Chirayita, Kiratatikta (Swertia chirayita) Part 2



Chirayita, Kiratatikta (Swertia chirayita) Part 2
By
Dr. Hemant Vinze 
                                            ( M. S.)

Identity, Purity and Strength   

Foreign matter: Not more than 2 percent
Total Ash: Not more than 6 percent
Acid-insoluble ash: Not more than 1 percent
Alcohol soluble extractive: Not less than 10 percent
Water-soluble extractive: Not less than 10 percent  

Tannin: On addition of Ferric chloride to aqueous or alcoholic extract of Chirayita (Swertia chirata) no blue black color develops.

Assay: Chirayita (Swertia chirata) contains Not less than 1.3 percent of bitter principle. [35]    

Heavy Metal Analysis
Permissible maximum limits for heavy metals in extracts of herbal medicines

Metal                     Maximum Permissible Limit (μg/g)
Iron (Fe)                                   300
Manganese (Mn)                       100
Copper (Cu)                               20    
Zinc (Zn)                                    50
Lead (Pb)                                   10 
Cadmium (Cd)                              0.2   [36]


Permissible Microbial Load

Name of bacteria                               WHO Limit
Escherichia coli                                        102        
Salmonella species                              Absence
Shigella species                                  Absence         
Enterobacter species                                104
Total bacterial Count                                107
Yeast and Mould                                      104    

Aflatoxins in Chirayita (Swertia chirata) extract

Fungi Aspergillus flavus and Aspergillus parasiticus colonize on agricultural and animal products. They produce aflatoxins. Aflatoxins are secondary metabolites. They are one of the most potent teratogens, mutagens, carcinogens and immunosuppressants. They cause some metabolic disorders resulting into damage of heart, lungs and kidney causing death both in human and animals. In present era there is increasing demand for herbal medicines in Asian and African communities. Aflatoxin contamination is a major concern, which has received worldwide attention due to their deleterious effects.       

A study showed that Chirayita (Swertia chirata) extract contains 9.87 μg /ml +/- 0.32 of Afflatoxin B1 and 9.18 μg /ml +/- 0.78 of Afflatoxin B2. [37]

Genetic Identity

By employing ISSR marker assay, random amplified polymorphic (RAPD) DNA study and PCR analysis accurate genetic identity and genotype of Chirayita (Swertia chirayita) has been established. [38] 

Chromosomal Identity

There is much overlap in morphologic and taxonomic appearance of Sweria species. Hence there is a need to establish chromosomal identity of Chirayita (Swertia chirata). The mosaic chromosome number counts in root tip cells were 11-24 chromosomes in Chirayita (Swertia chirata). [39]

Properties and Pharmacology

Ayurvedic Properties:

Rasa (Taste): Tikta (Bitter)

Weerya (Virya): Sheeta

Vipaka: Katu (Acrid, Pungent)

Guna: Laghu (Light), Rooksha (Dry)

Karma: Jwaraghna (Antipyretic), Swedajanan (Diaphoretic, Inducing perspiration), Kaphapittahara (Alleviates phlegm and pitta), Deepana (Appetizer), Paachana (Digestant), Aamapaachana (Free radical scavenger), Anulomana (Carminative), Raktashodhaka (Blood purifier), Vranashodhana (Disinfects wounds), Vranaropana (heals wounds and ulcers), Saaraka (Laxative), Pittasaaraka (Improves bile flow), Trishnaapaha (Relieves thirst), Shothaghna (Relieves edema, inflammations), Daahaghna-Daahanaashaka-Daahashamaka-Daahaprashamana (Relieves burning), Krimighna (Kills worms), Kandushaamaka-Kandughna (Relieves itching), Kushthagna (Anti-leprosy), Mehaghna (Antidiabetic, reduces polyuria), Katupaushtic (Bitter tonic), Stanyashodhana (Purifies milk), Shwasahara (Relieves dyspnoea), Hridya (Beneficial to heart)  

  Ayurvedic Gana

               Varga

        References

Charaka

Tikta, Skandha, Stanyashodhana, Trishna Nigrahana, Mahakashaya

Ch. Su. 4/14, 4; Ch. Vi. 8/143

Sushruta

Aaragwadhadi gana, Shaaka varga

Shsh. Su. 38/6, 46/262

Ashtaang Hridaya

Aaragwadhadi gana

Su. 15/17

Dhanwantari Nighantu

Aaragwadhadi gana

D. N. 33-35

Sodhala Nighantu

Guduchyaadi gana, Guduchyaadi varga

So. N. Part 1, Guduchyaadi varga 121-122

Madanpal Nighantu

Abhayaadi varga

M. N., Abhayaadi varga 143-144

Kaiyadeva Nighantu

Aushadhi varga

K. N. Aushadhi varga 889-891 

Bhaavaprakaasha Nighantu

Haritakyaadi varga

B. N. Haritakyaadi varga 153-155

Raaja Nighantu

Prabhadraadi varga

R. N. Prabhadraadi varga 15-18

Nighantu Aadarsh

Kiraataadi varga

Ni. A. Vol 1

Hridayadeepak Nighantu

Dwipaad varga

Hr. Di. Ni. 61

 Key:

Ch. =Charaka Samhita, Su. = Sootrasthana, Vi. =Vimaana Sthana, Sush.= Sushruta Samhita, D. N. Dhanwantari Nighantu , So. N. = Sodhala Nighantu, M. N. = Madanpal Nighantu, K. N.= Kaiyadeva Nighantu, B. N. = Bhaavaprakaash Nighantu, R. N. = Raaja Nighantu, Ni. A. =Nighantu Aadarsh, Hr. Di. Ni.= Hridayadeepak [40]

Effects on doshas: Tridosha (all the three doshas i. e. waata, pitta, kapha) predominantly on kapha and pitta. [41]

Phytochemistry

Important bioactive phytochemicals found in Chirayita (Swertia chirata) are:

Bitter glucosides: charatin, amarogentin, gentiopicrin

Bitter yellow acid: Ophelic acid

Xanthone: Swerchirin, 7-O-Me swertiarin  

Two Yellow crystalline phenols, a yellow crystalline compound

Swertanone, swertenol, episwertenol, chiratenol, gammacer-16-en-3β-ol, 21-a-H-hop-22(29)-en-3β-ol, taraxerol  

Oleanolic acid, ursolic acid, Monohydroxy terephthalic acid, Ascorbic acid
Swerta-7,9(11)-dien-3-β-ol, pichierenol, 1,3,6,7-tetrahydroxyxanthone-C-2-β-D-glucoside (Magniferin)

Alkaloids: Gentianine, gentiocrucine, enicoflavine    
   
Flavonoids, Steroids, Saponins,  
    
Swertinin, swertianin, swerchinin, decussolin, bellidifoten, friedelin, β- sitosterol, arginin, lucine, methionine, threonine, tryptophan, aspartic acid, glutamic acid [42], [43]

Modern view

Amarogentin
Molecular formula: C29H30O13
Structural formula:



Amarogentin is secoiridoid glycoside. It is one of the most bitter compounds found in nature. It tastes bitter even at a dilution of 1: 58,000,000. It can be extracted from Chirayita (Swertia chirayita Roxb). It activates the bitter taste receptor hTAS2R50. It is used as a scientific basis for measuring the degree of bitterness of any substance. It exhibits antileishmanial chemo-preventive effects.  [44], [45]
Amaroswerin
Molecular formula: C29H30O14
Structural formula:


   [46]



Amaroswerin is secoiridoid glycoside extracted from Chirayita (Swertia chirayita Roxb). It is gastroprotective.  [47]

Gentianine                                           
Molecular formula: C10H9NO2        
Structural formula:




Gentianine, also known as 4-(2-hydroxyethyl)-5-vinylnicotinate galactone. It is a member of the class of compounds known as pyranopyridines. Pyranopyridines are polycyclic aromatic compounds. Gentianine is soluble in water It is alkaline. It tastes bitter. It is also found in Methee-Fenugreek  (Trigonella foenum-graecum L) [48]
Gentianine is a sullen (dull), translucent monoterpene alkaloid. It possesses anti-inflammatory, analgesic, anesthetic, anticonvulsant, antipsychotic, antihistaminic, hypotensive, diuretic, antibacterial and antimalarial properties. [49]

Gentiocrucine
Molecular formula: C6H7NO3
Structural formula:



Gentiocrucine is a novel lactonic enamino ketone. It is an unusual alkaloid containing a stable primary enamide. [50]
Anti-hepatitis-B (anti-HBV) assay on HepG2.2.15 cell line in vitro showed that gentiocrucine inhibited the secretion of hepatitis B virus (HBsAg) surface antigen and hepatitis B virus e antigen (HBeAg). [51]

Enicoflavine
Molecular formula: C10H13NO4
Structural formula:




Enicoflavine is aromatic flavone. [52]
Belonging to flavonoid group of compounds, enicoflavine exhibits many properties of flavones for instance, anti-inflammatory, antioxidant, antibacterial, antiviral, antiulcer, antidiabetic and anticancer etc. [53]   

Swertinin
Molecular formula: C15H12O6
Structural formula:





[54]
Swertinin is anti-inflammatory, antioxidant, antibacterial, antiviral, antiulcer, antidiabetic and anticancer etc.  [55] 


Swertianin
Molecular formula: C14H10O6
Structural formula:



Swertianin has agreeable, pleasant perfume. It is used in cosmetics, soaps, skin care lotions, shampoos, toothpastes and perfume industry. [56]
Swertianin is anti-inflammatory, antimalarial, hypoglycemic and anticancer agent. [57]

Swerchinin

Swerchinin showed hypoglycemic activity in rats and in humans. It also showed hypoglycemic activity in normal as well as streptozotocin-induced diabetic rats. [58]


Swerchirin
Molecular formula: C15H12O6
Structural formula:




                                                                                  

Swerchirin is the 5-O-methyl derivative of bellidifolin. It belongs to the class of aromatic ethers known as xanthones and is a member of phenols. It exhibits hypoglycemic, hepatoprotective and weak chemo-preventive pharmacological effect. [59]

Swertiamarin
Molecular formula: C16H22O10
Structural formula:





Swertiamarin is a secoiridoid glycoside obtained from Chirayita (Swertia chirata Roxib). It shows anti-inflammatory, analgesic property. [60]

Charantin

Molecular fofmula: C26H35NO7
Structural formula:



The phytochemical charantin obtained from bitter gourd/Asian bitter melon (Momordica charantia) was first identified by Lolitkar and Rao in 1960. Charantin also known as naftidrofuryl or nafronyl is a member of the class of compounds known as naphthalenes. Charantin is sparingly soluble in water but is soluble in ether, methanol and ethanol. Charantin is actually a 1: 1 mixture of two steroidal saponins, β-sitosteryl glucoside (C35H60O6) and 5,25-stigmasteryl glucoside (C35H58O6). It is a whitish crystalline substance, neutral to pH, tasteless, melting at 266-2680 C. It shows hypoglycemic activity. [61]   

 
Gentiopicrin
Molecular formula: C16H20O9
Structural formula:



Gentiopicrin is a naturally occurring iridoid glycoside. Gentiopicrin could be absorbed rapidly in mice, but with a low bioavailability. Gentiopicrin is one of strongest myeloperoxidase inhibitor. Gentiopicrin is anti-inflammatory agent effective against fever, rheumatoid arthritis, digestive disorders, acute colitis and liver diseases. Gentiopicrin attenuates expression Tumor necrosis factor-α (TNF- α), Interleukin-1β (IL-1β), Interleukin-6 (IL-6), Inducible Nitric Oxide Synthase (iNOS) and Cyclooxygenase-2 (COX-2). Gentiopicrin inhibits reserpine-induced pain, depression by down-regulating glutamate inotropic receptors (GluN2B) in amygdale. Gentiopicrin injection has been approved by SFDA for the treatment of jaundice and chronic active hepatitis. [62] 

Magniferin

Molecular formula: C19H18O11
Structural formula:






Magniferin a xanthonoid is a glucoside of norathyriol. Magniferin was first isolated from the leaves and bark of mango (Magnifera indica). It can also be extracted from peels and kernels of mango. Magniferin has antioxidant, antibacterial, gastroprotective and anti-diabetic properties.  [63]
Magniferin (2-β-D-glucopyranosyl-1,3,6,7-tetrahydroxy-9H-xanthen-9-one) exhibits antioxidant, antiallergic, immunomodulatory, antidiabetic and hypocholesterolemic properties. By enhancing the capacity of monocyte-macrophage system magniferin shows antibacterial activity against gram positive and gram negative bacteria. Magniferin protects against many human cancers such as breast, neuronal, lung and colon cancer through the suppression of tumor necrosis factor-α (TNF-α) expression, inducible nitric oxide synthase potential, inhibition of proliferation of tumor cells and induction of apoptosis. [64]   


Friedelin

Molecular formula: C30H50O
Structural formula:





Friedelin is a pentacyclic triterpenoid. [65]
Administration of friedelin at 40mg/kg bodyweight significantly inhibited acute phase of inflammation, decreased the formation of granuloma due to chronic inflammation, decreased the vascular permeability induced by acetic acid, decreased the swelling and pain in the adjuvant-induced arthritis and showed strong analgesic activity in rats and mice. Friedelin also showed reduction in pyrexia depending on the dose administered. [66]   
In recent experimental studies friedelin showed anti-inflammatory, antioxidant, anti-free radical, analgesic, antihistaminic, antipyretic, anticonvulsant, antivenom, insecticidal, antimicrobial, antiulcer, antidiarrheal, hepatoprotective, hypolipidemic, hypoglycemic, diuretic, nephroprotective, cytotoxic, anticancer properties. [67]
Friedelin extracted from the leaves of Azima tetracantha showed gastroprotective effect against ethanol-induced gastric ulcer in rats. This effect was attributed to anti-inflammatory and antioxidant properties of friedelin. [68]
At 20mg/kg bodyweight friedelin significantly reduced the intestinal transit time.  Friedelin also exerted anti-enteropooling effects in rats. Additionally friedelin inhibited castor-oil induced diarrhea. It is suggested the antidiarrheal effect of friedelin was due to its anti-secretary and anti-motility properties. [69]
In vitro and in vivo friedelin isolated from the leaves of Azima tetracantha Lam displayed lipid lowering, antihypertensive and hepatoprotective activities. [70], [71]

References:


36. Source: WHO (2005)

37. Basant Kumar Sinha, Studies on the Inhibitory Effect of some Plant Extracts on Mycoflora and Aflatoxin Production, Acta Scientific Microbiology (ISSN: 2581-3226), Volume 1 Issue 6 June 2018

38. P. Joshi et al, Analysis of genetic diversity among Swertia chirayita genotypes, Biologia Plantanum, December 2007, Volume 51, Issue 4, pp 764- 768  

39. Tapojita Samaddara et al, Cytogenic and DNA fingerprinting analysis in three species of Swertia from Estern Himalaya, Caryologia: International Journal of Cytology, Cytosystematics and Cytogenetics, 2015

40. Sapkota Sabita et al, A review on Swertia chirata (Roxb. Ex. Flem.) Karsten: Comparative analysis of Ayurvedic Pharmacology, Experimental and Clinical Studies, International Research Journal of Pharmacy, 2019, 10 (7)


42. K. P. Sampath Kumar et al, J. Chem Pharm. Res. 2010, 2(1): 262-266

43. https://www.ayurvitewellness.com/2954/kiratatikta-swertia-chirata/

44. https://en.wikipedia.org/wiki/Amarogentin     

45. http://foodb.ca/compounds/FDBOO 7359

46. https://www.ebi.ac.uk/chebi/chebiOntology.do?chebiId=CHEBI:81152

47. http://foodb.ca/compounds/FDBOO 7359

48. http://foodb.ca/compounds/FDBOO7359      

49. K. P. Sampath Kumar et al, J. Chem. Pharm. Res. 2010, 2(1): 262-266

50. http://www.molbase.com/en/name-gentiocrucine.html                 

51. Wang HL et al, Gentiocrucines A-E, five unusual lactonic enamino Ketones from Swertia macrosperma and Swertia angustifolia, Planta Med 2012 Nov; 78(17): 1867-72             
52. https://pubchem.ncbi.nlm.nih.gov/compound/Enicoflavine

53. Prithviraj Karak, Biological activities of flavonoids: An overview, International Journal of Pharmaceutical Sciences and Research, Projected Impact Factor (2018): 083 


55. Prithviraj Karak, Biological activities of flavonoids: An overview, International Journal of Pharmaceutical Sciences and Research, Projected Impact Factor (2018): 083 


57. Jagmohan S Negi et al, Chemical constituents and biological importance of Swertia: A Review, Current Research in Chemistry 3(1):

58. https://herbalsupplementscare.com

59. https://pubchem.ncbi.nlm.nih.gov/compound/Swerchir

60. K. P. Sampath Kumar et al, J. Chem. Pharm. Res. 2010, 2(1): 262-266

61. http://food.ca/compounds/FDB006198

62. https://drugs.ncats.io/drug/0WE09Z21RC                  

63. https://en.wikipedia.org/wiki/Magniferin

64. Muhammad Imran et al, Magniferin: a natural miracle bioactive compound against lifestyle related disorders, Lipids Health Dis. 2017; 16:84; published online 2017 May 2.

65. https://pubchem.ncbi.nlm.nih.gov/compound/Friedelin

66. Antonisamy P et al, Anti-inflammatory, analgesic and antipyretic effects of friedelin isolated from Azima tetracantha Lam. in mouse and rat models, J Pharm Pharmacol. 2011 Aug; 63(8): 1070-7  

67. Prashith Kekuda et al, Phytochemistry, traditional uses and pharmacological activities of Azima tetracantha Lam (Salvadoraceae)-An Updated review, International Journal of Green Pharmacy 11(4): 217-229, October 2017  

68. Paulrayer Antonisamy et al, Protective effects of friedelin isolated from Azima tetracantha Lam. Against ethanol-induced gastric ulcer in rats and possible underlying machanisms, European Journal of Pharmacologym Volume 750, 4 March 2015; Pages 167-175

69. Paulrayer Antonisamy et al, Antidiarrhoeal activity of friedelin isolated from Azima tetracantha Lam. in Wistar rats, South Indian Journal  of Biological Sciences, 2014; 1(1): 34-37

70. Jinging Jiao, Antihyperlipidemic and antihypertensive effect of a triterpenoid-rich extract from bamboo shavings and vasodilator effect of friedelin on phenylephrine-induced vasoconstriction in thoracic aortas of rats, Phytotherapy research 18 July 2007

71. Christudas Sunil, Antioxidant, freeradical scaving and liver protective effects of friedelin isolated from Azima tetracantha Lam leaves, Food Chemistry, Volume 130, Issues 1-4, 15 August 2013, Pages 860-865


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