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Chemistry and Pharmacology of Rhubarb (Rheum Species)- a Review

Chemistry and Pharmacology of Rhubarb (Rheum Species)- a Review

Journal or Scientific & Industri al Research Yol.60, Jan uary 200 I, j:Jp 1-9

Chemistry and of (Rheum species)- A Review

Santosh K Agarwal *, Sudhir S Singh, Vijai Lakshmi+, Sushma Verma and Sushi! Kumar Central Institute of Medicinal and Aromatic (('SIR), Lucknow 226 015, India

+Central Drug Research Institute (CSIR), Luck now 226 00 I, India

Vari ous chemical constituents iso lated from rhubarb (Rheum ) species in clude an thraquinones, di anthrones, stilbencs. anth ocyanins, navonoids, anthragl ycos icles , polyphenols, organic acids, essential oi ls, vitamins, chromenes, chromanone and chromone glycosides. Notable biological ac ti viti es reported rro111 ,, ,l. va ri ous parts or th e and its iso lates arc cath arti c. an tibacteri al, fatal poisOfling, antiviral, anti inllammatory, mollu sciudal, anticoagulant , spas molyti c, cytotoxicity. chronic rcn;ll failure, chemiluminescence quencing and an ti -p latelet acti vities.

Introduction (R-28), R. webbianum (R-29), /?. willrockii (R-30) and R. qinlingense (R-31 ). About ten species are found in Rheum Linn (family ; English name: India. rhubarb), a large of perennial, stout herbs and dis­ tributed in the temperate and sub-tropical regions of the Indian rhubarb, which is official in Indian Phar­ world, chiefly in Asian countries, viz. India (Kashmir, macopoeia, consists of the dried of R. enwdi Assam, Sikkim), Nepal, Bhutan, China, Pak istan, Ko­ and R. webbian um and other species of Rheum. Rhizomes rea, , Russia and Tibet. Several species of this and of R. moorcroftianum and R. spicifonne are plant are used in medicine, some for culinary purposes also reported to be mixed with th e drug. The plant grows and few others are grown as ornamental plants. There wild at an altitude of about 4000 to 12000 feet. Rhubarb are three main types of rhubarb, viz. the Chinese Rhu­ has been successfully grown in certa in parts of Assam barb, the Indian or Himalayan Rhubarb and the Rhapontic also. Indian rhubarb occurs in sub-cylindrical or irregu­ Rhubarb u. Some known species of Rheum are R. lar pieces, rangin g from 2 to 20 em in length and 1.5 to acuminatum (R-1 ), R. alexandrae (R-2), R. altai cum (R- 2.0 em in diameter, much shrunken, li g ht in we ight. It is 3), R. australe (R-4), R. compactum (R-5), R. coreanum some what dark in colour, almost odourl ess or some­ (R-6), R.corodatum (R-7), R. delavayi (R-8), R. emodi what fragrant with a bitter and astringe nt taste. It con­ (R-9), R. franzenbachii (R- 10), R. hotaoense (R-11 ), R. tains derivatives and y ie ld s about 25-30 hybridium (R-1 2), R. kialense (R-1 3), R. /hasaense (R- per cent of ~·x tra c t soluble in 50 pe r cent aqueous alco­ 14), R. maximoviczii (R-15), R. moorcro.fiianum (R-16), hol'. In ayurvedic preparations, rhubarb has long been R. nobile (R-17), /?. offlcina/e (R-1 8), /?. pa/aestinwn used as an ingredient of purgatives, laxatives and sto­ (R-19), R. palmatum (R-20), /?. pami/um (R-2 1), /?. ribes machic-tonics ·' · ~. It is hoped th at the review would be (R-22), /?. rhabarbamm (R-23), R. rhaponricwn (R-24), useful to th ose workin g in th e fi e ld of phytochemical (R-13), R. lhasaense (R-14 ), R. maxim oviczii (R- 15 ), /( investigations of rhubarb. 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 (R- Chemistry 23), R. rhaponticum (R-24), R. spiciforme (R-25), R. A variety of const ituents have been isolated fro m tanguticum (R-26), R. tataricum (R-27), R. undu/atum Rheum species and the ir structures e lu c id ated. They be­ long to such classes as , clianthroncs, stil­ *Author for correspondence benes, anthocynins, rlavono icl s, anthrag lycosides, CIMAP Publi cat ion No.: 99 -11 R polyphenols, essenti al oi l. organic acid s, chromcnc, 2 J SCI IND RES VOL.60 JANUARY 2001

chromanone, chromone glycos id es and vitamins. Analy­ analyzed the rhubarb extract ( I 00 g) whi ch cont ained sis of samples of th e rhubarb contain ed (in percent ) ash, acet ic ac id (8 .5 -39.4), formi c ac id (9.'2-37. 1), oxa li c acid 9.3-4.9; protein , 1.1; fibre, 1.3-0.8; catha rti c acid , 3.5- ( 100-638), mali c ac id (3 05-1200) and citri c acid (207- 3.2; organi c acid s, 3.3-2.2 ; and su gar, 1.4- l. l ; res pec­ 340 mg). Trace amounts of lac ti c, succ in ic and fumari c tively' . acids were also detected' . Palmitic ac id content was found to be 49.3 1 per cent in the volatil e oil II of R. Essential Oil.\· tangu ti cu m. The essential oil s (0.05 per cent) obtain ed fro m rhi zomes of R. cmodi have charac teri sti c odour due to Stilbelles the presence of eugenol and meth yl heptyl k e ton e~ . The Rhubarb had many stilbene derivatives such as vo latil e oil from rhi zomes of R. polnw lun1 contain ed I 08 rhaponti ci n, deox yrhapo nt ic in , rh apon t ic i n-~ -D- g I uco­ vola til e components of whi ch 27.3 per cent we re terpe­ sid , desoxyrh aponti genin , rh apon ti genin, piceatann ol, noid s. The main constituent s were (per cent): palmitic 4'-0-meth y Ipic e id , rh apon t ige n in -3'-0- ~ -n-gl ucop­ aciu (22. 5) , pa eono l ( 16. 2), a -copa ene (9.8), met hyl yranoside, piceatannol- 3 '-0 - ~ - n -g i ucopy ran os idc (Table stearate (9.3), 8-cadinene (5.4), and meth yl-eugenol I). Rhapontin wh en ad ministered to ca~t r ated female rats (5. 4)('. (dose 600 ~L g) has been reported to restore the oestrous An 1h raquinones cycle. Also, tab lets containing 5 mg rhapontin and 90 mg of hops-extract ex hibited an ac tion sim ilar to th at of Many an thraq uin ones have been iso lated from dif­ the fo lli cular honnone in th e treatment of am enorrh oea, ferent spec ies of rhu ba rb. A few of th em are physcion, dysmenotTh oea and endomet ritis and in inh ibiting lacta­ ch rysophanol (c hrysophanic acid or chrysophan) , rh ein , tion 1. emodi n, aloe-, rh einal , hydroxy-meth yl an ­ th raq uin one and Jst izin. Out of these anthraquinone de­ Flo vonnids 7 rivatives, most of th e rhubarb spec it.:s contain ph ysc ion, Mainl y two spec ies, R. laWricum and R. \l'il/mckii. chr y ~op h anol, emodi n, al oe-emodin and rh ein as shown of rhubarb gave fl avono id s such as qu e rcetin, in Tab le I. Indian rhubarb (R. cmodi) was found to con­ isoguercetin , meratin, rutin (0.32 per ct: nt) and querce­ 13 tain free rhein (0.48), free chrysophanol (0.50) and gly­ tin-3 ,7-glu coarbinosides12· . Rutin ha s been iso lated cosidic rhein ( 1.52) and glycosidi c chrysophanol (0.4 1 from th e foll ow ing Rheum species (per cent ): R. cnwdi 1 pe r cent) . The antimicrobial acti vit y of rh ein was al so (0.32), R. officinale ( 1.30), R. rhapol/(icttlll (0.6 1) and observ ed again st Escherichia coli, Bacillus suhtiles, N. undulatum (0 . 7 0 ) 1 ~ . Alyukina ct a/.·1 found th at the Micrococcus luleus, Candida albicons. Clostrirliulil ground part of rhubarb (R. \l 'illmckii) conta ined 18 ph e­ 1 pe1ji-ingr'il.\' and Fusofacleriu/11 voriwn . We have also noli c compounds, seven of whi ch were flav onoids. The isolated a new anthraquin one deri vative rh einal (0.008 maximum amount of flav onoids was in th e fl owers and p,c r cent) from th e rh izomes of R. c n wd i ·~ . the immature fruit s (6.57 per cent) . fo ll owed by ripe fruits and buds (4.60 and4.1 8 per cent, respecti vely). Dianthrones Rh eidin A is a heterodianthrone co mposed of one mole of emodin and one mole of rhein anthrone, obt ai ned from 1<. palmatwnx. Simil arl y, three other di anthrones Anthocycutins 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 R. rh aponlicun1 and R. tawricum gave anth ocya­ chrysophanol), and rheidi n C (o ne mole of rhein

Organic Acids Vi to 111 in s Some orga ni c acids obtained from rhu barb spec ies arc: oxalic, pa lmitic, acetic, succ ini c, lacti c, ma li c, cit ­ Vit amin B. vitami n C (ascorbic acid) and vit am in ric , fumaric an d form ic (Table I). The oxa li c acid con­ D have been reported from rhubarb·1·1') Its juice proved a tent in In dian rhubarb 1 w;:s 1.3-t per ce nt. Mali c ac id fai rl y good source of vita min C. as tes ted by prophylac­ 1 w;,L predominant in al l th e v<~ri e ti es tested I 0. Yas uhiko tic experiment s . 3 AGGARWAL eta/.: CHEM ISTRY & PH ARMACOLOGY OF RH UBARB

Chromene, Chrornanone, and Chromone The drug is used in Ayurveda. ln th e Unan i sys­ Six chromone and chromanone deri vatives 211 have tem, it is a constituents of "[tri fa l Mulayy in ", used in been isolated from rhubarb together with two chromone ordin ary constipati on and other di gesti ve disorders, ''Hab 211 Shabya r" where headache of different intensity are con­ glu cosid es • These are : 2,5-dimeth yl- 7- hyd roxy­ chromene; 2-meth yl-5-acetyl-7-hydroxy-chromene; 2- sidered clu e to a disturbance in th e di gesti ve system, methyl-5-carboxy-meth yl- 7 -hydrox y-chromenc; 2-(2'­ "Haba Shafa", for an obstin ate type of cough and cold hydroxyl-propy 1-5-meth y 1-7 -hydroxychromene; 2- me­ and of "Roughan Aq rab", applied on pil es because or thyl-5-carbox-ymeth yl-7-hyd roxy chromanone; Aloe­ the astringent acti on of Rheum. "Qur Didan" is an an­ thelmintic' . so n e-7-0- ~-D- g lu co- p y ra n os id e and 2- methyl-5-(2'-oxo- 4'-hydroxypentyl)-7-hydroxy c hromon e -7-0 - ~ -D­ Rhubarb forms an important in gredi ent of a \'ari­ glucopyranos ide. ety of medicines. It is an excell ent remedy for irrit ation of the bowels, common among child ren during teething and in chroni c dysentry, du odenal catarrh or catarrh of Polyphenols th e biliary ducts with jaundice and in certain sk in dis­ A large number of polyphenols isolated from dif­ eases2. Fres h rhubarb juice showed anti scorbuti c activ­ ferent spec ies of rhubarb include: (-)-epi gall ocatechol, ity3 ( + )-ga ll ocatechol, (-)-epi gallocatechol-gall ocatec hol, The plant also possesses antibi oti c propcrti es 13 It ( + )-gall ocatec hol gall ate, (+)-catechol, (-)epicatechol is used as an antibacteri al again st Stapltvlococcus mm' us, gallate, catechin s, (-)-epicatechol, (- )-epicatechin ga llate, Escherichia coli or Brucella obortu . 1·~ . Rhubarb extract ga llic acid, glucoga llin, , 4,8'-bi s-3-0-galloyl­ had a laxative effec t due to it s content of hyd roxy me­ (-)-epicatechin , 4',8-3-0-gall oy 1-(-)-epicatechin-( +)-cat­ thyl anthraq uinone and tannins-' . It also has cathartic ef­ echin , d-catec hin , pyroga ll o l, carvacro l and 4- fect3·57 Cooked leaf and stems are harmless in moderate methoxygalli c ac id . The astrin gent principle consists quantities but th e leaves may cause fa tal pois o nin g ~. chi efl y of ga lli c ac id , present as gl ucoga ll in , together Rhubarb is used as an antiviral agent against Vori­ with small amount of tannin and possibl y catechin . cello zoster virus and He1pe.1· simplex virtt.\Tubello'x . The Glucogallin on hydrolysis yielded galli c acid and glu­ minimal inhibiti ve closes aga in st Voriccllo z.os rer and cose1. HcrJ"Jes simf'J iex vimsrubello G and JR, were I 00- 11\· J() - -1 Anthraglycosides 5000 mg/L. It has also shown antiinflammatory act i v- Anthraglycosides are found alm ost in all the spe­ ityl . Anthraquinones of rhubarb had mollu sc icidal ac­ cies of rhubarb and a few of them were: rheochrys in , ti vit y against th e sc hi stosome vector snail s Oncolllclu­ nio, Biomphalaria and Bulinw· 5 ~. Chrysophanic acid and aloe-emod in -8-0- ~ -D-g l ucos ide, emod in -6-0- ~-D -g l uco­ cl -catechin obtained from rhubarb had shown prolonga­ side, rh e in- 8- 0-~ -D-g lu cos i de, rhein os ide A, rh ein os ide ti on of prothrombin time which is a measure of coagu­ B, rh ein os id e C and rh ein os id e D, senn os id e A and i

Table I - Li st or compounds iso lated from illerent species or rhubarb

Sl. No. Name of compound Name or plant R e fe ren c e ~

Essential Oils Eugenol, bp, 255" R-9 4 2 Meth yl heptyl ket one R-9 4 3 Paeonol R-20 6 4 a -Copa ene. bp, 246-25 1" R-20 6

(aj0 - 6.3" (c= 1.2 in C HC I1). 5 Methyl stearate R-20 6 6 P-Cadi nene R-20 6

[a]o-25 1" 7 Meth yl-eugenol R-20 6

Anthraquinones 8 Physcion, mp. 2 10" Rhubarb, R-9, R-20. R- 18, 2 1-29 R-26. R- 10. R-22. R- 16. R-31 9 Chrysophanol or Chrysophan Rhubarb, R-9, R-20. R- 18. I. 2 1-31 Chrysophanic ac id , mp, 196" R-26. R-10. R-22, R- 16. R-24. R-27 10 Aloe-emodin, mp. 223-224" Rhubarb, R-9, R-20. R- 18. 4, 2 1-23. 25-28, 32 R-26, R-1 0, R-6

II Emodin, mp. 256-257" Rhubarb, R-9. R-20, R- 18, 4. 2 1-23. 25-3 1 R-26, R- 10, R ·24, R- 16. R-27 12 Hydroxy-methyl anthraqui none Rhubarb, 4 mp, 302"

13 Rhein, mp, 32 1-322" Rhubarb, R-9, R-20. R- 18. 1-4.2 1-24.26-28. 30 R-26. R- 10. R-22. R-24 14 Rhein al, mp, 236-238" R-9 2 15 Isti zin Rhubarb I , 33

Dian thrones 16 Rheidin A R-20 3, 8 17 Sennidin C Rhubarb 3.9 18 Rheidin B Rhubarb 3, 9 19 Rheidin C Rhubarb 3,9

Organi Acids 20 Oxali c acid, mp, 101 - 102" Rhubarb 4.5 2 1 Palmitic acid, mp, 63-64" R-20. R-26 22 Aceti c acid, bp, 11 8" Rhubarb 5, 10

- Contd. 5 AGGARWAL eta/.: C HEMISTRY & PHARMACOLOGY OF RH UBARB

Table I - Li st of compounds isolated from different species of rhubarb - Contd.

23 Succinic acid , mp, 185- 187" Rhubarb 5, 10 24 Lac ti c acid, mp, 53" Rhubarb 5, 10

[a]0 - 2.6" 25 , mp, 13 1-1 32" Rhubarb, R-1 2 5, 10 26 Citric acid , mp , !53" Rhubarb 5, 10 27 Fumaric acid, mp , 230" Rhubarb 10 28 Formic ac id , bp, I 00.5'' Rhubarb 10

Stilbenes 29 Rh aponti cin or Rhapontin Rhubarb, R-22, R-24, 24, 34-37 mp, 236-237"dcc R-20, R- 18, R- 11

[a] 0 - 59.5" (Acetone) 30 Deoxyrhaponticin R-24, R-30 34,38,39

3 1 Rh apo nti c in-~- D-g lu cos id e R-9, R- 20, R-24 4,40, 41 mp, 230-231 "

32 Desoxyrh apontigenin R-28 42, 43 33 Rhapontigenin, mp, 185" R-28, R-1 I 2!i , 37, 42, 43 34 Piceatannol, mp, 23 1-232" R-2 8, R-30 28, 39, 42, 43 35 4'-0-Methylpiccid R-20 41

36 Piceatannoi-4'-0- R-30 39

- ~ -D-g lu co p y ran oside

37 Rhapontigenin -3'-0- R-28 44

-~-D- g lu co p y r a n os id e

38 Piceatannol-3'-0-~-D­ R-28 37, 44 g lu copyranoside (Rheumin)

Flavonoids 39 , mp, 3 14" dec R-27, R- 30 12, 13 40 lsoquercetin, mp, 225-227" R-27, R-30 12, 13 41 Meratin, mp, 180" R-27 12 42 Rutin, mp, 2 14-2 15" dec Rhubarb, R-27, R-30, 12- 14

[a]0 + 13.82" (Eth anol) 43 Quercetin -3,7- glu coarbi nosid es R-30 !3

Anthocyanins

44 Cyanidin-3-glu coside mp, 205" dec Rhubarb, R-24 15-17

- Contcl. 6 J SCI IND RES VOL. 60 JANUARY 2001

Table I - Li st or compounds isol<11cd from di lfero.:n t species of rhubarb - Contd.. 45 Cya nidi n-3- rut inosidc Rhuh:1rb, R-24 15- 17 46 Ch rysa nt hcmin . mp. 205" dec R-27 18 47 Cyan in R-27 Ill

Sterols

48 ~-S it os t ero l . mp. 140" R- 11 37

fa iD- 37" (CHCI,J 49 Daucostcrol R- 11 37

Vitamins

50 Vit amin B Rhu ba rb 4 5 1 Vit am in C (Asco rbic acid) Rh ubarb 4, 6. 19 mp. 190-92", Ja iD + 4X" (MeOII)

52 Vitamin D Rh ubarb 4

Chnnncnc, Chromanone and Chmmonc

53 2.5-Dirncthyl-7 -hydroxy- chromcnc Rhubarb. R-30 20. ]<) 5-1 2-Mcthyl-5-acctyl-7- Rhu barb 20 hyJroxy-chro mc nc 55 2-Mcth yl-5-carboxy Rh ubarh 20 mcthyl-7 -hydroxy-c hromcnc 56 2-(2'- H ydro~y lp ropy l -5- Rh uba rb 20 mct hyl-7 -hydroxyc hromcnc 57 2-Mcth yl-5-c arboxymcth yl- Rhubarb 20 7-hydroxy chro manonc

5X A l ocso n c-7-0-~- D - Rhuba rb 20 gluco pyranos id c 59 2-Mcthyl-5-(2'-nxo-..J'- Rhubarb 20 hydroxypcnt yl )-7- hydroxy

chromnnc-7 -0- ~ - 1 )-glucopyranosidc

Polyphcnols 60 (- )-Epigall ocatec hul R- 15 45 ( +)- Gal locatcchol R- 15 -15 (- )-Epigallocatec hol- gal locatcchol R- 15 45 (±)-Ga llocat..:cho l-ga IIat..: R- 15 3. -16-..JX (+)-Catechol. mp. 212-2 16" R-2 0. R-27 . R-30. R-15 ] . ..J . 9. 27. -17 (-)-Epicatcc hol -gallatc R-20. R-27 46,-17

66 (- )-Epicatcchol R-27. R- 15 -1 7 . ..)<) 67 (- )-Epicatcchin-gal latc R-2 0. R-1 X. R-3. R- 10. R- 13 - Contd. AGGARWAL eta/.: C HEMISTRY & PHARMACOLOGY OF RHUBARB 7

Table I - List of compounds iso lated from different spec ies or rhubarb - Contd.

68 Gallic acid, mp. 235-240" 3

R-20. R- 18. R-3 3.37.48 69 Glucogall in R-20, R- 18, R-7 3 R-3. R- 10. R- 13

70 Kaempfcro l, mp. 276-278" Rhubarb 20

71 4.8'-bis-3 -0-Galloyl-(-)-epica techi n Rhubarb 50

72 4 .8'-3-0 -Galloyl-(-)-epica techi n Rhubarb 50 -(+)-catechin

73 Pyroga llol, mp. 13 1- 13:1''

74 Carvacrol, bp. 11 8- 122" R- 15 48

75 4-Methoxygallic acid R-1 5 48

Ant hraglycosides

76 Rh eochrys in R-20 51 77 Aloe-emodi n- 8-0-~-D-gl u cosid<: R-28. R-20 27.44. 51

mp 237-238"

78 Emod i n-6-0-~- 0 -g lucosidc R-20 27.51 79 Rhcin-8-0-0-D-glucoside R-13. R- 8. R- 30. 27. 52

mp, 260-266" R-2 1. R-1 4, R-26. R-20

Rhein- I 1 -0-~-D-gluw si dc R-9 2

mp. 247-25 1"

Rhcinoside A Rhubarb. R-2, R- 14. 52-54 R- 26. R- 8, R-20. R- 13

Rh ci nos ide 8 Rhubarb 53

Rhcinoside C Rhubarb. R-2. R-1 4. R-26. 52-54

R-8 . R-20. R-1 3. R-2 1. R-30 84 Rhcinos idc D Rhubarb. R-2. R-14. R-26, 52-54 R-8. R-20. R- 13. R-2 1. R-30

85 Scnnosidc A. mp. 200-240'' dec. R-30. R-14. R-6. R-26. R-8. 3.52.54. 55 [u.Jn - 164" (Acetone) R-2 0. R- 13

8(i Scnnnsidc B. mp. I Hll- 186" de c R-6. R-20 3. 55 fain- 100" (Acclonc•)

87 St.:nnosidc C. mp. I 1)7" Rhubarb

88 Scnn os idc D. 1np. 21( )" Rhubarb

C hrysoph a no 1-8-0- ~~ - R-28

-( 6' -gal loyl)-gluL , 'I') !'<'IH •side - Co ntd. 8 J SC I IND RES VOL.60 JANUARY 200 1

Table I - List of compounds iso lated from different species or rhubarb - Contd

90 A l oe-cmod in - 1 -0-~- - D-glu co pyra n oside R- 28 56

91 Tora c hr yso n e-8-0-~- Rhubarb, R-28 20 -D-glu copyranosidc

92 K aempferol-3-0-a-L-rhamnosidc Rhu barb 20

93 Ch rysophan ein. mp. 246" R-20 4

94 Ch rysoph an o i- 8-0-~-D-g lu cosi d c R-28. R- 3 1 44. 56 mp, 245-246"

95 Emod i n -8- 0 - ~-D- glucopy r a nnsi de R-28. R-3 1 44.56 mp, 2 10-2 11 "

96 C hr ysop h a n o i-1-0 -~- D-g l ucos i dc Rhu ba rb 4 1 mp. 248-249"

97 C hr ysop h a n o i- 8-0-~-D- R- 3 1 56 -(6'-malonyl)-glucopyranosidc

98 Physcion-8-0-~-D-glu cos id c R-3 1 56

in lo weri ng serum cholesterol concentrati ons , especiall y 4 Chopra R N, ayyar, Chopra, Clos.wrr o( Indian Medicinal 1 LDL cholesterol, in hypercholesterolemi c men ''. Plan is ( 1978) 212. 5 Yosu hi ko M , NiJ IJIO II S/wkuhin K ug\'o Cakkaishi, J I ( 1964) Conclusion 444-46: Chon Ah.11r, 64 ( 1966) 1269a. Rhubarb possesses wid e range of bi ological activi­ 6 Miyazawa M , Minami no Y & Kameoka 1-1 . Flavour Fmgro11n• ./, II ( 1996) 58-60. ti es and have revealed compound s of many chemi cal 7 Xiao P G, Chen B Z. Wa ng L W, Hn L Y & Lun SR. Guo Hang classes. Ninety eight compounds iso lat ed from these Zhou Yao 1-/sueh 1-/sueh Pao, 15 ( 1980) 3J-39: Che111 Ahsir. 93 species include five flavon oids , twelve anthraquinones, ( 1980) 2453301' ten stilbenes, sixteen polyphenols and tw enty-three 8 Lern li J. Dequckcr R & Cuvcc lc J. Plwnn \Veekblad, X9 (I %3) anthrag lycosides and rest others. It is be li eved that thi s 655-659; Che111 Ahsir. 60 ( I %4) 365g. rev iew would be of immense use for researchers work­ 9 Lernli J, Dequckcr R & Cuvcclc J. Phwm \Veekhlwl. 99 ( 1964)613-616:Che111Ah.l'll'. 61 (1964) 13 125c. in g in the fi eld of ph ytochemi cal in vest igat ions. 10 Blundstone H AW & Dickinson D . ./ SCI FoodAgric. 15 ( 1%4) 94- 10 I : Chen1 Ahslr. 60 ( 1964) 1357 011 . References II Wang X , Zheng J & Chen Q, Zhong~uo )l:w.rue Za::.hi. 30 (I t)f.J5) Ahmad Z, Jafri M A & Javed K , Indian Dmgs. ]5 ( 1998) 75- 7 19-20; Che111 Ahsir 124 ( 14) ( 19%) 18575 1r. 78. 12 Chumhalov V T K & Nurgalieva G M, Kh i111 Prir Srwdin. 3 2 Aganv:JI S K , Singh S S, Verma S & Kum;lr S. In c/ion .I Chen1 , ( 1% 7) 345 -346: Che111 A IJs lr, 6X ( 196X) 275 16p. 3813 ( 1999) 749-75 1. 13 A lyukina L S. BaigoLina V P & Rama7.anova Zh Tr. Ins/ /J oi 3 Thakur R S, Puri H S & Hussain A, Major Medicinal Plants oj' Akad Nauk Ku;. SSt?. 28 ( 1970) 170-178: Che111 Ahstr, 73 ( 19 70) In dia, ( 1989) 443-447. 127773s. AGGARWAL et a/. : C HEMISTRY & PHARMACOLOGY OF RHUBARB 9

14 Horhammer L & Muller K , Arch Pha r111 , 2X ( 195-+ ) 126: Ch('/11 42 Ko S K , Whang W K & Kim I H, Ya/.:!ta/.: HoeJi , 42 ( 199X) 1--+: AIJSfl·, 49 ( 1955) 5701. Med Aro111 PI Ahstr, 9802 ( 199ll) I OSX. IS Wrolstad R E & Struthers B J, .I Chm111 , 55 ( 1971 ) 405--+0~. 43 Ko S K , LeeS M & Wang WK. Arch Phamr Res. 22 ( 1999) 16 Wrolstad R E & Heathcrbcll D A , J Fo od Sci, 33 ( I % ll) 592- 40 1-403; Che111 Ahstr. 131 ( 1999) 29534 1j . 594. 44 Ko S K , Whang W K & Kim! H. Arch Phar111 Res. I X ( llJlJS) 17 Hctmanski W. Nvbo111 Nils Fmchtsafi l11d. 12 ( 190!\) 256-260: 282-288; Met! Aro111 PI Abstr. 9602 ( 1996) I mn. C/ret/1 Ahstr, 71 ( 1969) 29360u. 45 Pashinina L T & Chumhalov T K . Khi111 Prir Soedin. 3 ( 1%7) I S Nurgalicva G M & Chumbalov T K , Feno/inyo Soedin 1/.:h /Jiol 346-347: Client Ahstr, 68 ( 1968) 195441. F11n/.:ts Mat er Vses Si111p !st. ( 1966) 93-95: Client Ahstr. 71 46 Friedrich H & Hochbc J. Arch Phamr . 299 ( 1966) 857-X66; ( 1969) I 0257u. Client Abstr, 67 ( 1967) 26549p. 19 Allison R M , .I Sri Food Agric, 17 ( 1966) 554-557. -+ 7 Chu mbalov T K & Nurga licva G M . Khinr fJrir Soedin. 3 ( I% 7) 20 Kashiwada Y, Nonaka Gcrminacol & Nishioka I, fJhwochelllis­ 2~2 ; Chenr Ahstr, 67 ( 1967) 298591. try, 29 ( 1990) I 007-1009. 48 Chumbalov T K , Pashinina L T & Nurgalicva G M . l?ahot 2 1 Wang Z, Hong X & Li Z, Zhrm gg rw Zl11m grao Za:hi. I X ( 1993) Kafcdrv Ort;an K!ti111. ( 1962) 60-69: C!t ent Ahstr. 61 ( I%-+) 488-491; Che111 Abstr, 120 ( 1994) 27479w. 1101 21' 22 StahlE & Mcnsscn H G, Otsch Apoth Ztg, 125 ( 19X5) 1-+ni- -19 Chumbalov T K & Pa shinina L T, /Ji o/.:hillli1•a, 27 ( I %2) 65 1- 14 80; Che11t Abstr, 103 ( 1985) 109832u. 655; Chem Abstr. 57 ( 1962) 15 2381. 23 Ma X, Chen Y & Hui R, Chronrwogmphia , 27 ( 19X