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    CHE 432

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    CHE 432

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    Wa0001.

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    temazwidenxu
    CHE 432

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    Organic Spectroscopy Spectroscopic techniques deal with the interaction of matter (say, organic molecules) with energy (in the form of electromagnetic radiation). Electromagnetic spectrum is a continuum (shown below). dim viz cosmic rays 10-108 gamma rays... : 10-8 10! X-rays ie 10-* far ultraviolet .. aK 10-7 ultraviolet... visible 1o-* near infrared 1o-> 108 mid infrared 10-10"? (, 10? em=! far infrared 10" microwave 10> 108 1054 emote 10° 108 10 10” to? 108 toe 10? alternating current . The electromagnetic spectrum with wavelengths (i) and frequency (v) are shown ‘The sensitivity limits of the human eye extend from violet light through the rainbow colours to red light. The energy associated with regions of the electromagnetic spectrum related to wavelength and frequency by the following equations E=hw =he (w=) x x =nes (G+) x Where, E= energy of the radiation in joules (J) h= Planck's constant (6.626 x 10""* J s) quency of the radiation (Hz) [in reciprocal seconds, s“, or hertz, Hz (1s =1 Hz)] » = Wave number in reciprocal meters, m~ = velocity of light (2.998 x 10° x ms") 4.= wavelength (m) [meters, m or jim or nm scales can also be used) The electromagnetic radiation (light) has a w: ce propagation (as shown below) with velocity (c) = 2.998 x 10°x ms" ‘ : velocity Wavestike propagation of light 2.998 x 10 4.= wavelength, A = amplitude, ms"; ca.3x 10°ms* The various quantities and their relationship are given below. Quantity Relationship wavelength | wavenumber frequency (Hz) velocity mst ‘The amount of energy required to raise an electron/molecules in a given molecule from one level to a higher level is a fixed quantity. Because, the energy levels of a molecule are quantised. Only light with exactly the frequency corresponding to this amount of energy will cause the clectron/molecules to move to the higher level. The difference between these two energy levels (higher and lower energy levels) are given by AE =E;-Ey Beer’s and Lambert’s laws Beer's law relates that the absorption of light directly proportional to the concentration of absorbing solute, Lambert's law relates that the total absorption of light directly proportional to the optical path length of the sample (which is taken in a cuvette), ‘The combined Beer's and Lambert's law is written as follow. Aacl A=ecl-————— equation 1 ‘A= absorbance of the solution (also called as optical density of the solution, OD) e = molar absorptivity (also called as molecular extinction coefficient) (in m* mol" 107) ‘¢= concentration of solute (in mol I'(or) mol dm”) 1=path length of the sample (in crn (or) m 107) Ip is the intensity of incident light and I is the intensity of transmitted light. The intensity of transmitted light is measured using the formula given below. io 10"! Mp=10**! log (I/la)=-ec1 log I—log ly=-ee1 slog I+ log log Ip -log 1 log (Io/l) =ec1 According to Beer’s and Lambert's laws, A= «cL Therefore, A =log (Iy/l) =e! Absorbance, A = log (loll) ‘Molar extinction coefficient, «= A/c | ‘Transmittance (T) is the ratio of intensity transmitted light (I) and intensity of the incident light (19); T= Ilo. Transmittance, therefore, bears a reciprocal and logarithmic relationship to absorbance, The per cent transmittance is written by: %6T = (Wb) x 100. ‘Absorbance, A= £.¢1= log (fy) =Tog (1/7) ‘Molar extinction coefficient, ¢ = A/c] Transmittance, T= Wy Per cent transmittance, %T = (Wx) x 100 Infrared Spectroscopy (IR spectroscopy) (also known ax Vibrational Spectroscopy) When infrared light (%= 400-4000 cm’') is passed through a sample of an organic compound, some of the frequency (light) is absorbed, while other frequencies are passed through the sample without being absorbed. Absorption in the infrared region is due to changes in vibrational energy levels within the ground electronic state (i.e. Vo —> Vi, Vi-V etc, within the ground electronic state (Es). IR spectrum IR spectrum is obtained by plotting or absorbance (A, in ordinate) against wavelength (2, in abscissa) or by plotting % transmittance (%T, in ordinate) against wavenumber (%, in abscissa). Chemists prefer to plot % transmittance (%T) against wavenumber CPE Transmittance (T) is the ratio of intensity transmitted light (1) and intensity of the incident light (1a); T =o. Therefore, per cent transmittance is given by, %T = (Wl) x 100. ‘Absorbance wavelength ‘Wavenumber log (oll) = log (71) = ee! Transmittance Per cent transmittance HT = (Illy) x 100 Infrared spectrum of mixed long chain alkanes (liquid paraffin, Nujol) Different bonds (C-C, C=C, C, C-0, C=O, 0-H, N-H, ete.) have different vibrational frequencies. We can detect the presence of these bonds in an organic molecule by identifying this characteristic frequency as an absorption band in the infrared spectrum. In recording TR spectra, it is customary to use the following letters to indicate intensity; broad (br), strong (3), very strong (v. s), medium (m), weak (w) and variable (v). The essential requirement for a molecule to absorb in this IR region is that vibrations of molecule must give rise to an unsymmetrical charge distribution (dipole moment, 1).Dipole ‘moment is a vector quantity; it has magnitude and direction. Dipole moment, jt = charge « distance (11 = qr). Dipole moment is expressed in Debye unit. Carbon dioxide (0=C=0) (A linear molecule) The symmetrical stretching vibrations of CO, will not give an unsymmetrical charge distribution (dipole moment, u), CO2is a tinear molecule. The dipole moment caused by C-O (tr, in one direction is nullified by the dipole moment caused by another C=O (str.) which is ‘exactly in opposite direction, Therefore, the symmetrical stretching vibrations of CO: is IR inactive Ginear, non-polar mocule) dipole moment, =O ‘Modes of vibrations ‘A non-linear molecule can undergo number of vibrations. The two main types of vibrations are: 1. Stretching (vibrations along the bonds) sym. = symmetrical stretching; asym. = asymmetrical stretching (or) antisym. = antisymmetrical stretching 2. Bending (or) deformation (displacements perpendicular to bonds). STRETCHING MODES FoR CH, A single methylene groups (-CHs) shows several vibrational modes. The various modes of vibrations for AX2 system (CHa, NH;, NO; etc.) are given in the above Figure. For a nonlinear molecule with n atoms, the number of vibrational modes is (3-6) and for a linear molecule, the number of vibrational modes is (3n-S) (where, n = number of atoms). In some cases, other frequencies can be generated by modulation and other factors which include overtones or harmonics and combination or difference frequency. Molecular vibrations At ordinary temperatures organic molecules are in a constant state of vibration. Each bond has its own characteristic stretching and bending frequency. They are capable of absorbing light of that frequency. The vibrations of two atoms joined together by a chemical bond can be likened to the vibrations of two balls joined by a spring. Hooke's law correlates frequency with bond strength and atomic masses as shown below. bond strengh Vie atomic masses k mm /(m +m) vp=et|/ «x ana force constant of the bond ‘m, and mp are masses of the atoms = reduced mass; 4 = mjmy/(mj+ms) ‘Thus, as per Hook’s law, ‘C=C stretching requires higher frequency than C-C stretching, C=O stretching requires higher frequency than C-O stretching. Similarly, C-H stretching requires higher frequency than C-C stretching, O-H stretching requires higher frequency than O-C stretching, tion of IR spectroscopy 1. To identify various functional groups present in molecules Icis possible to determine the nature of functional group that is present in a compound based cn absorptions band in the IR spectrum. Different bonds (C-C, C=C, C=C, C-0, C=O, O- H, N-H, etc.) have different vibrational frequencies. infra-red spectrum of propan-1-ol, CHsCH2CH20H hy YN 4001 3000 2000 4500 1000 soo wavenumber (em!) 1005 ‘transmittance (%) Infra-red spectrum of propan-2-0l, CHsCHCHs OH 1005 vearsmitance (%) ° 4000 3000 2000 1500 1000 soo wavenumber (crm!) Structure of Menthone ar Wavenumber, em! IRespectrum of menthone 2957 8 | 1306 63 | 1246 G8 | 1079 77 | 867 77 2g2a 14 | 1377 50 | 1203 46 | ind 68 | 939 84 2a7z 21 | 135 45 | 1164 74 | 1030 77 | 740 64 1711 4 | 1336 62 | 1155 72 | 996 72 | 743 64 1456 37 | 1312 68 | 1145 72 | 985 77 | 61a 77 1447 43 | 1207 64 | 1117 2 | 950 81 | 608 77 l426 66 | 1267 70 | 1094 70 | 93) 81 | 653 74 Stretching frequency of CO group has wavenumber 1711em” and the stretching. frequency of overtone peak of CO group gives a weak peak and its wavenumber is 3422em"™ The position of absorption bands for some functional groups and single bond stretching and bending vibrations are given below. Position (em!) _ | Comments | 3550-3200) GH Gir), Strong, very broad | 3400-3250 N-H (str.); Weak, one band for NH aie and two bands for -NHs Cm | =3300 CH Gor); Sharp, Cis sp hybridised Saat 3100-3000 ~_ | Cis sp* hybridised { 3000-2850 C-H (sir.); Cis sp° hybridised 2975-2950 | C-H (asym. str.) 2885-2860 | C-H (sym. str.) 1470-1435. | C-H (def.) 1385-1370 | C-H (def) I 2830-2700 Two bands comes MiaetN 2260-2200 Medium c=c 2150-2100 Weak ° 1820-1650 C=O (sir; Strong (exact position | a ae ¢: aldehydes, ketones, carboxylic acids, keto group (str.) esters, etc.) 1660-1640 CC (sir); Often weak =1550 and ~1380 Both are strong 1300-1000 Strong Many single bond | ~ < 1400 Fingerprint region vibrations (stretching and bending) 2. Identification of an unknown compound by comparison of its fingerprint region with known IR spectra In IR spectra, the region that contains a large number of unassigned absorptions (peaks) is observed roughly from 900 cm” to 1400 em”. This general area of IR spectral region is often called the fingerprint region. The pattem of vibrations at this fingerprint region is uniquely characteristic of each molecule, Numerous absorptions at this fingerprint region are due to single bond stretches and variety of bending vibrations. Additionally, there are absorptions associated with the complex interacting vibrating systems in the molecule, To identify an unknown compound, one need only compare its infrared spectrum with a set of standard spectra recorded under identical conditions. Substances that give the same infrared spectra are identical. Although the entire spectrum must match, the fingerprint region provides the crucial test of identity. 3. To distinguish isomers o-Nirophenol and p-nitrophenol can be distinguished from cach other from their IR spectra. o-Nirophenol has intramolecular hydrogen bonding (chelation). On the other hand, p- nirophenol has intermolecular hydrogen bonding (association). The presence of hydrogen aes A Sabie clave absorption positions. Intermolecular hydrogen ondin trong int lcular hydrogen bonding. Therefore, O-H stretching vibration requires more energy in p-nitrophenol and consequently, the band for 0-H (str) is observed at ¥~3331 cm’. On the other hand, the O-H stretching vibration requires less ‘energy in o-nitrophenol and consequently, the band for O-H (str) is observed at ® ~3241cm". AR spectrum of o-nitrophenol Tatas wo=aeud ——[1r-ATon-6eae er hydrogen (Chelation) as =-9931 em! Ndrogen bonding, (assoclation), IR spectrum of p-nitrophenol SLY TBST on sseT Ten Rea KET ——— Mass Spectrometry Natural isotope abundances and isotopic masses ('?C=12.000 000) for some common elements Isotope | Natural Isotopic mass Abundance (%) Lie 99.985 1.007 825. |B CH) [0.015 “2.014 102 C989 12,000.00 mG Li 13.003 354 [So [99.76 15.994 915 "oO 0.04 16.999 133 *O 0.20 17.999 160 TN 99.64 14.003 074 [BN [036 15.000 108 The atomic mass of an atom (ihe atomic weight or mass number that is shown in the periodic table) is calculated based on averaging the atomic masses of the naturally occurring isotopes. For example, Natural | Natural Tsotopie mass Isotopes | Abundance (%) TH 99.985 1.007 825) DCH) [0.015 2.014 102, (99.985 x 1.007 825) + (0.015 x 2.914 102) 1 99,7673826 + 0.03021153 100 100 100.797594 = ———__ = 100797594 100 Electron impact (El) ionisation: Organic molecules are bombarded with electrons in two ways M-&> Mz or M—% Mt + 2e 1. Either an electron is captured by the molecule and gives a radical anion. e c M—>™M organic radical molecule anion s-e,70eV saa R—NH, ———> R—NH, be amine radical anion (electron is captured) (molecular ion) 2, Or an electron is removed from the molecule and gives a radical cation. The formation of radical cation is the most probable than radical anion. e + M—> M* 4+2¢ organic Pacieal molecule tation : (molecular ion or parent ion; highly energetic, undergoes further fragmentaion) ¢, 70 eV +. Hy ———> R—NH, amine radical cation (electron is removed) (molecular ion) The molecular ion is usually written in square bracket [M*] and partial square bracket “1 * can also be used especially for larger molecules. Neutral particles produced in the fragmentation, whether uncharged molecules (mz) or radicals (m), cannot be detected directly in the mass spectrometer. [Alternatives to electron impact ionisation are 1. Chemical ionisation (C), 2. Fast atom bombardment (FAB), 3. Field ionization and field desorption, 4. Secondary ion mass spectrometry (SIMS), 5. Laser ionization mass analysis (LIMA) and 6. Desorption by lasers (LD)). Molecular ion: The loss of an electron from a molecule leads to a radical cation called molecular ion. This process is represented as MM" The molecular ion is formed by the combination of most abundance isotopes of various elements present in a molecule. It is formed by loss of an electron from a molecule by bombardment with high energetic electron (e, 70 eV). The loss of an electron from a molecule leads to a radical cation. This radical cation is called molecular ion or parent ion. This process is represented as e + M—>M°* 4+2¢ organic radical molecule cation ‘molecular ion or parent ion Note: The molecular mass of a molecular ion corresponds to the sum of the masses of the ‘most abundant naturally occurring isotopes of various atoms that make up the molecule. Fragment ions: The molecular ion (M*) commonly decomposes to a pair of fragments, which may be an ion plus a radical or a radical cation plus a small molecule. Mt m* +m" or mt +m, The molecular ion (or parent ion) is high energetic since they acquired energy from electron (of 70 eV). Therefore, the molecular ion can break up into smaller ions called fragment ions or daughter ions. The Major Classes of Natural Products and their bioactivities: Carbohydrates Lipids (oils, fats, waxes and phospholipids) Fatty acids (saturated and unsaturated fatty acids) Amino acids, peptides, polypeptides and proteins: Terpenes and Terpenoids (Isoprenoids) Steroids Alkaloids Flavonoids. Phenolics ‘Coumarins Chalcones Macrolides Carbohydrates: Carbohydrates have the general formula of C,(H,0).. Carbohydrates are categorised into monosaccharides, disaccharides, oligosaccharides and polysaccharides. G0 co Ee | I Hots a yee w-chor E08 u—tpon Is f s we at #08 I ig e Chow Gio D(H)-Glucose DC) Fructose ‘ ‘ i Sue Monosaccharides (e-b.gonynnay! p-tetereniey (Disaccharides) Bioactivities of Carbohydrates: Carbohydrates are widely distributed both in plant and in animal kingdom. Carbohydrates are essential constituents of all living organisms. Carbohydrates are the main source of energy for humans and animals and serve as the primary fuel for muscles and brain. Carbohydrates have many pharmaceutical and cosmetic applications. Lipids (oils, fats, waxes and phospholipids): The term lipids embrace a variety of naturally ‘occurring compounds, Lipids include oils, fats, waxes and phopholipids. Oils and fats are referred as the simple lipids. Chemically, fats are esters of glycerol. Le. they are glyceryl esters also known as glycerides. 9 I) cH, h—OH =. ln, tho C—€ 5 HC—OH e—0—C—R, Heer Scie BeOS ecm ° Hy-OH, 0-8, HO FC CH-0—F—Catty glycerol ester of glycerol ester of glycerol Eerste (elyceride) (simple glyeeride) (nixed glyceride) (tristearin) Bioactivities of lipids: Lipids are important biomolecules. Lipids are one of the three classes ‘of foods; the other two are carbohydrates and proteins. When animals or humans eat more than they use up, they store the excess carbohydrates. They stored some carbohydrates as polysaccharide called glycogen. But they stored most carbohydrates as fats and released back ‘when the body requires energy during starvation. Coenzyme (CoA) Coenzyme A (HS-CoA, a thiol) and acetyl coenzyme (CH,-CO-SCoA, a thiol ester) are all important biomolecules which are associated with fats. Fatty acids and fatty esters (saturated and unsaturated): Fatty acids and fatty esters have a long hydrophobic hydrocarbon chain at one end and a hydrophilic acid or ester group in the other end. CH—eHi-ferts) coon H—eH-Eets}-coon CHE cH} cr=cu-fct ‘Stearic acta coon Palmitie acid Oleic acta (CigHOD) Unsaturated acid I=CH—CH—CH=CH-{CH;}—-COOH CH CH = Linoleic actd CH=CH-Clh—cit=cH—CH;—cr-=Ct-{cHs}- cook (CisHy20) Linolenie acid Unsaturated acid Caltoo ‘Unsaturated acid CHs—cta-tcu,y—coocn; CH —C#a-¢-cH:}-coocr, Methy palmitat a (Memny ester oF patiniette actd) ‘Meths! stearate (Methy ester of stearle acid) i RB 2 ie n-Hexadecanoic acid (Palmitic acid) Pe =$ See ° Methyl 9,12-octadecadienoate SS a 9,12 (Z,Z)-Octadecadienoic acid (Linoleic acid) Octadecanoic acid (Stearic acid) Bioactivities of fay acids and fatty esters: Fatty acids and their esters exhibited various biological and pharmacological activities which include antioxidant, antifingal, antibacterial, anti-acne, to reduce chronic blood glucose level, nematicide, pesticide, insectifuge, cancer preventive, hypochloesterolemic, antihydrogenic, hemolytic and lubricant activities. Amino acids, peptides, polypeptides and proteins: Amino acids: Amino acids have amino group (-NH,), carboxylic acid group (-COOH), anda side chain (R-). The side chain (R-) distinguishes one amino acid from another. -COOH, ~ NH2, -R groups and hydrogen all are bonded to a central carbon atom (a-carbon). They are termed c-amiino acids Hooe 00¢ TN t , amino acid ‘camino acid ieee (ewitter ion or inner salt) Only 20 different amino acids are present in the human body. Their names are abbreviated ‘with 3 letters; one letter abbreviations are also available. All a-amino acids (except glycine) are chiral because the a-carbon is attached to 4 different groups. In biological systems, only L-amino acids are incorporated into proteins. Essential amino acids: Essential amino acids are amino acids that cannot be synthesized by the human body and must be obtained from the diet. The essential amino acids are Arg, His, le, Leu, Lys, Met, Phe, Thr, Trp and Val. Names of the amino acids are usually abbreviated using 3 letters. One letter abbreviations are also used. Peptides and polypeptides: The linking of two or more amino acids forms a peptide. A peptide bond is an amide bond that forms when the -COOH group of one amino acid bonded with the -NH, group of the next amino acid. N-terminal of amino acid (amino terminus): Amino acid with free amino group on the left end of a peptide, C-terminal of amino acid (carboxyl terminus): Amino acid with free carboxyl group on the right end of a peptide. Dipeptide ~ 2 amino acids linked together ‘Tripeptide ~ 3 amino acids linked together Oligopeptide = 4-9 amino acids linked together peptide tinkage or amide bond Polypeptide = 10-40 amino acids linked together ot > taN—cn2— Ub Nu—ten— Neh Nf c00 i fanaa by N-terminal “terminal Gycine Glyeytatanine (Gly-Ata) Alanine A dipeptiae Peptides and proteins are polyamides derived from amino acids, The amide linkage is peptide bond. >40 residues confer proteins. Snake and spider venoms and some plants toxins are peptide in nature Proteins: Protein is « polypeptide chain of more than 40 amino acids. Funetions: Structural components, regulation of biological reactions and oxygen transport Primary structure: amino acid sequence e.g. - ~~ Ala-Phe-Ser -- - Secondary structure - results from hydrogen bonding between peptide bonds along the chain. ‘The secondary structures include a-telix, B-pleated sheet and triple helix. Tertiary Structure - folding of protein into a compact 3-D shape which results from hydrogen bonding between R groups of amino acids Globular proteins - have compact spherical shapes - Responsible for cell work Fibrous proteins have long, thin, fiber-like shapes - Responsible for structure of cells and tissues. Bioactivities of amino acids, peptides/proteins: Amino acids used to synthesise bioactive metabolites, particularly to synthesise alkaloids. Amino acids are used to produce peptides/proteins. A large number of plant proteins have been exhibited many biological and pharmacological activities, which include to stimulate segregation of growth hormones, lowering the blood pressure levels, lowering the cholesterol levels, antimicrobial, antioxidant, anticancer, antitumor, anti-fibrosis, cardio-protective, obesity and weight management, anti- diabetic, anti-inflammatory and anti-oestrogen Enzymes: Enzymes are globular proteins (biological molecules) that catalyze chemical reactions. In other words, enzymes are biological catalysts which are responsible for chemical transformation, Enzymes carry out this transformation more rapidly, more efficiently, under milder conditions and stereospecific manner. ‘The names of all enzymes have a suffix -ase (Oxidoreductases - catalyse oxidation-reduction reactions Isomerases - catalyse the rearrangement of atoms in a molecule to form an isomer ‘Transferases - catalyse transfer of a group between 2 compounds, Ligases - catalyse the formation of bonds between molecules using ATP Lyases - catalyse the addition or removal of groups to a double bond without hydrolysis, Terpenes and Terpenoids (Isoprenoids): Terpenes (have only hydrocarbons) and terpenoids (have functional groups) have a carbon framework of isoprene (2-methyl-1,3- butadiene) units, which is made up of five carbons. Isoprene units are joined to one another in a head-to-tail fashion, where the tail of one isoprene unit is connected to the head of the other isoprene unit Ay sepeann ms | eure ciactexe) mnt, eagles ey ead “te ait ai sete “tmonacycl (monocyclic monoterpenes) iy p-cymene thymol carvacrol (monocyclic aromatic monoterpenes) a9 Pinane 'YPe —fenchane type _thujane type eave (bicyclic monoterpenes) oo o-pinene cineole Terpenoids are classified into ‘Monoterpenoids (2 isoprene units) (10 carbon atoms) Sesquiterpenoids (3 isoprene units) (15 carbon atoms) Diterpenoids (4 isoprene units) (20 carbon atoms) Sesterpenoids (5 isoprene units) (25 carbon atoms) Triterpenoids (6 isoprene units) (30 carbon atoms) Tetraterpenoids (8 isoprene units) (40 carbon atoms) and Polyterpenoids (many isoprene units) (> 40 carbon atoms) Bioactivities of Terpenes/Terpenoids: Terpenes/Terpenoids are a larger group of secondary metabolites found in the plant kingdom. They have been exhibited many biological and pharmacological activities, which include antioxidant, antiseptic, antiulcer, antitumor, analgesic, antiviral, antihypertentive, antibacterial, antidiabetic, chemoproteetive, anti- dementia and anti-allergic antimalarial, antifungal, anthelmintic, anti-inflammatory, anti- parasitic and spasmolytic activities and used as colouring agents, appetisers, growth regulators and repellents. Steroids: Steroids are a group of biologicall of biologically important secondary metabolites. Steroids possess a eyclopentaphenanthrene carbon framework i.e, a phenanthrene moiety is fused to a cyclopentane ring as shown below: ‘The skeleton of steroids 0" pentacyli epenoi stleton hosters Steroids are modified trterpenoids = tetracyclic ring system of lanosterol; - lacking the three methyl groups at C-4 and C-14 (compare the pentaeyelic triterpenoid skeleton) Cholesterol - fundamental structure - modifications to the side-chain, create a wide range of biologically important natural products e.g. sterols, steroidal saponins, cardioactive glycosides, bile acids, corticosteroids and ‘mammalian sex hormones Testosterone is the male sex hormone that is made in the testicles. Estrone is female sex hormone that plays an important role in the normal sexual and reproductive development in on ott z > pies) fi k ee B-sitosterol helps to reduce cholesterol levels by limiting the amount of cholesterol that is eee Bioactivties of Steroids: Steroids find therapeutic applications in the traditional medicine. They also find applications in food and cosmetic industries. Plant steroids possess a variety of bioactivities, which include hypocholesterollemic, anticancer, antihelminthic, antimutagenic, ‘analgesic, antioxidant, immunoregulatory, antiinflammatory, antitumoral, anti-BPH, antimicrobial, antileishmanial, antigenicity antiarthythmie, antimalarial and antidiartheal activities. Steroids have been used as enzyme inhibitors and as growth regulatory, neuroprotective, hypolycemic and hepatoprotective agents. ae Be fehl are heterocyclic nitrogen containing organic compounds. Alkaloids are iste and are very poisonous but are used medicinally in very small quantity. The nitrogen atom contributes to their alkalinity (basi f asic) due t f clectron on the nitrogen atom. pee ee H Ho. y CH SS Nicotine HO Used as atimulant HO" i (from tobacco leaves) Morphine = Pain killer E N from Paper somniferum ()- Quinine (opium poppy) (from the bark of cinchona tree) used to cure malarial fever Bioactivities of alkaloids: Alkaloids are available in many species of plants, animals and microorganisms. Alkaloids possess a wide range of bioactivities which include anxiolytic, analgesic, antidepressant, anti-dysentery, psychotropic, antipsychotic, antipyretic, anti= inflammatory, antioxidant, antimutagenic, immunomodulatory, antiviral, antimalarial, tantifungal, antibacterial, anttumoral, anticancer, antisthma, antiarthrtis, antiprotozoal and repellent activities, In general, alkaloids (plant origin) are toxic but have been used in small {quantity for medicinal purposes. f consumed large quantity, they cause fatal to animals and Humans. For example, coniine is major component of poisonous hemlock (plant), which was used to kill Socrates. Flavonoids and isoflavonoids: Flavonoids (and isoflavonoids) are polyphenolic compounds and have a phenylbenzopyran functionality bearing C,-C,-C, carbon skeleton. In flavonoids, the phenyl group is attached to C-2 position of chromone. On the other hand, In flavonoids, the phenyl group is altached to C-3 position of chromone. The skeleton of flavonoids and isoflavonoids are given below. J 6 chromone (benzopyran) Aavones (anthoxanthines) Inoflavones The skeletons of flavonoids and isoflavonoids Flavonoids OH OH on OH HO. 0. Ho. 0. ‘OH ‘OH oH oO oH Catechin (Flavan-3-ol) Quercetin (Flavanol) Asoflavonoidy daidzein Bioactivities of flavonoids and isoflavonoids: Flavonoids exhibit verities of biological and pharmacological activities. Notably, they exhibit potent antioxidant activity due to their ability to donate protons. For example, catechin is present in tea (Thea sinensis or Cameltia sinensis). It serves as an effective antioxidant. Quercetin serves as a positive control in the determination of total flavonoid contents in a plant extract, Isoflavonoids: Several biological activities have been reported from isoflavones such as ~ helping to prevent heart attack and other cardiovascular diseases. - display significant anticancer activity, reduces Alzheimer’s disease. Food rich in isoflavonoids lessens the risk of breast and uterine cancer. Food rich isoflavonoids counteracts some of the side effects of the menopause in women. Genistein exhibits modest anticancer activity. The main food source of isoflavonoids is the: soya bean, which contains significant levels of daidzein and genistein. Phenolics: Phenolics are organic compounds that consist of at least one hydroxyl group. attached to an aromatic ring as a basic carbon framework. Ou on ©. on Keon, cay l Ho. a HO’ OH on ie ace Vanilin Engenol Gallic acid Bioactivities of phenolics: Phenolics exhibit varieties of biological and pharmacological activities. Notably, they exhibit potent antioxidant activity due to their ability to donate protons. Gallic acid serves as a positive control in the determination of total phenolic contents. present in a plant extract. ‘Coumarins: A group of o-hydroxycinnamic acid lactone derivatives are called coumarins. Coumarins are benzo-o-pyrones (lactones) derived fiom o-hydroxycinnamic acid by cyclization and ring closure between the o-hydroxyl and carbonyl groups. Scopolentin (Simple coumarin) Re 0" *o Bergapentene (Furanocoumarin) Bioactivity of coumarins: Several biological activities have been reported from various coumarins including toxic activity. For example, if animals consume spoiled sweet clover (Melilotus officinalis) causes them fatal haemorshages. The presence of pure compound,

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