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A, A, BOLDINOVÉ ALKALOIDY a PERSPEKTIVY JEJICH VYUŽITÍ

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A, A, BOLDINOVÉ ALKALOIDY a PERSPEKTIVY JEJICH VYUŽITÍ Chem. Listy 109, 846855(2015) Referát BOLDINOVÉ ALKALOIDY A PERSPEKTIVY JEJICH VYUŽITÍ a a ANNA HOŠŤÁLKOVÁ , TOMÁŠ SIATKA , jedním z nich jsou aporfinoidy, které jsou děleny do něko- a a JAKUB CHLEBEK , LUBOMÍR OPLETAL , lika podtypů. Aporfinové baze jsou současně jednou b a z početných skupin látek v rámci isochinolinových alka- PAVEL DRAŠAR a LUCIE CAHLÍKOVÁ loidů, bylo jich izolováno více než 500. Tyto sloučeniny, vycházející ze základní struktury 6-methyl-5,6,6a,7-tetra- a Katedra farmaceutické botaniky a ekologie, skupina hydro-4H-dibenzo[de,g]chinolinového skeletu, by se moh- ADINACO, Farmaceutická fakulta v Hradci Králové, Uni- ly zdát (až na výjimky) méně atraktivními než např. skupi- verzita Karlova v Praze, Heyrovského 1203, 500 05 Hra- b ny alkaloidů morfinanového, protoberberinového anebo dec Králové, Ústav chemie přírodních látek, Fakulta bisbenzylisochinolinového typu. Je pravdou, že jim byla potravinářské a biochemické technologie, VŠCHT, Tech- věnována pozornost spíše z čistě chemického hlediska, nická 5, 166 28 Praha 6 než z hlediska detailní biologické aktivity na rozdíl od [email protected] alkaloidů např. morfinanových. V posledních 15 letech však začíná být i této skupině věnována pozornost v oblasti biologických účinků. Výpis účinků by překračo- Klíčová slova: aporfinové alkaloidy, boldinový typ, val rámec tohoto sdělení a bude mu proto věnována pozor- biologická aktivita, perspektivy nost jinde, zajímavé je však uvést alespoň rámcově jejich aktivitu z hlediska vlivu na CNS. Disponují určitými do- paminergními5, noradrenergními6–9 a serotoninovými účin- ky10, resp. antagonizují adrenergní receptory a působí anti- Obsah serotoninově. Zdá se, že by se mohly uplatnit také u některých neurodegenerativních onemocnění, protože 1. Úvod působí navíc antioxidačně a protizánětlivě. Při sledování 2. Struktura boldinových alkaloidů a jejich izolace jejich dopaminergního účinku se vyskytla úvaha o mož- 3. Rozšíření v rostlinách ném ovlivnění Parkinsonovy choroby. Z hlediska ovlivňo- 4. Biologická aktivita vání neurodegenerativních procesů při Alzheimerově cho- 4.1. Antioxidační aktivita robě lze pokládat za zajímavé ty studie, které hovoří 4.2. Antiinvazní aktivita o oxoisoaporfinových derivátech ovlivňujících acetylcho- 4.3. Ovlivnění zánětlivých procesů a imunity linesterasu a agregaci β-amyloidu. Tento typ látek byl také 4.4. Vliv na centrální nervový systém sledován z hlediska enzymového duálního účinku – inhibi- 4.5. Interakce s adrenergními receptory ce acetylcholinesterasy/butyrylcholinesterasy11. Je zřejmé, 4.6. Ovlivnění kardiovaskulárního systému že se jedná o perspektivní skupinu látek, která může při- 4.7. Vliv na trávicí ústrojí a diabetes mellitus nést mnohá poznání v oblasti biologických účinků využi- 4.8. Zásah do metabolismu xenobiotik, telných při léčbě chorob. chemoprotektivita, genotoxicita 5. Perspektivy praktického využití 6. Závěr 2. Struktura boldinových alkaloidů a jejich izolace 1. Úvod (+)-Boldin je významným aporfinovým alkaloidem, jehož reálná využitelnost je nesporná. Z jeho struktury Isochinolinové alkaloidy představují hned po alkaloi- vychází několik dalších blízkých sloučenin, kterým je dech indolových druhou největší skupinu těchto látek ve v tomto přehledu věnována pozornost; výraz „boldin“ vyšších rostlinách. O jejich významu není pochyb: v ČR tvoří součást jejich názvu, případně je jejich strukturní existuje tradice studia těchto sloučenin a je jim věnována podobnost zřejmá (tab. I). pozornost i v poslední době např. separaci kvartérních Ačkoliv za poslední půl století existuje řada metod benzo[c]fenanthridinových alkaloidů z Macleaya cordata pro izolaci látek tohoto typu, je nutné říci, že hlavní meto- (sanguinarin a chelerythrin jsou součástí aditivních přísad dou je příprava primárního extraktu z vegetabilního mate- do krmiva hospodářských zvířat)1. Jsou také diskutovány riálu ethanolem nebo methanolem, po odpaření rozpouště- z hlediska využití při terapii onkologických onemocnění dla extrakce bazí z odparku zředěnou kyselinou chlorovo- (zejména alkaloidy jednoděložných rostlin)2,3. Neméně díkovou (pH 2–3), odstranění balastních látek nejčastěji důležitý je zájem o stanovení jejich obsahu v tak důležité chloroformem (nebo dichlormethanem), alkalizace na 4 surovině, jako je makovina . pH ~ 10 roztokem Na2CO3 nebo koncentrovaným rozto- Tyto alkaloidy zahrnují několik strukturních typů; kem NH4OH a vytřepání uvolněných bazí uvedenými 846 Chem. Listy 109, 846855(2015) Referát S-(+)-boldin-methochlorid (2) R4 R3 R2 R R1 N H R5 (1,4–8,11,12,15) (3) (9) (10,14) Tabulka I Boldinové alkaloidy a 1 2 3 4 5 Název R R R R R 1 (S)-(+)-boldin OH OCH3 OCH3 OH CH3 3 (S)-N-acetyl-(+)-laurolitsin OH OCH3 OCH3 OH COOCH3 4 (S)-(+)-N-methyllaurotetanin OH OCH3 OCH3 OCH3 CH3 [(S)-(+)-2-O-methylboldin] 5 (+)-predicentrin OCH3 OCH3 OCH3 OH CH3 [(S)-(+)-9-O-methylboldin] 6 (S)-(+)-isoboldin OH OCH3 OH OCH3 CH3 7 (±)-isoboldin OH OCH3 OH OCH3 CH3 8 O,O-dimethyl-(S)-(+)-isoboldin OCH3 OCH3 OCH3 OCH3 CH3 9 (R,R)-(+)-isoboldin-β-N-oxid OH OCH3 OH OCH3 CH3 10 (R)-(-)-norboldin OH OCH3 OCH3 OH H 11 (+)-laurolitsin OH OCH3 OCH3 OH H [(S)-(+)-norboldin] 12 (S)-(+)-norboldin-acetát OH OCH3 OCH3 OCOCH3 H 13 (S)-(+)-N-kyanomethylnorboldin OH OCH3 OCH3 OH CH2CN 14 (S)-(+)-laurotetanin OH OCH3 OCH3 OCH3 H 15 (S)-(+)-N-norisoboldin OH OCH3 OH OCH3 H a Dehydroisoboldin není v tomto přehledu uveden, protože jeho struktura je nekompletní a nedisponuje žádnými popisova- nými biologickými účinky chlorovanými uhlovodíky. Na rozdíl od jiných typů iso- aporfinů oproti chloroformu. chinolinových alkaloidů se neosvědčilo pro vytřepání pou- Dělení alkaloidních koncentrátů je prováděno nejčas- žití diethyletheru (ačkoliv jsou tak obecně získávány vý- těji na silikagelu; neutrální oxid hlinitý byl použit jen třepky s menším množstvím balastních látek a separace je v omezeném počtu případů, ačkoliv je jinak běžným ad- následně snazší). Je to z důvodu nižší rozpustnosti těchto sorbentem pro dělení alkaloidů. Existují také jiné metody 847 Chem. Listy 109, 846855(2015) Referát (např. chromatografie na Amberlite XAD-2, Sephadexu (+)-isoboldin (6): Aconitum, Annona, Anomianthus, Ber- LH-20, nebo iontově-párová chromatografie), z celkového beris, Cardiopetalum, Cocculus, Consolida, Corydalis, pohledu preparativní metodiky je však lze pokládat za Cryptocarya, Delphinium, Desmos, Guatteria, Laurelia, spíše okrajové. Litsea, Macrantha, Machilus, Monodora, Nectandra, Neo- litsea, Orophea, Papaver, Persea, Polyathia, Sarcocap- nos, Sassafras, Stephania, Thalictrum, Xylopia, 3. Rozšíření v rostlinách (±)-isoboldin (7): Cocculus, Glaucium, O,O-dimethyl-(+)-isoboldin (8) (syn. (+)-glaucin): Berbe- Z hlediska výskytu jsou aporfinové alkaloidy rozšíře- ris, Corydalis, Sarcocapnos, Thalictrum, Xylopia, ny v poměrně úzké skupině taxonomických jednotek, ná- (+)-isoboldin-β-N-oxid (9): Cryptocarya, Litsea, ležejících pouze do dvou podtříd. První jednotkou jsou (–)-norboldin (10): Dehaasia, Lindera, Phoebe, zástupci podtřídy Magnoliidae, resp. řádu Annonales, če- (+)-laurolitsin (11) (syn. (+)-norboldin): Actinodaphne, ledí Annonaceae (Alphonsea, Annona, Anomianthus, Car- Alseodaphne, Beilschmiedia, Cryptocarya, Dehaasia, diopetalum, Desmos, Duguetia, Fissistigma, Guatteria, Lindera, Litsea, Machilus, Nectandra, Neolitsea, Phoebe, Mitrephora, Monodora, Orophea, Polyalthia, Trivalvaria, Sassafras, Siparuna, Trivalvaria, Xylopia) a řádu Laurales, čeledí Atherospermataceae (+)-norboldin-acetát (12): Lindera, (Dryadodaphne, Laurelia, Nemuaron), Hernandiaceae (+)-N-kyanomethylnorboldin (13): Alseodaphne, (Hernandia, Sparattanthelium), Lauraceae (Actinodaphne, (+)-laurotetanin (14): Actinodaphne, Alphonsea, Annona, Alseodaphne, Aniba, Beilschmiedia, Cassytha, Cryp- Beilschmiedia, Cassytha, Corydalis, Cryptocarya, Deha- tocarya, Dehaasia, Lindera, Litsea, Machilus, Nectandra, asia, Dryadodaphne, Eschscholzia, Guatteria, Hedycarya, Neolitsea, Ocotea, Persea, Phoebe, Sassafras), Monimia- Hernandia, Laurelia, Lindera, Litsea, Machilus, Monimia, ceae (Hedycarya, Monimia, Palmeria, Peumus) a Sipa- Nectandra, Nemuaron, Neolitsea, Palmeria, Peumus, Pho- runaceae s rodem Siparuna; a řádu Magnoliales, čeledi ebe, Siparuna, Sparattanthelium, Xylopia, Magnoliaceae (Liriodendron). V druhé jednotce, třídě (+)-N-norisoboldin (15): Annona, Cocculus, Litsea. Ranunculidae, jsou to řády: Berberidales s čeleděmi Ber- beridaceae (Berberis, Nandina) a Menispermaceae (Cocculus, Stephania), Papaverales, s čeleděmi Fumaria- 4. Biologická aktivita ceae (Corydalis, Fumaria), Papaveraceae (Eschscholzia, Glaucium, Papaver, Sarcocapnos, Stylophorum) a Ranun- Ačkoliv čítá okruh základních boldinových alkaloidů culales zahrnující zde čeledi Helleboraceae (Aconitum, 15 sloučenin, je z literatury patrné, že největší pozornost Consolida, Delphinium) a Ranunculaceae (Thalictrum). z hlediska biologického studia i praktické použitelnosti je Zcela osamoceně byly tyto látky nalezeny v podtřídě Ro- věnována (+)-boldinu. Obecně vzato, je u perspektivních sidae, resp. řádu Rhamnales, čeledi Rhamnaceae (Phylica, látek nutné vzít v úvahu možnost jejich reálného získání Retanilla) a řádu Capparales, v čeledi Brassicaceae z rostlinného materiálu a v tomto ohledu se nabízí využití (Diceratella). ideální suroviny – „Boldo“, tj. listů boldovníku vonného Je pochopitelné, že metabolická cesta (+)-boldinu (Folium boldo; Peumus boldus Mol., Monimiaceae). Listy – zde nejdůležitějšího alkaloidu – zahrnuje celou skupinu tohoto neopadavého stromu z Chile a Peru jsou dostupné intermediátů, a proto se v rostlinách
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