phytochemicals from genus swertia and their biological...

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

Compounds name(Structure number)

I-Hydroxy-3 ,5-dirnethoxyxanthone ( I )

1,7-Dihydroxy-3-rnethoxyxanthone (2)

I ,3 -Dihydroxy-7-rnethoxyxanthone (3)

I-Hydroxy-3,7-dirnethoxyxanthone (4)

I-O-Styryl-3,5-dirnethoxyxanthone (5)

I-Hydroxy-4-methoxyxanthone (6)

8-Hydroxy-1 ,4-dirnethoxyxanthone (7)

I-Hydroxy-3 ,7,8-trirnethoxyxanthone (S)

1,7,8-Trihydroxy-3-rnethoxyxanthone (9)

1,3,5,8-Tetrahydroxyxanthone (10)

1,5,8-Trihydroxy-3-rnethoxyxanthone( II )

I ,8-Dihydroxy-3, 7-dirnethoxyxanthone ( 12)

I ,8-Dihydroxy-3,5-dirnethoxyxanthone (13)

I ,7-Dihydroxy-3,8-dirnethoxyxanthone (14)

I ,3-Dihydroxy-5,8-dirnethoxyxanthone ( IS)

\J ,7,8- Tetrahydroxyxanthone (16)

I-Hydroxy-3,5 ,8-trimethoxyxanthone (17)

1,7,8-Trimethoxy-3-hydroxyxanthone ( IS)

1,3,8-Trihydroxy-5-methoxyxan thone (19)

3.4-Dimethoxy-7,8-dihydroxyxanthone (20)

I ,5-Dihydroxy-3 ,8-dimethoxyxanthone (21 )

1,6,8-Trihydroxy-4-methoxyxanthone (22)

I ,3,8-Trihydroxy-7-methoxyxanthone (23)

I ,3 -Dihydroxy-4,5-dimethoxyxanthone (24)

I-Hydroxy-3,7,8-trimethoxyxanthone (25)

I-Hydroxy-2,3 ,5-trimet hoxyxanthone(26)

8-Hydroxy-1 ,3 ,5-trimethoxyxanthone (27)

3-Hydroxy-I ,7,8-trimethoxyxanthone (2S)

1,3,5-Trimethoxy-8-hydroxyxanthone (29)

I-Hyd roxy-3 ,5,7,8-tetramethoxy xanthone (30)

1,7-Dihydroxy-3,5,8-trimethoxy xanthone (31 )

I ,8-Dihydroxy-2.4 ,6-trimethoxy xanthone (32)

R

R

Triox ygenated Xanthones

OH HOMe

OH HOMe

01-1

01-1

O-St

0 1-1

OMe

1-1

1-1

1-1

1-1

1-1

0 1-1

OMe

OMe

1-1

1-1

Tetraoxygenated Xa nthones

0 1-1 1-1 OMe

0 11 II OMe

0 1-1

01-1

0 11

0 11

0 1-1

01-1

0 11

0 11

OMc

Oli

Ii

0 11

01-1

0 11

0 1-1

0 1-1

OH

OMe

OMc

OMe

1-1

1-1

II

1-1

II

II

I-I

II

II

II

II

II

II

II

II

II

OM~

II

II

II

01-1

OMe

OMc

OMe

OMe

0 11

01-1

OMe

0 11

Of-!

OMe

OMe

1-1

0 11

0 11

OMc

OMe

OMc

011

OMc

Pentaoxygenated Xanthones

0 11

01-1

0 11

II

II

OMc

OMe

OM..,

II

1-1

1-1

1-1

1-1

1-1

OMe

OMe

1-1

1-1

1-1

1-1

1-1

H

1-1

1-1

1-1

II

II

II

OMe

1-1

OMe

II

OMe

II

II

II

1-1

I-I

1-1

II

OMe

R~

OMe

1-1

1-1

1-1

OMe

1-1

1-1

1-1

1-1

0 1-/

0 1-1

1-1

OMe

1-1

OMe

1-1

OMc

II

OMc

II

0 1-1

II

II

OMe

II

o Ie

OMe

II

OMe

OMc

GMc

II

1-1

I-I

1-1

1-1

1-1

1-1

1-1

1-1

1-1

1-1

1-1

1-1

1-1

II

1-1

II

II

II

II

II

II

0 11

II

H

II

II

II

1-1

1-1

II

II

OM~

I-I

0 1-1

OMe

OMe

1-1

1-1

1-1

OMe

0 1-1

II

1-1

OMe

II

0 11

II

011

II

OMc

II

0 11

II

II

OMc II

OM.:

II

II

OM.:

1-1

OM.:

0 11

II

1-1

II

1-1

1-1

1-1

II

01-1

OMe

01-1

01-1

Oil

0 11

01-1

o e

01\ Ie

0 11

OMc

OMc

01 1

01-1

Ok 0 11

011 II

OMc

II

Oil

O1'.1c

011

OMc

OMc

011 ( 'ollld

568 INDIAN J CHEM, SEC B, AUGUST 2000

Compounds namc(Structurc nUlIIlJrr)

I-Hydroxy-3 ,4,7,8-tetramethoxy xanthone (33)

1,2,3-Trihydroxy-7,8-dimethoxy xanthone (34)

I-Hydroxy-3,4, 5,8-tetramethoxy xanthone (35)

1,7-Dihydroxy-3,4 ,8-trimethoxyxanthone (36)

I-Hydroxy-2,3,5,7-tetramethoxyxanthone (37)

1 ,3,7-Trihydroxy-4,8-dimethoxy xanthone (38)

1,3.6-Trihydroxy-2, 7-dimethoxy xanthone (39)

1 ,3.4.5,8-Pentamethoxyxanthone (40)

1,3.4,7.8-Pentamethoxyxan thone (41)

I -Hydroxy-2,3,4,7-tetramethoxyxanthone (42)

I-Hydroxy-2,3 ,4,5-tetramethoxy xanthone (43)

2-Hydroxy- 1 ,3,4, 7-tetramethoxy xanthone (44)

1 ,4-Dihydroxy-2,3, 7-trimethoxy xanthone (45)

I,3-Dihydroxy-4 ,5,8-trimethoxy xanthone (46)

1,3,6.7-Tetrahydroxy-2-C-glucosy lxanthonc (47)

7,R-Dihydroxy-J -ll1cthoxy-I-O

primeverosy lxanthonc (48)

3.7.8-Trimcthoxy-I-O-primcvcrosylxanthune (49)

1.5-Dihydroxy-3 -ll1cthoxyxan thone-

8-0-!3-o-glucosidc (50)

1.3,5-Trihydroxy-8-0 -!3-o-glucopyranosidc (51)

I-Hydroxy-8-glucusyloxy-3.5-dill1cthoxyxanthonc (52)

I-Glucosyloxy-3-hydroxy-5,8-dill1cthoxyxanthonc (53)

R-O-Prill1cvcrosy l bcllidifolin (54)

1.8-Dihydruxy-3-ll1cthoxy-

5-0-P-D-glucopyranosylxan thonc (55)

3. 7.R-Trill1ethoxyxanthunc- I -O-glucosidc (56)

7.8'-Dihydroxy-3-ll1ethoxyxanthon.:-1-0-glucosidc (57)

R-llydroxy-3. 7-dill1cthoxyxanthonc-I-O-g lucosidc (58)

R-I'lydroxy-3. 5-dill1cthuxyxanthon.:-I-O-glucos iclc (59 )

8-0-I.I-G lucusyl .. I .3 -dihyclroxy-5-ll1cthoxyxanthonc (60)

7-llydruxy-3.R-dill1dhoxyxan thonc- I-{)-glli cosidc (61 )

I-O-l'rill1cwrosy l-7- hydroxy

-3 .R-d i ll1cth oxyxanthonc (62 )

3.7.R-Trihydrox)'xan thom:-I-()-B-D-gl ucosidc (63 )

X-ll ydroxy-3. 7 -d i Il1cthoxyxantho lH:- I-()-p ri ll1c\,crosidc

(6" )

3 -11 ~ 'droxy ... ':'5-dill1cthoxy xanthonc-I -()- f.I-J)gillcopyranosidc (65 )

I-II ~ dro,) -<l .5-d ill1..:thuxyxantholl..: -3-( J-I.\-J) glucop) rano~ id c (66 )

OH

OH

OH

OH

OH

OH

OH

OMe

OMe

OH

0 1·1

OMe

0 11

0 1-1

1-1

OH

H

H

OMe

1-1

OMe

H

1-1

OMc

OMe

01-1

OMe

II

Xanthone glycosides

0 11

O-Pr

O-Pr

0 11

0 11

Oil

O-g lu

0 11

0 11

O-glu

O-g lu

O-glu

O-g lu

0 11

O-glu

O-!'r'

O- !' r

()- I'r'

()-g lu

OI l

C-glu

1-1

II

II

II

I I

II

II

II

II

II

II

II

II

II

I I

il

I I

I I

II

OMe

01-1

OMe

OMe

OMe

01-1

0 1-1

OMe

OMe

OMc

OMe

OMe

OMc

01-1

0 11

OMe

OMe

OMc

0 11

OMc

0 11

OMc

OM..:

OMc

OM c

OM..:

OM..:

Oil

OMc

OM ..:

0 11

OMc

()II

O-glu

OMe

H

OMe

OMe

H

OMe

H

OMc

OMe

OMe

OMe

OMe

01-1

OMe

II

II

II

II

II

II

II

II

II

II

II

II

II

II

II

II

II

II

OMc

OM..:

R~

H

1-1

OMe

1-1

OMe

H

1-1

OMe

II

H

OMe

1-1

II

OMe

II

II

II

01-1

0 11

OMc

OM..:

0 11

O-g lu

II

II

II

OMc

OM.:

II

II

II

II

OM c

OM.:

H

H

H

H

1-1

H

01-1

H

H

1-1

H

H

H

II

01-1

1-1

1-1

II

1-1

1-1

/I

II

II

II

II

II

II

II

II

II

II

II

II

II

OMe

OMe

II

0 1-1

o e

0 11

OMe

II

OMe

OMe

II

OMc

OMc

II

01 1

011

OMe

I I

H

II

II

!/

I I

O\ k

0 11

Oi\ 1c

II

II

( )11

Oil

Oil

O\ k

I I

I I

OMe

OMe

OMe

OMe

1-1

OMe

1-1

OMc

OMe

H

H

1-1

1-1

OMc

II

01-1

OMe

O-g lu

O-glu

()-glu

OMc

O-glu-xyl

0 11

Oi\'k

OIl

0 11

Oil

O-glll

OM..:

OM..:

Oil

0 11

II

II

('Olliel

J.

~

-;

PANT et al.: PHYTOCHEM ICALS FROM GENUS SWERTIA AND THEIR BIOLOG ICAL ACTIVITIES 569

Compou nds na me(St ru ct urc num be r) R, R2 RJ

3-0-B-o-G lucopyranosyl -I ,8-dihydroxy-5- OH H O-glu met hoxyxanthone (67)

1,7-Dihydroxy-3 -ll1ethoxyxanthone-8-0-glucoside (68) OH H OMe

3,8-Dihydroxy-7-ll1ethoxyxanthone- I-0-B-O- O-glu H OH glllcopyranoside (69)

4-B-o-G llicopyranosyl-1 ,3,6, 7-tetrahydroxyxanthone OH H OH (70)

2-B-o-G lucopyranosyl- 1 ,3,6, 7-tetrahydroxyxanthone OH O-glu OH (7 1 )

3,5,8-Trill1ethoxyxanthone-I-O-glucoside (72) O-glu H OMe

3.4.5.8-Tetrall1ethoxyxanthone- I-O-glucoside (73) O-glu H OMe

3,4,7,8-Tetrall1ethoxyxanthone-I-O-g l ucoside (74) O-glu H OMe

3-Methoxy- I-0-B-o - g lucopyranosyl-5 , O-glu H OMe

8-dihydroxyxanthone (75)

1-0-Prill1everosy l-3 , 7 ,8-trihydroxy xan thone (76) O-Pr H OH

7-0-( a-L-Rhall1nopyranosyl( 1-2)-B-o -xylopyranosyl)- OH H OMe 1.8-dihydroxy-3-ll1ethoxyxanthone (77)

Xa nth one-O-diglucos ides

I ,3.Di-B-o-glucopyranosyl -7, 8-d ihydroxyxanthone O-glu H (78)

8-0-(B-o-G lucopyranosyl ( 1-6)-B-o-glucopyranosyl)- OH H I. 7-dihydroxy-3 -ll1ethoxyxanthone (79)

glu- Glucopyranoside Xyl-Xylopyranoside Pr-Prill1everoside Rhll1- Rha ll1 nopyranoside C-Glu-C-glucoside (ie glucoside lin ked through to carbon)

MeO

Chin lanin (80)

OMe

OMe

Gentianine (83); R-H, R1-CH=CH2

Gentianamine (84); R-CHzOH, R1-CH=CHz Gentianadine (85); R-H, R1-H

HO

OH

Luteolin (81)

OHc;;1 MeX N J ~

H

GentioOavine (86)

O-glu

OMe

OH

R4 R~ R6 R7 R3

H OMe H H OH

H H H OH O-glu

H H H OMe OH

O-glu H OH OH H

H H OH OH H

H H H OMe OMe

OMe OMe H H OMe

OMe H H OMe OMe

H H H OH OH

H H H OH OH

H H H O-Rh- OH Xyl

H H H OH OH

H H H OH O-glu

:x5' e

MHO: ""80

o "' 9.C: Syring.resinol (82)

H~~ o 0

Gentiocr ucine (87) EnicoOavine (88)

570 INDIAN J CHEM, SEC S, AUGUST 2000

OH

Swertifrancheside (89)

R

Swertipunicoside (91) ; R=Me

3-0-Demethyl swertipunicoside (92); R=H

Rl OH

R4 R

R

Rl R2

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

X2 OGJu M(Q

HO --, ~

I GJu H eOOH

;entiopicroside 1l03) Loganic acid (lO~)

Swertiablsunthont - r (90)

R ":::: OH

C7

Isoorienti0-6'-arabinoside (93); R=OH IsovitexirH'-arabinoside (94); R=H

o 0

~o rn,oo(J0H

R3 R4 ~Ji OMe H OMe H H ~ H

OH H OMe Glu OH H Amarogentin ( 101 ) ; R=lll

O-Glu H Amaroswerin (102 ) ; R= OH

o 0

~ ~'O" ~OH

I ~o 0 0

~ 1I0 HO HO H H H HO OH

011 OH

Swertiapunimarin (l05) BiphenC>side-B (106)

all

~

OH

PANTet al. : PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES 571

BlpbeliOilde - A (107)

SMrtiaSide ( 111 )

Senburiside - I ( 112 )

Senbbwiside - n ( 113 )

5 ( 3'-O-B-D-slucopynDOsyl)

~H

:r~ ... ~ lloR

R

H

H

~OH 'U

R RI

Beamyloxy geatisic add ( 114 ) H H

2.6-Dimetboxy-4-bydroIY OMe OR pheDOI-I-O-B-D~lueopynDO.1de ( 115 )

SwertiamacfO.lde (108)

RI

-Glu

-Glu

H

R OMe

572 INDIAN J CHEM, SEC S , AUGUST 2000

Swertiamarin ( 116 ) 2-O'-Acetylswertiamarin (117) Swe ..... ide (118 ) 2'-O-Acetyl-4 '-O-trans-Ceruloylswertiamarin ( 119)

2'-O-Acetyl-4'-O-cisCe ruloyl-swertiamarin ( 120 )

2'-O-Acetyl-4'-O-trans-p-coumaroylswertiamarin ( 121 )

2'-O-Acetyl-4'-O-cis-p-coumaroylswertiamarin ( 122 )

4'-0-Traas-p-coumaroyl-lwertiamarin ( 123 )

SMro.ide-2'-O-3",3"',5"-tribydroxybipbenyI-2"-carboxylie acid ester ( 124 )

SwertanoDe (125) j R, -0, ~ 7 (I )

Swertenol (126) j R,a -H, p -OH, ~7(1) Episwertcnol (127) j R, a -OH, P -H, ¢. 7

(I)

Swcrta-7,9(II)-diene-3- p-ol (130) j R, P -OH, a -H, ~ 7 .9(11)

Pichierenol (131) ; R, a -H, p -OH, ~'(II)

R

on OH H

OH

OH

OH

OH

OH

B

~ :~

OR.

Rl

H COCH3

H

COCH3

COCH3

COCH3

COCH3

H

~~ ;:".. 1

9' 1 ~ OH

Oleanolie acid (128) OH

Unolie acid (129) OH

....

R2

H H H

0

~OMe ;:".. OH

~OMe o ~ OH

0

~ ~ 1 OH

~ o ~ OH

0

~ ;:".. I OH

H

H H Me

H H

PANT et al.: PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES 573

Hederagenin (132) ; R, -CH10H; Rh -COOH

Erythrodiol (136)

HO

2l-a-H-Hop-22(29)en-3-p-ol (139)

HO

Kairatenol (142)

Lupeol (134) ; R, - CHJ

3- ~-Hydroxylup-12-eDe-28-oic acid (135); R, -COOHAIl(IJ)

'i' - Taraxasterol (137) ( Heterolupeol )

Chirateool (140)

HO

Gammacer-16-eo-3-~-ol (138)

HO

Taraxerol(141)

3-p-Hydroxylup-13-(18)-eoe (143)


cJ<R. ,~~

R

cSsR

'

Isoscmbltrin (144) ; R, -CH=CHz; Rh -H NeoscmburiD (146) Isoswertiol (147) ; R, -CH~Hz; R .. -H

Stmburin (145) ; R, -H; R" -CH=CHz

rrr ~rH

Swertiol (148) ; R, -H; Rh -CH=CHz

~ o

IsoDeoswertiol (149) ; R, -CH=CHz; Rh-H 3-PropylidcDe-S-peD taDolide (IS I) Erythroctntaurin (152)

Neoswcrtiol (ISO} ; R, -H ; R .. -CH=CHz

w· o

2-Methoxy-I,4-napthoquinone (153) Swertialactone-C (154) Swertialactone·D (ISS)

OM.

yQ~ Oglu OMe XX:0OR1

~I R300C ~ R2

Rl Rz

Monobydroxy-terepbtbalic acid (158) H H

ThysaDolactoDf (156) I-O-Sinapoyl.,D-e1ucopyranoside (157) 2,5-Dihydroxy- terephthalic acid (159) H H

RJ

H

H

i

~

H

OH

S.No.

1.

2.

3.

PANTel af. : PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES

3-0-Stearyl-3· ... • .S.7-tetra-0-methylquerc:etin (160)

~: y COOMe

l-Hydroxydimethyl terephthalate (161)

MeO 11 XJ'b HO GluO 0

OH

Mllngostin (162) Gentiopicrin (163) Choleretic: Sweroslde (164)

Table ~Biological activIty of diffcrent extracts from Swer/ia species

Plant Species Different plant extracts Biological activity

S. japonica Ethyl acetate soluble fraction, ether insoluble Hypoglycemic activity fraction

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

Semi looper (Anomis ~~.!!_u!ifera)

Ethanolic extract Anticholinergic activity Benzene extract Antiinflammatory activity

S calycina Methanolic and dichloromethane extract Antifungal activity

Table I~Biological activity of different compounds from Swer/ia sps S.No Plant species Bioactive compounds (Str. No.) Biological activitiy

I. 2.

3.

4.

S moleensis S calycina

S franche/iana

Sjaponica

Sweroside (118) 2-Methoxy-I ,4- naphthoquinone(IS3)

Swertifrancheside (89)

Swertiamarin (116)

Bellidofolin (II) Methylbellidofolin (13) Swertiamarin (116) 1,3.7;8-Tetrahydroxy xanthone (16) and its 3-methyl or 3.7-dimethyl ethers

Antihepatitis drug Strong antifungal activity against Cladosporium cucllmerinum. Candida albicans

Potent inhibitor of HIV reverse /rans-criptase

Antibacterial action against Staphylococcus aureus, Hypoglycemic activity Hypoglycemic activity Anticholinergic activity Antituberculous activity

Ref.

12

13, 14 IS IS

16.17 18

19 20 21

Ref.

22 21

575

23,24

2S

26 10.26 27 28

Contd.


Table II-Uiological activity of different compounds from Swerlia sps S.No Plant species l3iollctive compounds (Str. No.) Biological activitiy

5.

6.

7.

Antiinflammatory agent Secoiridoids Gentianine (S3) CNS depressant, Antiulcerogenic actions.,

Inhibit

Tetrahydroxyswertianollin (50), Bellidifolin(11 ),Methylbellidifolin (13),

Gastric secretion Hepatoprotective activity

Antioxidant activity

S. purpurascens

Swertianin (9), Methylswertianin (12), Nor· swertianin (16), Desmethylbellidifolin (10) Norswertianolin (51), Isoswertianolin (55) CNS depressant, stimulant and Cardiovascular

anticonsvulsant activity

S. randaiensis Swertianolin (50) 1,3,5-Trihydroxyxamhone-8 -O-glucoside (51)

Antitubercular activity Tuberculostatic activity

S. chirata Swerchirin (13) Hypoglycemic principle(Blood-sugar lowering)

1,3,7,8-Tetrahydroxy xanthone (16) & its 3-methyl and 3,7-dimethyl ether derivative Mangiferin (47), Mangostin (162) Swerchirin (13)

Antitubercular activity

Antiinflammatory activity Antimalarial activity

Table III--Chemical Compounds of Swerlia spp

S.No. Plant species (Plant Parts) Compounds (Str. No.)

I . S. mileensis (aerial parts) Swertiamarin (116)

2'-O-Acetylswertiamarin (117)

Amarogentin (101)

2. S. calycina (whole paint)

I-Hydroxy-2,3 ,5 -trimethoxyxanthone (26)

Sweroside( lIS)

2'-O-Acetyl-4'-O Irans-fcruloylswertiamarin (119)

2'-O-Acetyl-4'-O-cis- fcruloylswertiamarin (120)

2'-O-Acetyl-4'-O-lrans-p-coumaroylswertia-marin (12 1)

2'-O-Acetyl-4'-O-cis-p-coumaroylswertia-marin (122)

4'-O-lrans-p-coumaroylswertiamarin (123)

8-Hydroxy-1 ,4-dimethoxyxanthone (7)

2-Methoxy - I ,4-napthoquinonc (153)

Sweroside( lIS)

Dccussatin (S)

Swertianin (9)

Gcntiopicroside (103)

Mangiferin (47)

Isogentiakochianoside (4S)

I-Hydroxy-3 ,5-dimcthoxyxanthone ( I )

3, 7,8-Trimethoxy-I-O-primeverosy lxanthonc (49)

3. S. ! rancheliana(Whole plant) Swerti francheside (S9)

4. S. cordata (Aerial parts) I-Hydroxy-3,5,7,8-tetramcthoxyxanthone(30)

1,7-Dihydroxy-3 ,5,8- trimethoxyxanthonc(J I)

Swertianolin (50)

Mangiferin (47)

Ursol ic acid (129)

5. S. macrosperma(Whole plant) Swertiabisxanthone-I (90)


Norswertianolin (5 1)

Ref.

39

39

39

40

41

39

39

39

39

39

42

2 1

2 1

2 1

2 1

2 1

2 1

2 1

21

2 1

23

43

43

43

43.44

44

45

45

45

Ref.

29 30

31

32

33,34

35

11 ,36. 37 28

20 38

Conld.

PANT et ul.: PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES 577

Table III-Chemical Compounds of Swertia spp-Conld

S.No. Plant species (Plant Parts) Compounds (Str. No.) Ref.

I-O-trans-caffeoyl-6-0-a-L rhamnopyranosyl-I3-D- 46 glucopyranoside( lOS)

6. S pseudochinensis(~eeds) Swertiamarin (1 16) 47,48 Gentiopicroside (103) 48 Sweroside (lIS) 48 Amaroswerin (102) 48 Amarogentin (10 I) 48 Isovitexin (99) 48

7. S speciosa (Aerial parts) I-Hydroxy-8-glucosyloxy-3 ,5-dimethoxy xanthone 50 3-Methoxy-1 ,5,8-trihydroxyxanthone (11) 50 I ,8-Dihydroxy-3 , 7- dimethoxyxanthone (12) 50 I ,8-Dihydroxy-3.5-dimethoxyxanthone (13) 51 Mangiferin (47) 51 Ursolic acid (129) 50

(Roots) 1,7-Dihydroxy-3-methoxyxanthone (2) 51 I ,3-Dihydroxy-7-methoxyxanthone (3) 51 I-Hydroxy-3, 7-dimethoxyxanthone (4) 51 1,7,8-Trihydroxy-3-methoxyxanthone (9) 51 1,7-Dihydroxy-3 ,8-dimethoxyxanthone (14) 51

8. S punicea(Aerial parts and Decussatin (S) 52 from Cultured tissue also)

Gentiacaulein (14) 52 Methyl swertianin ( 12) 52 I-I-Iydroxy-3 ,5,7,8-tetramethoxyxanthone (30) 52 1,8-Dihydroxy-2,4,6-trimethoxyxanthone(32) 52 Swertiapunimarin (1 05) 53

(Whole plant) Swertipunicoside (91) 54 3-0-Demethylswertipunicoside (92) 55

9. Spetio/ata(Aerial parts) I ,3-Dihydroxy-5,8-dimethoxyxanthone (15) 56 2-Hydroxydimethyl terephthalate(161) 56 I-Glucosyloxy-3-hydroxy 5,8-dimethoxyxanthone (53) 57 I ,8-Dihydroxy-3 ,5-dimethoxyxanthone (13) 57 1,3 - Dihydroxy-7-methoxyxanthone (3) 57 1,7-Dihydroxy-3-methoxyxanthone (2) 57 1,7-Dihydroxy-3-methoxyxanthone-8-0-glucoside (6S) 58

(Whole Plant) 3-I3-Hydroxylup-13-( 18)-ene(143) 59 3-I3-Hydroxylup-12 ene-28-oic acid (135) 59 Ursolic acid (129) 59 Swertialactone-C (154) 60 Swertialactone-D (155) 60

10. Sjaponica(Whole Plant and Bellidifolin (11) 10,26,6 1,62 from Hairy roots also)

Methylbellidifolin (13) 10,61 Swertianin (9) 10,62

" Methylswertianin( 12) 10,62 1-H ydrox y-3,7 -d imethoxyxanthone (4) 10 Norswertianin (16) 62 Desmethylbellidiolin (1 0) 62

Conld

578 INDIAN] CHEM, SEC B, AUGUST 2000

Table III-Chemical Compounds of Swerlia sprr--Conld


5,8-Dihydroxy-3-methoxyxanthone-I-O-glucoside (75) 63 ,64

Thysanolactone (156) 10

Oleanolic acid(128) 10

Swertiamarin (116) 25 ,65,66,67

8-0-Primeverosylbellidifolin (54) 61

Swertianolin (50) 61

Amarogentin (101) 61 ,65,66,67

Amaroswerin (102) 61,65,66,67

(whole plant) Swertiaside (III) 68

Senburiside-I (112) 69

Senbburiside-II (113) 70

5'(3'-O-B-o-glucopyranosyl) Benzoyloxy-gentisic acid (114) 71

2,6-Dimethoxy-4-hydroxy-phenol -1-O-6-o-glucopyranoside 71 (115)

I-O-Sinapoyl-6:-0 glucopyranoside (157) 71

(whole plant) Tetrahydroswertianolin 72

Semburin (145) 73

Isosemburin (144) 73

Neosemburin (146) 73

Soswertiol (147) 73

Swertiol (148) 73

Isoneoswertiol (149) 73

Neoswertiol (150) 73

3-Propylidene-5-pentanolide (151) 73

Biphenoside-A (107) 66

Biphenoside-B (106) 66

Isoswertianolin (55) 73

Gentiopicroside (103) 48.67,74

Sweroside (118) 48

Choleretic sweroside( 164) 75

Swertisin (95) 76.77,78

Swertiajaponin(96) 77,78

Iso-orientin (97) 78

(Root part) Isovitexin (99) 49

Gentianine (83) 79

II. S. panicuiala(whole plant) Swerchirin (13) 80

I ,8-Dihydroxy-3, 7-dimethoxyxanthone( 12) 80

Bellidifolin ( II) 80

1,7,8-Trihydroxy-3-methoxyxanthone (9) 80,81

I-Hydroxy-3 ,5.8-trlmethoxyxanthone (17) 80

I.7,8-Trimethoxy - 3 hydroxy Xanthone (18) 80

1-1-lydroxy-3,4,7.8-tetramethoxyxanthone (33) 80

I-Hydroxy-3.7.8-trimethoxyxanthone (8) 80

1,3,8-Trihydroxy-5-methoxyxanthone (19) 80

3-Hydroxy-I ,7.8- trimethoxyxanthone (18) 80

(stem) B-Amyrin (133) 82

!.I-Sitosterol (109) 81 ,82

Swertisin(95) 82

Conld

PANTel al.: PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES 579

Table III----Chemical Compounds of Swerlia spp----Conld


Isoswertisin (9S) 82

(whole plant) Hederagenin (132) 80

3,7,8-Trimethoxyxanthone-I-O-glucoside (56) 80

7,8-Dihydroxy-3-methoxyxanthone-I-O-glucoside (57) 80

8-I-Iydroxy-3 ,7-dimethoxyxanthone -I-O-glucoside (58) 8

8-I-Iydroxy -3 ,5- dimethoxyxanthone- I-O-glucoside(59) 8

(Aerial pi arts) Urso li c acid (129) 81

12. S. decussala(leaves & flowers) Swertinin(20) 83 Oleanolic acid. (12S) 83 f.I-Sitosterol (109) 84 3-I-Iydroxy - triterpene 84 3-I-Iydroxy-17-methylo l-triterpene 84 Decussatin (S) 83 1,7,8-trihydroxy-3-methoxyxanthone (9) 85

13 . S. randaiensis(whole Plant) Norswertianolin (5 1) 86 Isovitexin (99). 49 Oleanolic acid( 12S) 87 Gentianine (S3) 87

14. S.chirala(whole plant) Oleanolic acid(I2S) 88,89 Ursolic acid (129) 90 p-Amyrin (133) 89,91 Gentianine (S3) 92 Gentiocrucine (S7) 92 Enicoflavine (SS) 92 Swertanone (125) 90,93 Swertenol( 126) 90 Episwertenol ( 127) 90 Gammacer-1 6-en-3-Ll-ol( I3S) 90 2 1-a-I-I-hop-22(29)-en-3-f.l-o l (139) 90 Chiratenol (140) 90,94 Taraxero l(141 ) 90

(Aerial parts) Syri ngares inol(S2 ) 95 Mangiferin (47) 95 ,96 Mangostin(162) 20 Bell idifolin (II) 95,96 I-I-Iydroxy-3 ,5,8-trimethoxyxanthone (17) 95 ,96 I-I-Iydroxy-3 ,7,8-trimethoxyxanthone (25) 95,96 Amarogentin (101) 95,97,98 Sweroside(IIS) 88,95 Amaroswerin (102) 88,95 Swerta-7,9( II )-dien-3-f.l-ol (130) 99 Pichierenol (13 1) 99 Lupeo l (134) 91 ,99 Erythrodiol (136) 99 I.J'-TaraxasterolorI-leterolupeol (137) 99 Swerchirin (13) 96, 100,101 Chiratanin (SO) 102 Chiratol (21) 101

Contd

580

S.No.

15 .

16.

17.

INDIAN J CHEM, SEC B, AUGUST 2000

Table III---Chemical Compounds of Swertia spp---Contd

Plant species (Plant Parts) Compounds (Str. No.)

S. hookeri(whole flowering plants)

S. connata(Roots & rhizomes)

(Roots & aerial parts)

(Aerial parts)

S. angllstifolia(whole pl ant)

(Aerial parts)

7-0-Methylswertianin(12)




Monohydroxyterephthalie aeid (158)

2,5-Dihydroxyterephthalic aeid (159)

Kairatenol (142)

f3-Sitosterol-3-f3-0-glueoside (110)

Sweroside-2'-O-3",3" ,5" -trihydroxy biphenyl-2"earboxylic aeid ester (124)

Swertinin (20)

Swertianin (9)

Deeussatin (8)

Isobellidifolin (22)

I-O-Stearyl-3 ,5-dimethoxyxanthone (5)

3-0-Stearyl-3',4',5,7-tera-0-methylquerctin (160)

8-0-f3-Glucosyl-1 ,3-dihydroxy-5-methoxy xanthone (60)

I-Hydroxy- I ,4-dimethoxyxanthone (6)

Gentiabavaroside (62)

Gentiaeau lein (14)

Mangiferin (47)

Gentiacau lein-I-O-glucoside (61)

Bellidifoloside (55)

Gentianamine (84)

Gentianadine (85)

Gentiollavine (86)

1,5- Dihydroxy-3-methoxyxanthone-8-0-f3-0-g1 ueoside .( 50)


1.3.4 .5,8-Pentamethoxy xanthone (40)

I ,3,4,7,8-Pentamethoxyxanthone (41) 1,3,7.8-Tetrahydroxyxanthone (16)

I-Hydroxy-2,3 ,4,7-tetramethoxyxanthone (42)

1.8-Dihydroxy-3 ,5-dimethoxyxanthone (13)

1.8-Dihydroxy-3.7-dimethoxyxanthone (12)

3,5.8-Trimethoxyxanthone-I-O - glucoside (72)

3,7,8-Trimethoxyxanthone-I-O-primeverosylxanthone (49)

3.4,5,8-Tetramethoxyxanthone-I-0-glucoside (73)

3,4,7,8-Tetramethoxy xanthone-I-O-glucoside (74)

I-Hydroxy-3 ,7,8-trimethoxyxanthone (8)

I ,3,8-Trihydroxy-7-methoxyxanthone (23)

3-Hydroxy-4.5-d imethoxyxanthone - 1-0- (3-0-gl ucopyranoside (65)

3-Methoxy-I-0-f3-0-glucopyranosyl-7,8-dihydroxyxanthone (57)

Ursolic acid (129)

13- Sitosterol (109)

Bellidifolin (II)

Ref.

96,101

96

96

96

103

103

104

88

88

lOS 105

105

105

106

106

106

107

107

108

108

108

108

109

109

109

110

III

III

111

III

III

III

III

III'

III

III

III

III

III

III

III

81

81

81. 111

Conld.

PANT et af. : PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES 581

Table lII~hemical Compounds of Swertia sp~ontd

S.No. Plant species (Plant Parts) Compounds (Str. No.) Re f. j

18. S. davida Gentianine (2) 112 19. S. iberica(Above ground Bellidifoloside (55) 11 3

parts)

Mangiferin (47) 11 3

1-0-13-o-Glucopyranosyl-3 ,7,8-trihydroxyxanthone (63) 114

1-0-13-Primeverosyl-3,7,8-trimethoxyxanthone (49) 11 3, 114

1-0-Primeverosyl-3, 7 -8-trihydroxyxanthone(76) 114 (Roots) Swertiaperennin (12) 115

Decussatin (8) 11 5 Gentiachochianine(9) 11 5 Norswertianin (16) 11 5 Isogentiakochianin (23) 115 Swertiaiberin (34) 11 5

20. S. mussoti 3- 0-13- o-Glucopyranosyl-I ,8-dihydroxy-5-methoxyxanthone 11 6 (67)

Oleanolic acid . (128) 117 Mangiferin . (47) 117

8-0-(I3-o-glucopyranosyl-( 1-6)-I3-o-g lucopyranosyl) 1,7- 11 6 Dihydroxy 3-methoxyxanthone (79) 7-0 -(a-I-Rhamnopyranosyl-( 1-2)-13-o-xylopyranosyl) 1,8- 11 6 dihydroxy-3-methoxy xanthone (77)

I-Hydroxy-I ,4-dimethoxyxanthone (6) 118 8-HydroxY-I,3,5-trimethoxyxanthone(29) 118 1,3,8-Trihydroxy-5-methoxyxanthone (19) 118 1.7-Dihydroxy-3,4,8-trimethoxyxanthone(36) 118 I-Hydroxy-3,7,8-trimethoxy xanthone (8) 118 1,3 ,6-Trihydroxy-2, 7-dimethoxyxanthone (39) 11 9 1,3 ,7-Trihydroxy-4,8-dimethoxyxanthone (38) 11 9

2 1. S. alata(Roots and aeria l O leanolic ac id(128) 120 parts)

Swertisi n(95) 120 , Swerti amarin ( 116) 120

, Bellidifolin ( II ) 120

22 . S. pllrpurascens(whole plant) O leano lic ac id( 128) 121 Norswertianolin (51 ) 33 Swertianolin (50) 33 Isoswertianolin (55 ) 33

(Aeri al parts) I-HydroxY-3 ,5,7,8-tetramethoxyxanthone (30) 122 (whole pl ant ) Bellidifolin ( II ) 122

1-llydroxy-3,4,5,8-tetramethoxyxan thone (35) 123 1,3,8-Trihydroxy-5-methoxyxanthone ( 19) 123 I-Hydroxy-3 ,7,8-trimcthoxyxanthone (8) 123 1,3, 7,8-Tetrahydroxyxanthone( 16) 123 1,3,5,8-Tetrahydroxyxanthone ( 10) 123 I-Hyd roxy-3,4,7.8-tetramethoxyxanthone (33) 123

23 . S. perennis(Aeri al parts) 1-3-Di-B-o-glucopyranosyl-7,8-dihydroxy xanthone (78) 124 1.8-Dihydroxy-3. 7-di-methoxyxanthone ( 12) 85

(Root extract) 1,3,7,8-Tctrahydroxyxanthonc ( 16) 125 1,7-Di-hydroxy-3 .8-d imcthoxyxanthonc \ 14) 125

COllld

582 INDIAN J CHEM, SEC 8 , AUGUST 2000

Table III-{;hemical Compounds of Swertia spp--Contd


I-l-Iydroxy-3 ,7,8-trimethoxyxanthone (8) 125

3,7,8-Trihydroxyxanthone-I-O-I3-o-glucoside(63) 125

3.7,8-Trimethoxyxanthone-I-0-primeverosylxanthone (49) 125

8-l-Iydroxy-3 , 7-dimethoxyxanthone-I-0-primeveroside (64) 125

(Stem and leaf extract) 1,5,8-Trihydroxy-3-methoxyxanthone (II) 125

I ,5-0 i hyd rox y-3 -methox yxanthone-8-0-f3-o-g1 ucoside( 50) 125

Mangiferin (47) 125

I-Iomoorientin (97) 125

Isovotexin (99) 125

Isoorientin 6-a-L -arabinoside (93) 125

Isovitexin 6-a-L-arabinoside (94) 125

24. S. lawii I ,3,7,8-Tetrahydroxyxanthone (16) 126

1,7,8-Trihydroxy-3-methoxyxanthone (9) 126

I ,8-Dihydroxy-3. 7-dimethoxyxanthone (12) 126


I-l-Iydroxy-3 ,4,7,8-teramethoxyxanthone (33) 126

1,3,5,8-Tetrahydroxyxanthone(10) 126

1-l-Iydroxy-3 ,5,8-trimethoxyxanthone (17) 126

Erythrocentaurin (152) 127

25. S. marginata Gentianamine (84) 128

Gentianine (83) 128

Gentioflavine (86) 128

26. S. graciliflora Gentianamine (84) 128

Gentianine (83) 128

Gentioflavine (86) 128

27. S. caroliniensis Gentiopicroside (103) 129

(Crude root extract) Loganic acid (104) 129

28. S. bimaculata Isovitexin (99) 49 I ,3-Dihydroxy-4,5-dimethoxyxanthone (24) 130

3 -l-Iydroxy-4,5-dimethoxyxanthone-I-O-I3-o-glucopyranoside 130 (65)

1-l-Iydroxy-4,5-dimethoxy-3-0-I3-o-glucopyranoside (66) 130

I ,8-Dihydroxy-3,5-dimethoxyxanthone (13) 131

1,3,5-Trimethoxy-8-hydroxyxanthone (29) 131


1-l-Iydroxy-2,3,4,5-tetramethoxyxanthone (43) 131

I-l-Iydroxy-2,3,4,7-tetramethoxyxanthone (42) 13 1

2-l-Iydroxy-1 ,3,4, 7-tetramethoxyxanthone (44) 13 1

1 ,4-Dihydroxy-2,3, 7-trimethoxyxanthone( 45) 131

1 ,3-Dihydroxy-4,5,8-trimethoxyxanthone( 46) 131

29. S. diluta Isovitex in (99) 49

Norswertianin (16) 132

Swertianin (9) 132

Methylswertianin (12) 132

Gentiacaulein (14) 13 2

30. S. racemosa Decllssatin (8) 132

Demethylbellidifolin ( 10) 13 2

31. S. nervosa Bellidifolin (II) 132

COllld

j

+

PANT et al.: PHYTOCHEMICALS FROM GENUS SWERTIA AND THEIR BIOLOGICAL ACTIVITIES 583

Table II I---Chemical Compounds of Swertia spp-Contd


32. S gracilescens Methylbellidifolin (13) 132 Oleanolic acid( 128) 132

33. S. tosaensis Swertianolin (50) 33 Swertinol (I I) 133 Swerchirin (13) 133 Desmethylswertianol( 10) 133 Oleanolic acid(128) 133

34. S vivace Gentiopicrin (163) 134 35. S swertopsis Norswertianin (16) 135

Swertianin (9) 135 Methylswertianin (12) 135 Decussatin (8) 135 Methylbellidifolin (13) 135 Isovitexin (99) 135 Homoorientin (97) 135 Mangiferin (47) 135

36. S cuneata(Aerial parts) I-Hydroxy-3,7,8-trimethoxyxanthone (8) 136 1,7,8-Trihydroxy-3-methoxyxanthone (9) 136 1 ,8-Dihydroxy-3.5-dimethoxyxanthone (13) 136 1 ,8-Dihydroxy-3 . 7-dimethoxyxanthone (12) 136 New glucosyloxy - 3. 7.8-trimethoxyxanthone 136

37. Sthomsonii 1,7-Dihydroxy-3.8-dimethoxyxanthone (14) 137 Swertianin (9) 137 Ursolic acid (129) 137

38. S patens I-Hydroxy-I ,4-d imcthoxyxanthone (6) 138 39. S tetrapetala l-hydroxy-2,3,5-trimcthoxyxanthone (26) 139

Luteolin (81) 139 Luteol in-7-0-glucoside (100) 139 I-Hydroxy-2,3.5 ,7-tctramethoxyxanthone (37) 139 1 ,8-Dihydroxy-3 ,5-c1imethoxyxanthone (13) 139

40. S. verticilhfolia 3,8-Dihyclroxy-7-mcthoxy- I-O-f3-o-glucopyranoside (69) 140 Swertianolin (50) 140 Norswertianolin (5 1) 140

41. S elongata 4-f3-o-Glucopyranosyl-I.3 ,6.7-tctrahydroxy xanthone (70) 14 1 2-f3-o-Glucopyranosyl-I.3 .6,7-tetrahydroxy xanthone (71) 14 1

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.

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