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A comprehensive overview of terpenoids, also known as isoprenoids, which are natural products found in plants and marine organisms. It delves into their classification, biosynthesis, and various uses, particularly focusing on monoterpenoids and sesquiterpenoids. The document highlights the importance of terpenoids in the perfume industry, culinary herbs, and medicinal applications. It also discusses the extraction methods, chemical properties, and biological activities of specific terpenoids, such as camphor, cineole, menthol, and terpin hydrate.
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Terpenoids Classification and Uses of Terpenoids
aka ISOPRENOIDS natural products whose structures may be divided into isoprene units (C5H8) ⭐ ISOPRENE UNITS HAS 5 CARBONS
2 isoprene units (C10H16) GENARYL DIPHOSPHATE isolated from higher plants and marine organisms can be found in defense and pheromonal secretion of insects CHARACTERISTICS volatile and intensely pungent odors most common component in plants responsible for fragrance and flavor USES perfume industry culinary herbs
ketone Source: Cinnamomum camphora Family: Lauraceae crystalline products in clefts in the woody stems and roots, and to a greater extent, dissolved in the volatile oils AMOUNT the wood is chipped and distilled with steam, and 1 lb of crude camphor is obtained from 40lbs of chips METHOD OF EXTRACTION the crude camphor is then freed from oil by centrifugation and pressed into familiar cakes SPECIFIC ROTATION: top +4 to +43 (to the right)
MENTHOL or MENTHAN-3-OL
formed by the action of nitric acid on rectified turpentine oil in the presence of alcohol it is cis-p-menthane-1-8-diol hydrate USES expectorant
antipruritic at 0.1% to 1% counterirritant at 1-16% concentration, often combined with camphor in small doses, menthol has Carminative action; however, larger doses will have a depressant effect on the heart combined with camphor and eucalyptus oil in ointments, cough drugs, nasal sprays and inhalants to relieve symptoms of bronchitis, sinusitis and nasal congestion
alkaloid Plants: Cinnamon Clove Nutmeg Peppermint
phenol
3 isoprene units, C15H FARNESYL DIPHOSPHATE widely distributed in nature the largest class of terpenoids SOURCES B-cadinene -> from oil of Jade (Juniper tar, Juniperus oxycedrus) B-caryophylene -> from clove oil, Eugenia caryophyllus ABSCISIC ACID essential plant hormone controls growth and development SESQUITERPENOIDS LACTONES chemically distinct through the presence of an a-methylene, y-lactone system also contains a, B-unsaturated carbonyls as well as epoxides these functional groups represent reactive receptor sites for biological nucleophiles such as thiol and amino groups of enzymes with antimicrobial and antitumor activity
alkaloid Plants: Cinnamon Clove Nutmeg Peppermint
phenol
3 isoprene units, C15H FARNESYL DIPHOSPHATE widely distributed in nature the largest class of terpenoids SOURCES B-cadinene -> from oil of Jade (Juniper tar, Juniperus oxycedrus) B-caryophylene -> from clove oil, Eugenia caryophyllus ABSCISIC ACID essential plant hormone controls growth and development SESQUITERPENOIDS LACTONES chemically distinct through the presence of an a-methylene, y-lactone system also contains a, B-unsaturated carbonyls as well as epoxides these functional groups represent reactive receptor sites for biological nucleophiles such as thiol and amino groups of enzymes with antimicrobial and antitumor activity PLANT HORMONES or PHYTOHORMONES GIBBERELLINS lengthens the steam between nodes hastens maturity period in conifers promotes early seed production and germination 100 types AUXIN first growth hormone to be discovered first isolated from human urine found in growing stems and roots promotes stem growth towards the sun - phototropism ETHYLENE gaseous hastens fruit ripening increases root growth and root hair formation --> increasing absorption area CYTOKININS exists in areas where rapid cell division takes place delays leaf senescence or aging ABSCISIC ACID induces dormancy in seeds and helps seed withstand unfavorable growth conditions promotes leaf senescence stress hormone
Other name: Colforsin Source: Coleus forskohlii Uses: vasodilator, weight loss aid
4 isoprene units C20H GERANYLGERANYL DIPHOSPHATE RESINS ACIDS (Abietic acid) exuded from the woods of trees, especially in conifers, and protect the tree from infection and attack GIBBERELINS plant hormones that stimulate plant growth PRODOLACTONES plant inhibitors
Source: Gingko biloba Characteristics: flavone glycodies of rutin Ginkgolides A,B,C, and M-diterpenoid they inhibit platelet aggregating factors (PAF). it will result in blood fluidity and circulation Uses: Dietary supplement - inhibit platelet aggregating factor TAXOL Other name: Paclitaxel Source: Taxu brevifolia Characteristics: complex diterpenoid with a taxane ring system Uses: one of the promising antineoplastic drug or anticancer Limitation: limited supply of the drug, difficult to synthesize
6 isoprene units C30H EXAMPLES OF DITERPENOIDS TETRAPENOIDS or CAROTENOIDS 8 isoprene units C40H Vitamin A Major form: RETINAL major natural form of the vitamin, but known forms include the acetate and the palmitate esters of the alcohol and such oxidation products are: TRETINOIN or all-transretinoic acid ISOTRETINOIN or 13-cis retinoic acid Sources:
defense against herbivory QUASSINOIDS antileukemic property (bruceantin) SAPONINS toxic to cold blooded animals
TETRAPENOIDS or CAROTENOIDS Beta-carotene aka Provitamin A most common carotenoid in higher plants responsible for the yellow, orange, red, and purple colors seen in living organism USES In plants and microorganism photoprotective agents photosynthetic accessory pigments membrane stabilization components In animals source of vitamin A and other retinoids as photoprotective antioxidant prevents oxidative damage to cells General use colorants for foods animal feeds pharmaceutical and cosmetics
chemical constituents of volatile oils and spices may be divided into 2 broad classes, based on their biosynthetic origin: Terpenoid derivatives formed via the acetate-mevalonic acid pathway Aromatic compounds formed via the shikimic acid-phenyl propanoid route dried, fragrant, aromatic, or pungent plant parts that contain a volatile oil used in food as seasoning agent rather than for nutrition
Volatile oils and Spices Characteristics of Volatile oils Biosynthesis Method of extraction Uses of Volatile oils Classification of Volatile oils SPICES AKA essential oils or ethereal oils General uses: Spice and condiments Flavoring and odorant Carminative - expel gas Characteristics of Volatile oils characterized by high refractive indices optically active immiscible with water miscible in ether, alcohol, and most organic solvents on exposure to light and air they oxidize and resinity (fixed oil: rancidity) they don't leave permanent grease on paper cant be saponified with alkalies
⭐ volatile oils occur in specialized secretory structure such as glandular hairs (Lamiaceae)
essential for the manufacture of soaps, toiletries, and deodorizers to mask and provide odor to household cleaners, polishers, and insecticides TWO MAJOR COMPONENTS OF VOLATILE OILS Eleoptene hydrocarbon portion of oil is liquid liquid volatile oil Stereoptene oxidized hydrocarbon portion of oil is usually solid examples: menthol camphor thymol hydrocarbon alcohol aldehyde ketone phenol phenolic ether oxide ester Turpentine oil
Source: Pinus palustris Family: Pinaceae distilled from Pinus palustris largest volume essential oil uses: counterirritant Rectified Turpentine oil distillation from an aqueous solution of NaOH uses: expectorant Terpinol or Terpin hydrate formed by the action of nitric acid on rectified turpentine oil in presence of alcohol uses: expectorant, stimulant to mucous membrane usual dose: 85mg TO Rectified TO^ Terpinol TO + NaOH RTO + NA + alcohol
Source: Mentha piperita Family: Lamiaceae Source: Elettaria cardamomum Family: Zingerberaceae Source: Coriandrum sativum Family: Umbeliferae Source: Rosa gallica Family: Rosaceae
Peppermint oil
distilled with steam fresh over round parts of flowering plant ALCOHOL VOLATILE COMPONENT: menthol USES: counterirritant carminative stimulant Cardamom oil distilled dried, ripe seed ALCOHOL VOLATILE COMPONENT: cineol USES: flavor carminative Coriander oil steam distillation dried ripe fruit ALCOHOL VOLATILE COMPONENT: linalool USES: flavor carminative Rose oil aka Otto of Rose distilled fresh flower ALCOHOL VOLATILE COMPONENT: geraniol citronellol nerol USES: perfume
Source: Cinnamomum cassia Family: Lauraceae Source: Citrus sinensis Family: Rutaceae Source: Cymbopogon winterianus Family: Poaceae ALDEHYDE VOLATILE COMPONENT: Citronellal USES: insect repellant
Cinnamaldehyde, cinnamic aldehyde, cinnamyl aldehyde USES: carminative pungent aromatic antiseptic ⭐ Mannitol- imparts sweetness of cinnamon
Cinnamon oil
aka Saigon cinnamon, cassia cinnamon, ceylon cinnamon steam distillation of leaves and twigs Orange oil expression of the fresh peel ripe fruit ALDEHYDE VOLATILE COMPONENT: Citronellal USES: flavor Citronella oil steam distillation of the fresh peel dried leaves
Source: Hamamelis virginiana Family: Hamamelidaceae Source: Citrus limon Family: Rutaceae
2 hexen 1-al USES: astringent in OTC hemorrhoidal preparation ⭐ Tannins - secondary metabolite of Hamamelis virginiana
Hamamelis water
distilled witch hazel extract steam distillation of dried dormant twigs ALDEHYDE VOLATILE COMPONENT: citral (combination of neral and geranial), hesperidin, tannin, calcium oxalate USES: stimulant flavoring agent stomachic Lemon peel
