Izolovanje i identifikacija diarilheptanoida iz biljnih vrsta crna jova (Alnus gltinosa (L.) Gaertn.) i zelena jova (Alnus viridis (Chaix) DC. subsp. viridis) i njihova biološka aktivnost

Abstract

Rod Alnus Mill. (jove), sa više od 30 vrsta, pripada familiji Betulaceae. Alnusvrste koje rastu u Srbiji su A. glutinosa (crna jova), A. viridis subsp. viridis (zelena jova)i A. incana (siva jova). U ovom radu izolovani su i okarakterisani diarilheptanoidi izkore crne jove i zelene jove i određena je njihova biološka aktivnost.Biljke ovog roda su u tradicionalnoj medicini korišćene u brojne svrhe, kaoalterativi, astringenti, purgativi, emetici, antipiretici, hemostatici, antiparazitici iantihelmintici, za lečenje različitih bolesti, uključujući tumor. Jedinjenja izolovana izjova poseduju širok spektar bioloških aktivnosti, a najvažnija su citotoksična,antitumorska, antivirusna, anti-inflamatorna, antimikrobna i antiparazitska.Vrste roda Alnus su bogat izvor diarilheptanoida. Oni se u biljci prvenstvenonalaze u kori i lišću, kao prosti, glikozidi ili složeni - diarilheptanoid glikozidiesterifikovani različitim fenolnim kiselinama, najčešće cinamičnim. U okviru ovedisertacije iz kora zelene i crne jove izolovano je i okarakterisano 39 jedinjenja, odkojih je 19 novih prirodnih proizvoda. Iz zelene jove izolovano je 13 jedinjenja (1-13), aiz crne 28 (1, 5, 14-39), pri čemu su diarilheptanoidi platifilozid (1) i acerozid VII (5)izolovani iz obe biljne vrste. Od 13 jedinjenja izolovanih iz zelene jove, 11 pripadagrupi diarilheptanoida (1-11), od kojih je 6 novih prirodnih proizvoda (3, 7, 8, 9, 11 i13). Svih 28 jedinjenja izolovanih iz crne jove su diarilheptanoidi, a 13 (19, 27, 29-39)je novih. Strukturne karakteristike diarilheptanoida zelene jove su da isključivo imaju phidroksifenilgrupe kao aromatične sisteme i da se, pored prostih, sreću glikozidi koji sesastoje iz mono- i disaharida. Složeni diarilheptanoidi su retki, izolovan je samo jedansa galnom kiselinom (3). Za većinu diarilheptanoida crne jove karakteristično je daimaju bar jednu kateholsku grupu. Od glikozida su zastupljeni isključivo oni samonosaharidnom jedinicom, prvenstveno glukozidi i ksilozidi. Za crnu jovu sukarakteristični složeni diarilheptanoidi sa različitim cinamičnim kiselinama, pretežnoonim sa metoksi grupama...

The genus Alnus Mill. (Alder), with more than 30 species, belongs to theBetulaceae family. Alnus species growing in Serbia are A. glutinosa (black alder), A.viridis subsp. viridis (green alder) and A. incana (gray alder). In this work,diarylheptanoids from the bark of black alder and green alder were isolated andcharacterized, and their biological activity was determined.Plants of this genus have been traditionally used for numerous purposes, e.g. asan alterative, astringent, cathartic, emetic, febrifuge, hemostatic, parasiticide, vermifuge,in the treatment of various diseases, including tumors. Compounds isolated from theAlder species possess a wide spectrum of biological activities and the most importantare cytotoxic, antitumoral, antiviral, anti-inflammatory, antimicrobial and antiparasitic.Alnus species are a rich source of diarylheptanoids. These are predominantlyfound in the bark and leaves as simple diarylheptanoids, glycosides and complexdiarylheptanoids – diarylheptanoid glycosides esterified with some phenolic acid, mostcommonly with some cinnamic acid. In this work, 39 compounds were isolated andcharacterized from the barks of green and black alder, of which 19 are new naturalproducts. Thirteen compounds were isolated from green alder (1-13), and 28 from blackalder (1, 5, 14-39), of which diarylheptanoids platyphylloside (1) and aceroside VII (5)were isolated from both species. Of the 13 compounds isolated from green alder, 11belong to diarylheptanoids (1-11) from which 6 are new natural products (3, 7, 8, 9, 11,and 13). All 28 compounds isolated from black alder are diarylheptanoids and 13 (19,27, 29-39) are new. The structural characteristics of the diarylheptanoids isolated fromgreen alder are that they have only p-hydroxyphenyl groups as aromatic systems andthat besides simple diarylheptanoids, diarylheptanoid glycosides are found whichconsist of mono- and disaccharides. Complex diarylheptanoids are rare and only onewas isolated with gallic acid (3). For the most diarylheptanoids isolated from black alderthe presence of at least one catechol moiety as an aromatic component is characteristic...