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

Fish, F.; Gray, Alexander I.; Waigh, Roger D.; Waterman, Peter G.

doi:10.1016/s0031-9422(00)89011-1

Cited by 18 publications

(20 citation statements)

References 7 publications

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“…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.…”

Section: Methodssupporting

confidence: 90%

“…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.…”

Section: Introductionmentioning

confidence: 99%

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

Still

Sacalis

et al. 2001

Phytotherapy Research

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Four pyranocoumarins; dipetaline, alloxanthoxyletin, xanthoxyletin and xanthyletin; and two lignans; sesamin and asarinin were isolated from the northern prickly ash, Zanthoxylum americanum. To varying degrees, all inhibited the incorporation of tritiated thymidine into human leukaemia (HL-60) cells. Dipetaline was the most active with an IC(50) of 0.68 ppm, followed by alloxanthoxyletin (1.31 ppm), sesamin (2.71 ppm), asarinin (4.12 ppm), xanthoxyletin (3.48 ppm) and xanthylletin (3.84 ppm).

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Section: Methodssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

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

Still

Sacalis

et al. 2001

Phytotherapy Research

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“…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 .…”

Section: Introductionmentioning

confidence: 99%

“…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].…”

Section: Introductionmentioning

confidence: 99%

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

Vlachou

Gabriel

Litinas

2018

Journal of Heterocyclic Chem

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Dipetalolactone and 4‐methyldipetalolactone are prepared in excellent yield by a one‐pot tandem propargylation/Claisen rearrangement/cyclization reaction of the corresponding 5,7‐dihydroxycoumarins with 3‐chloro‐3‐methylbut‐1‐yne in the presence of Cs2CO3 under microwave irradiation. The analogous reactions of propargyl chloride with esculetins or 5,7‐dihydroxycoumarins led to dipropargyloxy derivatives. The later by treatment with gold nanoparticles supported on TiO2 or BF3.Et2O in N,N‐dimethylformamide (DMF) under microwave irradiation resulted in very good to excellent yield to the corresponding fused dipyranocoumarins. The reactions of esculetins with 3‐chloro‐3‐methylbut‐1‐yne gave mainly exomethylene fused dioxino[g]coumarins.

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“…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.…”

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confidence: 99%

Natural and Synthetic 2,2-Dimethylpyranocoumarins with Antibacterial Activity

et al. 2005

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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 (10-15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products. The type of fusion of the pyrano ring in all cases has been established by 2D NMR spectroscopy. The compounds have been studied for their in vitro antibacterial activity, which has been compared with that of some previously synthesized seselin derivatives. The most active compounds were 3, 7, 8, 11, and 14. Some structure-activity relationships are discussed.

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

Cited by 18 publications

References 7 publications

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

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

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

Natural and Synthetic 2,2-Dimethylpyranocoumarins with Antibacterial Activity

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