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Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
Polyketide lignan-phenylpropanoids
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Polyketide lignan-phenylpropanoids

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  • 1. Lignans & Phenyl-propanoids Priyanka Goswami
  • 2. IntroductionLignan • • • • • 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.
  • 3. Introduction-Lignan • 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
  • 4. Introduction-Phenylpropanoids • diverse family of organic compounds that are synthesized by plants from the amino acid phenylalanine. • 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 phenylpropanoid biosynthesis. • Phenylpropanoids are found throughout the plant kingdom, where they serve as essential components of a number of structural polymers, provide protection from ultraviolet light, defend against herbivores and pathogens, and mediate plantpollinator interactions as floral pigments and scent compounds.
  • 5. IntroductionPhenylpropanoids • Concentrations of phenylpropanoids within plants are also altered by changes in resource availability. • 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
  • 6. 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 • GS: America (US-Virginia, Kentucky, North carolina, Tennessee, Indiana, Canada) Indian: Tibet, China, Afghanistan, Himalayas • Collection: The rhizome which is about 1 m in length, is dug up cut into pieces about 10 cm in length and dried.
  • 7. • 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 Starch P. hexandrum 6-12% Resin 40% podophyllotoxin
  • 8. • Chemical Test: Alcoholic ext. + strong copper acetate- brown ppt with Indian podophyllum & green color without ppt with american podophyllum • USES: -Cyto-toxic, venereal disease -Podophyllotoxin is semisynthetically converted to etoposide potent anticancer agent for lung & testicular. -Its GIT irritant, drastic purgative in moderate uses
  • 9. 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, betacaryophyllenoxide, 4-terpineol, linalool, geranyl acetate, angelicin, psoralen, bakuchiol
  • 10. Psoralen Psoralidin • Chemical Test: 1) psoralen, dissolved in alcohol + NaOH  UV light observation yellow fluorescence 2) Psoralen, dissolved in small amount of alcohol, 3 times propylene glycol, 5 times acetic acid, 40 times water UV light observation blue fluorescence • USES Aphrodiasic, antibacterial, astringent, cytotoxic, deobstruent, diaphoretic, diuretic, stimulant, stomachic , tonic, lower back pain, skin disease, bed wetting, leprosy, hair loss
  • 11. 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
  • 12. 3. Ammi majus • Constituents: furanocoumarins, xanthotoxin, imperatorin, bergapten, isopimpilin
  • 13. 4. Phyllanthus (Lignan) • Syn: Bhumyamlaki, Stone breaker • Source: dried leaves and stem of Phyllanthis niruri • Family: Euphorbiaceae • GS: trophical zone • Uses: Kidney stones treatment Antibacterial Anti inflamatory Anti hepatotoxic Antiespasmodic Anti viral Hepatotonic Choleretic Inmuno stimulant
  • 14. • 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.
  • 15. 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
  • 16. • Constituents: -5% yellow resin: anthelmintic property -Oleoresin: phloroglucinol dvt. -Monocyclic dvt.: butyryl phloroglucinol, aspidinol and acylfilicinic acid -Bicyclic: albaspidin, flavaspidic acid -Tricyclic: filicic acid

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