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Chirality in natural products

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Valliappan Kannappan
Valliappan Kannappan
VALLIAPPAN K
Professor of Quality Assurance (Retd.)
Department of Pharmacy
Annam...

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Valliappan Kannappan
Valliappan Kannappan
Ascorbic acid
Ascorbic acid
Quinidine
Quinidine
N
A
T
U
R
A
L
O
R
I
Chiral Bio
C...

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Valliappan Kannappan
Valliappan Kannappan
F
F
R
R
A
A
G
G
R
R
A
A
N
N
C
C
E
E
S
S
(S) Limonene  (R)
Lemon odor Orange od...

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Chirality in natural products

  1. 1. Valliappan Kannappan Valliappan Kannappan VALLIAPPAN K Professor of Quality Assurance (Retd.) Department of Pharmacy Annamalai University INDIA 2021 Chirality in NPs 15 min.
  2. 2. Valliappan Kannappan Valliappan Kannappan Ascorbic acid Ascorbic acid Quinidine Quinidine N A T U R A L O R I Chiral Bio Chiral Bio- -active molecules active molecules 2021 Chirality in NPs (-)-Hyoscamine (-)-Hyoscamine Fungicides I G I N
  3. 3. Valliappan Kannappan Valliappan Kannappan F F R R A A G G R R A A N N C C E E S S (S) Limonene  (R) Lemon odor Orange odor 2021 Chirality in NPs caraway spearmint (S) Caravone  (R)
  4. 4. Valliappan Kannappan Valliappan Kannappan F F L L A A V V O O R R S S (S)  Asparagine  (R) bitter sweet NH2 (R) HO O O NH2 H H2N (S) OH O O H2N H 2021 Chirality in NPs sweet bitter (S, S)  Aspartame  (R, R) (S) N H (S) O O HO O O NH2 H H
  5. 5. Valliappan Kannappan Valliappan Kannappan F F U U N N G G I I C C I I D D E E (S)  Metalochlor  (R) inactive 2021 Chirality in NPs (R)-enantiomer is 1000x more active in vitro than (S) -isomer (S)  Metaxylyl  (R) N (R) CH3 O O O O H N (S) H3C O O O O H 
  6. 6. Valliappan Kannappan Valliappan Kannappan fungicide Plant growth regulator N N N (S) (S) CH3 CH3 CH3 OH H H Cl F F U U N N G G I I C C I I D D E E 2021 Chirality in NPs (2R,3R) Paclobutrazol (2S,3S) The chiral twins of Paclobutrazol exhibit wildly differing biological activities
  7. 7. Valliappan Kannappan Valliappan Kannappan H E R B C I D E (R)-Mecoprop; Herbicidal activity (inhibition of the activity of the plant growth hormone, indole- 3-acetic acid) resides virtually in the R-enantiomer eutomer 2021 Chirality in NPs N H O (R) NHC2H5 O O H CH3 (R)-Carbetamide; eutomer; developed as pure enantiomer
  8. 8. Valliappan Kannappan Valliappan Kannappan ( S,2R,3R)- Deltamethrin  3 2 I I N N S S E E C C T T C C I I D D E E 2021 Chirality in NPs Deltamethrin is Pyrethroid insecticide; Chemically an ester of m-phenoxybenzaldehyde cyanohydrin; has three stereogenic centers and is sold as an enantiopure molecule with configuration (S,R,R).
  9. 9. Valliappan Kannappan Valliappan Kannappan (-)-Morphine O O L L D D C C D D 2021 Chirality in NPs  Millennia-old-unichiral drug is the opioid agent morphine; Opium powder is the dried juice from the unripe seed capsule of the poppy Papaver somniferum; analgesic and euphoric;  Pentacyclic 3amine (alkaloid) with 5 stereogenic centers (25 = 32 stereoisomers) and the natural product is the (-)-enantiomer – analgesic activity (-)-Morphine
  10. 10. Valliappan Kannappan Valliappan Kannappan (+)-Ascorbic acid 2021 Chirality in NPs (+)-Ascorbic acid  (+)- Ascorbic acid exhibits the redox activity, where as the (-)- enantiomer is inactive and cannot be used to treat scurvy
  11. 11. Valliappan Kannappan Valliappan Kannappan The herb Ephedra sinica contains ephedrine and Pseudo-ephedrine Sympathomimetic amine (alkaloid); CNS Stimulant, , treat hypotension, Bronchodilator, appetite suppressant (1R,2S)-2-(methylamino)-1-phenyl- propan-1-ol (-)-1R,2S-Ephedrine O O L L D D C C D D 2021 Chirality in NPs The herb Ephedra sinica contains ephedrine and Pseudo-ephedrine as its principle active ingredients; Ephedrine has two stereogenic centers, exhibits enantiomerism and is unichiral ; (1R,2S)- and (1S,2R)-enantiomers are designated ephedrine, (1R,2R)- and (1S,2S)-enantiomers as pseudoephedrine In April 2004, USFDA banned the sale of ephedrine and dietary supplements containing ephedrine due to serious adverse effects
  12. 12. Valliappan Kannappan Valliappan Kannappan Antimalarial activity (-)-Quinine 2021 Chirality in NPs Antimalarial activity  Most fascinating old chiral drug, from historical point of view is Quinine (1600s); Bark of Cinchona tree;  Contains two major fused ring systems: aromatic quinoline and bicyclic quiniclidine  Stereoselective synthesis of quinine was successfully done in 2001, 181 years after compound was first isolated
  13. 13. Valliappan Kannappan Valliappan Kannappan (-)-Quinidine (S) (R) O HO N (S) (R) H (R) (S) O HO N (S) (R) H (-)-Quinine 2021 Chirality in NPs Quinidine is a diastereomer of Quinine and is employed as an antiarrythmic agent; Stereoisomeric alkaloids exhibiting different therapeutic effects N N antimalarial Antiarrythmic
  14. 14. Valliappan Kannappan Valliappan Kannappan (-)-Cocaine The Coca Plant; Erythroxylon coca 2021 Chirality in NPs (-)-Cocaine  Cocaine is a tropane alkaloid obtained form the leaves of coca plant; employed topical anesthetic in eye and nasal surgery, although it is now predominantly used for nasal and lachrymal surgery.  (-)-cocaine was found have 50 x more affinity than its enantiomer Erythroxylon coca
  15. 15. Valliappan Kannappan Valliappan Kannappan N O OH H3C O Stereochemically atropine is an interesting case; This racemic substance is believed not to occur in naturally 2021 Chirality in NPs (-)-Hyosciamine  (-)-Hyoscyamine occurs in several Solanaceae plant species and is racemized to atropine during isolation  (S)-(-)-Hyoscyamine was found to be 12-20 X more potent than the (+)-enantiomer in a variety of pharmacological effects viz. mydriasis, salivary secretion , etc.
  16. 16. Valliappan Kannappan Valliappan Kannappan Thanks for Thanks for your your time time 2021 Chirality in NPs valliappan valliappan Chirally Yours Chirally Yours

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