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Terpenoids Terpenoids T E R P E N O I D S COMPOUNDS DERIVED FROM MEVALONIC ACID • The largest and most variable group of natural compounds (monoterpenes, sesquiterpenes, diterpenes, sesterpenes, triterpenes, polyterpenes) • Relative both in general biosynthetic origin and reciprocal structural relationship • Formed by multiples of five carbon unit • Pyrolysis produces carbohydrate isoprene (2-methylbutadiene) → isoprenoids. Isoprene is not a natural compound. TERPENOIDS - OCCURRENCE • Prevalent majority of terpenoids is found free in plant tissues (Lamiaceae, Asteraceae, Rosaceae, Rutaceae, Apiaceae….) • Exceptionally glycosides • Esters with organic acids • Combination with proteins • Lower members of group (C10 and C15 substances) are volatile – distillation with water steam (hydrodistillation) (essential oils – olea etherea, Etheroleum menthae) • Higher members (C20 and more) are not volatile – extraction with organic solvents 1 ISOPRENE RULE 6 8 5 7 OH 4 3 2 OH isoprene 1 myrcene geraniol farnesol O camphor CO H OH 2 carvon guajol dextropimaric acid WAYS OF C5 UNITS CONDENSATION „HEAD – HEEL“ monoterpenes sesquiterpenes diterpenes 2 WAYS OF C5 UNITS CONDENSATION 6 5 7 4 8 p-menthane type 3 2 1 type: thujane camphan head-heel 2,6-dimethyloctane pinane carane 8 6 7 5 type of cantharidine 4 3 2 1 heal-heel 2,7-dimethyloctane 6 5 7 type of fenchane 4 3 2 1 heel-side 2,3,6-trimethylheptane BASIC SUBDIVISION OF NATURAL TERPENOIDS LABELING NUMBER OF C5 OCCURRENCE HEMITERPENES 1 constituent of ergot alkaloids; some C5 acids MONOTERPENES 2 volatile constituents of essential oils (geraniol, menthol, camphor) SESQUITERPENES 3 constituents of essential oils (farnesol, farnesen); some bitter substances (artabsin) DITERPENES 4 constituents of essential oils, resins, balsams (for example abietic acid); vitamin A; gibberellins (phytohormones); constituent part of some alkaloids (Aconitum); phytol (building block of chlorophylls) TRITERPENES 6 squalene; pentacyclic triterpenes; steroids; cardioactive glycosides; some bitter substances TETRATERPENES 8 carotenoids; xanthofylls; some lipophilic plant pigments POLYTERPENES n cautchuc (cis) gutta-percha (trans) 3 BIOGENETIC ORIGIN H C OH 3 C HOOCH2C CH2CH2OH (R)-mevalonic acid BIOGENETIC ORIGIN OF IPP (1) (takes place in cytoplasma of plant cell) CH COCH CO SCoA CoA SH 2 CH3CO SCoA 3 2 + acetylcoenzyme A acetoacetylcoenzym A CH3CO SCoA NADP+ HMG-CoA synthase OH NADPH OH CH C CH CO H CoA SH 3 2 2 CH3 C CH2CO2H + CH CH OH HMG-CoA reduktasa 2 2 CH2CO SCoA mevalonic acid -hydroxy--methylglutaryl-CoA 3 H C ATP 3 3 4 C CH2CH2OPP H C ADP 2 3-methyl-3-butenyldiphosphate = isopentenyldiphosphate (IPP) H3C OP -CO C 2 - HOP isomerase H2C CH2CH2OPP H C 3 C 3 2 HO O C CHCH2OPP H3C 3-methyl-2-butenyldiphosphate = 3,3-dimethylallyldiphosphate (DAPP) 4 BIOGENETIC ORIGIN OF IPP (2) (takes place in plastides) 1 CH3 2 C=O - 1 CH COO 3 2 C=O + Pyruvic acid H + H O C H 3 3 CHO H C OH 4 H 4 C OH 5 CH2OP CH OP 5 2 1-deoxy-D-xylulose-5-phosphate GAP HO HO 2 4 2 4 1 OP 1 3 3 OP OPP O OH OH OH IPP 2-C-methyl-D-erythritol-4-phosphate 3-methyl-3-butenyl-diphosphate Lange B.M., Croteau R.: Biochem. Biophys. 365 (1), 170-174 (1999) Isoprenoid biosynthesis via a mevalonate-independent pathway in plants: Cloning and heterologous expression of 1-deoxy-D-xylulose-5-phosphate reductoisomerase from peppermint. POLYMERISATION REACTIONS CH CH3 3 C CH OPP C CH OPP PPO CH H C CH 2 CH CH 2 2 + 2 2 2 H2C CH IPP + HOPP CH C H C CH C 3 3 H C CH DMPP 3 3 geranyldiphosphate PPO CH OPP 2 CH2 CH2 = + CH OPP + 2 CH OPP 2 CH OPP IPP 2 farnesyl-PP IPP geranyldiphosphate farnesyl-PP 2x farnesyl-PP CH2OPP squalene geranylgeranyl-PP 5 FORMATION OF BASIC TERPENOIDS DAPP + IPP H - P C10 monoterpenes GERANYL-PP (C10) H - P IPP C15 sesquiterpenes FARNESYL-PP (C15) H - P : condenzation "head - heel" 2x P-P P - P : kondenzation " heal - heal " C30 PP H - P squalene IPP C30 triterpenes GERANYL-GERANYL-PP (C20) C19-21 steroids (IPP) (IPP)n n H - P H - P P-P C diterpenes 20 2x gutta-percha cautchuc phytol (trans) (cis) giberillines C40 carotenoids HEMITERPENES 2 2 1 4 3 1 4 3 CH2OH CH2OH 3-methyl-2-buten-1-ol 3-methyl-3-buten-1-ol 2 O O 2 O O 3 1 4 3 1 4 CH O P O P OH CH2 O P O P OH 2 OH OH OH OH 3-methyl-2-butenyldiphosphate 3-methyl-3-butenyldiphosphate 3,3-dimethylallyldiphosphate (DAPP) isopentenyldiphosphate (IPP) 6 MONOTERPENES CH OH OH OPP 2 + H O + H - H2O 2 CH2OH geranyl-PP geraniol citronelol ocimene linalol + limonene + -pinene + 3-carene GERANIOL; NEROL; LINALOL CH CH3 3 H3C OH H 6 8 5 7 OH 4 3 H OH 2 1 Geraniol Nerol Linalol CH CH CH CH 3 3 3 3 1 H CH OH 7 5 3 7 5 3 2 8 6 4 2 8 6 4 2 CH OH H 1 2 7 BICYCLIC MONOTERPENES camphane linear type p-menthane pinane fenchane carane thujane IRIDOIDS 11 4 6 5 3 7 O 8 9 1 10 Iridane Cyclopentanotetrahydropyrane 8 IRIDOIDS CH GERANYL - PP H O CH O O citronellal iridodial COOCH3 HO alkaloids O O Glc loganine HO O O RO O O CH2OR HOH C 2 O Glc O O aucubine O Glc valepotriates gentiopikroside SESQUITERPENES • THE MOST WIDESPREAD GROUP OF NATURAL COMPOUNDS • GENERAL ORIGIN IN ORIGINAL CATIONOID PRECURSORE • BETWEEN SINLE GROUPS SHARP DISTINCTIONS • OCCURENCE OF SOME GROUPS CHEMOTAXONOMICALLY LIMITED TO CERTAIN PLANT SPECIES • USEABLE FOR CHEMOTAXONOMY 9 ACYCLIC SESQUITERPENES H 2 3 CH2OH CH3 trans-farnesol (geraniol) CH2OH 2 3 H CH3 cis-farnesol (nerol) OH nerolidol (linalol) SESQUITERPENIC CARBOHYDRATES H H H3C CH3 -farnesene trans--farnesene cis--farnesene 10 CYCLIC SESQUITERPENES 5 8 6 8 7 4 9 5 6 7 1 2 9 2 10 4 10 3 1 3 OPP OPP trans, trans - farnesyl-PP cis, trans - farnesyl-PP + OPP + carbocation carbocation OPP 14 2 1 9 10 3 8 4 5 7 6 13 bisobolane humulane 15 11 germacrane guajane ( ) cadinane ( ) caryophylane 12 ( ) eudesmane -BISABOLENE + - H+ x cis-farnesyldiphosphate carbocation -bisabolene O CH2OH -curcumene turmerone lanceol 11 SESQUITERPENIC LACTONES (Asteraceae) - H+ HO+ O + precursor O oxidation - H+ + COOH CH2OH CH2OH OH cyclization O C COOH O OH HO H O O O O O O artemisine santonine artabsine O O ANTIFEEDANTS Sesquiterpenic dialdehyde COH Plants of Polygonaceae, COH Canellaceae, Winteraceae families H Mollusces (class Arthropoda) Polygodial Only once the fish try to eat… 12 DITERPENES +C +C CH 5 5 CH2 2 CH2 OPP OPP OPP CH2OPP geranylgeranyldiphosphate OH geranyllinalol part of jasmine essential oil DITERPENS H3C CH2CH3 CH N CH3 H2C N Mg N CO H3C N H H3C H COOCH3 H CH2CH2 COO chlorofyll a phytol CH3 H3C O HO -tocoferol (vitamin E) CH3 O CH3 O vitamin K1 13 BASIC TYPES OF CYCLIC DITERPENES DITERPENES ACYCLIC MONOCYCLIC BICYCLIC 20 20 20 13 15 12 12 11 14 11 14 12 14 16 15 19 19 13 19 18 13 15 5 11 1 18 18 4 6 9 1 9 10 2 10 8 2 10 8 7 3 5 7 3 5 7 3 2 9 4 4 6 17 8 6 1 16 17 retinol type 16 17 labdane type TRICYCLIC TETRACYCLIC 15 15 14 14 16 pimarane type abietane type caurane type MONOCYCLIC DITERPENES -caroten CH2OH 2 vitamin A1 (retinol) CH2OH vitamin A2 (3-dehydroretinol) 14 BICYKLIC AND POLYCYCLIC DITERPENES OH OH O HO O O O O H CH marubiine picrosalvine OH N H OH H atisine H HO2C H HO2C H pimaric acid podocarpic acid TRITERPENES squalene squalene-2,3-epoxide O tetracyclic HO intermediate lanosterol HO cycloartenol Animals lower and higher Fungi photosyntetizing plants HO cholesterol HO -sitosterol HO -amyrine 15 FORMATION OF AGLYCONS OF CARDIOACTIVE GLYCOSIDES steroidal steroidal saponins alkaloids OH 20 HO HO cholesterol 20-hydroxycholesterol CH2OH CH3 C O C O OH HO O H progesterone 5-pregnan-3,14,21-triol-20-on O CH C 3 SCoA C3-unit O O O O OHC OH OH HO HO OH H digitoxigenine hellebrigenine BIOSYNTHESIS OF TETRATERPENS geranylgeranyldiphosphate geranyllinaloydiphosphate phytoene (3 conjugated double bonds, 1 x cis ) H neurosporine (9 conjugated double bonds, all-trans) lycopene (11 conjugated doubl bonds, all-trans) -carotene -carotene 16 TETRATERPENES O OH HO capsanthine TETRATERPENES OH 3' 6' 1' 1 3 HO Luteine (3R,3'R,6'R)-,-carotene-3,3'-diol 3,3'-dihydroxy--carotene • Belongs to carotenoids of xanthophyll group • Contains the same chromophore as α-carotene, it is isomeric with zeaxanthine. • Yellow pigment, present together with carotene and chlorophyll in all green plant parts • Present in many yellow and red flowers and fruits, it was observed also in animals, for example in feathering, yolk, and in corpus luteum. • Can be present as free substance or as ester; it possesses no activity of vitamine A. • Luteine was firstly obtained in crystalline state 1907 by Willstätter from stinking nettle, later from chicken yolk. Structure was resolved by P. Karrer in 1951. • Protectum, Vitalux Plus 6, Ocuvite … macular defects of eye. 17 POLYTERPENES H H C H H H3C 3 H3C H3C H * n * cautchuc (all - cis) degree of polymerisation 20.000 CH3 CH3 CH3 CH3 * * n H H H H gutta-percha (all - trans) degree of polymerisation 2.000 18.
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