Flora da Reserva Ducke, Amazonas, Brasil: Annonaceae

Maas, P.J.M.; Maas, Hiltje; Miralha, J. M. S.; Junikka, Leo

doi:10.1590/2175-7860200758307

Cited by 18 publications

(23 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…However, A. amazonica produces as its major secondary metabolite, the pimaradiene-type diterpene acanthoic acid (1), as evidenced by the surprising and extraordinary appearance of large glassy prism crystals in very high quantities, practically 65% of the hexane extract, which allowed their direct collection and investigation by spectrometric methods, mainly by NMR analysis, without the need of any additional purification procedure. 18 These findings, confirmed by 13 C NMR data as well as by one-bond and long-range heteronuclear 1 H-13 C correlations from HSQC and HMBC experiments, along with the MS fragmentation pattern, mainly by the ion at m/z 234, attributed to an elimination of 2-methylbutadiene by a retro-Diels-Alder process, allowed us to establish the structure of 1 as acanthoic acid. 18 Additionally, all relative configurations in 1 were established by 1D nOe experiments, as follows.…”

Section: Chemical Studiesmentioning

confidence: 57%

Section: General Proceduresmentioning

confidence: 95%

“…13 and 100.61 MHz, respectively. 1 H- 13 C correlation (HSQC and HMBC) experiments were performed with the average coupling constant 1 J(C,H) and LR J(C,H) optimized for 140 and 8 Hz, respectively. The 1D nOe experiments were obtained by selective excitation of each 1 H NMR frequency and gradient selection using the double-pulsed field gradient spin-echo (DPFGSE)-nOe experiment with constant mixing time of 500 ms. IR spectra were recorded in KBr pellets on a Perkin-Elmer Spectrum 2000 spectrometer.…”

Section: General Proceduresmentioning

confidence: 95%

“…In Brazil this species commonly occurs in the Amazon, mainly in the states of Amazonas and Pará. 13 To the best of our knowledge, only one previous phytochemical study has described the isolation and identification of cyanogenic constituents from this species. 14 Here we describe the isolation and structural identification of the chemical constituents from the stems of A. amazonica, including acanthoic acid (1), a Acanthoic Acid and other Constituents from the Stem of Annona amazonica (Annonaceae) J. Braz.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae)

Pinheiro

Xavier

Souza

et al. 2009

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

O presente trabalho descreve o isolamento, a partir do caule de Annona amazonica, do ácido acantóico, um diterpeno do tipo pimaradieno que possui várias e importantes atividades biológicas descritas na literatura. Neste estudo foi verificado que este composto apresenta significante atividade tripanocida contra as formas epimastigotas de Trypanosoma cruzi. Também foi constatado que este diterpeno é o constituinte majoritário da planta, encontrado em cerca de 65% do extrato hexânico, demonstrando que A. amazonica é uma nova fonte natural renovável desta substância. Além do ácido acantóico, a investigação química resultou no isolamento dos alcalóides liriodenina e cassiticina, entre outros compostos, tais como terpenos, esteróides e ácidos graxos. Adicionalmente, é descrita a completa e inequívoca atribuição dos deslocamentos químicos de RMN de 1 H e 13 C da cassiticina.The present work reports the isolation of acanthoic acid, a promising pimaradiene-type diterpene with several important biological activities described in the literature, from the stems of Annona amazonica. We found that acanthoic acid has significant trypanocidal activity against the epimastigote forms of Trypanosoma cruzi. This diterpene is the major constituent of the plant, comprising at least 65% of the hexane extract, demonstrating that A. amazonica is a new renewable natural source for this compound. The chemical investigation also resulted in the isolation of the alkaloids liriodenine and cassythicine, and other compounds including terpenes, sterols, and fatty acids. Additionally, the complete and unequivocal 1 H and 13 C NMR chemical shift assignments for cassythicine are provided. Keywords: Annona amazonica, Annonaceae, acanthoic acid, cassythicine, trypanocidal activity IntroductionThe family Annonaceae, comprised of tropical and subtropical species with about 135 genera and more than 2500 species and widely distributed in South and Central America, Africa, Asia, and Australia, 1 is known for its edible fruits and the medicinal properties of several species. 2 In Brazil, there are 26 genera with about 260 species, including the genus Annona, which contains approximately 120 species. 3 Chemical investigations of species of Annonaceae have revealed their high chemical diversity in terms of secondary metabolites, such as alkaloids, acetogenins, terpenoids and lactones. These compounds have shown important biological activities, including antiparasitic, in particular against Leishmania sp., Plasmodium falciparum, and Trypanosoma cruzi. [4][5][6][7][8][9][10][11][12] Annona amazonica R.E. Fries is a tropical tree that grows up to 20-25 m tall and 35-60 cm in diameter, and is found from Panama to South America. In Brazil this species commonly occurs in the Amazon, mainly in the states of Amazonas and Pará. 13 To the best of our knowledge, only one previous phytochemical study has described the isolation and identification of cyanogenic constituents from this species. 14 Here we describe the isolation and structural identification of the chemica...

show abstract

Section: Chemical Studiesmentioning

confidence: 57%

Section: General Proceduresmentioning

confidence: 95%

Section: General Proceduresmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Acanthoic acid and other constituents from the stem of Annona amazonica (Annonaceae)

Pinheiro

Xavier

Souza

et al. 2009

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…1 Some species of this genus, such as Xylopia aethiopica, X. sericea and X. aromatica are used as condiments, as well as for medicinal purposes. 2 Previous phytochemical investigations on some species of this genus have indicated the presence of terpenoids, 3 alkaloids, 4 and flavonoids, 4 exhibiting several pharmacological activities such as antifungal, 3 antioxidant, 2,4 antileishmanial, 5 cytotoxic, 6 antinociceptive, 7 acaricidal, 8 and insecticidal properties.…”

Section: Introductionmentioning

confidence: 99%