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Dr Leonie Curtolo

No direct function on growth and development = Secondary metabolites, secondary products or natural products Primary metabolites:
Chlorophyll, amino acids, nucleotides, simple carbohydrates or membrane lipids Recognized roles in photosynthesis, respiration, solute transport, translocation, nutrient assimilation and differentiation Throughout plant kingdom

Secondary metabolites:
Restricted distribution in plant kingdom Certain only found in one plant species / taxonomically related group of species

1.

2.

Funtions: Defends plants against being eaten by Herbivores and infection by pathogens Plant defenses evolved to maintain reproductive fitness
Evolution of metabolites lead to greater reproductive fitness than undefended plants as long as the metabolic cost of producing them was not excessive Defended plants left more descendant than undefended ones and passed their defensive traits on to the next generation.

Interesting that defense compounds to increase reproductive fitness by warding off fungi, bacteria and herbivores also make them undesirable as food for humans. Certain crops artificially selected to for producing low levels of compounds, can make them more susceptible to insects and disease and leads to more chemicals being used to protect crops

Three principle groups of secondary metabolites:


1.

Nitrogen-containing 2nd ary products


Alkaloids, biosynthesized from amino acids

2.

Phenolic compounds:
Aromatic substances, via shikimic acid pathway or malonic acid pathway

3.

Terpenes:
lipid synthesized, from acetyl CoA or basic intermediates of glycolysis

5 major subclasses: monoterpenes, sesquiterpenes, diterpense, triterpenes and polyterpenes Synthesized from IPP (Isopentenyl pyrophosphate) and DMAPP (Dimethyallyl pyrophosphate)

Monoterpenes (C10): Important agents of insect toxicity Plants contain mixtures of volatile monoterpenes and sesquiterpenes = ESSENTIAL OILS Lamiaceae family: peppermint (monoterpene = menthol), lemon (monoterpene = limonene), basil and sage Conifers (f.e. pine and fir): Resin monoterpenes accumulate in resin ducts in needles, twigs and trunks = -pinene, B-pinene, limonene and myrcene Toxic to insects and beetles Found in glandular hair on epidermis advertise toxicity of plant, repelling insects and other herbivores Essential oils: extracted via steam distillation (commercially used to flavour foods and making perfumes)

Sesquiterpene lactones (C15): Compositae family Glandular hair Characterized by lactone ring (cyclic ester) Feeding repellants to herbivores and mammals = taste BITTER Solanaceae

Diterpenes (C20) Toxins and feeding detergants Resins, from pines and tropical leguminous trees contain abietic acid Euphorbiaceae (Spurge family): diterpene esters of phorbol When resins canals are pierced by insect feeding the outflow of resin may physically block feeding and serve and chemical deterrent to continued predation Phorbol type diterpenes tumor promoters in animals Pacific yew (Taxus brevifolia) contain taxol anti-cancer drug

Abietic acid

Phorbol

Triterpenes (C30)
Steroids Found in plasma membranes Phytoecdysones by insects disrupts molting and other developmental processes often with lethal consequences Limonoids:

Bitter substances in citrus spp. Most powerful deterrent to insect feeding from Neem tree

(Azadirachta indica) from Africa or Asia

Triterpenes (C30) Cardenolides Glycosides (compounds containing an attached sugar) Bitter tasting extremely toxic to higher animals Humans: dramatic effects on the heart muscle (influence on Na+/K+ activated ATPases); regulated doses they strengthen the heartbeat. Foxglove (Digitalis) cardenolides extracted to treat heart disease Digitoxigenin (aglycone sugarless triterpene portion of naturally occuring digitanides)

Glycosides

aglycone + sugar

Triterpenes (C30) Saponins Steroids and tripterpene glycosides Soaplike properties: soapy lather when shaken with water Both lipid-soluble (triterpene) and water-soluble (sugar) elemens in one molecule gives saponins detergent properties Toxicity due to ability to form complexes with sterols May interfere with sterol uptake from the digestive system or disrupt cell membranes after absorption into bloodstream
Yam (Dioscorea villosa) Yamogenin Used as starting materials in synthesis of progesterone like compounds for birth control pills.

Polyterpenes ((C5)n) rubber

Functions:
1. 2. 3. 4.

Defense mechanisms Mechanical support in attracting pollinators and fruit dispersers Absorbing harmful ultraviolet radiation Reducing the growth of nearby competing plants Shikimic acid pathway
COH converted to aromatic amino acids In plants, fungi and bacteria but not animals Phenylalanine Cinnamic acid Simple phenolics / lignin / flavonoids / condensed tannins Phenylalanine ammonia lyase (PAL) catalyses formation of phenylalanine to cinnamic acid activity increased by environmental factors, such as low nutrient levels, light, and fungal infection.

Synthesized from 2 different pathways

Malonic pathway

Simple Phenolic Compounds

Furanocoumarins non toxic until activated by UV-ligth / sunlight. Activated furanocoumarins insert themselves into double helix DNA bind to pyrimidine bases cytosine and thymine blocking transcription and repair leading to cell death
Umbelliferae (cellery, parsnip and cellery)

Allelopathic activity (inhibiting growth of other plants: cafeic acid and ferrulic acid
From leaves roots and decaying litter release substances into

enviroment

Lignin: primary and secondary roles


Most abundant after cellulose Strengthening Bonds to cellulose and protein, reduces digestibility Blocks growth of pathogens and response to infection or wounding

Flavonoids
Largest class of plant phenolics 15 carbons in a arrangement with 2 aromatic rings connected by a 3 carbon bridge

Fusion of 2 parts synthesized from 2 different pathways

shikimic acid pathway and the malonic acid pathway

Anthocyanins
Coloured flavonoids that attract animals for pollination and

seed dispersal (mutualism) 1 of 2 principles colored pigments flavonoids (other carotenoids terpenoid compound accessory compounds in photosynthesis yellow, orange and red) Red, pink, purple, blue colors in plants Anthocyanin anthocyanidins + sugars

Anthocyanins Anthocyanidins: Pelargonidin (organge red) Cyanidin (Purplish red) Delphinidin (Bluish purple) Peonidin (Rosy red) Petunidin (purple) Anthocyanins and carotenoids responsible for variety of colours in plant kingdom. Colour one type of signal to animal also monoterpenes provide attractive scents.

Flavones and flavonols


Absorb light at shorter wavelengths, not visible to human eye Visible to bees and insects may indicate the location of pollen and nectar

Isoflavonoids Defense compounds synthesized immediately following infection by fungi or bacteria Leguminosae Tannins Plant phenolic polymer 1st used to describe compounds that could convert raw animal hides into leather in the process known as tanning Tannins bind to collagen proteins of animal hides, increasing resistance to heat, water and microbes 2 categories:

Tannins 1. Condensed tannins 2. Hydrolyzable tannins Astringents taste due to binding of salivary proteins General toxins that reduce growth and survivorship, most mammals avoid, but humans often prefer certain level of astringency in tannin containing foods apples, blackberries, tea and red wine Inactivate herbivore digestive enzymes and create complex aggregates of tannins and plant proteins that are difficult to digest

Nitrogen in structure Alkaloids Poisonous if taken in sufficient quantity Strychnine, atropine, coniine (poison hemlock) Lower doses useful pharmacologically Morphine, codeine, atropine and ephedrine Stimulants or sedatives Cocaine, nicotine and caffeine Mechanism of action: 1. Interfere with components of the NS, esp. chemical transmitters 2. Others affect membrane transport, protein, or miscellaneous enzyme activities

Cyanogenic glycosides

Release poison hydrogen cyanide

Glucosinolates (mustard oil glycosides)


Also release volatile toxins Cruciferae

bitter principles release of gastrin Release of gastrin increases:


Gastric acid & pepsin secretions Pancreatic digestive secretions Intestinal juice production Hepatic bile flow Hepatic bicarbonate production Brunners glands secretions Intrinsic factor secretinos insulin, glucagon & calcitonin secretions Muscle tone of lower oesophageal sphincter Muscle tone of stomach and small intestine Cell division & growth of gastric & duodenal mucosa Cell division & growth of pancreas

Indications : Increase appetite and digestive secretions Enable body to digest, assimilate vital nutrients Eliminate wastes efficiently Food = nourishment also present immunological challenge Low stomach secretions enteric infections Antigen penetration through gut wall (f.e. dysbiosis - candida, food allergies) Autoimmune problem coinciding with depressed digestion Stimulate the totality of digestive activity

Stimulate the totality of digestive activity


Protect gut tissue Promote bile flow Enhance pancreatic function Tonics Nervous disorders and emotional disharmony

Also,
Bitter tonics Hepatics Choleretics (improves amounts of secretions) Cholagogues (stimulates gallbladder contraction to improve secretions)

Compositae family Especially useful in hypercholesterolaemia Cautions:


Allergy to Compositae family


Contact dermatitis not oral ingestions

Cholelithiasis (gallstones)

Compositae family Relates spp

A. annua, A. afra, A abrotanum etc Dyspepsia

Aromatic bitter

Safety:
Contra-indicated in pregnancy No longer than 4-6 wks High doses

CNS toxin cause hallucinations & addictions

Mustard Oil Glycosides Glycosides / glucosilinates Cruciferae family Mostly used externally as rubefacients (increases local bld flow) or vesicants Goitrogenic (substances that suppress the function of the thyroid gland by interfering with iodine uptake) if consumed in large amounts Miscellaneous Pungent Constituents Pungent alkaloids: capsaicin (Capsicum spp) Volatile oils (Zingiber off) Sulphur-containing constituents (Allium spp) Rubefacient, vesicant, counter-irritants (therapeutic inflammation, without destructive inflammatory agents) Stimulate circulation at a local level Stimulate stomach acid production Carminative Disinfects lungs and expectorates

Mixture of fragrant compounds Extracted by steam distillation Wide range of pharmacological activities

Antimicrobial and spasmolytic, carminative (mint, sage, rosemary, cardamon, dill), diuretics (juniper), expectorant (aniseed), sedative (lavender), anxiolytic (melissa), anaesthetic (clove), analgesic (lemongrass), rosemary (stimulant activity), diaphoretic, anti-inflammatory, antiulcer and oestrogenic activities

Tea tree Chamomile Lemon balm Buchu

Plant pigments Flavus = pigment Anti-oxidant activity, reducing capillary fragility and permeability, duiretcs, anti-spasomodic, antiinflammatory, antiseptic Yarrow Elder

Resins (Pinus spp), oleo-resins (Pinus spp), Oleo-gum-resins and gum resins (Commiphora molmol, Boswelia spp), balsamic resins (Styrax spp) and balsams (Myroxylon pereira) Uses: antiseptic, anti-inflammatory Commiphora molmol Potentilla erecta

Treating wounds and burns Haemostatics Anti-inflammatory Especially usefull in diarrhoea Potentilla erecta

Bulk laxatifes Inflammations in the respiratory, urinary and GIT Ulmus fulva

Highly toxic cause lysis of bld cells Sapo = soap Glycosides


On injections cause lysis of bld cells, haemolysis and are highly toxic On oral ingestion hydrolysi occus splittin the glycosie into its sugar and aglycone / sapogenin. Sapogenin does not posses the haemolytic properties and is safe.

2 classes:
1.

Steroidal saponins structural relationship to steroidal hormones, cardioactive glycosides and vitamin D
Dioscin from Dioscorea villosa used to manufacture sex hormones

Triterpenoid saponins Trigonella dioscin and diosgenine may also act as a precurosr to female hormones and adrenal hormones Glycyrrhiza glabra saponins mimic adrenocorticotrophi chomrone and potentiate glucocorticoid, prgesterone and aldosterone actigity by inhibiting their metabolism Anti-inflammatory (Solidago candensis, stellaria media) Diuretic (Betula spp) Antispasmodic (Nigella sativa) Adaptogens (Glycyrrhiza glabra, panax ginseng) Stimulating expectorants (Lobelia inflata, verbascum thapsus, Viola spp, Glycyrrhiza glabra) Treatment of vascular disorders (Centella asiatica, Achillea millefolium) Used to increase bioavailability of other components Facilitates absorption of nutrients.