Professional Documents
Culture Documents
Chemistry and Pharmacology of Rhubarb Species) - A Review: (Rheum
Chemistry and Pharmacology of Rhubarb Species) - A Review: (Rheum
,,,l.
Introduction
Rheum Linn (family polygonaceae; English name:
rhubarb), a large genu s of perenni a l, stout he rbs and distributed in the temperate and sub-tropical regions of the
world, chiefly in Asian countries, viz. India (Kashmir,
Assam, Sikkim), Nepal , Bhutan, China, Pak istan , Korea, Turkey, Ru ss ia and Tibe t. Seve ral species of this
plant are used in medicin e, some for culinary purposes
and few others are grown as ornamental plants. The re
are three main types of rhubarb , viz. the Chinese Rhubarb, the Indian or Himalayan Rhubarb and the Rhapontic
Rhubarb u. Some known s peci es of Rh e um are R.
acuminatum (R-1 ), R. alexandrae (R-2), R. altai cum (R3), R. australe (R-4), R. compactum (R-5), R. coreanum
(R-6), R.corodatum (R-7), R. delavayi (R-8), R. emodi
(R-9), R. franz enbachii (R- 10), R. hotaoense (R-11 ), R.
hybridium (R-1 2), R. kialense (R-1 3), R. /hasa ense (R14), R. maximoviczii (R-15 ), R. moo rcro.fiianum (R-16),
R. nobile (R-17 ), /?. offlcina /e (R-1 8), /?. pa/aestinwn
(R-19 ), R. palmatum (R-20), /?. pami/um (R- 2 1), /?. ribes
(R-22), /?. rhabarbamm (R-23), R. rhaponricwn (R-24),
(R-13 ), R. lhasaense (R-14 ), R. max im oviczii (R- 15 ), /(
moorcrojtianum (R- 16), /?. nobile (R- 17), /?. oJficina /e
(R-1 8), R. palaestinum (R- 19), R. pa/matuiii (R-20), /?.
pamilwn (R-21 ), R. ribes (R-22) , R. rhabarbarwn (R23), R. rhaponticum (R-24), R. spiciform e (R-25), R.
tanguticum (R-26), R. tata ricum (R-27), R. undu/atum
*Author for correspondence
CIMAP Publi cat ion No.: 99-11 R
Chemistry
A varie ty of co nst itu ents ha ve been iso lated fro m
Rheum spec ies and the ir stru ctures e lu c id ated. They belong to such classes as anthraquin o nes, clianthron cs, stilbenes, anthocynin s, rla vo no icl s, an thrag lycosid es,
polyphenols, esse nti a l oi l. o rga nic ac id s, chromcnc,
chromano ne, chromone glycos ides and vitamins. Analysis of sampl es of th e rhubarb contained (in perce nt ) as h,
9.3-4.9; protein , 1. 1; fibre, 1.3-0.8; catha rti c acid , 3.53.2; orga ni c ac ids, 3.3-2.2 ; and sugar, 1.4- l . l ; res pectively' .
Essential Oil.\
The essential oil s (0.05 per ce nt) obtained fro m
rhi zo mes of R. cm odi have charac teri sti c odo ur due to
the prese nce of eugenol and meth yl heptyl k e ton e~ . The
vo latil e oil from rhi zo mes of R. poln w lun1 co ntained I08
vola til e components of whi ch 27.3 per cent we re terpenoid s. The main cons tituent s were (per cen t): palmitic
aciu (22. 5) , paeo no l ( 16. 2), a -co paene (9.8), met hyl
stea rate (9.3), 8-cadinen e (5.4), and meth yl-e uge no l
(5. 4)('.
An 1h raquinones
Many an thraq uin ones have bee n iso lated from different spec ies of rhu ba rb. A few of th em are physcion ,
ch rysop hanol (c hryso phani c acid or chryso phan) , rh ein ,
e modi n, aloe-emodi n, rh e inal , hydroxy-me th yl an th raq uin one and Jst izin. Out of these anthraqu inone derivatives, mos t of th e rhubarb spec it.:s co ntain 7 ph ysc ion,
chry ~op h anol, emodi n, al oe-emodin and rh ein as shown
in Tab le I. Indian rhubarb (R. cm odi) was found to co ntain free rhein (0.48) , free chrysophan ol (0.50) and g lycosidic rhein ( 1.52) and glycos idic chrysophanol (0.4 1
pe r cen t) 1. The antimicrobi al acti vit y of rh ein was al so
obse rv ed aga in st Esche richia coli, Bacillus suht iles,
Microco ccus lule us, Candida alb icons. Clost rirliulil
pe1ji-ingr'il.\' and Fusofacle riu/11 voriwn 1. We have also
Dianthron es
Rh eidin A is a heterodianthrone co mposed of one
mole of emodin and one mole of rhein anthron e, obtai ned
from 1<. palmatwnx. Simil arl y, three other di anthrones
se nnidin C (o ne mole of aloe-emodin and one mole of
rhcin ), rhci din B (one mole of rhein and one mole of
chrysopha no l), and rheidi n C (o ne mole of rhein <lll d one
mole of physc ion) we re isolated from rhubarb roo ts') .
Stilbelles
Rhubarb had many stilbene derivativ es such as
rhaponti cin, deox yrhapo nt ic in , rh apon t ic in-~ -D- g Iucosid , desoxy rh apo nti genin , rh apon ti genin, piceatann ol,
4'-0- meth y Ipice id , rh apon t ige n in -3'-0- ~ -n- gl ucopyranosid e, piceatann ol- 3'-0 - ~ - n -g i ucopy ran os idc (Table
I). Rhapontin wh en ad ministered to ca~t rated female rats
(dose 600 ~Lg) has been reported to res tore the oes trous
cycle. Also, tab lets containin g 5 mg rhapontin and 90
mg of hops-ex tract ex hibited an ac tion sim ilar to th at of
the fo lli cular honn one in th e treatment of am enorrh oea,
dysmenotTh oea and endomet ritis and in inh ibitin g lactation 1.
Flo vonnids
Mainl y two spec ies, R. laWricum and R. \l'il/ mckii.
o f rhubarb gave fl avo no id s s uch as qu e rce tin ,
isoguercetin , meratin, rutin (0.32 per ct: nt) and que rcetin -3 ,7-g lucoarbinosides 12 13 . Rutin ha s been iso lated
from th e foll ow ing Rh eum spec ies (per cent ): R. cnwdi
(0.32), R. officinale ( 1.30), R. rhapol/(icttlll (0.6 1) and
N. undulatum (0 . 7 0 ) 1 ~ . Alyukina ct a/. 1 found th at the
ground part of rhubarb (R. \l'illmck ii ) con ta ined 18 phenolic compounds, seven of whi ch were flav onoids. The
maximum amount of flav onoid s was in th e fl owers and
the immature fruit s (6.57 per cent) . fo ll owed by ripe fruits
and buds (4.60 and4 .1 8 per ce nt, respecti vely).
Anthocycutin s
R. rhaponlicun1 and R. tawricum gave anth ocyanin and th eir deri va ti ves such as cya niclin-3-g lucoside.
cya nidin -3- rutin os ide, chrysa nth emin , ;t nd cya nin 1' 1x.
Organic Acids
Vi to 111 in s
Vit amin B. vitami n C (asco rbic acid) and vit am in
D have been reported from rhubarb11') Its juice proved a
fai rl y good source of vita min C. as tes ted by prophylactic expe riments 1.
Polyphenols
A large number of polyphenols isolated from different spec ies of rhubarb include: (-)-epi gall ocatec hol,
(+ )-ga ll oca tec hol, (- )-epi gallocatec ho l-gall ocatec hol,
(+ )-gall ocatec ho l ga ll ate, (+)-catec hol, (-)epicatec hol
gallate, catechins, (-)-epicatec hol, (- )-epicatechin ga llate,
ga llic acid, glucoga llin, kaempferol, 4,8'-bis-3-0-galloyl(-)-epicatec hin , 4',8-3-0-galloy 1-(-)-epicatec hin-(+)-catec hin , d-cate c hin , pyroga ll o l, ca r vacro l a nd 4met hoxyga llic ac id . The ast rin ge nt principl e co nsists
chi efl y of ga llic ac id , prese nt as glucoga ll in , together
with small amount of tannin and poss ibl y catec hin .
Glucoga llin on hydroly sis yielded ga lli c acid and glucose1.
The dru g is used in Ayurveda. ln th e Unan i system, it is a constituents of " [tri fa l Mulayy in ", used in
ordin ary constipati on and other di gesti ve disorders, ''Hab
Shabya r" where headache of different intensity are co nsidered clue to a disturbance in th e di ges ti ve system,
" Haba Shafa", for an obstin ate type of co ugh and cold
and of " Roughan Aq rab", appli ed on pil es beca use or
the astrin gent acti on of Rh eum. "Qur Didan" is an anthelmintic' .
Rhubarb forms an important ingredi ent of a \'a riety of medicines. It is an exce ll ent remedy for irrit ation
of the bowels, comm on amon g child ren durin g tee thin g
and in chroni c dyse ntry, du odenal catarrh or ca tarrh of
th e biliary ducts with jaundi ce and in certain sk in d iseases2. Fres h rhubarb juice showed anti sco rbuti c act ivity3
The plant also possesses antibi oti c propcrti es 13 It
is used as an antibacteri al aga inst Stapltvlococcus mm' us,
Esche richia coli or Brucella obortu.1~ . Rhubarb extract
had a laxative effec t due to its co ntent of hyd roxy methyl anthraq uinone and tannin s-' . It also has catharti c effect357 Cooked leaf and stems are harm less in modera te
quantities but th e leaves may cause fa tal pois o nin g ~.
Rhubarb is used as an antiviral agent against Voricello zoster virus and He1pe.1 simplex virtt.\Tubello'x . The
minimal inhibiti ve closes aga in st Voricc llo z.osrer and
HcrJ"Jes simf'J iex vims rubello G J() and JR -,-1 were I 005000 mg/L. It has also shown antiinflammatory act ivityl . Anthraquinones of rhubarb had mo llu sc icidal acti vit y against th e sc hi stoso me vector snail s On colll clunio , Biomphalaria and Bulinw 5 ~. C hrysophanic acid and
cl-catec hin obtained from rhubarb had show n prolongati on of prothrombin time which is a measure of coagui<lting activityn w. Chrysop hano l had been show n to be
res ponsibl e for spas molytic act ivityli 1.
11\
Anthraglycosides
Anthraglycos ides are found almost in all the species of rhubarb and a few of them were: rheochrys in ,
aloe-emod in-8-0- ~ -D-g l ucos ide, emod in-6-0- ~-D-g l ucoside, rh e in- 8- 0-~ -D-g lu cos i de, rheinos ide A, rh einos ide
B, rh ein os ide C and rh e in os ide D, se nn os ide A and
se nn os ide B, t o rac hryso n e - 8 -0-~-D- g lu co p y ra n os id e,
ka e mpfe ro 1- 3-0-a- L-rh a mn os id e, c hryo- phan e i n,
chrysop han o l- 8-0- ~- D-g l ucos id e, emod in -8-0- ~- Dgluco-pyranos ide, chrysop h ano i - 1 -0- ~ -D-g lu cos id e and
rh e in-II - O-~-D-g lu cos id e 2 (Ta ble I).
Pharmacology
Ant i-platelet aggregati on activity of stiIbene dcri \'ali ves fr o m /?. undttlurttnt has a lso bee n obser\'ed.
Rh aponti ge nin and deso xyrh apo nti gen in ha ve shown
strong inhi biti on of agg rega ti on induced by arachid onic
acid and co ll age n11 . The rhubarb stalk fibre is c!Tccti ve
Table I -
Sl. No.
Name o f co mpound
Name o r plant
R e fe ren ce ~
Essential Oils
Euge no l, bp, 255"
R-9
R-9
Paeono l
R-20
R-20
Methyl stearate
R-20
P-Cadi ne ne
R-20
R-20
2 1-29
(aj 0
5
6
[a]o-25 1"
Anthraquinones
C hrysophano l or Chrysophan
10
II
R-24. R-27
4, 2 1-23. 25-28, 32
4. 2 1-23. 25-3 1
Rhubarb ,
1-4.2 1-24.26-28 .
mp , 302"
13
Rh ein, mp , 32 1-322"
30
R-26. R- 10. R-22. R-24
14
Rhein a l, mp , 236-238"
R-9
15
Isti zin
Rhu barb
I , 33
R-20
3, 8
Dian thrones
16
Rh eidin A
17
Sennidin C
Rhubarb
3.9
18
Rhe idin B
Rhubarb
3, 9
19
Rhe idin C
Rhubarb
3,9
Rhu barb
4.5
Organi Acids
20
21
22
Aceti c ac id , bp , 11 8"
R-20. R-26
Rhubarb
5, 10
- Contd.
Table I -
Contd.
23
Rhubarb
5, 10
24
Rhubarb
5, 10
[a] 0
2.6"
25
Rhubarb , R-1 2
5, 10
26
C itric ac id , mp , !53"
Rhubarb
5, 10
27
Rhubarb
10
28
Formic ac id , bp , I 00.5''
Rhubarb
10
24, 34-37
mp, 236-237"dcc
R-20, R- 18, R- 11
Stilbenes
29
[a] 0
30
R-24, R-30
34,38,39
31
4,40, 41
R-28
42 , 43
33
R-28 , R-1 I
2!i , 37 , 42 , 43
34
Piceata nn o l, mp , 23 1-232"
R-2 8, R-30
28 , 39 , 42 , 43
35
4'-0-Methylpiccid
R-20
41
36
R-30
39
R-28
44
R-28
37 , 44
37
38
Piceatannol-3'-0-~-D
Flavonoids
39
R-27, R- 30
12, 13
40
R-27, R-30
12, 13
41
R-27
12
42
12- 14
R-30
!3
Rhubarb , R-24
15-17
Anthocyanins
44
Contcl.
45
15- 17
46
R-27
18
47
Cya n in
R-27
Ill
R- 11
37
S terols
48
~-S it os t ero l .
49
Daucostcrol
R- 11
37
50
Vit amin B
Rhu ba rb
51
Rh ubarb
4, 6. 19
Rh ubarb
mp. 140"
Vitamins
52
Vita min D
53
Rhubarb. R-30
20.
5-1
2-Mcthyl-5-acctyl-7-
Rhu barb
20
Rh ubarh
20
Rh uba rb
20
Rhubarb
20
Rhuba rb
20
Rhubarb
20
R- 15
45
(+)-Gal locatcchol
R- 15
-15
R- 15
45
R- 15
3. -16-..JX
]<)
2-Mcth yl-5-carboxy
mcthyl-7 -hydroxy-c hro mcnc
56
57
5X
A l ocso n c-7-0-~- D-
gluco pyranosidc
59
Polyphcnols
60
R-20. R-27
46,-17
66
(- )-Epicatcchol
R-27. R- 15
-17 . ..)<)
67
(- )-Epicatcchin-gal latc
Contd.
Tabl e I 68
69
Glucogall in
Contd.
3
R-2 0. R- 18. R-3
3.37.48
R-3. R- 10. R- 13
70
Rhub arb
20
71
Rhubarb
50
72
Rhubarb
50
-(+)-catechin
73
74
R- 15
48
75
4-Methoxygallic acid
R-1 5
48
An t hraglycosides
76
Rh eochrys in
R-2 0
51
77
R-28. R-20
27.44. 51
mp 237-238"
78
R-20
27 .51
79
Rhcin-8-0-0-D -glucoside
R-13. R- 8. R- 30.
27. 52
mp, 260-266"
Rhein- I 1 -0-~-D-gluw si dc
R-9
52-54
Rhcinoside A
R- 26. R- 8, R-2 0. R- 13
Rh ci nos id e 8
Rhubarb
53
Rhcinoside C
52-5 4
Rhcin os idc D
85
R-2 0. R- 13
R-6 . R-20
52-54
8(i
fain-
3.5 2.5 4. 55
3. 55
100" (Acclonc)
87
Rhubarb
88
Rhubarb
C hrysoph a no 1-8-0- ~~ -
R-28
- Co ntd.
Table I -
- Contd
90
R- 28
56
91
Rhubarb, R-28
20
K aempferol-3-0-a-L-rhamnosidc
Rhu barb
20
93
R-20
94
R-28. R- 3 1
44. 56
R-28. R-3 1
44.56
Rhu ba rb
41
R- 3 1
56
R- 3 1
56
mp, 245-246"
95
96
mp. 248-249"
97
C hr ysop h a n o i- 8-0-~-D-
98
Physcion-8-0-~-D-glu cos id c
Conclusion
Rhubarb possesses wide range of bio log ica l activ iti es and have revealed co mpound s of many chemi cal
classes . Ninety eight co mpound s iso lated from these
species include five flavon oids , twe lve anthraquin ones,
ten stilbenes, sixteen po lyphenols and tw enty-t hree
anthrag lycos ides and rest others. It is believed that thi s
rev iew would be of immense use for resea rchers workin g in the fi eld of ph ytochemi ca l in vest igat ions.
References
4
5
6
7
9
10
II
78.
Aganv:JI S K , Singh S S, Verma S & K um;lr S. In c/ion .I Chen1 ,
3813 ( 1999) 749-75 1.
Thakur R S, Puri H S & Hussain A, Major Medicinal Plants oj'
In dia , ( 1989) 443-447.
12
13
42
594.
Hctmanski W. Nvbo111 Nils Fmchtsafi l11d. 12 ( 190!\) 256-260:
C/ret/1 Ahstr, 71 ( 1969) 29360u.
I S Nurgal icva G M & Chumbalov T K , Feno/inyo Soedin 1/.:h /Jiol
F11n/.:ts Mat er Vses Si111p !st. ( 1966) 93-95: Client Ahstr. 71
( 1969) I 0257u .
19 Alli son R M , .I Sri Food Agric, 17 ( 1966) 554-557.
20 Kashiwada Y, Nonaka Gcrminacol & Ni shioka I, fJhwochelllis try, 29 ( 1990) I 007-1009 .
2 1 Wang Z , Hong X & Li Z, Zhrm gg rw Zl11m grao Za:hi. I X ( 1993)
488-491; Che111 Abstr, 120 ( 1994) 27479w.
22 StahlE & Mcnsscn H G , Otsch Apoth Ztg, 125 ( 19X5) 1-+ni1480; Che11t Abstr, 103 ( 1985) 109832u.
23 Ma X, Chen Y & Hui R, Chronrwogmphia , 27 ( 19X<J) -+6546 6.
24 Meri cli A H & Tuzl aci E. Fit oteratJia , 61 ( 1990) J75.
25 Yang F, Zh ang T, Ti an G , Cao h, Liu Q & It o Y, .I Chm 111 A, XSS
( 1999) I 03-1 07; Client AIJstr. 132 (2000) 26717h.
26 Li C L , Zhu P L & Liu M C, .I Clnmn A , 857 ( 1999) 167-17-+:
Chenr Abstr, 131 ( 1999) 342 103v.
27 Ko suge T & Ishida H. Che11r Phar111 1?1111. 33 ( 19X5 ) 150.11506.
28 Yan g X , Zhao J, Zhang Y, Li J, Ma C, Hatori Y & Nanba T,
Zhong caorao , 29 ( 1998) 289- 293; Che1n Abstr 129 ( 19 9~)
3 13336d
29 Rawa t M S M, cgi D S, Pawar MS. Pant G, Shibata S, Okada
Y, Oshima Y & Oku ya rn a T. Phamw:ie, 44 ( 198<.)) 509-5 10;
Mcd Arant PI AIJSu, 9005 ( 1990) 2264.
30 Cavclli V & Giuli ano R, Fwm co, 12 ( 1957) I X4-9 1; Che111
Abstr, 54 ( 1960) 2663c.
3 1 Chumbalov T K & Nurga licva G M , Khinr Prir Soedi11 . 3 ( 1967)
144; Chem Abstr. 67 ( 1967) 298591.
32 Masao U & Tas hi ro M , Che11r Phar111 /J111f. 9 ( 196 1) 23-+-236.
33 Blcir W, Sci P!tamt , 44 ( 1976) 140-142: C!te111 Ahstr. 74 ( 1976)
182460k.
34 Csupor L, Arch Phar111 (Wcinheim ). 304 ( 1971) 32-35: C!tenr
Ahstr, 74 ( 197 1) 111 945g.
35 Czlonkowsb G, Bitna-Szlaehta A & Gradecka J, AJIIcch Delo ,
IS ( 1966) 77-79; C!te111 Ain u. 66 ( 1967) 79628c.
36 Schra tz E & Witt H. De11t Af/Oth Ztg. 106 ( 1966) 1437- 1441;
C!te11r Abstr, 66 ( 1967) 17041 z.
37 Li J, Li J, He W, Wang A, Kong M, Zlwngcaoyao 29 ( 19<)8)
721-723; Cirelli Abstr, 130 ( 1999) 234656y.
38 Csupo r L , Arch P!tar111 ( Weinheim) , 303 ( 1970) 68 1 -6~7 : Chem
Abstr, 74 ( 1971) 12742j.
3<J Min D, Xu L, Zhang Z. Wang H, Huang D , Guo D & Zheng J,
Zhongg 11o Z!tongmo Za: hi. 23 ( 1998) 486-48~; C!tcnr Alwr.
44
14
IS
16
43
17
40
41
45
46
-+ 7
48
1101 21'
Chumbalov T K & Pa shinina L T , /Jio/.:hillli1a, 27 ( I %2 ) 65 1655; Chem Abstr. 57 ( 1962) 152381.
50 Hi samitsu Pharm . Co I nc Japan. Ko/.:ai To/.:kro Kolw. JP ' I 92 .
28],25 Jul. , 198 1: Chm1 Abstr, 96 ( 1982) 3509 1nt.
5 1 Rama nova AS. Ban'kovskii A I. Tr Vses Na uch- lssf,,d ln.,r Lt'/.:
A ronrat l?a st, I 5 ( 1969 ) 5404 -51 0; Che111 Ahstr, 75 ( 197 1)
3 1304e.
52 Zhcng J, Zhang L & Lou Z, Beijing Yi/.:e n a.w e Xu ehuo. 2.'\
( 199 1) 5 1-53; C/r,'nt Ahstr, 117 ( 1992) 66653f.
53 Takashi Y, M akoto N , Mit suhiko I. Kuri o H. Gcncltiro N &
l tsuo N, C!tenr Phar111 Uu/1 . 35 { 1987) 3 132 -313X.
54 Zhcng J, Hu ang Q, Zhang Z. Gao S, & Lou Z. Beijin g Vi /.:e
Da.m e X11 ehao. 23 ( 199 1) 139- 1-+ I: Chl'/11 Ahstr. 11 7 ( 1992)
66652c.
55 Murata T , K arasaki S & Shiozub T. Na t11ral Met!. -Hi ( 19lJ-I)
~2 - ~5; Med Armtt PI Abstr, 9502 ( 1995) 11 33.
56 Mat suda H , K ageura T. Morikawa T, Toguchida I. ll a r im ~t S &
Yoshikawa M , !liom~~ M('{/ Chem Lcll , 10 (2000) 32.1 -.\27.
57 T surumik K , Hayas hi M, Hibino R & Fujimura II. it'f/{)1/
Ya/.:11rigak11 Zasshi. 65 ( 196<J) 643-648; Cirelli Ahstr, 73 ( 1970)
129 191 z.
58 Wang P. Xi an Y. Xu S. Wang G . Sony Y. Xu H. Yao P. Wang Z
& Wang Y, Slwndong Yi/.:e Da.m e X11ehao. 34 ( 1996) 166-169;
Clr enr Abstr, J 25 { 1996) 3 16.127c.
59 Liu Sy, Sporer F, Wink M , Jourdanc J, Hcrrnin g R. L i Y L &
Rurpcl A, Tm fi M('{/ l11st 1-/ea /th. 2 ( 1997) 179-1 X8.
60 H amsaveni G R & Puru shotlt aman K K. 13111/ Jilted /:.rlurohot
Res, 5 ( 1984) 171- 177.
6 1 Kh etwal K S & Pathak R P, .I Indian Clu111 Soc . 65 ( I <JX8)
227-22 8.
62 Sato H, Kurosak i Y, Hir :~yama H & Mi zug::1 ki M. Ya/.:11ga/.: 11
Zasshi , 110 ( 1990) 55 -5X ; Met! Aronr PI Alnn, 9105 ( 1991)
3 144.
63 Li L S. Chines" Med ./. I 09 ( 1996) 35-37: MNI Amm PI Ahstr.
9606 ( 1996) 3-14 1.
64 Li L S & Liu Z H , Chines(' .lollma/ ln teg rat ed Tratlitionalll'estem Med, ll ( llJ9 1) 392-396: Med Am111 PI Ahstr. 9205 ( ll)Sl2 )
2889.
65 Gocl V, Ooraik uiB Ba:-.u TK . .I Am Col! Nutr. 16 ( 19lJ7) 600604.
-19