Populoside and grandidentoside from the bark of Populus grandidentata

Erickson, Richard L.; Pearl, Irwin A.; Darling, Stephen F.

doi:10.1016/s0031-9422(00)85193-6

Cited by 24 publications

(18 citation statements)

References 10 publications

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“…Compound 9 is a novel compound. Related structures with p -hydroxycinnamoyl or caffeoyl in the 2-position of the glucoside and with a cis -1,2-cyclohexanediol moiety have previously been isolated from Populus grandidentata , , Salix fragilis , and S. purpurea …”

Section: Resultsmentioning

confidence: 99%

Dovyalicin-Type Spermidine Alkaloids from Dovyalis Species

et al. 2006

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Phytochemical investigations of Dovyalis abyssinica, D. hebecarpa, and D. macrocalyx revealed two new spermidine-type alkaloids, dovyalicin E (3) and dovyalicin F (4), along with the previously described dovyalicin A (1), dovyalicin B (2), and dovyalicin C (5). In addition, a new phenol glucoside, 4-hydroxytremulacin (7), and the new 1,2-cyclohexanediol glucoside 9, as well as the known compounds methyl 1-hydroxy-6-oxocyclohex-2-enecarboxylate (6) and tremulacin (8), were isolated. The structures were established using homo- and heteronuclear two-dimensional NMR experiments and chiroptical methods. At ambient temperature, the N-disubstituted amide 4 exists as a mixture of cis and trans conformers. Variable-temperature (1)H NMR studies showed that time-averaged spectra are obtainable at 348 K, and the activation parameters determined for the rotation about the amide bond were DeltaH++ = 89 +/- 4.6 kJ/mol, DeltaS++ = 65 +/- 14 kJ/mol.K, and DeltaG++(298K) = 70 +/- 4.5 kJ/mol.

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Section: Resultsmentioning

confidence: 99%

Dovyalicin-Type Spermidine Alkaloids from Dovyalis Species

et al. 2006

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“…Additionally, enzymatic [17] hydrolysis afforded glucose [19]; alkaline [18] hydrolysis yielded p-coumaric acid and catalpol Ic [21] portions of hexane until defatting was completed. In a similar manner a methanolic extract was prepared affording after evaporation in vacuo, 26 g of a dark crude solid.…”

Section: Introductionmentioning

confidence: 99%

Isolation of 6-O-(p-Coumaroyl)-Catalpol from Tabebuia rosea¹

Compadre¹,

Jáuregui²,

Nathan³

et al. 1982

Planta Med

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From the bark of Tabebuia rosea, the iridoid 6-O-(p-coumaroyl)-catalpol (specioside) was isolated. Antimalarial properties have been attributed to the infusion prepared from this part of the plant, although the compound failed to exhibit antimicrobial activity. The structure was corroborated by comparison with reported data for specioside as well as some additional chemical and spectroscopic data described herein.

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“…Consequently, 1 was determined to be salicyl alcohol l-0^-D-(3'-benzoyl)glucopyranoside, i.e., 3'-benzoylsalicin, and named chaenomeloidin. In the Salicaceous plants, many kinds of acylated salicin derivatives, which are usually esterified at C-2' or C-6' in the glucose moiety, have been reported (6)(7)(8)(9)(10)(11)(12)(13)(14). To the best of our knowledge, chaenomeloidin is the first example of a 3'-benzoyl ester of salicin.…”

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confidence: 99%