Terpenoid iridoid

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Terpenoid iridoid

  1. 1. Iridoids & Misc. compounds
  2. 2. Introduction- Terpenoid • Terpenes constitute one of the most important groups of essential oils. • The group includes constituents such as limonene, phellandrene, cedrene etc. and their oxygenated derivatives such as geraniol, citral, carvone, camphor, cineol and many others. • These compounds arise at the geranyl pyrophosphate and fernesyl pyrophosphate levels respectively, in the acetate mevalonate pathway from the fundamental building block termed as isoprene (C5H8) unit. 2-Methyl-1,3-butadiene
  3. 3. Terpenoid-Classification SR NO. NO. OF CARBON ATOM VALUE n CLASS 1 10 2 MONOTERPENOIDS (C10H16) 2 15 3 SESQUITERPENOIDS (C15H24) 3 20 4 DITERPENOIDS (C20H32) 4 25 5 SESTERPENOIDS (C25H40) 5 30 6 TRITERPENOIDS (C30H48) 6 40 8 TETRATERPENOIDS (C40H64) 7 >40 >8 POLYTERPENOIDS (C5H8)n
  4. 4. Introduction-Iridoids  Monoterpene  Cyclopenta[c]pyranoid skeleton  Iridane skeleton cis-2-oxa-bicyclo-[4,3,0]-nonane  Type: Secoiridoids by cleavage of the 7,8 bond of the cyclopentane ring  Some authors limits the definition up to: Methyl cyclopentane  Iridoid glycosides (>300)  Secoiridoid glycoside (>100)  Non-glycoside compounds (>100)
  5. 5. Iridoids: How derived? • Named after ants of the Iridomirmex genus, from which were isolated compounds involved in the defence mechanism of the insects: iridoidal, iridomyrmecin and related compounds. • Exists in plants as well: nepetalactone from Nepeta cataria (Lamiaceae), or teucriumlactone C from Teucrium marum have marked properties • Nepeta cataria: effects on cats, so termed as Catnip, katzenmelisse, herbe-aux-chats • Iridoid: generally 10 carbons, may even have more or multiple structure variation up to polycyclic structures
  6. 6. Iridoids: Structure
  7. 7. Iridoids: Occurence • Biosynthetically homogenous • Insects: ants • Plants: dicotyledon: Angiosperm • Plant family: Dipsacales, Gentianales, Lamiales, Scrophulariales • Iridoid glycoside: glucoside- glycosidic linkage between –OH group on anomeric carbon of D-glucose and the –OH group in the 1-position of aglycone • Small no. of structure: 1 sugar portion is oligosaccharide (e.g. Rehmaniosidesa) • Glucose is linked to: 11-hydroxylmethyl group (e.g. ebuloside in caprifoliaceae • Non-glycosidic iridoid: alkaloid: skytanthine
  8. 8. Iridoids: Occurrence 10 carbon atom • Polycyclic compounds: Plumericin, Polyesters(valepotriates) or intramolecular ethers (Rehamaglutin B) • Non-glycosidic secoiridoids: Syringa spp., Olea spp. • C-11: carboxymethyl group (loganin, geniposide) or part of carboxylic acid (monotropein) • Hydroxymethyl group: Valerianceae, Caprifoliaceae • Aldehyde or methyl group: Lamioside • C-11 is absent: Aucubin, Catalpol, Harpagoside
  9. 9. Iridoids: Occurrence 10 carbon atom • Pyran ring is exceptionally open: gentiobiosides of Iridodidal & Nepatariaside (precursor of nepetalactone) • Methyl group at C-8: aucumbin, monotropein, epoxide (valtrate) & rarely absent (deutzioside) • Unsaturation at 7,8 position: Geniposide, Aucumbin • Vinyl group at C-9: gentiopicrin • Oleoside: ethylidene-hydroxyethylidene at C-9 • Carboxy group is esterified: Oleuropein
  10. 10. Iridoids: biosynthesis
  11. 11. Iridoids: Extraction • Delicate due to their great instability • Instability darkening that takes place soon after plant collection in many species containing iridoids • Extraction with polar solvent alcohols of various concentration • Initial separation, re-dissolving the extraction residue in water, then re-extracting this with immiscible solvents of increasing polarity • Fractionation: chromatography on alumina on charcoal (with risk of irreversible adsorption), on porous polymers (e.g. XAD- 2) with polar eluents & more and more by polar reverse phase HPLC • Purification TLC, HPLC • Detection Trim and Hill color reagent: Dilute solution of CuSO4 and HCl, blue color • Detection spray: vanillin H2SO4, Hot HCl
  12. 12. Iridoids: Biological- Pharmacological properties • Defensive function in ants • Anti-inflammatory: weak by oral route and stronger by topical route • 1 mg of aucubin, verbenalin or loganin have an activity almost similar to that of 0.5 mg of indomethacin on the TPA induced mouse ear edema
  13. 13. Drugs category Iridoids: 1. Gentian (bitter glycoside) 2. Picrorrhiza (bitter glycoside) Modified Terpenoids 1. Quassia (bitter, triterpenoid lactone) 2. Tinospora (sesquiterpene glucoside) 3. Artemisia (sesquiterpenoid) 4. Taxus (diterpenoid) 5. Andrographis
  14. 14. 1. Gentian • Syn: yellow gentian root • Source: dried fermented roots and rhizomes of Gentiana lutea • Family: Gentianaceae • GS: Mountainous regions of Central and south Europe, Turkey, Yugoslavia • Now: France, Italy, Germany • Use: bitter tonic, GIT problems, anti- inflammatory, wound healing, choleretic-stimulating bile production, anti-oxidant, hepato-protective, anti- fungal, anorexia
  15. 15. Constituents & Structures • Bitter glycoside, alkaloids, yellow coloring agent, sugar, pectin, fixed oil • Seco-iridoid: gentiopicroside (gentiopicrin-gentiomarine) • Hydrolysis product: gentiogenin + glucose • Biphenolic acid ester of gentiopicrosideamarogentinhighest bitter • Sweroside, swertiamarine • Yellow color is due to Xanthonegentistin or gentiamarine, isogentistin, gentioside, gentisic acid • Alkaloid: gentianine, gentialutine
  16. 16. 2. Picrorrhiza • Syn: Kutki, Yellow gentian • Source: dried rhizomes of Picrorrhiza kurroa • Family: Scrophulariaceae • GS: North-west Himalaya region at 3000- 4000 m • Use: Bitter tonic, Hepatoprotective, Immunomodulator, curing different types of jaundice, skin disease, improves eye sight, Cholagogue- stimulates gallbladder contraction to promote bile flow
  17. 17. Constituents & Structures 1. Iridoid glycoside: • Picroside I • Picroside II • Kutkoside • Pikoroside • Picrorhizinon hydrolysispicrorhizetin + dextrose 2. Phenolic glycoside: • Picein • Androsin 3. Cucurbitacin glycoside
  18. 18. 3. Quassia • Syn: Bitter wood, Jamaica Quassia • Source: dried wood of the stem of Aeschrion excelsa (Picroena or Picrasma excelsa) • Family: Simaroubaceae • GS: West indies, Jamaica, Guadeloupe, Martinique, Barbados, St. Vincent • Use: Bitter tonic, Insecticide, vermicide for thread worms, slightly narcotic & acts on flies, increase appetite
  19. 19. Constituents & Structures 1. Terpenoid : Amaroid • quassin, an intensely bitter lactone • Neoquassin • Isoquassin (picrasmin) • 18-hydroxy quassin • Scopoletin 2. Alkaloid: Cathine-6-one 3. Volatile Oil 4. Inorganic salt: CaCl2, NaCl, sulphate of lime, oxalate, ammonical, KNO3, Neoquassin
  20. 20. 4. Tinospora • Syn: Guduchi, Gulvel, Heartleaved moonseed • Source: dried matured stem of Tinospora cordifolia • Family: Menispermaceae • GS: Himalaya, South India, Srilanka • Use: Rejuvenator, Hypoglycemic,Detoxifier, Immonuomodulatory, astringent, antipyretic, blood purifier, anti- neoplastic, cardiotonic, anti-asthamatic, pyrexia, skin disease
  21. 21. Constituents & Structures 1. Furanoditerpenoids: • Columbin • Tinosporaside-lignan • Tetrahydrofuran 2. Alkaloid: • Jactrorhizine • Palmatine • Berberine • Tembeterine 3. Sesqui terpene glucoside 4. Phenylpropene disaccharide Cordifolioside A, B Tinosporic acid, Tinosporone, Tinosporal, Choline
  22. 22. 5. Artemisia • Syn: A.cina (Santonica, wormseed) A. annua (Sweet annie, Qinghaosu) • Source: dried un-expanded flower heads of Artemisia cina, A. annua, A.brevifolia, A.maritima & other spp. Of Artemisia. • Family: A. cina (Compositae) A. annua (Asteraceae) • GS: A. cina (Pakistan, Turkestan), A. annua (China-native, Europe, US, Turkey, Australia, Iran, Vietname, India (GJ, UP, JK, HP, KA)
  23. 23. Constituents & Structures A. Cina • Sesquiterpene lactone:santonin • Artemisin • Irone A. annua • Artemisinin • Deoxyartemisinin • Artemisic acid • Arteanniun A, B • Cadinene type sesquiterpene Santonin Artemisin Artemisinin
  24. 24. USES • A.cina: Strong althelmintic against round worms and less effect against thread worms. • A.annua • Artemisinin: Chloroquine resistant Plasmodium falciparum and particularly cerebral malaria • Derivative: Artesunate, Artemether: effective • Artemisic acid: anti-inflammatory, cytotoxic, antibacterial
  25. 25. 6. Taxus • Syn: Yew • Source & GS: dried bark of • Taxus baccata (Europe) • Taxus brevifolia & • T. canadensis (North america) • Taxus cuspidata (Japan) • Taxus wallichiana (Himalaya) • Family: Taxaceae
  26. 26. Constituents & Structures Tricyclic diterpenoids: • Taxane skeleton • Taxusines • Taxagifen • Baccatin-III • Taxine • Taxol • Cephalomannine • Taxicine
  27. 27. USES • Paclitaxel: mitotic spindle poison • M/a: it promotes assembly of tubulin dimers into microtubules which is stabilized by inhibiting their depolymerization • Indication: Advanced ovarian cancer, metastatic breast cancer • S/e: neutropenia, peripheral neuropathy, CVS, alopecia • Posology: 135-175 mg/m2 • Docetaxel: • Indication: breast cancer • S/e: severe neutropenia, hypersensitivity reaction, water retention, cutaneous reaction • Posology: 100 mg/m2
  28. 28. 7. Andrographis • Syn: Kalmegh, King of bitter, kirayet • Source: leaves and entire aerial part of Andrographis paniculata • Family: Acanthaceae • GS: growing -India, Pakistan, Srilanka, Indonesia • Cultivated-China, Thailand, west indies, Mauritius • Use: bitter tonic, febrifuge-reduce fever, anthelmintic, astringent, cholagoggue, cholera, diabetes, weakness, blood purifier, jaundice, GI disturbances, itching
  29. 29. Constituents & Structures • Diterpene lactone: kalmeghin • Andrographolide • Neoandrographolide • 14-deoxy-11,12- didehydroandrographolide • 14-deoxy-11-oxo- • Andrographolide • Andrographiside
  30. 30. Carrot • Syn: Gajar, Queen annie’s lace • Source: dried roots of Daucus carota • Family: Umbelliferae • GS: Temperate regions of Asia, Africa & Europe • Use: food, condiment, Anthelmintic, flatulence, Immunomodulatory, antioxidant, Vitamin A supplement
  31. 31. Constituents & Structures Diterpenoids Carotene Carotol Daucol Trans-asarone Pinene Limonene Geraniol Retinol Asarone C a R O T E n e
  32. 32. Chirata • Syn: Indian gentian, Indian balmony, chirayta • Source: entire herb of Swertia chirata • Family: Gentianaceae • GS: India, Nepal, Bhutan • Use: ingredient of Mahasudrashan & Sudarashan churna, chronic fever, bitter tonic, stimulant, liver protective, promoting flow of bile, cures constipation and useful in treating dyspepsia
  33. 33. Constituents & Structures Chirata: • chiritin, gentiopicrin and amarogentin • Amarogentin: phenol carboxylic acid ester of sweroside: related to gentiopicrin • Ophelic acid • Gentianine • Gentiocrucine

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