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Corchorus Species—A Source of Cardiac Glycosides, Triterpenoids, Ionones, Flavonoids, Coumarins, Steroids and Some Other Compounds

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Corchorus Species—A Source of Cardiac Glycosides, Triterpenoids, Ionones, Flavonoids, Coumarins, Steroids and Some Other Compounds Journal of Scientific & Industrial Research Vol. 65, April 2006, pp 283-298 A comprehensive review on the chemistry and pharmacology of Corchorus species—A source of cardiac glycosides, triterpenoids, ionones, flavonoids, coumarins, steroids and some other compounds M S Y Khan*, S Bano, K Javed and M Asad Mueed Centre for Interaction between University & Industry, R & D Extension and Projects Office, Hamdard University, New Delhi 110 062 Received 08 February 2005; revised 24 January 2006; accepted 03 February 2006 An exhaustive literature survey on the secondary metabolites of Corchorus species has been carried out. Cardiac gly- cosides, triterpenoids, sterols, phenolics, ionones, carbohydrates and fatty acids have been reported from different species. Many of these compounds have been found to possess significant biological properties e.g. digitalis glycosides like action, anticonvulsive activity, antiesterogenic action, anticancer activity and antipyretic activity etc . Keywords : Biological properties, Carbohydrates, Cardiac glycosides, Corchorus sp, Ionones, Phenolics, Sterols, Triterpenoids Introduction cies 6-10 but no definite conclusions could be drawn Corchorus (Family: Tiliaceae ) is a genus of annual regarding the structures of these compounds. Similar herbs. Nearly 40 species are known to occur in nature was the fate of capsularin 11 , chorchoritin 12 and and distributed in the tropics of both the hemi- corchsularin 13 . In the same manner, a number of agly- spheres 1. Seeds of C. acutangulus are used as a tonic, cones namely corchsugenin 13 , corchortoxin 14 and cor- stomachic, purgative, in fever and in obstruction of chorgenin 15,16 were isolated. A significant advance- the abdominal viscera. Leaves of C. capsularis , ment was made when these aglycones were chemi- C. depressus and C. olitorius are demulcent, bitter, cally identified as strophanthidin 1 17 , the familiar tonic, laxative, carminative, refrigerant, febrifuge, aglycone of the cardiac glycoside strophanthin. This diuretic, useful in chronic cystitis, gonorrhoea and was followed by identification of 2-deoxy riboside dysuria 1-3. C. depressus is given to increase the vis- and 2-deoxy-3-O-methyl riboside of strophan- cosity of the seminal fluid 4. Corchorus species have thidin 18,19 , though the position of the sugar residue been reported to increase sexual ability in males. The was not defined. evaluation is based on real experience and collective Two digitalis glycosides, corchoroside A 2 {m p information from the local people who used them in o 20 o 188-90 , [ α]D = +11 (MeOH)} and corchoroside B their daily routine 5. 20 0 20 o 15 {m p 222-24 [ α]D = +68 }, were isolated re- In view of the important medicinal properties at- spectively from C. capsularis and C. olitorius . Both tributed to this genus, this paper presents a compre- showed similar colour reactions. A monoglucoside 21-24 hensive review giving chemical constituents (Table 1) of corchoroside A from C. olitorius , a diglucoside and and the biological activities of Corchorus , besides a triglucoside 25 of corchoroside A were also identified structures of the compounds, wherever known in seeds of C. capsularis . Monoglucoside of corchor- (Chart 1). oside A was named as olitoriside 3 26 . Seeds of C. acutangulus yield helveticoside 4, cor- Cardiac Glycosides, their Aglycones and a few Un- choroside A 2 and an uncharacterized glycoside A (m characterized Glycosides/Aglycones o p 155-60 ), which on hydrolysis gave the sugar digi- Several glycosidic compounds, referred to as cor- toxose 9 while the aglycone part remained uncharac- chorin, were isolated from different Corchorus spe- terized. An amorphous mixture of a glycoside, which —————— on mild hydrolysis followed by chromatography gave *Author for correspondence Tel: 91-11-26059686-88/extn 5890; Fax: 91-11-26059663 strophanthidin 1 and strophanthidol 10 , was also ob- E-mail: [email protected] tained. The sugar part (paper and TLC examination) 284 J SCI IND RES VOL 65 APRIL 2006 Table 1 Chemistry of Corchorus Species Sr No Corchorus Species Compounds isolated References Cardiac glycosides 1 C. capsularis 2, 15 (seeds) 20 Strophanthidin glycoside (seeds), 31b capsulasone, corchorol, Capsularol (leaves) 44 2 C. olitorius 2,15 (seeds) 20 3 (seeds) 26 Strophanthidin trioside (seeds) 31a Coroloside, deglycocoroloside (seeds) 32 6, 7, 8, 13 (seeds) 33, 34 16-20 (seeds) 35 3 C. acutangulus 2, 4 (seeds) 27 3, 5 (seeds) 30 4 C. trilocularis 14,15 (seeds) 43 Triterpenes 5 C. capsularis 21 (roots) 49a 25, 26, Oxo-corocin (roots) 50 35, 36 (leaves) 59, 60, 61 6 C. olitorius 21 (roots) 49a 25, 26, Oxo-corocin (roots) 50 25a (leaves) 51 7 C. acutangulus 27, 28, 29, 30 (aerial parts) 52, 53 8 C. fascicularis 31 (whole plant) 54 9 C. depressus 22, 23, 24 (whole plant) 55 32, 33 (whole plant) 56 Depressosides C & D 57 34, Depressoside F 58 10 C. trilocularis 37, 38, 39 (whole plant) 62 Ionones 11 C. olitorius 40, 41, 42, 43, 44 (leaves) 63 Phenolics 12 C. capsulari 45, 46 (bark) 64 46 (leaves) 64 13 C. acutangulus 47 (whole plant) 65 14 C. depressus 47, 48 (leaves & flowers) 66 49, 50 (whole plant 55 56, 57 (whole plant) 58 15 C. olitorius 51, 52 (leaves) 63 53, 54, 55 (leaves) 51, 67 58, 59 (leaves) 63 60, 61 (leaves) 63, 67 62 (seeds) 68 (Contd ) KHAN et al : REVIEW ON THE CHEMISTRY AND PHARMACOLOGY OF CORCHORUS SPECIES 285 Table 1 Chemistry of Corchorus Species —Contd Sr No Corchorus Species Compounds isolated References Sterols 16 C. capsularis 63 (seeds, leaves, roots) 69, 44, 46, 49a 64 (leaves) 44, 70 17 C. olitorius 63 (roots) 49a 64 (leaves) 51 18 C. depressus 64 (whole plant) 55 19 C. fascicularis 63 54 Fatty acids 20 C. olitorius 65,66,67,68,69,70 (leaves) 70 Glyceryl monopalmitate (leaves) 51 was found to be a mixture of digitoxose 9 and boivi- narigenin 3-O-β-D-glucopyranosyl-(1 →4)-O-β-D- nose 11 along with another uncharacterized fast mov- allomethylpyranose/altromethylopyranose 13 , canno- ing sugar possibly 2,6-di-deoxy monomethoxy hex- genol 3-O-β-D-glucopyranosyl-(1 →4)-O-β-D-boivi- 27 28 ose . Loshkarev reconfirmed the presence of cor- nopyranoside 6, periplogenin 3-O-β-D-gluco- choroside A in the seeds of C. olitorius . An extract of pyranosyl-(1 →4)-O-β-D-digitoxopyranoside 7 and the seeds of C. olitorius and C. capsularis , after en- digitoxigenin 3-O-β-D-glucopyranosyl-(1 →6)- O-β- zymic hydrolysis, gave a fair yield of corchoroside A, D-glucopyranosyl-(1 →4)- O-β-D-digitoxopyranoside while this extract without enzymic treatment gave a 29 8 and some new cardiotonic oligoglycosides corcho- lower yield of the expected product 2 . Two other 36 30 rusosides A-E 16-20 . C. olitorius seeds from Japan polar glycosides isolated from seeds of C. acutan- contained cardiac glycosides (approx 1.0% level wet gulus were identified as olitoriside ( 3, m p 205-08 o) o weight). The dark greyish green seeds contained more and erysimoside ( 5, m p 178-82 ). The structures of cardiac glycosides as compared to the dark greyish these compounds were determined based on chemical yellow or yellowish green seeds. The methanolic ex- and IR spectral data, the sugars were characterized by tract of seeds gave digitoxigenin glycosides, coro- paper chromatography. Seeds of C. olitorius , besides loside and glucoevatromonoside, as well as strophan- erysimoside, gave a cardenolide glycoside, trioside of thidin glycosides, erysimoside, olitoriside, corchor- strophanthidin, having a structure identical with the 31a oside A and helveticoside, as the main cardiac gly- polar glycoside of C. capsularis . cosides. Seeds of C. capsularis gave a polar glycoside 31b , Chloroform - butanol (1:3) fractions from the O-D- glucopyranosyl-β-(1 →3)-O-D- glucopyranosyl 37 β-(1 →4)-D- boivinopyranosyl-β-(1 →3)- strophan- seeds of C. capsularis yielded polar glycosides A thidin. Energetic hydrolysis yielded glucose and no and B. Chloroform - alcohol (2:1) extracted residue other hexose or pentose, whereas mild acid hydrolysis gave glycoside B and a new polar glycoside C. Com- provided strophanthidin as an aglycone. Controlled parison with an authentic sample showed glycoside A enzymic hydrolysis with β-glucosidase gave olito- to be erysimoside, which had not previously been re- ribiose, glucose and boivinose, suggesting the sugar ported from C. capsularis seeds. Glycoside C crystal- residue to be gluco-olitoribiose. Complete enzymic lized from isopropanol-methanol-ether, m p 200- hydrolysis of the product gave corchoroside A sug- 10°/218-25° and was not identical with any com- gesting that the glycoside is a higher homologue of pound isolated earlier from any Corchorus species. 38 corchoroside A. The periodate oxidation studies sug- Fermented seeds of C. hirtus gave strophanthidin gested that the nature of the linkage of glucose units is heterosides, glycosides a, b, c and d. Glycoside c was 1→3- β- linkage (laminaribiose residue). Lami- found to have boivinose 11 however a, b, and d were naribiose residues were found for the first time as part found to have boivinose and glucose as sugars. Petro- 39 of the cardiac glycosides 31b . leum ether extracted seeds of C. capsularis and C. 0 Seeds 32-35 of C. olitorius gave glycosides, coro- olitorius gave helveticoside ( 4, m p 168-71 , 20 0 loside and deglycocoroloside, cardiac glucosides, ca- [α]D =+31.9 ± 2 ). Its structure was confirmed by 286 J SCI IND RES VOL 65 APRIL 2006 chemical and IR spectral data. Seeds 40 of C. capsu- KHAN et al : REVIEW ON THE CHEMISTRY AND PHARMACOLOGY OF CORCHORUS SPECIES 287 288 J SCI IND RES VOL 65 APRIL 2006 KHAN et al : REVIEW ON THE CHEMISTRY AND PHARMACOLOGY OF CORCHORUS SPECIES 289 290 J SCI IND RES VOL 65 APRIL 2006 KHAN et al : REVIEW ON THE CHEMISTRY AND PHARMACOLOGY OF CORCHORUS SPECIES 291 292 J SCI IND RES VOL 65 APRIL 2006 (61 ) 3,5-Dicaffeoylquinic acid (62 ) 4,7-dihydroxycoumarin KHAN et al : REVIEW ON THE CHEMISTRY AND PHARMACOLOGY OF CORCHORUS SPECIES 293 laris on autofermentation followed by extraction with dianhydroperiplogenin 12 and canarigenin 13 , which methanol gave monosides corchoroside A 2 and might be artifacts.
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