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Senna glycosideKratika Daniel (Ph.D)Assistant professorMANDSAUR INSTITUTE OF PHARMACY,Mandsaur
Introduction Category – Anthraquinone glycoside •They possess anthracene or their derivatives as aglycone •Hydrolysis of t...
Types of anthraquinone glycoside 1. O-glycosides where the aglycone moiety is 1,8    dihydroxyanthraquinone derivatives, e...
3. C-glycoside where the aglycone structure (anthrone der.)                                            O                  ...
SOURCE•Consists of the dried leaflet of Alexandrian or Khartoumsenna, Cassia senna (C.acutifolia), Tinnevelly senna(C.angu...
1.Similar anthrone moiety (Homo-dianthrones) i.e., 2 rhein anthronemoieties condensate through two C-10 atomes. Thus it ca...
Extraction & IsolationI            Dry Senna powdered                       90% methanol or 50%                       Acet...
SenzymeBiosynthesis   O                           O       O       O                      O        O       O       O       ...
chrysophanol anthrone                        -CO 2                                                                        ...
Identification test  1. Borntrager’s test   3ml extract        +            Boil & filter         To cold filtrate   Dil. ...
TLC    Solvent system – dichloromethane:     methanol: formamide(8:2:1)                        ethyl acetate: n – propanol...
SAR:1. Glycosilation:The purgative action of anthracene bearing drugs is   owed to their anthracene glycosidal content rat...
4.   The nature of substances at C-3:Derivative with CH2OH (as     in aloe emodin) are more active than those with CH3    ...
USE & ACTION1. Used as effective cathartic agents for long time.2. Their action is due to their anthracene constituents ac...
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Senna glycoside

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Senna glycoside

  1. 1. Senna glycosideKratika Daniel (Ph.D)Assistant professorMANDSAUR INSTITUTE OF PHARMACY,Mandsaur
  2. 2. Introduction Category – Anthraquinone glycoside •They possess anthracene or their derivatives as aglycone •Hydrolysis of these glycoside yields aglycone which are di, tri, or tetra hydroxy anthraquinone Anthraquinone Anthrone Anthranol O O OH 8 1 8 1 7 9 2 4H 7 9 2 6 10 3 6 10 3 5 4 5 H H 4 O H O 2H 8 1 7 9 2 6 10 3 5 H 4 OH Oxanthrone Kratika Daniel (Ph.D)
  3. 3. Types of anthraquinone glycoside 1. O-glycosides where the aglycone moiety is 1,8 dihydroxyanthraquinone derivatives, e.g.,Gl O O OH O 1 Gl O OH Gl O O OH 1 1 8 9 2 8 9 2 8 9 2 10 CH2 OH 10 10 5 4 COOH CH3 5 4 5 4 O O O Aloe-emodin-8-glycoside Rhein-8-glycoside Chrysophanol-8-glycoside2. O-glycoside where the aglycone moiety partially reduced 1,8 dihydroxy anthraquinone, e.g., Oxanthrone-type. Gl OH OH H O 7 8 9 1 2 6 10 3 5 4 Kratika Daniel (Ph.D) Emodin-oxanthrone-9-glucoside O
  4. 4. 3. C-glycoside where the aglycone structure (anthrone der.) O OH OH 7 8 9 1 2 6 10 4 3 5 CH2 OH H C6 H11 O5 Barbaloin4. O-glycosides where the aglycone moiety is di-anthrone der. (i.e.,dimmer) e.g., Sennosides where there is C-C bridge between theanthranol units. Sennoside A&B Gl O O OH 7 8 9 1 2 6 10 4 3 COOH 5 H H COOH Gl Kratika Daniel (Ph.D) OH O O
  5. 5. SOURCE•Consists of the dried leaflet of Alexandrian or Khartoumsenna, Cassia senna (C.acutifolia), Tinnevelly senna(C.angustifolia).Constituents: - Dimeric anthracene glycosidesderived from two anthrones moieties which may be: O OH OH 1 O OH OH 8 9 1 2 8 9 2 10 CH2 OH 10 5 4 COOH 5 4 Aloe-emodin anthrone Rhein anthrone Kratika Daniel (Ph.D)
  6. 6. 1.Similar anthrone moiety (Homo-dianthrones) i.e., 2 rhein anthronemoieties condensate through two C-10 atomes. Thus it can be exist intwo optical forms, Sennoside A (L- form) & Sennoside B (meso form). Gl O O OH 7 8 9 1 2 6 10 4 3 COOH 5 H H COOH Sennosides A &B Gl O OH O2. Or different (Hetero-dianthrones) i.e., one rhein-anthrone & oneemodin anthrone, Sennoside CO(L- form) and Sennoside D (meso form). Gl O OH 7 8 9 1 2 6 10 4 3 CH2 OH 5 H H COOH Kratika Daniel (Ph.D) Sennoside C&D Gl OH O O
  7. 7. Extraction & IsolationI Dry Senna powdered 90% methanol or 50% Acetone for 6 hrs. Extraction with cold water for 4 hrs 17% of solid extract Contain 60 – 65% sennosideII Powdered Senna leaf Citric acid in methanol Extraction with methanol – toluene Mixture & ammonia Extract treated with CaCl2 Calcium salt of sennoside A & B Kratika Daniel (Ph.D)
  8. 8. SenzymeBiosynthesis O O O O O O O O 8 acetate unit O CH3 O O O Senzyme O O O O poly β - keto methylene acid intramolecular condensation CH3 COOH OH O HO Kratika Daniel (Ph.D) chrysophanol anthrone
  9. 9. chrysophanol anthrone -CO 2 OHO CH3 HO CH3 COOH OH O OH OH O Emodin - 9 -anthrone Endocrocin [O] O HO CH3 O HO CH3 [O] HO OH CH3 OH O OH emodin OH OH Kratika Daniel (Ph.D) emodin dianthrone
  10. 10. Identification test 1. Borntrager’s test 3ml extract + Boil & filter To cold filtrate Dil. H2SO4 Add benzene / CHCl3 & shake Add NH3 Ammonia layer turns pink / red Separate the organic layer2. Modified Borntrager’s test 5ml extract + Δ for 5 min. Boil & filter 5ml of FeCl3 To cold filtrate Add benzene + / CHCl3 5ml of Dil. HCl. & shake Ammonia layer turns Add NH pink / red 3 Separate the organic layer3. Magnesium acetate solution test: - in methanolic extract add magnesium acetate solution give orange color. Kratika Daniel (Ph.D)
  11. 11. TLC Solvent system – dichloromethane: methanol: formamide(8:2:1) ethyl acetate: n – propanol: water (4:4:3) Detecting reagent – ammonia vapors or spectrophotometry.Properties1. Sennoside occurs as a brownish powder.2. Sennoside soluble in alcohol but sparingly soluble in acetone3. Purgative activity of senna is mainly due to sennoside A & B while C & D exerts a powerful synergistic effect upon purgative activity. Kratika Daniel (Ph.D)
  12. 12. SAR:1. Glycosilation:The purgative action of anthracene bearing drugs is owed to their anthracene glycosidal content rather than their content of free anthracene aglycones (i.e., glycosylation is the main requirement for activity, as the sugar moiety serve to transport the aglycone to the site of action in the large intestine).2. Hydroxylation:Hydroxylation of C-1, C-8 is essential for activity. Increase hydroxylation leading to increase solubility.3. Oxidation level:The degree of oxidation at positions C-9 & C-10 plays an important role in the pharmacological activity. Higher oxidation level at C-9 & C-10 caused lowering of activity. i.e., anthrones and anthranols are more potent than their corresponding oxanthrones, which in turn more active than their corresponding anthraquinones. Complete reduction of C-10 &C-9 lead to complete loss of activity. Kratika Daniel (Ph.D)
  13. 13. 4. The nature of substances at C-3:Derivative with CH2OH (as in aloe emodin) are more active than those with CH3 substitution. The latter more active than derivative with COOH substitution at C-3. Anthraquinone glycosides containing adimer more active than a monomer.5. Effect of storage on the active of anthracene glycosides: Prolonged storage of anthracene bearing drugs may bring oxidation of anthranols and anthrones to give the less active anthraquinones. Thus, the activity of drugs decreases by time. However, anthraquinone glycosides do not cause any griping action (like anthranol and anthone), Senna preparations retain their activity for a long time Kratika Daniel (Ph.D)
  14. 14. USE & ACTION1. Used as effective cathartic agents for long time.2. Their action is due to their anthracene constituents acting on the large intestine. The sugar moiety helps to transport anthracene aglycon intact to large intestine, where aglycon is liberated by enzyme.3. Anthracene derivative without sugar moiety are broken down & only small amount reaches to intestine to exert cathartic action.4. It also used as purgative, cathartic, laxative & in acute constipation.5. Gripping action – occurs due to its resin or emodin6. Used in haemhoridial, after anorectal operation, anal fissure.7. For evaluation X – ray Kratika Daniel (Ph.D) from intestine contrast media

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