Phytochemical Study of Hippeastrum diniz-cruziae Dutilh & Semir and Hippeastrum glaucescens (Mart.) Herb. (Amaryllidaceae)
Name: VANESSA DIAS DOS SANTOS
Type: PhD thesis
Publication date: 28/08/2019
Advisor:
Name |
Role |
|---|---|
| WARLEY DE SOUZA BORGES | Advisor * |
Examining board:
| Name |
Role |
|---|---|
| ÁLVARO CUNHA NETO | Internal Examiner * |
| FERNANDA OLIVEIRA DAS CHAGAS | External Examiner * |
| RICARDO MACHADO KUSTER | Internal Examiner * |
| THIAGO ANDRE MOURA VEIGA | External Examiner * |
| WARLEY DE SOUZA BORGES | Advisor * |
Summary: The interest in the study of the Amaryllidaceae family is related by yours relevant chemical and biological potential that has presented over the years. The objective of this work is the isolation and characterization of alkaloids present in two Brazilian species, Hippeastrum diniz cruziae (leaves, bulbs and roots) and Hippeastrum glaucesce ns ( Initially, an acid base extraction was performed in the methanolic extracts and liquid liquid partition of the vegetal parts, obtaining the acid AcOEt and alkaloid enriched fractions. These extracts were analyzed by GC MS and indicated to Hippe astrum diniz cruziae 39 known alkaloids and 24 unidentified compounds. For Hippeastrum glaucescens 12 known alkaloids and 9 unknown compounds were identified. These extracts were subjected to various chromatographic separation techniques in order to isolat e and purify these compounds. As a result, 5 Hippeastrum diniz cruziae alkaloids were isolated: cruzinine ( I), 7 deoxy narciclasine ( II), licoryne ( III), pseudolycorine and ungiminorine ( V), with cruzinine being an unpublished alkaloid of the type homolicorin, elucidated by GC MS, one and two dimensional NMR, Circular Dichroism and, mainly, X ray Crystallography. This compound presented a unique characteristic within Amaryllidaceae alkaloids, evidenced by the stereochemistry of positions H 1 and H 10b. Fractions of Hippeastrum glaucescens resulted in 20 alkaloids: 2α 7 dimethoxyhomolicorin e N oxide (VI), 7 Methoxy O methylillorenine N oxide ( VII), Candimine N oxide
VIII), N oxide albamaculin e ( IX), 2α methoxyhomoly corin e ( XX), 2α hydroxyhomoly corin e ( XXI), albomaculin e ( XXII), 2α hydroxya lbomaculin e (XIII), 2α, 7 dimethoxyhomoly corin e ( XIV), 7 Methoxy O methyllico rin e (XV), candimine ( XVI), hyppeastrin e ( XVII), haemantidine ( XVIII), 6 epi haemantidine ( XIX), 11 hydroxyvitatin e ( XX), tazetine ( XXI), pretazetin e (XXII), 3 epi machrine ( trisfaeridine (XXIV) and ismine ( XXV), compounds (XI), ( XVIII), (XIX) and ( being obtained in three mixtures. The compounds (VI), and (VIII) were isolated for the first time in this study , being identified by 1 H NMR and high resolution masses. for the compound ( also high resolution masses. Previous studies of Hippeastrum glaucescens have indicated relevant alkaloid and biological potential, with potential inhibitory enzyme acetylcholinesterase. For Hippeastrum diniz cruziae this is the firs t phytochemical study performed, and its previous report has reported its high moebicide power and low toxicity. In this sense, this evidence gives great relevance in the continuation of the respective chemical and biological studies with the respective sp ecies.
