Phytochem Class 6 PDF

Class 6 • Sesquiterpene • Patchoulol • What is this? • A terpene that contain 15 carbons • What is this? • A sesquiterpene • That is commonly found in patchouli (Pogostemon cablin) • Where can they be found? • Most of them are volatile (evaporate at room temperature), so they can be found in aro...

Class 6 • Sesquiterpene • Patchoulol • What is this? • A terpene that contain 15 carbons • What is this? • A sesquiterpene • That is commonly found in patchouli (Pogostemon cablin) • Where can they be found? • Most of them are volatile (evaporate at room temperature), so they can be found in aromatic plants or human made products • This is group is commonly thought to contain the highest number of terpenes, chemical formulas. It contains various subgroups • Linear, branched, or cyclic terpenes • Like monoterpenes they contain linear and cyclic arrangements • What forms does it have? • Several isomers • Thing to know • This is thought to play a major role in the scent of patchouli • Patchoulol • Have displayed antibacterial and insecticidal activity • Commercially • Plays a huge role in the perfumery industry • Is a great replacement for Pacific Yew trees when producing a chemotherapeutic agent called Taxol, used for the treatment of breast cancer Class 6 • Artemisinin • An Oddity • • • What is this? • A sesquiterpene • That is commonly found in sweet wormwood (Artemisia annua). Thing to know • • • This herb has been used in TCM for over 2,000 years and has been used to treat jaundice, bacterial dysentery, in malaria and tuberculosis, for the treatment of wounds and hemorrhoids, in viral and bacterial infections, and autoimmune diseases Since the 1970s this herb has been recognized to contain a compound called artemisinin that successfully treats malaria and parasitic worm infections Artemisinin • While this compound has been rather successful over the past 50 years, concerns are being raised regarding its efficacy i.e., cost of extraction, low yield by the plant, poor bioavailability, and the development of resistance • As malarial resistance begun to pop up throughout SE Asia in 2008 multi-drug therapies have been considered a more effective form of practice • In 2018, a lab modified form of A. annua was grown and tested to generate more of this sesquiterpene. On average, dried leaves contain between 0.1-1% total dry leaf weight, however, the GMO crop yielded levels as high as 3.2% total dry weight of the leaves • Abscisic Acid • Is a sesquiterpene, secondary metabolite, and a primary metabolite, hormone • Found in plants and human How does it behave in a plant? • A hormone that alters endogenous functions i.e., plant development, growth, and stress responses (closes stomata – where gas is exchanged, and water vapour is lost) • So, this hormone encourages growth? • It suppresses the growth of plants, by counteracting other hormones that encourage it • How does it assist with plant development other than suppressing growth? • It plays a key Class 6 • Diterpenes • What is this? • A terpene that contain 20 carbons • Where can they be found? • In plants and fungi • Under normal circumstances these compounds are not volatile, too heavy • Can be found in very small amounts as part of some essential oils • What roles do diterpenes serve within plants? • Defense against biotic and abiotic stressors • Hormones • Ginkgolides – A, B, C, K • What is this? • A diterpene lactone (lactone possess a O2-carrying ring structure with a carbonyl function = CO, functional group) • That is commonly found in Ginkgo biloba • What forms does it have? • Five isomers • Where can it be found within the plant? • Can be found within leaves of the tree • Thing to know • This is viewed to possess a variety of medicinal benefits in humans • Ginkgolides • Have displayed anti-allergic, antioxidant, PAF antagonising, anti-inflammatory, and neuroprotective actions in humans Class 6 • Phorbol • Phorbol • • • What is this? • A diterpene • A diterpene • This will be found in manchineel (Hippomane mancinella) also known as manzanilla de la Muerte (little apple of death) • This will be found in manchineel (Hippomane mancinella) also known as manzanilla de la Muerte (little apple of death) What forms does it have? • • • • What is this? • • A variety of isomers Thing to know What forms does it have? • A variety of isomers Thing to know • Do not play with the tree when dry or wet outside, not a good time • Do not play with the tree when dry or wet outside, not a good time • Habitat ranges from the southern USA throughout the Caribbean to northern reaches of South America • Habitat ranges from the southern USA throughout the Caribbean to northern reaches of South America • Phorbol Phorbol • Blisters, strong contact dermatitis, severe pain, and swelling occur after touching this tree • Blisters, strong contact dermatitis, severe pain, and swelling occur after touching this tree • This compound can be found within the fruits, leaves, roots, and stem of the tree • This compound can be found within the fruits, leaves, roots, and stem of the tree When raining • When raining • Rain bouncing off of leaves on this tree can produce contact dermatitis • Rain bouncing off of leaves on this tree can produce contact dermatitis • Can peel paint off if enough rain falls, for hours • Can peel paint off if enough rain falls, for hours Class 6 • Sesterterpenes • Triterpenes • What is this? • A terpene that contain 25 carbons • What is this? • A terpene that contain 30 carbons • Where can they be found? • In plants, fungi, marine organisms • These compounds are not volatile, too heavy • What roles do diterpenes serve within plants? • Typically, anti-tumor activity has been noted from this class of terpene • Uses by plants for defense are poorly understood currently • Where can they be found? • In plants, fungi, humans • These compounds are not volatile, too heavy • What are some unique things about this terpene? • To provide stability ring structures are typically used • This area is heavily studied by humans as steroids are a group of triterpenes, which we produce • What roles do triterpenes serve within plants? • They can act as primary or secondary metabolites Steroids • Synthesis • In animals • Cholesterol, a triterpene, is produced with 30 C • Next, 3 C are removed to bring the total down to 27 • A OH is then added to this modified triterpene • You have now created a steroid • In plants • Cholesterol is not required for synthesis • Instead, the 30 C unit is assembled directly into a steroid • Phytoecdysones • Brassinosteroids • Thing to know • This is intended to mimic a steroid referred to as ecdysones as a defense mechanism • This steroid can be found amongst crabs, insects, snakes, etc. • Hormones • Animals contain estrogen, testosterone, and progesterone • Plants contain brassinosteroids • How much of this compound is synthesized to maintain function? • Very little as it is quite a potent primary metabolite • Where can this be found within a plant? • Throughout each organ of a plant • What roles do they exert? • Responsible for cellular growth, response to biotic and abiotic stressors, pollination, and vascular differentiation • What is this? • A triterpene • A steroid • Found amongst hundreds of different species, if not more • What forms does it have? • Innumerable number of isomers • Phytoecdysones • As a mimic it is attempting to tell the insect to shed its exoskeleton uncontrollably • The process of shedding requires a lot of energy, on behalf of the insect, and each time it sheds the organism is exposed/defenseless Class 6 • Saponins • What is this? • A triterpene with aglycone attached • Aglycone = carbohydrate • Thing to know • They behave like detergent, soap, an amphipathic molecule • If enough of these compounds are consumed, they can cause harm to the gastric tract by dissolving tissues • Furostanol Saponins • What is this? • A triterpene • This can be found in puncture vine (Tribulus terrestris), with the highest levels displayed in Bulgarian grown varieties • What forms does it have? • A variety of isomers • Thing to know • This plant has been used amongst cultures throughout Eastern Europe, the middle east, India, and China for thousands of years • The leaf and berry have been viewed as aphrodisiac tonics • Saponins • Are believed to exert anabolic/androgenic activity by activating endogenous production of sex steroid hormones i.e., testosterone and LH which may stimulate muscle growth • This activity has been consistently identified in animal study whereas in humans' data obtained has been inconsistent Class 6 • Sesquarterpenes • What is this? • A terpene that contain 35 carbons • Where can they be found? • Found in plants but primarily bacteria • These compounds are not volatile, too heavy • What are some unique things about this terpene? • Not much is known about this group of terpenes as they were only organized in 2011 • Tetraterpenes • What is this? • A terpene that contain 40 carbons • Where can they be found? • In plants • These compounds are not volatile, too heavy • What are some unique things about this terpene? • They are most commonly understood as pigments i.e., what pops out in the fall after chlorophyll is no longer produced and is eventually all destroyed • Carotenes • What does carotene mean? • Recall, they are orange or red pigments in plants • They are tetraterpenes with various isomers and contain no O2 • What are examples of carotenes in nature? • Beta-carotene, lycopene, lutein, and zeaxanthin • Aren’t carotenoids the same as carotenes? • They are similar and literally translate to “carotene like” as they contain some O2 • Xanthophyll's are an example of carotenoids • Where can they be found? • These can be found in some photosynthetic bacteria, some species of fungi, algae, plants, and animals • When we here about them we will typically think of foods i.e., bell peppers, broccoli, cantaloupe, oranges, mangoes, etc. also within leaves of plants • What roles do they have in nature? • To prevent the buildup of free radicals • Act as attractants • Assist with photosynthesis i.e., incase chlorophyll misses any light Class 6 • Animals • Astaxanthin • What sort of effects do carotenes exert in animals? • Antioxidant • Sexual development • This affects the development of gonads within birds, mammals, and reptiles bust most profoundly affects the former • Carotenes have the capacity to override the chromosomal influence of sex. So, the more that is consumed the more likely this will occur • Vision • Beta-carotene is a tetraterpene that when split in half makes retinal a diterpene • What is this? • • A carotenoid Where can it be found in nature? • Most commonly within algae, egg yolks, salmon (provides the pink colouration when wild grown), and krill (commercially) • Bioaccumulation plays a large role here • • • Defined as an increase in the concentration of a chemical in a biological organism over time, compared to the chemical’s concentration in the environment In plants but mostly as a flower pigment What type of therapeutic effects does it contain? • This a fat-soluble antioxidant • Recall that vitamin E is found to be one of the strongest lipid soluble forms and astaxanthin is not as strong as it but more effective than vitamin A Class 6 • Rubber • What is this? • A Polyterpene • Polyterpenes • What is it made up of? • They are made up of thousands of isoprene units • What is this? • A terpene that contain >40 carbons • Where can they be found? • In plants • These compounds are not volatile, too heavy • What are some unique things about this terpene? • They typically contain thousands of carbons • Rather than focussing on their chemical structure to differentiate between patterns are sought after instead • The patterns they seek will point out similar functions to other chemicals • Thing to know • When the bark of a rubber tree is damaged white latex is released; this is a physical rather than a chemical defense • How does that show up? • If an insect attempts to enter this type of plant, it will quickly receive a mouthful of liquid eraser • This then dries and causes the insect to die due to starvation • The rubber has stuck to their mouth and cannot be wiggled off • In 2013, German researchers modified one key enzyme in a Kazakh variety of dandelion, T. koksaghyz, to now have the potential to commercially cultivate this crop to produce rubber • Humans uses • The first use of rubber comes from Olmec culture in Mesoamerica where they used it to produce rubber balls and later by the Aztec and Maya cultures to waterproof textiles