Indian Journal of Chemistry Vol. 398, August 2QOO, pp. 565 - 586 Review Article Phytochemicals from genus Swertia and their biological 'lctivities Neerja Pant , D C Jain* & R S Bh akuni Central In stitute of Med ic in al & Aromati c Plant s, P. O. CIMAP, Lucknow 2260 15 , Ind ia Swerlia spec ies (fami ly - Ge nti anaceae) widespread in nature, are frequentl y utili zed fo r the treatment of hepatiti s, cholecystitis, pneumonia, dy sent ery, scabies. pain and ne ur as th e mi a. The Swertia herbs are also ex tens iv ely used as bitter tonics and febrifuges in th e Ayurved ic system of medicine. This review summari zes th e che mi cal co nstitue nt s and their biological activi ti es repo rt ed till Dec. 1 998. The plants of th e ge nu s Swerlia are ri ch sour ces of xa nthono id s. fl avo noid s, irri - do id s and terpeno id s. Introduction Th e ge nu s Swe rtia L. (fam: Gentianaceae) comprises 170 species, of which 79 species are di stributed in China l . About 20 species of thi s ge nu s have been used in chinese traditional medicine for the treatmen t of hepatic, choleric and inflammatory d iseases 2J . In In dia , Sw e rtia C hirata Bu ch-Ham, co mm o nl y kn ow n as ch irayala is used as a crude drug repo rt ed in Indian ph a rm acopoe ia. It is grown in the temperate Him alayas fr om Kashmir to Bhutan and in Kai sa hill s4. The extract is used as a bitter sto ma chic, febrifuge , anthelmintic, antimalaria l and antidiarrhoea l 5 . The he rb of S. pwpurasce ns is used in Pa ki stan as a substitute of S c hirata a nd in Japan S. japonica Makino (Japanese name - Senburi) is an important bitter stomac hi c 6 . 7 The pl a nt s of SlI'ertia ge nu s are ri ch sources of xa nth ones, fl avono id s, irrid o id a nd secoirido id g lu cos id es a nd te rp eno id s. The compila ti on of th e chemical constituents on Swertia ge nu s ha s been done by Wang et al 8 in 1992 , a nd Rahman el al 9 in 199 7. The prese nt rev iew is an attempt to compile and tabulate al l th e che mi ca l con stitu e nt s of th e ge nu s SIVcrtia a nd th e ir bi ological activities available in th e literature till Dec. 1998. Ti ll now 1 64 compounds have been isolated a nd cha ra cter ized from 4 I different SIVertia spe cies. Tvvo xa nthones- Bellidifolin from S japonica and swe rchirin from S. chirata have been isolated a nd characte ri ze d to possess ma rk ed hypoglyce mi c .. I d " d 10 I ' ac ti v ity w len a mlntstere to rats " . The bioactive compounds a nd biologically ac ti ve extracts from different Swer t iel s r.ec ies have been sllmmarised in Ta bl e 1 11 ,11 a nd II L ,.1S The che mi ca l constituents is olated from different plant parts of Swertia species have been given in th e Table I11 39 ,14 1. Chemical constituents of Swertia species Different c la sses of compounds have been isolated from differe nt spec ie s. They are as fo ll ows: Xanthonoids: The ma in components isolated from th e Swerlia species are th e xa nth ones a nd their g lu cosides. About 46 xa nthones of trioxygenati on ( 1- 7) tetra - (8-29) a nd pentaoxygenation (30-46) a nd twenty- n in e xanthone-O-glucosides (48-77) have been isolated from various Swer lia .sp. O nl y one xanthone -C-g lllc os id e i, e. man g if e rin 47 has been reported frol11 nine plant species - S. calyc ina, S. co rda/a, S. spe ciosa, S. c hiral a, S. co neata, S. iberica, S. musso /ii, S. percnnis and S. slVert ops is. Two xa nthone - O-diglucosides (78, 79) fro m S. . d S' .. 11 6 124 b' I I . . p erc nl1l s an . musso tll . , tsxa nt lone c 1 tratan 111 80 from S c hirata l02 , One bi sxanthone 90 fro m S. . fran che/iana 23 and two bi sxa nth one g lu cos id es ( 91 ,92) from th e whole plant of S. 55 have been isolated, Lignan : Only one hepatoprotec ti ve li gnan (-) sy rin gares in ol (82) has bee n iso lated from S. chirata a nd is id entified by its spect ral data l oo . Alkaloids: About six a lk a lo id s (83-88) ha ve been reported from different SIVe rtia species'o. 79.S7,Q2. I09. 1 18 Flavonoids: A fl avone, Illt eo lin 81 from S terepc tala l. 19 , a fl avone-xa nthone g lu cos id e dim e I' , swertifranehes id e 89 fro m S. ./i·anchesidc",1.1 . two of th e fl avone - dig lu cosides (93, 94) frolll S. !}( !rCllllis I 15 , six flavone g lu cos id es (95-100) 1'1' 0 111 diff erent pl ant species have been iso lated. IlTidoid and Sccoil'idoid : Thirteen secoirido id g lu cos id es ( 101 -103, 105, 116-124) have been
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Indian Journal of Chemistry Vol. 398, August 2QOO, pp. 565 - 586
Review Article
Phytochemicals from genus Swertia and their biological 'lctivities
Neerja Pant, D C Jain* & R S Bhakuni
Central Institute of Med icinal & Aromatic Plants, P. O. CIMAP, Lucknow 2260 15, India
Swerlia species (fami ly - Genti anaceae) widespread in nature, are frequentl y utili zed fo r the treatment of hepatiti s, cholecystiti s, pneumonia, dysentery, scabies. pain and neurasthemia. The Swertia herbs are also extensively used as bitter tonics and febrifuges in the Ayurved ic system of medicine. This review summarizes th e chemical constituents and their biological act ivi ti es reported till Dec. 1998. The plants of the genus Swerlia are ri ch sources of xanthonoids. fl avonoids, irri do ids and terpeno ids.
Introduction
The genus Swertia L. (fam: Gentianaceae) comprises 170 species, of which 79 species are di stributed in China l. About 20 species of thi s genus have been used in chinese traditional medicine for the treatment of hepatic, choleric and inflammatory d i seases2J .
In In dia , Swertia Chirata Buch-Ham, commonly known as chirayala is used as a crude drug reported in Indian pharmacopoe ia. It is grown in the temperate Himalayas from Kashmir to Bhutan and in Kai sa hill s4. The extract is used as a bitter stomachic, febrifuge, anthelminti c, antimalaria l and antidiarrhoea l5. The herb of S. pwpurascens is used in Paki stan as a substitute of S chirata and in Japan S. japonica Makino (Japanese name - Senburi) is an important bitter stomachic6
.7 The plants of SlI'ertia
genus are ri ch sources of xa nthones, fl avonoid s, irridoid and seco iridoid g lucos ides and terpenoids.
The compil ation of the chemical constituents on Swertia genus has been done by Wang et al8 in 1992, and Rahman el al9 in 1997. The present rev iew is an attempt to compile and tabulate al l the chemi ca l constitu ents of the genus SIVcrtia and their biologica l activities available in the literature till Dec. 1998. Ti ll now 164 compounds have been isolated and character ized from 4 I different SIVertia species.
Tvvo xa nthones- Bellidifolin from S japonica and swerchirin from S. chirata have been iso lated and characteri zed to possess marked hypoglyce mic
.. I d " d 10 I ' acti vity w len a mlnt stere to rats " . The bioactive compounds and biologically ac ti ve
extracts from different Swert iel sr.ec ies have been sllmmarised in Ta ble 111,11 and II L
, .1S The chemi ca l
constituents isolated from different plant parts of Swertia species have been given in the Table I11 39,141.
Chemica l constituents of Swertia species Different classes of compounds have been iso lated
from different spec ies. They are as foll ows: Xanthonoids: The main components iso lated from
the Swerlia species are the xanth ones and their glucosides. About 46 xanthones of trioxygenati on (1-7) tetra - (8-29) and pentaoxygenati on (30-46) and twenty-n ine xanthone-O-glucosides (48-77) have been iso lated from various Swerlia .sp. Only one xanthone -C-glllcos ide i,e. mangiferin 47 has been reported frol11 nine plant species - S. caly cina, S. corda/a, S. speciosa, S. chirala , S. coneata, S. iberica, S. musso/ii, S. p ercnnis and S. slVertopsis.
Two xanthone - O-diglucos ides (78, 79) fro m S. . d S' .. 11 6 124 b' I I . . p ercnl1ls an . mussotll . , tsxant lone c 1 tratan 111
80 from S chirata l 02, One bi sxanthone 90 from S.
.franche/iana23 and two bi sxanth one glucosides (91 ,92) from the who le plant of S. punicea5~, 55 have been isolated,
Lignan : Only one hepatoprotecti ve li gnan (-) syringaresinol (82) has been iso lated from S. chirata and is identifi ed by its spectral data loo .
Alkaloids : About six alka lo ids (83-88) have been reported from different SIVertia species'o. 79.S7,Q2. I09. 118
Flavonoids: A fl avone, Illteo lin 81 from S terepctala l.
19, a fl avone-xanthone glucos ide dim eI',
swertifraneheside 89 from S. ./i·anchesidc",1.1 . two of the fl avone - dig lucosides (93 , 94) frolll S. !}(!rCllllis I15
,
six flavone glucos id es (95-100) 1'1'0 111 different plant spec ies have been iso lated.
IlTidoid and Sccoil'idoid : Thirteen secoiridoid glucosides (101 -103, 105, 116-124) have been
566
I i
INDIAN J CHEM, SEC B, AUGUST 2000
Miss Neerja Pant PA is currently working as a research scholar in Department of Phytochemical Technology Division, CIMAP, Lucknow. She obtained her MSc degree in chemistry in 1996 from Lucknow University and has a throughout first class carreer. Her field of research is mainly based on the bioactive natural product compounds.
Dr 0 C Jain, Scientist-E, Central Institute of Medicinal and Aromatic Plants (CIMAP) Lucknow, India received his master' s degree in organic chemistry from the University of Rajasthan, Jaipur, India and Ph.D. from the University of Indore in 1982. In 1982 he joined CIMAP. Dr Jain has wide research interest in natural products chemistry and developed a new antimalarial drug arteether from the plant Artemisia annua. He is author of 60 publications and 10 patents including two international patents.
Dr R S Bhakuni, Scientist, Central Institute of Medicinal & Aromatic Plants, Lucknow, India received his M.Sc degree in 1978 and Ph.D. in 1987 in organic chemistry from Kumaun University, Nainital. He has worked 011 anticancer drug Taxol as PDF with Prof K V Rao at the University of Gainsvi-lle, Florida USA for two years. Working in natural products chemistry since 1981 , he has published 31 research papers, 7 patents including cone international patent.
iso lated from Swertia species. Tliese are the bitter components present in the plant. Amarogellt in 101, Amaroswerin 1()2 and Swertiamarin 116 are the most importan t bitter components reported from Swertia species.Three irrido id g lucosides (111-113) have been isolated from S, japonica68
. 69. 70 and one 104 is
. reported 7.1. Three lac to nes have al so been reported
( 154-156)1 0.1>0 . A quinone derivative 153 is reported fro m S. calycillc/ I A few compou nds (l 06-11 0, 114-115, 152, 157-164) have also bee n iso lated fro m different Swerlia species.
d 1': S I' " 1)1) reporte 1 rom . caro Imensls - . Triterpenoids: Till now nineteen triterpenoids
( 125-143) have been reported from thi s large genus. The triterpeno ids are the other major components from Swerlia species .
Miscellaneous: The steam-vo latil e const ituents of S. j aponica have been studied and 7 1 components of the oi l have been identified. About e ight compo und s ( 144-151) o f the steam-vo lat il e const ituents have been
Biological Activities of Swertia species
H ypoglycemic activity. A lcoho lic and hexane ex tracts of S. chirala have a remarkab le blood sLigar lowerin g effect in a lbino rats l 6
.17 A xa nthone iso lated
from hexane fraction of S. cliirala, ident ifi ed as swerchirin (I ,S-dihydroxy-3 ,5-d imethoxyxanthone: 13) possesses a very signifi cant blood sugar- lower in g effec t in fast, fed , g lucose loaded and to lbutamide pretreated a lbino rat mode ls II . .1(, .:17
PANT et a/.: PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES 567
Swe rtis in (95 ) H Glu Swe rna ja po Din (96 ) OH Glu Homoorientin ( 97) OH Glu Isoswe rtisio (98 ) H Glu Isovitexin (99 ) H Glu Luteolin-7-O-g1ucoside (100) OH H
S c/Jirala Hexane fraction Hypoglycemic activity Alcohol and water extracts CNS depressant activity Petroleum ether extract, aleohol and water ex- Antimicrobial activity tract Hexane fractions and 9S% ethanol fraction Blood sugar-lowering in rats Ethyl acetate extract Antifeedant property against Jute
An ethyl acetate soluble fraction of S. japonica and its ether insoluble fraction also showed a potent hypoglycemic activity 12. A xanthone named bell idifol in 11 isolated from ethyl acetate fraction of S. japonica showed a potent and dose-dependent hypoglycemic activity in streptozotocin-induced diabetic rats by both ora l and intraperitoneal administration26 Both bellidifo lin 11 and methyl be llidifo lin 13 showed a significant activity but be llidifo lin was found to be more potent than methylbell id ifo l in 26
jrancheliana was found to be a potent inhibitor of the DNA polymerase activity of human immunodeficiency virus-I reverse Irans-criptase (HIV -I RT) with 50% inhibitory doseD, 24 . It binds to DNA and was shown to be a compet it ive inhibitor with respect
Anti-H IV activity . Swertifranches ide 89, a new flavone xanthone glucoside isolated from S.
I . 74 to temp ate-pnmer- .
Antitubercular Activ ity. Xanthones and their glucosides showed antituberculosis activity i ~o l ated
from S. purpurascens. Swertianolin 50 and Norswertiano lin 5 1 produces a weak antitubercular activit/ 4 The aglycone of norswertianolin appeared to be more active than corresponding I-O-glucosyl der ivative suggesting importance of free hydroxyl
584 INDIAN J CHEM, SEC 8 , AUGUST 2000
group at one pos ition for the activity34 . Compound 51 isolated from S. randsaiensis also showed tuberculostatic activity35.
Anticholinergic activity. The anticholinergic action of S. japanica is used in Japan as a bitter stomachic. A secoirridoid glycos ide named swertiamarin 116 was found to be about 30% active wi th an anticholinergic action. The effect of 116 was not as rapid in onset as that of atropine, used as reference drug but its effect was 10nglasti ng27 . The ethanolic extract of S. chirata a lso showed anticholinerg ic activity' 9.
Antimalarial activity. Swerchirin 13 a tetraoxygenated xanthone from S. chirata was tested for antimalarial activity by Goyal el al. Compound 13 was proved to be effective even at 115 of standard dose primaquine by both ora l and subcutaneous routes . The drug is effective at both the routes i.e. at 1.6 mg/kg and 320 f1 gm/kg by reaching nil parasitaemia in infected rats38
.
Antiinflammatory activity . Xanthone glucos ide mangiferin (47) as well as preny lated xanthone Mangostin (162) have been found to exert pronounced antiinflammatory activity against different models of experimental inflammation20
.
Antimicrobial activity. S. chirala extracts are more active against gram-pos itive than against gramnegative bacteria. They were inactive against all the fungi. Alcohol and water extracts of S. chirata showed that it possesses CNS depressant activity. Higher doses produced CNS depression without the loss of reflexes.
Several xanthones and their D.g lucos ides showed antimicrobial activity' s. Swertiamarin 116 iso lated from S. japonica showed antibacteria l act ivity agai nst Staphylococcus aureus25
.
Antifungal activity. The methanolic and dichloromethane extracts of S. calycina exhibited a strong antifungal activity aga in st Cladosporium cucumerinum and Candida albicans. The com pound responsible for thi s activity has been identified as 2-methoxy- 1,4- naphthoquinone21 153.
Antifeedant property. Different extracts of S. chirala were investigated to assess their antifeedant effects aga inst Semilooper (Anomis sabyuliferaguen) . Only the ethy l acetate extract showed antifeedant
. • 18 activ ity .
Acknowledgement
Authors are thankful to Dr Sushil Kumar, Director, CIMAP for the necessary laboratory facilities,
constant encouragement and for the award of senior research fellowship to Ms Neerja Pant.
References
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