METABOLIT SEKUNDERg

8/10/2019 METABOLIT SEKUNDERg

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PENGANTAR METABOLIT

SEKUNDER

FARMAKOGNOSI 1

DTTIF BOGOR


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Constituents

The huge number of chemical

substances that are present in theplant-kingdom and animal kingdom in

one form or the other are termed asconstituents. These constituents may

be further divided into two main

categories, namely:

(a) Active Constituents, and

(b) Inert Constituents.


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Active Constituents

The chemical entities that are solely responsible for

existing pharmacological, microbial or in a broader-

sense therapeutic activities are usually termed as

active constituents. Most drugs like:

alkaloids,glycosides,

steroids,

terpenoids,phenil propanoid

bitter principles are the bonafide members of this

particular category.


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Inert Constituents

The chemical compounds, thoughpresent in plant and animal kingdom,

which do not possess anydefinite therapeutic values as such but

are useful as an adjunct either in the

formulation of a drug

or in surgery are collectively known as

inert constituents.


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Plant Drugs: The following inert constituents are invariably

present in plants, namely:

Cellulose: Microcrystalline forms of cellulose are used

as combination binderdisintegrants in tabletting. Collodalcellulose particles aid in stabilization and emulsification of

liquid;

Lignin: To precipitate proteins, and to stablise asphalt

emulsions;Suberin: Esters of higher monohydric alcohols and

fatty acids;

Cutin: -do-

Starch: As pharmaceutic aid i.e.; tablet filler, binder

and disintegrant;

Albumin : Soyabean albuminsas emulsifiers;

Colouring Matters : Cochineal for colouring food

products and pharmaceuticals.


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(b)Animal Drugs: The under mentioned inert

constituents are mostly present in animals,

namely:Keratin: For coating enteric pills that

are unaffected in the stomach but dissolved

by the alkaline into intestinal secretions;Chitin: Deacylated chitin (chitosan)for

treatment of water; sulphated chitinas

anticoagulant in laboratory animals.


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GLIKOSIDA

The Glycosidic Linkages The exact point of linkagebetween the carbohydrate (sugar) and non

carbohydrate (aglycone) moieties is an oxygen

bridge that essentially connects the reducinggroup present in carbohydrate to either an alcoholicor a phenolic group present in the noncarbohydrate.

O-glycosides;

S-glycosides;

N-glycosides;

C-glycosides.


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The most acceptable classification of glycosides is based on

the chemical nature of the aglycone moiety present in

them, namely:

(i)Anthracene glycosides(ii) Phenol glycosides

(iii) Steroid glycosides

(iv) Flavonoid glycosides(v) Coumarin and Furanocoumarin glycosides

(vi) Cyonogenetic glycosides

(vii) Thioglycosides(viii) Saponin glycosides

(ix) Aldehyde glycosides

(x) Bitter glycosides


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PHENYLPROPANOIDS

Phenylpropanoids represent a large conglomerate of naturally occurring phenolic

compounds essentially derived from the aromatic amino acids phenylalanine and

tyrosine or in certain specific instances the intermediates obtained from Shikimic

Acid Biosynthetic Pathway. In other words, these compounds comprise of a

phenylring to which is attached a 3C-side chain; and may also contain one or more

C6C3 residues.

Interestingly, the unique combination of the phenyl-propane side chain (i.e., 3C-atom)

evidently present in phenylpropanoids are absolutely devoid of nitrogen atom,

which is observed to be in contradiction to such other vital class of natural

products, namely: alkaloids, cyanogenic glycosides, and glucosinolates. Obviously,

the phenylpropanoids are distinctly phenolic in character by virtue of the

presence of one or several hydroxyl groups attached to the aromatic ring (C6 H6),

they are more often known among the phytochemists as plant phenolics.


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The phenylpropanoids may be classified on the

basis of their basic chemical moieties as

enumerated below:(i) Hydroxycinnamic Acids

(ii) Phenylpropenes

(iii) Coumarins

(iv) Abridged phenylpropanoids

(v) Biphenylpropenoid derivatives(vi) High molecular weight phenylpropanoids


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ALKALOIDS

The alkaloids, as an important and enormously largeconglomerate of naturally occurring nitrogencontainingplant substances having very specific as well as mostdiversified pharmacological properties may be classified in a

number of modes and means.* Salts of Alkaloids: that are used frequently arehydrochloride, hydrobromide, hydroiodide perchlorate,nitrate, oxalate and picrate.

Another school of thought classifies alkaloids in the following

four heads, namely:(a) Biosynthetic Classification

(b) Chemical Classification

(c) Pharmacological Classification

(d) Taxonomic


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(a) Biosynthetic Classification

In this particular instance the significance solely lies to

the precursor from which the alkaloids in question are

produced in the plant biosynthetically. Therefore, it is

quite convenient and also logical to group together all

alkaloids having been derived from the same

precursor but possessing different taxonomicdistribution and pharmacological activities.

Examples

(i) Indole alkaloids derived from tryptophan.

(ii) Piperidine alkaloids derived from lysine.

(iii) Pyrrolidine alkaloids derived from ornithine.

(iv) Phenylethylamine alkaloids derived from tyrosine.

(v) Imidazole alkaloids derived from histidine.

b) h l l f


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(b) Chemical Classification

It is probably the most widely accepted and common mode of classification of

alkaloids for which the main criterion is the presence of the basic

heterocyclic nucleus (i.e., the chemical entity).

Examples(i) Pyrrolidine alkaloids e.g., Hygrine;

(ii) Piperidine alkaloids e.g., Lobeline;

(iii) Pyrrolizidine alkaloids e.g., Senecionine;

(iv) Tropane alkaloids e.g.,Atropine;

(v) Quinoline alkaloids e.g., Quinine;(vi) Isoquinoline alkaloids e.g., Morphine;

(vii) Aporphine alkaloids e.g., Boldine;

(viii) Indole alkaloids e.g., Ergometrine;

(ix) Imidazole alkaloids e.g., Pilocarpine;

(x) Diazocin alkaloids e.g., Lupanine;(xi) Purine alkaloids e.g., Caffeine;

(xii) Steroidal alkaloids e.g., Solanidine;

(xiii) Amino alkaloids e.g., Ephedrine;

(xiv) Diterpene alkaloids e.g.,Aconitine.

( ) h l i l Cl ifi i


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(c) Pharmacological Classification

Interestingly, the alkaloids exhibit a broad range of very specific

pharmacological characteristics. Perhaps this might also be used as a strong

basis for the general classification of the wide-spectrum of alkaloids derived

from the plant kingdom, such as: analgesics, cardio-vascular drugs, CNS-stimulants and depressants, dilation of pupil of eye, mydriatics,

anticholinergics, sympathomimetics, antimalarials, purgatives, and the like.

However, such a

classification is not quite common and broadly known.

Examples(i) Morphine as Narcotic analgesic;

(ii) Quinine as Antimalarial;

(iii) Strychnine as Reflex excitability;

(iv) Lobeline as Respiratory stimulant;

(v) Boldine as Choleretics and laxatives;(vi)Aconitine as Neuralgia;

(vii) Pilocarpine as Antiglaucoma agent and miotic;

(viii) Ergonovine as Oxytocic;

(ix) Ephedrine as Bronchodilator;

(x) Narceine as Analgesic (narcotic) and antitussive.

(d) T i Cl ifi i


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(d) Taxonomic Classification

This particular classification essentially deals with the Taxoni.e., the taxonomic

category. The most common taxa are the genus, subgenus, species, subspecies,

and variety. Therefore, the taxonomic classification encompasses the plethora of

alkaloids exclusively based on their respective distribution in a variety of Plant

Families, sometimes also referred to as the Natural order. A few typical

examples of plant families and the various species associated with them are

stated below, namely:

(i) Cannabinaceous Alkaloids: e.g., Cannabis sativa Linn., (Hemp, Marijuana).

(ii) Rubiaceous Alkaloids: e.g., Cinchona Sp. (Quinine); Mitragyna speciosa

Korth (Katum, Kratum, Kutum); Pausinystalia johimbe (K. Schum) (Yohimbe).

(iii) Solanaceous Alkaloids: e.g., Atropa belladona L., (Deadly Nightshade,

Belladona); Brunfelsia uniflorus (Pohl) D. Don (Manaca, Manacan); Capsicum

annuum L., (Sweet Peppers, Paprika); Datura candida (Pers.) Saff.

(Borrachero, Floripondio); Duboisia myoporoides R. Br. (Corkwood Tree,

Pituri); Hyoscyamus niger L. (Henbane, Henblain, Jusquaime); Mandragora

officinarum L. (Mandrake, Loveapple); Nicotiana glauca R. Grah. (Tree

Tobacco); Seopolia carniolica Jacq. (Scopolia); Solanum dulcamara L.,

(Bittersweet, Bitter Nightshade, Felonwood); Withania somniferum (L.)

Dunal (Ashwagandha), etc.


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TERPENOIDS

A plethora of naturally occurring plant products have been found to be related

wherein they are comprised of one or more units of isoprene (C5H8Terpenoids are

broadly classified on the basis of the number of isoprene units incorporated into

a specific unsaturated hydrocarbon terpenoid molecule, such as:

(a) Monoterpenoids: These are built up of two isoprene units and have the

molecular formula C10H16;

(b) Sesquiterpenoids: These are composed of three isoprene units and have the

molecular formula C15H24;

(c) Diterpenoids: These are comprised of four isoprene units and have the

molecular formula C20H32;(d) Triterpenoids: These contain six isoprene units and have the molecular

formula C30H48; and

(e) Tetraterpenoids These are made up of eight isoprene units and have the

molecular (or Carotenoids): formula C40H64.

d h d b f id i


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Based on the extensive distribution of terpenoids in

the vast plant kingdom they are classified broadly

as follows, namely:

(i) Monoterpenoids

(ii) Sesquiterpenoids

(iii) Diterpenoids

(iv) Triterpenoids

(v) Tetraterpenoids and Carotenoids

(vi) Volatile Oils (or Essential Oils)

(vii) Resins and Resin Combinations

(viii) Oleoresins

(ix) Oleo-Gum-Resins

(x) Balsams


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BITTER PRINCIPLES

Bitter principles have been judiciously classified intosix categories based on the typical chemical

structures present in them, namely:

(a) Phenolic Bitter Principles,(b) Lactone Bitter Principles,

(c) Chromone Bitter Principles,

(d) Coumarin Bitter Principles,(e) Coumarone Bitter Principles, and

(f ) Miscellaneous Bitter Principles.


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ANTIBIOTICS

Antibiotics are broadly classified on the basis of their inherentchemical structures as stated below:

(i) Aminoglycosides,

(ii) Anthracyclines,

(iii) Cephalosporins,

(iv) -Lactams,

(v) Lincosamides,

(vi) Macrolides,

(vii) Penicillins,

(viii) Polypeptide antibiotics,

(ix) Tetracyclines, and

(x) Miscellaneous antibiotics.


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DRUG MOLECULES OF MARINE

ORGANISMS

The enormous quantum of newer and potent drug molecules

derived from the wide spectrum of marine organisms across

the world may be judiciously and logically classified based on

their specific pharmacologic actions as stated below:(i) Cytotoxic/Antineoplastic Agents

(ii) Cardiovascular active drugs

(iii) Marine Toxins

(iv) Antimicrobial drugs(v) Antibiotic substances.

(vi) Antiinflammatory and Antispasmodic Agents

(vii) Miscellaneous pharmacologically active substances

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