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Amaryllidaceae Alkaloids

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Amaryllidaceae Alkaloids Seminaris de Recerca de la Facultat de Farmàcia 27 de setembre de 2016 RECERCA EN PRODUCTES NATURALS Plantes ornamentals de la família Amaryllidaceae com a font de compostos bioactius Dr. Laura Torras Claveria; Luciana Tallini, Dr. Francesc Viladomat, Dr. Jaume Bastida Hymenocallis littoralis Phaedranasa dubia Crinum x powellii Galanthus nivalis Lycoris radiata Narcissus cv. Pinza AMARYLLIDACEAE Natural Products 1981-2010 All new approved drugs Natural product and/or natural product structures play a highly significant role in the drug discovery and development Newman & Cragg, J Nat Prod 2007, 70, 461-477 Newman & Cragg, J Nat Prod 2012, 75, 311-335 Research and development of new products FDA Production/ New drugs Pre-clinic Clinic assays (Phases I-III) Revision Phase IV 10.000 1 approved compounds 250 compunds 5 compounds drug Presentación NDA Presentación Presentación IND Presentación FDA 5 Years 1,5 Years 6 Years 2 Years 2 Years Average time in each step IND: Investigational New Drug NDA: New Drug Application Amaryllidaceae family • Bulbous plant family with ornamental and medical value • 3 subfamilies: Agapanthoideae, Allioideae, and Amaryllidoideae (previously 3 families) • Term “Amaryllidaceae” corresponds with subfamily Amaryllidoideae Amaryllidaceae medical uses through History Hippocrates of Kos Dioscorides (40-90 AD) Pliny the Elder (23-79 AD) (460-370 BC). Soranus of Ephesus (98-138 AD) Topic use Narcissus oil Same therapy Narcissus extracts Uterus tumors Bible Middle Ages European doctors Narcissus tazetta Chinese medicine, N Africa Hymenocallis caribaea Anti-tumor therapy Narcissus oil tumors – inflammation Amaryllidaceae geographical distribution Amaryllidaceae: Africa Amaryllidaceae: America Hymenocallis coronaria (Alabama) Amaryllidaceae: Asia Amaryllidaceae: Europe Mediterranean area Caucasus Narcissus poeticus (Vall d’Aran, Catalonia) Amaryllidaceae alkaloids 12 11 OH 3 2 4 HO 4 2 HO 1 MeN 3 3 4a 5' 10 10b H 4 10 H 10b HO 4' 6' 9 10a MeO 9 10a 1 2 5 1 O 11 4a 6 H H H NH N 12 O HO 3' 1' O 8 6a MeO 8 6a 6 2' ' 7 6 7 norbelladine lycorine homolycorine O OH 2 2 2 1 3 OH 1 3 OMe 1 OH 11 11 3 10 10 OH 10 H 4 O 9 10a 4a 4 O 9 10a 4a 4 O 9 10a 10b 10b 10b OH H 12 H 12 4a N N NH O 8 6a O 8 6a O 8 6a 6 7 6 7 6 7 crinine haemanthamine OH O narciclasine OMe 1 OMe 3 10 11 11a 2 2 2 4 3 OH O 9 10a OH 1 H 4a 1 4a 3 O 10 NMe 12 10 10b 9 10a 4 MeO 9 10a O 11 4 10b 12 O 8 6a H N 4a OH 7 6 11 12 O O 8 6a montanine 8 6a NMe 7 6 7 6 tazettine galanthamine Other Amaryllidaceae alkaloids OMe H NMe 10b O O R NMe R 4a O N H O O O O Graciline Plicamine OH Graciline PlicNonami ndimerice dinitrogenated compound DibenzoEsquele[tob,d di]b piranenzo[skeletonb,d]pirano Compuesto dinitrogenado no dimérico AbsoluteConfigur aconfigurationción absoluta 4aR/10bR 4aR/10bR CenSpirotro s pcenteriro = T =a Tazettinezettina [O[O/N]/N] GalanthusGalanthusgracilis gracilis GaGalanthuslanthus plicplicatusatus sspssp. by zByzantinusantinus GalanthusGalanthusplicatus plicatusssp. ssp Byzantinusbyzantinus CyrCyrthantusthantus oblobliquusiquus Pancratium maritimum Pancratium maritimum Narcissus broussonetii Exceptions NMe O 2 OMe OMe OMe OMe NMe2 O N OH N O Me Me amisine mesembrenol mesembrenone Aizoaceae Aizoaceae Aizoaceae Hymenocallis arenicola Crinum oliganthum Narcissus pallidulus Z Chem 1980, 20: 298 Z Chem 1981, 21: 358 J Nat Prod 1989, 52: 478 O O HO NMe NMe O O MeO NH H O O H HO Me H salsoline O MeO Chenopodiaceae (Salsola richteri) O Galanthus woronowii (-)-capnoidine (+)-bulbocapnine Fumariaceae Papaveraceae, Fumariaceae y Biochem Syst Ecol 2013, 51, 276 Lauraceae Galanthus nivalis ssp cilicicus Biochem Syst Ecol 2004, 32, 1059 Chemotaxonomic value Behria tenuiflora Greene NMe NMe O COO O Shihunine NMe H COOH Dehidroshihunine Amaryllidaceae Alliaceae Bastida, Sellés, Codina, Viladomat, León de la Luz Planta Medica 1996, 62, 575-577 Amaryllidaceae alkaloids biosynthesis 1.- Enzimatic preparation of precursors HO NH2 L-Phe L-Tyr COOH H2N COOH PAL hydroxylasesPAL TTyryr-decarboxylasedecarboxylase R1 -oxidation HO HO reduction R2 COOH HO CHO tyramine trans-cinnamic acid, R1=R2=H protocatechuic aldehyde H2N para-coumaric acid, R1=OH, R2=H caffeic acid, R1=R2=OH Amaryllidaceae alkaloids biosynthesis 2.- Primary ciclation HO HO HO CHO protocatechuic aldehyde tyramine H2N HO HO HO HO HO N NH H N HO O H Schiff's base HO (isomeric structures in solution) HO OH HO NH HO norbelladine Amaryllidaceae alkaloids biosynthesis 3.- Enzimatic preparation of intermediary agents HO HO HO 4' MeO 4' NH NH HO HO norbelladine O-methylnorbelladine Amaryllidaceae alkaloids biosynthesis 4.- Secondary ciclation. Diversification HO MeO 4' NH HO O-methylnorbelladine ortho-para' para-para' para-ortho' types types types lycorine crinine galanthamine homolycorine haemanthamine tazettine narciclasine montanine Amaryllidaceae alkaloids biosynthesis 4.- Secondary ciclation. Diversification OH MeO NH HO O-methylnorbelladine ortho-para' para-para' para-ortho' types types types lycorine crinine galanthamine homolycorine haemanthamine tazettine narciclasine montanine Amaryllidaceae alkaloids biosynthesis 4.- Secondary ciclation. Diversification OH OH MeO NH O-methylnorbelladine ortho-para' para-para' para-ortho' types types types lycorine crinine galanthamine homolycorine haemanthamine tazettine narciclasine montanine Natural Products Research SCREENING STRUCTURAL CHARACTERIZATION 1980 1983 I 1993 II 2005 III 2011 Study of Study of Study of genus Catalan flora Amaryllidaceae galanthamine Narcissus spp. used in producer species [Spain-Portugal] TradMed [Chemotaxonomy] [SA/Ibero- America] Phytochemical screening SCREENING • Collection, Drying, Storage • Taxonomic Determination 1980 1983 • Obtaining genus information • Simple method rapid selection Catalan flora > 1000 samples Green plants & Fungus different habitats from Catalonia Narcissus assoanus Duf. =N. requienii Roem. =N. juncifolius Lag. (Amaryllidaceae) Natural Products Research SCREENING STRUCTURAL CHARACTERIZATION 1980 1983 I 1993 II 2005 III 2011 Study of Study of Study of genus Catalan flora Amaryllidaceae galanthamine Narcissus spp. used in producer species [Spain-Portugal] TradMed [Chemotaxonomy] [SA/Ibero- America] Selection of genus Narcissus In base of: • High content in exclusive Amaryllidaceae alkaloids • Biological and pharmacological activity of extracts and alkaloids previously isolated from this family species • Poor studied genus • Influence area: Mediterranean (easy to work) Selection of genus Narcissus • 80-100 species • Narkào (=narcotic) penetrating smell of flowers from some species • Growing from lowlands to highlands • Flowering at the end of winter - spring • Distribution South Europe (Iberian Peninsula and Italy) (also in North Africa and East Mediterranean) * * * * Methodology Spectroscopy Plant Pure UV, IR, MS, Extracts Fractions material compounds NMR (1D/2D), X Ray Structure elucidation Alkaloids from genus Narcissus OH 2 HO 1 3 10 10b H 4 9 10a O 11 H 4a N 12 O 8 6a 7 6 Lycorine, Narcissus pseudonarcissus Gerrad, 1877: isolation Nagakawa et al., 1956: characterization New alkaloids from Narcissus R OMe MeO O MeO N NMe N MeO O MeO roserine bicolorine vasconine R= H tortuosine R= OMe OR2 R1O H HO MeO H N N MeO MeO O 1-O-acetylpseudolycorine R1= Ac, R2= H 2-O-acetylpseudolycorine R1= H, R2= Ac oxoassoanine MeN MeN H H H H R O 9 R O 9 1 R 1 R H 3 H 3 O O R2O R2O O OMe 9-O-demethylhomolycorine R1=H, R2= Me, R3= H O-methyllycorenine R1=R2= Me, R3=H dubiusine R1= COCH2CHOHMe, R2= Me, R3= OAc 2-hydroxy-6-O-methyloduline R1+R2= CH2, R3=OH 9-O-demethyl-2-hydroxyhomolycorine R1= H, R2= Me, R3= OH 8-O-acetylhomolycorine R1= Me, R2= Ac, R3= H New alkaloids from Narcissus OAc OH OMe OMe 11 OAc MeCOOCH2 HO 9 HO 9 O O O H H H H N N N N MeO MeO O O cantabricine 9-O-demethylmartidine 11-O-acetylhaemanthamine bujeine OMe HO H NMe O NH O O O OH O O N O N H OH O nangustine obesine pallidiflorine OMe O HO OH OH OH O O O MeO MeO MeO NH NH N O epinorgalanthamine epinorlycoramine H N-formylnorgalanthamine Bastida, Lavilla, Viladomat. The Alkaloids 2006, 63, 87-179 Natural Products Research SCREENING STRUCTURAL CHARACTERIZATION 1980 1983 I 1993 II 2005 III 2011 Study of Study of Study of genus Catalan flora Amaryllidaceae galanthamine Narcissus spp. used in producer species [Spain-Portugal] TradMed [Chemotaxonomy] [SA/Ibero- America] Amaryllidaceae in traditional medicine KwaZulu-Natal 200.000 Traditional healers (Year 2004 – licences authorization) South Africa Amaryllidaceae in traditional medicine Brunsvigia Crinum Cyrtanthus Nerine B. josephinae C. sthulmanii C. elatus N. filifolia B. orientalis C. kirkii C. sanguineus B. radulosa C. delagoense C. obliquus B. littoralis C. macowanii pregnancy B. bosmeniae (facilitate birth) sexually transmitted stomach pain urinary diseases (STD) Leprosy affected areas lactation problems South Africa Amaryllidaceae in traditional medicine Ammocharis Boophane A. tinneana B. flava Used by indigenous population (Xhosa, Shoto, San, Zulu ...) Infusions of bulbs [> 200 years]. A lot of species from genus Boophane, Brunsvigia, Crinum and Nerine are used to treat ♀ infertility South Africa Methodology Mass spectrometry GC-MS, LC-MS Spectroscopy Plant Pure UV, IR, MS, Extracts Fractions material compounds NMR (1D/2D), X Ray Biological assays Structure elucidation Amaryllidaceae alkaloids OAc OR2 OAc HO R1O 1 R1 O O H OH H H N O N N R2 O R delagoensine R1+R2= OCH2O josephinine 3 delagoenine R1= R2= OMe 1-epibowdensine R1= R2= Ac, R3= OMe 1-epidemethoxybowdensine R1= R2= Ac, R3= H 1-epideacetylbowdensine
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