Phytochemical investigation of the branches of Annona foetida Mart. led to isolation from the CH2Cl2 extract of four alkaloids: Atherospermidine (1), described for the first time in this species, liriodenine (2), O-methylmoschatoline (3), and annomontine (4). Their chemical structures were established on the basis of spectroscopic data from IR, MS, NMR (1D and 2D), and comparison with the literature. Compounds 2–4 showed potent trypanocidal effect when evaluated against epimastigote and trypomastigote forms of Trypanosoma cruzi.
Bicyclogermacrene (35.12%), (E)-caryophyllene (14.19%) and α-copaene (8.19%). The antimicrobial and antileishmanial activities were investigated. The oil showed potent antimicrobial activity against Candida albicans and Rhodococcus equi. The oil also showed significant antileishmanial activity, giving the best results against Leishmania guyanensis. A preliminary cytotoxicity assay for this oil was carried out on hamster and mice (Balb/c) peritoneal macrophages. The results obtained were similar to pentamidine and considered not to be cytotoxic to macrophages.
1 January 2009 in Journal of the Brazilian Chemical Society
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 ¹H and 13C NMR chemical shift assignments for cassythicine are provided.
Gustavia augusta is used in the folk medicine against leishmaniosis and showed anti-inflammatory action. The phytochemical studies of the plant stem bark have led to the isolation of (22E)-stigmasta-7,22-dien-3beta-ol, 24alpha(S)-ethyl-5alpha-colesta-7,trans-22-dien-3-one, D-friedoolean-14-en-3beta-ol, D-friedoolean-14-en-3-one and D-friedoolean-14-en-3alpha-ol along with stigmasterol, alpha-amyrin, beta-amyrin, lupeol, 3alpha-hidroxi-lupeol and betulinic acid. The structures of these compounds were identified by IR, GC/MS, ¹H and 13C NMR spectral analysis and comparison with literature data.
Miraruira is a medicinal plant-based product (MPBP) that is widely used in the state of Amazonas for the treatment of diabetes, though its botanical identity remains unclear, which raises concerns about authenticity and therapeutic consistency. One solution to this problem is the use of mass spectrometry-based approaches, which have emerged as powerful tools for verifying botanical origin based on chemical composition. Thus, to confirm the botanical authenticity of miraruira, direct-injection mass spectrometry (DI-MS) and chemometric analyses (PCA and HCA) were conducted on methanol fractions of Salacia impressifolia and Connarus ruber, both suspected sources of miraruira, as well as commercial samples obtained in street markets in Manaus, Brazil. Additionally, the hexane extracts of C. ruber and the commercial samples were screened for benzoquinones using DI-MS, as these compounds are recurrent in the genus Connarus. The DI-MS and PCA analyses revealed distinct chemical profiles for each species, and identified mangiferin and epicatechin as chemical markers for S. impressifolia and C. ruber, respectively. Furthermore, PCA demonstrated that all the commercial samples exhibited chemical profiles closely aligned with C. ruber. However, the HCA indicated variability among these samples, suggesting C. ruber or related Connarus species are the primary sources of miraruira. Moreover, embelin, rapanone, and suberonone were identified as the main compounds in the hexane extracts of C. ruber and the commercial products. This study successfully confirmed the botanical authenticity of miraruira, identified key bioactive compounds related to its traditional use in the treatment of diabetes symptoms, and demonstrated the effectiveness of DI-MS as a valuable tool for addressing authenticity issues in MPBPs.