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Abietane Diterpenoids As Potential Drugs

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Abietane Diterpenoids As Potential Drugs 5 CATALYZER THE FIFTH ISSUE OF CATALYZER MAGAZINE 19/07/2020 ABIETANE DITERPENOIDS AS POTENTIAL DRUGS Abietanes are naturally word “turpentine”. Each isoprene occurring diterpenoids that unit also called a “C5 building haveAbietane been isolated Diterpenoids from several as Potentialblock” or Drugs hemi-terpene; they terrestrial plant families are linked to form terpenes in includingGülaçtı Topçu Lamiaceae (Labiatae), “head-to-tail” fashion, in general. Asteraceae, Celastraceae, Therefore, monoterpenes are and Boraginaceae, and resins formed from 2 isoprene units (10 Abietanes are naturally occurring diterpenoids that have been isolated from several terrestrial Sildi: which from conifers belonging to the C’s), sesquiterpenes from 3 units familiesplant families Cupressaceae, including Lamiaceae Pinaceae, (Labiatae), (15Asteraceae, C’s), diterpenes Celastraceae, fromand Boraginaceae 4 units , Podocarpaceae,and resins from conifers Phyllocladaceae, belonging to the families(20 Cupressaceae,C’s), and sesterterpenes Pinaceae, Podocarpaceae, from andPhylloclad Araucariaceae.aceae, and Araucariaceae. 5 units (25 C’s), while triterpenes Sildi: e are from 6 units (30 C’s) and Secondary metabolites metabolites of plants of can be classifiedtetraterpenes, namely as fromterpenoids 8 units and (40 steroids, Sildi: ; plantsflavonoids can and be other classified, phenolics, namelyand alkaloids, C’s). which all play an important role in their asdefense terpenoids mechanisms, and such steroids, as fighting with herbivores, pests, and pathogens as well as other Sildi: to flavonoidstypes of external and damage other. Asphenolics, one of the secondaryMono- metabolites and sesquiterpenoids of plants, terpenoids are Sildi: s and alkaloids, which all play an are the main constituents composed of isoprene (2-methyl-1,3-butadiene) units. The name "terpene" is derived from the Sildi: formed important role in their defense of the essential oils of all mechanisms,word “turpentine”. such Each isopreneas fighting unit also calledplants a “C5 building and flowers block” or and hemi they-terpene ; they Sildi: , withare linked herbivores, to form terpenes pests, in and“head -to-tail” fashion,give in them general. their Therefore, special monoterpenes smell are pathogensformed from 2 as isoprene well asunits other (10 C’s), types sesquiterpenes and taste. Diterpenoids from 3 units (15 C’s), diterpenes are from of4 units external (20 C’s), damage. and sesterterpenes As one offrom 5 unitscomposed (25 C’s), wh ofile fourtriterpenes isoprene are from units 6 units the(30 C’s) secondary and tetraterpenes metabolites from 8 unit ofs (40 C’s). with a core molecular formula Sildi: e plants, terpenoids are composed C20H32to form different skeletons, ofMono isoprene- and sesquiterpenoids (2-methyl-1,3- are the main constituentssuch as of abietane,the essential kaurane,oils of all plants and butadieneflowers and )they units. give The them name their special smell andatisane, taste. Diterpenoids labdane, jatrophane,are composed of four Sildi: which occur “terpene” is derived from the tigliane, lathyrane, or taxane. isoprene units with a core molecular formula C20H32 to form different skeletons, such as abietane, kaurane, atisane, labdane, jatrophane, tigliane, lathyrane, or taxane. Sildi: h Sildi: , etc Abietane skeleton Abietic acid Dehydroabietic acid Ferruginol Abietane diterpenoids have three 6-membered cyclic rings (trans-fused A-B, and trans-fused B-C rings) with an isopropyl side chain attached to C-13 on ring C. A simple example of them Sildi: is abietic acid (7,13-abietadien-18-oic acid), and dehydroabietic acid, which has an aromatic Sildi: The Sildi: for INTERNATIONAL CHEMISTRY OLYMPIAD MAGAZINE / ISTANBUL - TURKEY 2020 Taxodione Salvinolone 6-Hydroxysalvinolone Abietane diterpenoids have three six-membered cyclic rings (trans- Some Salvia species afforded abietane diterpenoids that have opened Taxodione Salvinolone 6-Hydroxysalvinolone fused A-B, and trans-fused B-C rings) with an isopropyl side chain ring A, which are called seco-abietanes, such as aethiopinone and Some Salvia species afforded abietane diterpenoids that have opened ring A, which are called Sildi: which attached to C-13 on ring C. A simple example of them is abietic acid salvipisone [2,8]. (7,13-abietadien-18-oic acid), and dehydroabietic acid, which has seco-abietanes, such as aethiopinone and salvipisone [2,8]. Some Salvia species afforded abietane diterpenoids that have opened ring A, which are called Sildi: which an aromatic ring C, previously obtained during chemical studies starting from abietic acid. Another simple abietane diterpene withseco the -abietanes, such as aethiopinone and salvipisone [2,8]. aromatic ring C is ferruginol, first isolated in 1939 from the resin of thering miro C, previouslytree (Podocarpus obtained ferrugineus during chemical) endemic studies to starting New Zealandfrom abietic [1]. acid. Another simple abietane diterpene with the aromatic ring C is ferruginol, first isolated in 1939 from the resin Aromatic abietanes comprise the largest group of naturally occurring abietanesof the miro [1] t reeand (Podocarpus are the main ferr secondaryugineus) endemic metabolites to New ofZealand the Salvia [1]. Sildi: M Sildi: h L. (sage) plants belonging to the family Lamiaceae. The genus Salvia Aethiopinone Salvipisone Aromatic abietanes comprise the largest group of naturally occurring abietanes [1] and are the Sildi: species is represented by over 900 species throughout the world, and the bestmain known secondary Salvia metabolites species are of the S. miltiorrhizaSalvia L. (sage) (Danshen plants belonging or Tanshen) to the in family Lamiaceae. Sildi:Aethiopinone the Salvipisone China and other Asian countries, S. officinalis L. in Europe (sage), and Sildi: The genus Salvia is represented by over 900 species throughout the worldThe, and most theThe bestinteresting most known interesting re-arranged re-arranged abietanes abietanes were obtained were obtainedfrom endemic from Anatolian Salvia Sildi: M S. fruticosa Mill. (syn: S. triloba L.) in Mediterranean countries, and S. Sildi: d endemic Anatolian Salvia species, such as S. microstegia Boiss. et M divinorumSalvia species L., a hallucinogenicare S. miltiorrhiza species, (Dansh enwhose or Tanshen) origin indates China back and tootherspecies Thethe Asian m,ost such couinteresting ntriesas S., S.microstegia re-arrangedSildi: (BrandtBoiss. abietanes ve etNeubauer Bal were. 1939)grow obtaineding in fromthe Binboğaendemic MountainsAnatolian Salvia(Turkey) , Sildi: Sildi: n Bal. growing in the Binboğa Mountains (Turkey), which afforded a Mazatecofficinalis hallucinogenic L. in Europe sage.(sage), Most and SalviaS. fruticosa species Mill. are (syn: rich S. in triloba abietanespecies L.) in , Mediterraneansuch as S. microstegia Sildi: Boiss. family et Bal. growing in the Binboğa Mountains (Turkey), Sildi: n which affordedrearranged a rearranged tricyclic abietanetricyclic diterpene.abietane diterpene. Its structure Its structurewas elucidated was elucidated by a diterpenoids, while S. divinorum is rich in neo-clerodane diterpenoids. Sildi: most countries, and S. divinorum L., a hallucinogenic species, whose originwhich dates affordedby back a series toa rearrangedthe of NMR techniques,tricyclic 1abietane such 13asditerpene. 1H and 13ItsC NMR,structure COSY was elucidated by a In Turkey, Salvia species are represented by over 100 species (114series of NMR techniques, Sildi:such h as H and C NMR, COSY and 1D-NOE and SINEPT taxa),Mazatec and hallucinogenichalf of them are sage endemic. Most Salvia to Anatolia species (Asian are rich part in abietane of Turkey). seriesditerpenoids ofand NMR ,1D-NOE while techniques, S. and SINEPT such a experimentss 1H and 13C asNMR, well COSYas HRMS and analysis. 1D-NOE and SINEPT experimentsExamination as well as of HRMS its unusualSildi: analysis. Mediterra carbonnian Examination skeleton ofsuggested its unusual that carbon this skeleton suggested divinorum is rich in neo-clerodane diterpenoids. In Turkey, Salvia speciesexperiments are represented as well by as HRMSSildi: analysis. hallusinogenic Examination of its unusual carbon skeleton suggested During our group studies on Salvia species by Prof. Ulubelen and that this compound might be derived biogenetically fromfrom regularregular abietane abietane diterpene having a Sildi: its byover Prof. 100 Topcu, species over (114 140 taxa) abietane, and half diterpenoids of them are endemic were isolated to Anatolia (Asianthat this part diterpenecompound of Turkey ).havingmight be a threederived six-membered biogenetically Cfrom skeleton regular by abietane ring A diterpene having a three–six-membered C skeletonSildi: of theby ring A cleavage between C-4 and C-5, followed by Sildi: [2,7], at least half of them being new, and most ofring them C, previouslyhave an obtainedcleavage during chemical between studies C-4 and starting C-5, followed from abietic by recyclization acid. Another of sim C-4ple three–six-membered C skeletonSildi: beingby ring A cleavage between C-4 and C-5, followed by Sildi: Sildi: aromaticDuring ourring group C. Their studies structures on Salvia were species elucidated by Prof. basedUlubelen on and 1D- by and recyclizationProf. Topcu,to C-11. overof C Therefore, -1440 to C-11. the Th finalerefore, product, the final named product microstegiol,, named microstegiol with a , with a seven- abietane diterpene with the aromatic ring C is ferruginol, first isolated in 1939 from the resin Sildi: 2D-NMRabietane and diterpenoids
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  • Paleovegetational Reconstruction and Implications on Formation
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