New Euphorbiaceae from Trinidad and Tobago

Philcox, D.

doi:10.2307/4117268

Cited by 4 publications

(6 citation statements)

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“…It is interesting that both tembamide acetate [1] and alatamide [2] were isolated from the plant P. guayranum, while there was no evidence of tembamide [3], their putative biogenetic precursor. Further, it is noteworthy that ß-phenylethylamine-derived amides, which are of taxonomic significance in the Rutaceae family, have now been isolated from a member of the Piperaceae.…”

Section: Mild Hydrolysis Of Compound 1 Gavementioning

confidence: 99%

“…The plant material was air-dried (ca. 30°) for 1 Compound 2 was also obtained as white needles (6 mg), mp 188-189°( petroleum ether/ Me2CO) [lit. (11) 178-180°]; uv (MeOH) X max 204, 222, 308 nm (e 10700, 13400, 17200); irv max 3320, 1640, 1290, 1250, 1170, 1030,945 cm" '; eims mlz (%) [M]+ 253 (40), 150 (6), 149 (6), 148 (6), 135 (13), 134 (21), 121 (11), 105 (100), 77 (30); *H nmr see Table 1.…”

Section: Mild Hydrolysis Of Compound 1 Gavementioning

confidence: 99%

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β-Phenylethylamine-Derived Amides from Piper guayranum

Maxwell¹,

Ramprasad²

1989

J. Nat. Prod.

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The acetone extract of the aerial parts of Piper guayranum yielded tembamide acetate [1] and alatamide [2] but not tembamide [3]. Compound 1 has not been previously reported as a natural product while both 2 and 3 has only been encountered so far in species of Rutaceae.Piper guayranum C.DC. (Piperaceae) is a tall, slender shrub that is found in shady, elevated regions of Trinidad, Tobago, and Venezuela (1). There is no record of folkloric medicinal use of this plant, and there appear to be no reported chemical studies either. We wish to report the results of our studies on the aerial parts of P. guayranum occurring in Trinidad.Repeated vacuum liquid chromatography (vie) of the Me2CO extract resulted in the isolation of three crystalline compounds. The most polar compound 1 was obtained as white needles, mp 159°( petroleum ether/Me2CO). High resolution eims gave an [M]+ (at mlz 313 -1308) which indicated a molecular formula of C18H19N04 ([M}+ calculated 313.1314). Four bands, at 208, 225, 270, and 278 nm, were observed in the uv spectrum. The ir spectrum exhib-OMe ited absorptions at 3315, 1727, 1645, 1532, and 1510 cm-1 indicating the presence of both amide and ester groups.*H nmr (Table 1) suggested a 1,4-disubstituted aromatic ring (AB type fourproton doublet of doublets at 6.92 and 7.35) as well as a monosubstituted one (five-proton multiplet at 7.45-7.83).Acetate (three-proton singlet at 2.12) and aromatic methoxy (three-proton singlet at 3.82) groups were also indicated. On complete exchange after the

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Section: Mild Hydrolysis Of Compound 1 Gavementioning

confidence: 99%

Section: Mild Hydrolysis Of Compound 1 Gavementioning

confidence: 99%

β-Phenylethylamine-Derived Amides from Piper guayranum

Maxwell¹,

Ramprasad²

1989

J. Nat. Prod.

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“…accounted for three of these while the other two appeared at 1.68 and 1.78. Seven allylic methylene groups were also indicated for 1 (as opposed to five in 6).…”

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confidence: 94%

“…H-6', 10', 14'........ 5.12 (m) 5.10(m) 5.11 (m) 5.16 (m) 5.12(m) H-16' . 1.68 (brs) 1.68 (brs) 1.68 (br s)…”

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confidence: 99%

Novel Prenylated Hydroxybenzoic Acid Derivatives from Piper saltuum

Maxwell¹,

Rampersad²

1989

J. Nat. Prod.

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The acetone extract of the aerial parts of Piper saltuum yielded three new prenylated hydroxy benzoic acids, 1, 2 and 3, the structures of which were determined principally by spectroscopic methods.Piper saltuum C.DC (Piperaceae) is a relatively rare species in the New World(1) and has not been previously studied.We examined the aerial parts of P. saltuum occurring in Trinidad and wish to report the isolation of three new prenylated hydroxy benzoic acid derivatives.Despite extensive study of Piperaceae, this class of compounds has only very recently been isolated from Piper species (2-5).Compound 1 was obtained as a yellow, viscous oil. Its uv spectrum showed bands at 217 and 258 nm and its ir spectrum exhibited absorptions at 3400 (br), 1675, and 1601 cm \ which suggested an aromatic carboxylic acid. Indeed, the *H-nmr spectrum of 1 (Table 1) was very similar to that of the previously reported compound 6 (4-6). However, in the case of 1 five vinyl methyl groups, rather than the four that would be expected for 6, were indicated. The signal at

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“…C. DC., which occurs in moist, shady regions in Trinidad (1) and has not been previously studied. We wish to report the isolation, from the aerial parts of the plant, of a new dihydrocinnamoyl 2-pyrrolinone amide 1 and three prenylated hydroxy benzoic acids previously isolated from Piper saltuum (2).…”

mentioning

confidence: 99%