate yields by refluxing in pyridine. Dipetalolactone has been obtained also by the pyrolysis in N , N ‐diethylaniline at 180°C of bis(1,1‐dimethylpropargyl) ether, derived from the reaction of 5,7‐dihydroxycoumarin and 2‐chloro‐2‐methylbut‐3‐yne [15c].…”

Natural and Synthetic 2,2-Dimethylpyranocoumarins with Antibacterial Activity

“…A new efficient synthetic approach to the natural coumarins 5-hydroxyseselin (5), 5-methoxyseselin (3), and (() cis-grandmarin (9) is described as well as the synthesis of some new derivatives in the 5-methoxyseselin series (10)(11)(12)(13)(14)(15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products.…”