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Biomedical subjects

S W Pelletier

Publications and source records attributed to S W Pelletier.

At least 19 recordsLinked to original sources
PubMed2001

Insect repellent activity of diterpenoid alkaloids.

Diterpenoid and norditerpenoid alkaloids were tested against Tribolium casteneum (Herbst.) in order to assess their repellent activity. Of 29 tested alkaloids, 21 compounds showed promising insect repellent activity, while eight of them were not found to be active. The alkaloids were obtained from Delphinium, Consolida and Aconitum species. The highest activity was found in hetisine, a diterpene alkaloid (59.37%) and the lowest activity in another diterpene alkaloid venulol (31.25%).

Animals↗
PubMed2001

Norditerpenoid and diterpenoid alkaloids from Turkish Consolida orientalis.

From the aerial parts of Consolida orientalis collected in Turkey, a new diterpenoid alkaloid designated as consorientaline has been isolated along with the known norditerpenoid alkaloids delsoline, delcosine, gigactonine, and takaosamine. The structure of consorientaline (1) was established by spectroscopic studies and chemical correlation with dihydroajaconine (2).

Alkaloids↗
PubMed2001

Diterpenoid alkaloids from Delphinium virgatum poiret.

From the aerial parts of Delphinium virgatum Poiret, which is an endemic plant growing wildly in Turkey, a new norditerpenoid alkaloid, N-deethylperegrine alcohol, has been isolated along with the known alkaloids peregrine, peregrine alcohol, davisinol, hetisine, hetisinone and atisine.

Alkaloids↗
PubMed2000

Diterpenoid alkaloids from the aerial parts of Aconitum anthora L.

Isolation and identification of six diterpenoid alkaloids, from Aconitum anthora L. are described. All proton detected 2D NMR techniques have been used for unambiguous 1H and 13C chemical shift assignments of guan-fu-base-Y (6). This is the first investigation of the diterpenoid alkaloids of this plant species.

Alkaloids↗
PubMed1998

Certain norditerpenoid alkaloids and their cardiovascular action.

Thirteen new derivatives of norditerpenoid alkaloids, namely, 8-deacetyl-8-p-aminobenzoyldelphinine (1), 8-deacetyl-8-anthranoyldelphinine (2), 8-deacetyl-8-(4-hydroxy-3-methoxycinnamoyl)delphinine (3), 16-demethoxy-15,16-didehydro-8-p-anisoyl-14-benzoyldelpho nine (4), 6-acetylheteratisine N-oxide (6), 3,8-diacetylfalconerine (7), 8-stearoylfalconerine (8), 8-linolenylfalconerine (9), 13-acetylpyrodelphinine (11), 13-acetyldelphinine N-oxide (13), N-deacetyl-8,9-diacetyllappaconitine (14), 8, 9-(methylenedioxy)lappaconine (15), and 16-epipyroaconitine N-oxide (17), were prepared, and their structures were established by analysis of spectroscopic data (1D and 2D NMR, HRFABMS). The preliminary in vivo cardiovascular action (hypotensive, bradycardic, and ventricular arrhythmias) of these new compounds was tested in male Sprague-Dawley rats. The results are reported herein.

Alkaloids↗
PubMed1997

Selective demethylation of some aconitine-type norditerpenoid alkaloids.

Demethylation of some aconitine-type norditerpenoid alkaloids was carried out with trimethylsilyl iodide and with HBr in glacial AcOH. Aconitine (10), cammaconine (23), delphinine (3), falconerine (18), lappaconitine (22), and talatizamine (24) afforded partially demethylated products. When methoxyl groups are present at the C-16 and C-18 positions, these are demethylated, and the methoxyl group at the C-1 position underwent demethylation in none the alkaloids studied except falconerine (18). With HBr-AcOH, in the case of alkaloids possessing a C-3 hydroxyl group, the methoxymethyl at C-18 formed a tetrahydrofuran, cyclizing at the C-6 position. Detailed NMR spectral studies (1H, 13C, 1H homonuclear COSY, HETCOR, and selective INEPT) carried out on the demethylation products have enabled accurate chemical shift assignments to be made for the demethylated alkaloids.

Aconitine↗
PubMed1997

Study of the acid-catalyzed isomerization of dihydroveatchine.

A study of the acid-catalyzed isomerization of dihydroveatchine (5) resulted in the isolation of a single major compound, the aldehyde 6. Structure 6 has been derived from its spectral data. Reduction of 6 with NaBH4 gave compound 7, which was characterized through detailed NMR studies including 1D, 2D, and selective INEPT experiments, as well as preparation of its mono- and bis(p-nitrobenzoyl) derivatives 8 and 9. A plausible mechanism for the formation of 6, derived from the spectral data of the isomerized product obtained by deuterium labeling, is reported. Interestingly, the acid-catalyzed isomerization products of the allylic alcohols garryfoline (1) and dihydroveatchine (5) are different and appear to be dependent on the configurational orientation of the C(15) hydroxyl group. Unambiguous NMR chemical shift assignments for 5 are also reported.

Alkaloids↗
PubMed1996

Diterpenoid alkaloids from Delphinium davisii.

Three new hetisane-type diterpenoid alkaloids, davisinol (6), 18-benzoyldavisinol (7), and Davisin (9) have been isolated from Delphinium davisii Munz. and their structures established by detailed spectroscopic studies. Accurate 1H- and 13C-NMR assignments have been made for kobusine (8), a related hetisane-type alkaloid, and karakoline (5), a norditerpenoid alkaloid. The known norditerpenoid alkaloids 14-acetylperegrine (4), 6-deacetylperegrine (3), and karakoline (5) and the diterpenoid alkaloids hetisine and hetisinone were also isolated.

Alkaloids↗
PubMed1996

Diterpenoid alkaloids from Consolida oliveriana.

From the aerial parts of Consolida oliveriana (DC) Schröd. a new norditerpenoid alkaloid consolidine (2) has been isolated, in addition to the known alkaloids pubescenine (1), gigactonine, and delsoline and the diterpenoid alkaloid ajaconine (4). The structure of alkaloid 2 was established on the basis of its physical and spectroscopic data including detailed NMR studies. A detailed NMR study on ajaconine (4) resulted in the revision of 11 13C chemical shift assignments.

Diterpenes↗
PubMed1995

Effect of diterpenoid alkaloids on cardiac sympathetic efferent and vagal afferent nerve activity.

The diterpenoid alkaloid, lappaconitine, at a dose of 150 micrograms/kg (i.v.) increased cardiac vagal afferent nerve activity (16.2%) and reduced cardiac sympathetic efferent nerve activity (12.5%). A polar analog, N-deacetyllappaconitine, at this same dose, increased cardiac vagal afferent nerve activity (40%) and reduced cardiac sympathetic efferent nerve activity (23.5%). Both of these agents also reduced arterial blood pressure and heart rate. A larger dose of lappaconitine (300 micrograms/kg i.v.) produced the same changes in nerve activities and cardiac function as the lower dose. Two other structurally related agents, lycoctonine and aconine, failed to alter these variables in doses up to 300 micrograms/kg. These data suggest that certain diterpenoid alkaloids activate autonomic reflex receptors, including cardiac reflex receptors. The polar agent, N-deacetyllappaconitine, appears to be more effective on cardiac reflex receptors than the non-polar agent, lappaconitine. Such agents may be useful in the treatment of hypertension.

Aconitine↗
PubMed1995

Two new norditerpenoid alkaloids from Delphinium elatum var. "black night".

Two new norditerpenoid alkaloids, blacknine [1] and blacknidine [2], have been isolated from the whole plants of Delphinium elatum var. "black night" along with six known alkaloids. The structures of the new alkaloids 1 and 2 were derived from their spectroscopic data (1H, 13C, DEPT, COSY, HETCOR, and selective INEPT nmr experiments). The phytochemistry of this plant variety has not been examined previously.

Alkaloids↗
PubMed1995

Structure-activity relationships of norditerpenoid alkaloids occurring in toxic larkspur (Delphinium) species.

Fourteen norditerpenoid alkaloids present in larkspur (Delphinium) species associated with cattle poisoning on grazing land in the western United States have been toxicologically assessed in a mouse bioassay. Toxicity data for these alkaloids have established the tertiary nitrogen atom and anthranilic acid esterification as important structural features necessary to impart toxicity to lycoctonine-type norditerpenoid alkaloids. Variation in C-14 functionality of the toxic alkaloids is also a factor that influences toxicity in these compounds. The relationship of the structure-activity information of this study to previous in vitro neuromuscular studies is discussed.

Alkaloids↗
PubMed1995

N-oxides of some norditerpenoid alkaloids.

Eight new N-oxides [1-8] of the norditerpenoid alkaloids aconitine, ajacine, delphinine, delphisine, deltaline, heteratisine, lappaconitine, and N-deacetyllappaconitine have been prepared with m-chloroperbenzoic acid. The structures of these compounds were established on the basis of their spectroscopic data (1H, 13C, DEPT, COSY, HETCOR, and selective INEPT nmr experiments). The complete nmr chemical shift assignments for all eight N-oxides are reported. Table 2 shows the differences between the 13C-nmr shifts of the N-oxides compared with those of the parent alkaloids.

Chlorobenzoates↗
PubMed1994

Long-chain fatty acid esters of some norditerpenoid alkaloids.

Several C-8 long-chain fatty acid esters of aconitine-type norditerpenoid alkaloids namely, aconitine, delphinine, delphisine, falconerine-8-acetate, mesaconitine, and pseudaconitine bearing a C-8 acetyl group, have been prepared. Preparation was achieved by heating the alkaloids with the neat fatty acid under vacuum. All the compounds have been fully characterized by physical and spectroscopic data. Identification and characterization of reaction byproducts are also included.

Alkaloids↗
PubMed1990

Structure of a photodimer of 3-acetoxy-2-inden-1-one: 9,10-dioxoindano[2',3':4,3]cyclobuta[1,2-b]indan-4b,4c-diyl diacetate.

C22H16O6, Mr = 376.37, monoclinic, P21/c, a = 9.555 (3), b = 15.664 (2), c = 12.300 (4) A, beta = 100.08 (2) degrees, V = 1812.5 (5) A3, Z = 4, Dx = 1.379 g cm-3, lambda(Cu K alpha) = 1.5418 A, mu = 8.0 cm-1, F(000) = 784, room temperature, R = 0.047, wR = 0.064 for 3203 observed reflections [I greater than 3 sigma (I)]. The molecule exists as the syn-trans isomer in the crystal. The crystal structure exhibits a number of C--H...O intermolecular contacts.

Chemical Phenomena↗
PubMed1990

Structure of delvestine: a norditerpenoid alkaloid from Delphinium vestitum Wall.

C32H46N2O8, Mr = 586.73, m.p. 458-460 K, monoclinic, P2(1), a = 9.187 (2), b = 14.979 (3), c = 11.474 (2) A, beta = 104.09 (2) degrees, V = 1531.5 (9) A3, Z = 2, D chi = 1.27 g cm-3, lambda(Cu K alpha) = 1.5418 A, mu = 7.1 cm-1, F(000) = 632, room temperature, R = 0.039, wR = 0.053 for 3077 observed reflections [I greater than 3 sigma(I)]. The aminoethyl C(21) atom is disordered. There is an intramolecular hydrogen bond between O(1)--H(O1) and N(1) atoms, and between O(3)--H(O3) and O(4), stabilizing the boat conformations adopted by the rings A and D.

Alkaloids↗