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Pandey M. B, Rai N, Singh A. K. Constituents of Zizyphus Species: A Review. Biosci Biotech Res Asia 2006;3(2a).
Manuscript received on : July 13, 2006
Manuscript accepted on : October 04, 2006
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Constituents of Zizyphus Species: A Review

M. B. Pandey, Nisha Rai and A.K. Singh

Department of Chemistry, S.G.R. Post Graduate College, Dobhi Purvanchal University, Jaunpur - 222 149 (India) Department of Medicinal Chemistry, Institute of Medical Science, Banaras Hindu University, Varanasi - 221 005 India  

ABSTRACT: Most of the Zizyphus species available in India finds use system of medicine for the treatment of scabies, throat troubles, skin diseases, abdominal pain, diarrhoea, dysentery, healing of wounds, colds, coughs, bilious affection and also as an important source of the fruit. In view of this, a review on chemical constituents has been presented upto the year 2003 which may be of great help to the workers in this area.

KEYWORDS: Zizyphus species.

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Introduction

The Zizyphus species of family Rhamnaceae are evergreen trees and shrubs distributed in wild states1. Around 50 species are growing in tropical and sub-tropical regions of the worlds of which 17 species are found in India1,2.

The freshly drupes of several species are eaten, Z. mauritiana is a source of one of the common fruits (Ber) in India and is found in both wild and cultivated states. The fruits has a high nutritional value and a great commercial potential. Z. jujuba Mill. Is the Chinese plant and the correct name of the Indian plant mentioned in most Indian floras as Z. jujuba Lam., a later homonym is Z.mauritiana. Lam. The fruits have been in cultivation for the last 400 years in both China and India1.

There are two main groups of Jujubes found in India: (i) The Chinese jujube (Z. jujuba Mill.) and (ii) the Indian of jujubes of which Z. mauritiana, with its several cultivated varieties, is important as a source of the fruits which are said to excel even apples in their content of protein, carotene and vitamin C, while another species, Z. nummularia is a prized for its leaves which provide fodder for livestock in summer moths, particularly in the folder-deficient areas of Punjab, Haryana and Rajasthan1.

Most of the Zizyphus species available in India finds use in Indian System of Medicine for the treatment of scabies, throat troubles, skin diseases, abdominal pain, diarrhoea, dysentery, healing of wounds, colds, coughs, bilious affections and also as tonic3,4. The seed of the Zizyphus species were evaluated pharmacologically, which revealed the central nervous system depressant activity, tranquilising and sedative activities5. The flavonoids and saponins isolated from Zizyphus species have shown neuroleptic activity by neurol deficit but do not have anticonvulsant or muscle relaxant activity6. The seeds of Zizyphus jujuba have exhibited sedative activity, which has been used since ancient times in medicine as a remedy for insomnia, and sleepiness must derive mainly to totally from the jujubogenin glycoside7.

It is reported that Zizyphus species contains considerable amount of cyclopeptide alkaloids and these alkaloids have antibiotic and antifungal properties. The use of Zizyphus species in the treatment of diarrhoea, dysentery, skin diseases and healing of wounds are well supported by the presence of these alkaloids270.

A review of literature revealed the presence of a number of cylcopeptide alkaloids, isoquinoline alkaloids, flavonoids, steroids, terpenoids and many other chemical constituents from different Zizyphus species. The chemical investigation of as many as 22 species of Zizyphus genus as mentioned below in Table -1 has been reported so far.

Zizyphus species are found to be a rich source of cyclopeptide alkaloids. A list of cyclopeptide alkaloids that have so far been isolated from different Zizyphus species are thus listed in Table -2 and other chemical constituents are listed in Table -3.

Table 1:

1 Zizyphus abyssinica Hoechst. Ex A. Rich
2 Z. amphibia A. Cheval
3 Z. hysodrica
4 Z hutchinsonii.
5 Z. joazeiro Mart.
6 Z. jujuba Mill.
7 Z. lotus
8 Z. mauritiana Lam.
9 Z. murcronata Willd.
10 Z. nummularia Wight and Arn.
11 Z. oenoplea Mill.
12 Z. rugosa Lam.
13 Z sativa Gaerrn.
14 Z. spina-christi.
15 Z. spinosus Semen
16 Z. trinervia  Roxb.
17 Z. vulgaris Lam.
18 Z. xylopyra Willd.
19 Z. rotundifolia
20 Z. obstusfolia
21 Z. mistol
22 Z. acidojujuba


Table 2: Cyclopeptide alkaloids reported from Zizyphus species

Name of the Plant source Name of the cyclopeptide alkaloids Plant source (References)
Zizyphine-A Z. oenoplia20,22,40 Mucronine-D Z. mucronata38,116,125
Z. jujuba129 Z. mummularia50
Z. jujuba57,132
Z. sativa69,93
Zizphine-B Z. enoplia20,31,40,44 Amphibine-F Z. spina-christi53
(Zizphinine) Z. mauritiaan47
Z. amphibia41
Amphibine-A Z. amphibia34 Amphibine – G Z. amphibia41
Z.spina-christi52
Amphibine-H Z. amphibia41
Z. mummularia50
Z. jujuba57
Amphibine-B Z.amphibia35 Z. xlopyra100
Z.mauritiana47 Z. spina-christi110,133
Z.oneoplia123
Amphibine-I Z. amphibia43,134
Amphibine-C Z.amphibia35
Murcronine-E Z. mucronata44
Amphibine-D Z.amphibia35 Murcronine-F Z. mucronata44
Z.mauritiana36,47 Murcronine-G mucronata44
Z.rugosa75
Z.vulgaris var. spinous109   
Amphibine-E Z. amphibia35,36 Zizyphine-C Z. oenoplia50
Z. mauritiana47
Z. spina-christi52 Zizyphine-D Z. oenoplia50
Mauritine-A Z. mauritiana36 Zizyphine-E Z. spina-christi110
Z. spina-christi52
Z. jujuba57 Zizyphine-F Z. oenoplia51
Z. spina-christi110
Mauritine-B Z. mauritiana36
Zizyphine-G Z. oenoplia51
Frangulanine Z. mauritiana36 Nummularine-D Z. nummularia55
Z. sativa93
Z. vurgaris Nummularine-E Z. nummularia55,105
var. spinousus99,101,109 Z. hysodrica75
Z. spinosus semen99
Z. jujuba100,102,132 Nummularine-F Z. nummularia55
Z. nummularia100
Z. lotus 122 Jubanine-A Z. jujba57
Z. oenoplia123,136 Z. spira-christi110
Z. nummularia91
Frangulanine Z. jujuba45,132 Abyssenine-C Z. abyssinica44
Z. sativa69 Z. mucronata48
Maruitine-D Z. mauritiana47 Sativanine-F Z. sativa90,93
Z. xylopyra95
Z. nummularia97 N-desmethyl- Z. nummularia91
Z. oenoplia123 jubanine-B
Marutine-E Z. mauritinana47 Nummularine-O Z. nummularia92
Marutine-F Z. mauritiana47 Sativanine-H Z. sativa94
Z. rugosa108
Nummularine-A Z. nummularia49
Z. jujuba57 Nummularine-P Z. nummularia97
Z. rugosa108
Nummularine-B Z. nummulaira49,86
Z. jujuba57,132 Rugosanine-A Z. rugosa103
Z. sativa69,93
Z. xylopyra95 Daechunie-S3 Z. jujuba107,132
Nummularine-C Z. nummularia49,132 Daechuine-S8-1 Z. jujuba107,132
Nummularine-G Z. nummularia61 Numularine-T Z. nummularia118
Nummularine-H Z. nummularia61 Sativanine-G Z. sativa87,93
Nummularine-K Z. nummularia61 Tscheschamine Z. sativa106
Z. xylopyra100
Daechuine-S6 Z. jujuba107,132
Five known Z. jujuba67
cylclopetide alkaloids Daechuine-S7 Z. jujuba 107,132
Daechuine-S10 Z. jujuba107,132
Sativanine-A Z. sativa69,93 Sajoinine-B Z. vulgaris var. spinosus99,109
Z. spina-christi96 Z. spinsosus Semen99
Sativanine-B Z. sativa69,93,137
Known 13- Z. jujuba76 Sanjoinine-F Z. vulgaris var, spinosus99,109
Membered Z. lotus122
cyclopeptide alkaloids
Daechunine-S5 Z. jujuba107,132
Daechuine-S15 Z. jujuba132
Lotusanine-A Z. lotus122
Sativanine-C Z. sativa85,93
Scutianine-C Z. jujuba129
Nummularine-N Z. nummularia86 Sanjoinenine Z. vulgaris var. spinosus99,109
Z. spinsosus Semen99
Sativanine-E Z. sativa88,93 Z. lotus122
Sativanine-D Z. sativa88,93
Sativanine-K Z. sativa98 Spinanine Z. spina-christi110
Nummularine-R Z. nummularia100 Nummularine-S Z. nummularia104
Two new Z. mucronata116 Hysodricanine-B Z. hysodrica112
cyclopetide alkaloids Hysodricanine-C Z. hysodrica128
Nummularine-M Z. nummularia86 Sanjoinine-Ah Z. jujuba113
1 Z. vulgaris var. spinosus113
(epimer of
Sanjoinine-A)
Franganine Z. spina-christi96
Z. jujuba132 Jubanine-C Z. jujuba115
Lotusine-A Z. lotus114,130
New cyclopeptide Z. jujuba115
Lotusine-D Z. lotus114,130 alkaloid
Mucronine-J Z.mucronata125 New 13-membered Z. oenoplia121
cyclopetide alkaloid
Lotusine-G Z. lotus130
Lotusein-B Z. lotus117,130 Lotusine-F Z. lotus117
Lotusien-C Z. lotus117,130 Sanjoinine-D Z. vulgaris var, spinosus99,109
Z. spinosus Semen99,111
Mauritine-J Z. mauritiana124
Daechuine-S24 Z. jujuba132 Sanjoinine-G Z. vulgaris var, spinosus99,109
Z. spinosus Semen99
Lotusine-E Z. lotus117,130
Jlubanine-D Z. jujuba120 Sanjonine-G2 Z. vulgaris var, spinosus99,109
Z. spinosus Semen99
Z. lotus122
Zizyphin-I Z. oenoplia119 Sanjoinine-A Z. vulgaris var, spinosus101,107
Jubanine-C Z. jujuba129 Z. jujuba127Z. spinosus Semen99
Lotusanine-B Z. louts122 Jubanine-B Z. jujuba57
Z. nummularia91,92
Deachucyclopeptide-1 Z. jujuba102,107,132
(Daechuine-S26)
Mucronine-A Z. muconata37 Hysodricanine-A Z. hysodrica58
Z. abyssininca44 Z. hutchinsonii75
Mucronine-B Z. mucronata37
Z. abyssinica44 Mauritine-H Z. mauritiana58
Mucronine-C Z. mucronata37 Sanjoinine-G1 Z. vulgaris var, spinosus126
Rugosanine-B Z. rugosa108 Abyssenine-A Z. abyssinica44
Z. mucronata48,125
Mauritine-C Z. mauritiana47 Z. oenoplia50
Z. spina-christi52,96
Z. nummularia91 Abyssenine-B Z. abyssinica44
Z. mucronata48
Aduetine Z. jujuba45,132 Z. oenoplia50
Table - 3: Chemical constituents, other than Cyclopeptide alkaloids reported from Zizyphus species Table 3: Chemical constituents, other than Cyclopeptide alkaloids reported from Zizyphus species
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