Terpenoids PDF - PHINMA Education

TERPENOIDS MODULE 13 LEARNING OUTCOMES: 1. Define monoterpenoids & others and their basic chemical structure. 2. Explain the biosynthesis process, key enzymes, and intermediates. 3. Identify medicinal plants with monoterpenoids and their pharmacological uses. 4. Describe extraction and p...

TERPENOIDS MODULE 13 LEARNING OUTCOMES: 1. Define monoterpenoids & others and their basic chemical structure. 2. Explain the biosynthesis process, key enzymes, and intermediates. 3. Identify medicinal plants with monoterpenoids and their pharmacological uses. 4. Describe extraction and purification methods. 5. Discuss ecological roles and industrial applications. Terpenoids a.k.a isoprenoids Any of a class of hydrocarbons that consist of terpenes attached to an oxygen-containing group. Terpenoids are widely found in plants, and can form cyclic structures such as sterols. Classifications of Terpenoids: Monoterpenoids (C10): Derived from geranyl pyrophosphate. Found in volatile oils. Examples: Gentian, Centaury, Valerian, Devil’s claw. Sesquiterpenoids (C15): Derived from farnesyl pyrophosphate. Examples: Chamomile, Feverfew, Artemisinin. Diterpenoids (C20): Derived from geranylgeranyl pyrophosphate. Examples: Gingko, Forskolin, Taxol. Classifications of Terpenoids: Triterpenoids (C30): Examples: Neem, Quassia wood. Tetraterpenoids/Carotenoids (C40): Examples: Lycopene, Carotene. Polyterpenoids: Examples: Rubber, Gutta-percha.  MONOTERPENOIDS 1. Iridoids Cyclopentan-[c]-pyran monoterpenoids are a growing group of compounds derived from Iridomyrex ants, which use them as defensive secretions.  MONOTERPENOIDS 2. Gentian SN: Gentian lutea (Gentianaceae) AC/s: gentiopicroside (a.k.a gentiopicrin and gentiamarin), genistic acid (2,5-dihydroxybenzoic acid), gentianose and gentiobose Uses: used to treat various gastrointestinal conditions, anti-inflammatory and wound healing agent, choleretic, antioxidative, hepatoprotective and antifungal activities MONOTERPENOIDS 3. Centaury SN: Centaureum erythraea, C. majus, C.suffruticosum AC/s: centapicrin, swertiamarin, sweroside and gentiopicroside Uses: employed as bitter, stimulating the appetite and increasing the secretion of bile and gastric juice  MONOTERPENOIDS 4. Bogbean leaf SN: Menyanthes trifoliata (Menyanthaceae) AC/s: menthiafolin and loganin Uses: diuretic, treatment of various rheumatic conditions 5. Plantain SN: Plantago major AC/s: iridoid aucubin Uses: expectorant, diuretic, antihaemorrhagic properties  MONOTERPENOIDS 6. Valerian SN: Valeriana officinalis (Valerianaceae) AC/s: bornyl acetate, valerenic, valerenolic acid, acetoxyvalerenolic acid, valepotriates Uses: anti-anxiety, sleep aid 7. Devil’s claw (Harpagophytum) SN: Harpagophytum procumbens AC: harpagoquinone Uses: treatment of rheumatic disease, anti-inflammatory and analgesic  SESQUITERPENES 1. Chamomile SN: Matricaria recutita (Asteraceae) AC/s: bisabolol, bisaboloxides, prochamazulene Use/s: anti-inflammatory, antispasmodic 2. Feverfew SN: Tanacetum parthenium (Asteraceae) AC/s: Parthenolide Uses: antipyretic, migraine, serotonin antagonist  SESQUITERPENES 3. Artemisinin/Qinghaosu SN: Artemisia annua (Asteraceae) Use: Potent blood schizontocide (malaria) 4.Arnica flowers SN: Arnica montana (Compositae/Asteraceae) AC/s: methylated flavones, sesquiterpene lactones of the pseudoguaianolide, esters of helenalin Uses: astringent, treatment of sprain and bruises ❖ Arnica gel - was the first traditional herbal medicine to be granted registration in UK  SESQUITERPENES 5. Chicory SN: Cichorium intybus (Compositae/Asteraceae) AC/s: sesquiterpene lactones, cichorioside A and picriside B Uses: Lactucin and lactucopicrin - antimalarial Diuretic, antihepatotoxicity 6. Fish berries (cocculus indicus) SN: Anamirta cocculus (Menispermaceae) AC/s: Picrotoxin, Picrotoxinin Use/s: Used intravenously in poisoning by barbiturates and other narcotics Very small quantities of the fruits are sufficient to stupefy fish  SESQUITERPENES 7. Orris SN: Iris florentina, Iris germanica, Iris pallida (Iridaceae) AC/s: irone, ionone Use: Perfumery (fixative for artificial violet perfumes) ❖ Mogadore orris - it is usually inferior to the European, the rhizome being smaller, darker and less fragrant  SESQUITERPENES 8. Santanonica flowers SN: Artemisia cina (Compositae/Asteraceae) AC/s: santonin Use: anthelmintic 9. Gossypol SN: Gossypium spp. Uses: male antifertility agent, treatment of menorrhagia, leiomyoma and endometriosis DITERPENOIDS 1. Gingkgo SN: Gingkgo biloba (Ginkgouceae) AC: Ginkgolides Use: reduce capillary fragility and reduce blood loss (ischemic brain damage) 2. Forskolin or colforsin SN: Coleus forskohlii Uses: cardiomyopathy, bronchial asthma, glaucoma, hypertension DITERPENOIDS 3. Taxol/paclitaxel SN: Taxus brevifolia (Taxaceae) Use: treatment of metastatic carcinoma of the ovary and breast TRITERPENOIDS 1. Neem SN: Azadirachta indica AC: limonoid azadirachtin Use/s: antifeedant TRITERPENOIDS 2.Quassia wood (Jamaica Quassia) SN: Picroena excelsa, Aeschrion excelsa (Simaroubaceae) AC/s: amaroid, neoquassin, scopoletin Uses: bitter tonic, insecticide, enema for the expulsion of thread worms Other quassinoids (Simaroubaceae) Uses: for cancer, amoebic dysentery, malaria Quassinoid (simaroubolide) Uses: antileukaemic, anti-viral, anti-inflammatory, antifeedant  TRITERPENOIDS 3. Black horehound SN: Ballota nigra (Lamiaceae) 4. White horehound SN: Marrubium vulgare (Lamiaceae) AC/s: Marrubiin TETRAPENOIDS 1. Lycopene 2. Carotene Obtained from carrots used to prevent xerophthalmia  POLYTERPENOIDS 1. Rubber SN: Hevea brasiliensis (Euphorbiaceae) 2. Gutta-percha SN: Parthenium argentatum (Compositae/Asteraceae) AC/s: Polymerized hydrocarbon gutta Uses: for covering moist dressing, manufacture of surgical instruments  POLYTERPENOIDS 3. Chicle (sapodilla plum) SN: Manilkara zapota (Sapotaceae) Use: chewing gum