Polyketide lignan-phenylpropanoids


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Polyketide lignan-phenylpropanoids

  1. 1. Phenyl propanoids & related compounds
  2. 2. Phenolic compounds • Phenols probably constitute the largest group pf plant secondary metabolites. • Phenols are utilized as Colouring agents. Flavouring agents, aromatizers and antioxidants. E.g. • Simple phenolic compounds • Tannins • Coumarins and glycosides • Anthraquinones and glycosides • Naphthaquinone and glycosides • Flavones and related flavonoid glycoside • Anthocyanidins and anthocyanins • Lignans and lignin
  3. 3. Monomeric derivatives • p-Coumaryl alcohol • Coniferyl alcohol • Sinapyl alcohol
  4. 4. Lignan: Dimeric derivatives • Dimeric compounds formed essentially by the union of the two molecules of a phenylpropene derivative. • Not synthesized by lignin biosynthetic pathway. • Unlike lignin, optically active and probably arise by stereospecific, reductive coupling between the middle carbons of the side chain of monomer. • Some 300 lignans have been isolated and categorized into a number of groups according to structural features. • Important pharmaceutical examples are the lignans of Podophyllum spp. which appear to be formed from two molecule of coniferyl alcohol or the corresponding acid with subsequent modification; apparently, a sinapic acid derivative, as might be expected by the inspection of the podophyllotoxin molecule, is not involved.
  5. 5. Podophyllotoxin (Podophyllum) Macelignan (Nutmeg)
  6. 6. Introduction-Lignan • Lignans, cited are not however, necessarily the therapeutically active constituents of the plant. • Neo-lignans are also derived from the same unit as lignans but the C6-C3 moieties are linked head to tail or head to head and not through the beta-beta’ carbons. • They occur in the heart wood of trees of the Mangoliaceae, Lauraceae and Piperaceae. • Example: Guaicum officinale resin Guaicum sanctum • Myristica fragrans, Piper cubeba • Magnolia officinalis Magnolia obovata: • Magnolol: CNS Action: depressant, muscle relaxant, anti platelet, antimicrobial, anti-tumour, anticancer, insecticidal
  7. 7. Introduction-Lignin • It is an important polymeric substance, (C6-C3)n, laid down in a matrix of cellulose microfibrils to strength certain cell wall. • It is an essential component of most woody tissues and involves vessels, tracheids, fibers and sclreids. • Lignins from different biological sources vary in composition, depending on the particular monomeric units in which they are composed. • Variations in lignin constitutes also arise as a result of random condensations of the appropriate alcohols with mesomeric free radicals formed from them by the action of a laccase type (oxidase) enzyme. • As there is no template for this non-enzymatic condensation the lignin molecules formed vary in structure and so it is not possible to isolate lignin as a compound of defined composition.
  8. 8. Introduction-Lignin • In the wall, it appears to occur chemically combined with hemicellulose and built up in greatest concentration in the middle lamellae and in the primary walls. • Lignified cell walls after treatment with Schultze’s macerating fluid (HNO3+ Potassium chlorate) will show cellulose reactions. • Acid Aniline sulphate  bright yellow • Phloroglucinol + conc. HCl  pink/red • Chlor-zinc-iodine  yellow
  9. 9. Introduction-Phenylpropanoids • diverse family of organic compounds that are synthesized by plants from the amino acid Phenyl alanine. • Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of cinnamic acid, which is synthesized from phenylalanine in the first step of phenyl propanoid biosynthesis. • Phenylpropanoids are found throughout the plant kingdom, where they serve as essential components of a number of structural polymers, provide protection from UV light, defend against herbivores and pathogens, and mediate plant-pollinator interactions as floral pigments and scent compounds. • Concentrations of phenylpropanoids within plants are also altered by changes in resource availability.
  10. 10. Introduction- Phenylpropanoids • Phenylpropanoids and other phenolics are part of the chemical composition of sporopollenin. • This substance found in pollen is not exactly known, due to its unusual chemical stability and resistance to degradation by enzymes and strong chemical reagents. Analyses have revealed a mixture of biopolymers, containing mainly long chain fatty acids, phenylpropanoids, phenolics and traces of carotenoids. • Tracer experiments have shown that phenylalanine is a major precursor, but other carbon sources also contribute. It is likely that sporopollenin derives from several precursors that are chemically cross-linked to form a rigid structure
  11. 11. 1. Podophylum: Lignan & Polyketide • Syn: May apple, Wild mandrake • Source: dried roots and rhizomes of American: Podophyllum peltatum & India: Podophyllum hexandrum (P.emodi) • Family: Podophyllaceae (Berberidaceae) • GS: America (US-Virginia, Kentucky, North carolina, Tennessee, Indiana, Canada) • Indian: Tibet, China, Afghanistan, Himalayas
  12. 12. • The rhizomes and roots are obtained from wild grown plants growing at an altitude of 3000 to 4000 m. • Underground rhizomes remain dormant in winter and produce aerial shoots in April to May. • Shoots flower during summer and die in November • Rhizomes and roots are dug up in spring or autumn, washed, cleaned and dried in the sun • The drug collected in the month of may has higher resin content than the collected in November. • Actually the roots contain more resin than rhizomes and hence roots are preferred.
  13. 13. • Constituents: • P. peltatum • 2-8% resinous material as podophyllin, Lignan dvt: podophyllotoxin, alpha & beta peltatin, (Lignan: in form of glycoside), Desmethyl podophyllotoxin, desoxypodophyllotoxin, podophyllotoxone, • Flavonoid: quercetin, kaempferol, essential oil, Starch • P. hexandrum • 7-15% Resin as Podophyllin • 40% podophyllotoxin
  14. 14. • Chemical Test: • Alcoholic ext. + strong copper acetate- brown ppt with Indian podophyllum & green color without ppt with American podophyllum • USES: • Cyto-toxic, venereal disease, Warts, • Podophyllotoxin is semisynthetically converted to etoposide potent anticancer agent for lung & testicular. • Its GIT irritant, drastic purgative in moderate uses
  15. 15. Podophyllum species • American Podophyllum • Not so • The CaOx crystals are fewer and smaller (30-60-100 Micro meter) • Less resin 2-8 % • Contains alpha & beta peltatin • Podophyllotoxin is less • Indian Podophyllum • Vascular bundles are more elongated radially. • The CaOx crystals are fewer and smaller (20-30-60 Micro meter) • More resin up to 7-15% • No constituents • Podophyllotoxin is more
  16. 16. 2. Psoralea Furanocoumarins • Syn: Bavchi, Malaya tea • Source: dried ripe fruits and seeds of Psoralea corylifolia • Family: Leguminosae • GS: India, China, Srilanka, Nepal, Vietnam • Constituents: coumarin like psoralen, isopsoralen, psoralidin, isopsoralidin, carylifolean, bavachromanol and psoralenol, Fixed oil 10%, essential oil 0.05% and resin • Seeds: Flavonoids: bavachalcone, bavachinin, isobavachalcone, bavachin and isobavachin • Seed oil: limonene, aelemene, beta- caryophyllenoxide, 4-terpineol, linalool, geranyl acetate, angelicin, psoralen, bakuchiol
  17. 17. • Chemical Test: • psoralen, dissolved in alcohol + NaOH  UV light observation yellow fluorescence • Psoralen, dissolved in small amount of alcohol, 3 times propylene glycol, 5 times acetic acid, 40 times water UV light observation blue fluorescence • Uses: • Aphrodisiac, antibacterial, astringent, cytotoxic, diaphoretic, diuretic, stimulant, stomachic , tonic, lower back pain, skin disease, bed wetting, leprosy, hair loss Psoralen Psoralidin
  18. 18. 3. Ammi majus • Syn: Bishop’s weed, Laceflower, Toothpick ammi, Large bullwort • Source: dried fruits of Ammi majus • Family: Umbelliferae • GS: Europe, Egypt, West africa, India • Constituents: furanocoumarins, xanthotoxin, imperatorin, bergapten, isopimpilin • CT: 1) drug+ waterboilstrainfiltrate+ NaOH no rose color  distinct from Ammi visanaga 2) Alc. Ext of fruit blue fluorescence under UV light • Uses: furanocoumarin: stimulate pigment production in skin when exposed to bright sunlight and hence  treatment of vitiligo and psoriasis
  19. 19. 3. Ammi majus • Constituents: furanocoumarins, xanthotoxin, imperatorin, bergapten, isopimpilin
  20. 20. 4. Phyllanthus (Lignan) • Syn: Bhumyamlaki, Stone breaker • Source: dried leaves and stem of Phyllanthus niruri • Family: Euphorbiaceae • GS: trophical zone • Uses: Kidney stones treatment Antibacterial, Anti inflammatory Anti hepatotoxic Antispasmodic Anti viral Liver tonic Choleretic Immuno-stimulant
  21. 21. • Constituents • Lignans: phyllanthin, hypophyllanthine, phyltetralin, lintetralin, niranthin, nirtetralin, nirphylline, nirurin, niruriside. • Terpenes: Cymene, limonene, lupeol and lupeol acetate. • Flavonoids. Quercetin, Quercitrin, Isoquercitrin, astragalin, rutin, physetinglucoside. • Lipids: Ricinoleic acid, dotriancontanoic acid, linoleic acid, linolenic acid. • Benzenoids: Methylsalicilate. • Alkaloids: Norsecurinine, 4 - metoxy - Norsecurinine, entnorsecurinina, nirurine, phyllantin, phyllochrysine. • Steroids. Beta-sitosterol. • Alcanes: Triacontanal, Triacontanol. • Others. Vitamin C, tanins, saponins.
  22. 22. 5. Male fern (polyketide-resin) • Syn: Filix Mass, Rhizoma filicis Maris • Source: dried rhizome and its surrounding frond bases of Dryopteris filix-mass • Family: Polypodiaceae • GS: Europe, England, Germany, India: JK, HP, SK at high altitude of 5000-10000 ft. • Use: Potent taenicide, kills worms and expel it out, absorption from GIT blindness, in large dose: irritant poison
  23. 23. • Constituents: -5% yellow resin: anthelmintic property -Oleoresin: phloroglucinol dvt. -Monocyclic dvt.: butyryl phloroglucinol, aspidinol and acylfilicinic acid -Bicyclic: albaspidin, flavaspidic acid -Tricyclic: filicic acid