Alkaloids and other compounds from Psychotria correae

Planta Medica, 1993

From extracts of the leaves and/or the roots of Psychotria correae, isodolichantoside and the new alkaloids correantoside, 10-hydroxycorreantoside, correantines A to C, and 20-epi-correantine B were isolated, in addition to two cerebrosides and some isoprenoids. Structures were established by spectroscopic studies in combination with chemical interconversions and partial synthesis.

Journal of the Brazilian Chemical Society, 2011

Os extratos orgânicos das folhas e raízes de Psychotria stachyoides forneceram o novo alcaloide indólico monoterpênico glicosilado N-desmetil-correantosida, além de bizantionosida B, a-amirina, éter metílico da alizarina, rubiadina, escopoletina, ácido barbinévico e uma mistura de b-sitosterol e estigmasterol glicosilados. A caracterização estrutural dos compostos isolados foi estabelecida com base na espectroscopia no infravermelho (IR), espectrometria de massa (MS) e particularmente ressonância magnética nuclear (RMN) 1D e 2D.

Journal of the Brazilian Chemical Society, 2012

A continuidade do estudo fitoquímico de P. prunifolia com a análise dos extratos etanólicos obtidos a partir de suas raízes e galhos levou ao isolamento de cinco alcaloides indol-b-carbolínicos dos quais, dois derivados, o 10-hidróxi-iso-deppeaninol e o N-óxido-10-hidróxi-antirhina são descritos pela primeira vez. As estruturas foram determinadas por análise de técnicas espectroscópicas de IV, EMAR e RMN ( 1 H e 13 C, 1D e 2D). A avaliação da atividade frente à Leishmania amazonensis e Trypanosoma cruzi, mostrou que os extratos brutos e os alcaloides 14-oxoprunifoleína e estrictosamida inibiram as formas promastigotas de L. amazonensis, com valores de CI 50 de 16,0 e 40,7 mg per mL, respectivamente.

Journal of Ethnopharmacology, 1996

Psychotria viridis and P. carthagenensis are often discussed in relation to the hallucinogenic beverage Ayahuasca, used for religious, medicinal and social purposes. The significance of including P,D'chotriu species in this beverage has been understood on the basis of substantial amounts of tryptamine alkaloids detected on leaves of both P. ciridis and P. carthagenensis. Nevertheless, there is a long lasting debate over the identification of which Po,chotria species are actually traditionally employed. We here report that a P. carthagenensis leaf ethanol extract was found to be devoid of alkaloids. The extract significantly decreased mice body temperature (350 and 500 mg/kg). Toxicity assessment revealed that the extract induced sedation and slight ptoses (75% of animals treated with 1000 mg/kg). Lethality was not observed within 48 h. The data indicate that P. carthagenensis does have bioactive compound(s), possibly active at the central nervous system, but unlikely to be tryptamine alkaloids as in the case of P. viridis. Therefore, if P. carthagenensis is indeed used by ayahuasqueros, its chemical and pharmacological significance have yet to be elucidated.

The Open Bioactive Compounds Journal, 2009

Many important molecules have been discovered from tropical and sub-tropical plant biodiversity. However, the largest part of the chemical profile of such biodiversity remains unknown. Combining ethnopharmacological and chemotaxonomical investigation can be a good strategy in bioactive compound discovery. South American Psychotria species studied by this approach proved to be a rich source of new bioactive alkaloids, some of which bear unique chemical skeletons.

J Nat Prod, 1997

CHEMICAL & PHARMACEUTICAL BULLETIN, 2006

The genus Turraeanthus (Meliaceae) occurs in tropical and subtropical regions and comprises about four species in Cameroon. 1) These species have been used in Cameroonian traditional medicine for the treatment of cardiovascular disease, stomach ache, rheumatism pains, and asthma. 2) Phytochemical studies on the seeds of Turraeanthus africanus (WELW. ex. C.D.C.) PELLEGR. revealed the presence of labdane diterpenoids and a limonoid. In this paper, we describe the isolation and structural elucidation of two new alkaloids from T. africanus. The dried and ground stem bark of T. africanus was extracted with methanol. This extract was concentrated to dryness under a vacuum. Extensive column chromatography of the residue on silica gel yielded pure 10-O-demethyl-17-O-methyl isoarnottianamide (1) and 11-demethoxyl-12methoxyl oxynitidine (2), together with two known compounds that were characterized based on their spectral data, and identified as decarine, and oxynitidine. 6) Alkaloid 1, obtained as brown crystals, mp 237-239 °C, reacted positively to FeCl 3 reagent suggesting the presence of a phenolic hydroxyl group. Its high resolution electrospray-TOF mass spectrum (HR-ES-IMS) showed a pseudomolecu-lar ion peak (MϩH) ϩ at m/z 382.1283 (Calcd for C 21 H 20 O 6 N, 382.1285). The odd mass at m/z 381 indicated that it contained a nitrogen atom in the molecule. Its IR spectrum showed absorption bands for free hydroxyl at 3450 cm Ϫ1 , olefin (1631, 1517 cm Ϫ1 ), carbonyl (1663 cm Ϫ1 ), and ether (1285, 1142 cm Ϫ1 ) functionalities. The UV spectrum of compound 1 exhibited absorption maxima at 237, 291, and 332 nm. The 1 H-NMR signals at d 2.90 (3H) and d 8.25 (1H) were typical of an N(CH 3 )CHO group in compound 1. 7) This was confirmed in the 13 C-NMR spectrum by signals at d 32.6 and 163.3. Alkaloid 1 has also characteristic signals due to four aromatic protons appearing as, singlets at d 7.01, 7.40, 6.60, and 6.51, and a pair of doublet at d 7.80 (1H, Jϭ8.7 Hz) and 7.25 (1H, Jϭ8.7 Hz). On the other hand, the singlets of the aromatic rings should be located in para positions, and the two doublets indicated that the two aromatic protons were

Biochemical Systematics and Ecology, 2014

The phytochemical investigation of Psychotria vellosiana aerial parts yielded five compounds, including two triterpenes (squalene and lupeol), two steroids (stigmasterol and sitosterol), and one coumarin (scopoletin). The structures of the isolates were established based on analysis of their spectroscopic data and comparison with literature. All metabolites isolated were previously detected in Psychotria, excepting squalene that is being described for the first time from this genus. This study adds a new species to a number of reports showing the absence of alkaloid in Psychotria.

Biochemical Systematics and Ecology, 2001

S 0 3 0 5 -1 9 7 8 ( 0 1 ) 0 0 0 5 9 -X

Biochemical Systematics and Ecology, 2010