Phytochemistry and Pharmacology of Indian Medicinal
Plants Zizyphus Mauritiana Lamk
Nikhat
F*, D Satyanarayana and Subhramanyam EVS
Department of Pharmaceutical
Chemistry Nitte, Gulabi, Shetty, Memorial,
ABSTRACT
The object of this review is
to highlight the importance of multipurpose indigenous plant Zizyphus mauritiana Lamk Belonging to
the family Rhamnaceae . It has been used for centuries as folk remedy in
Keywords: Zizyphus mauritiana Lamk, Rhamunaceae,
antidiabetic, antioxidant, anti-inflammatory,
alkaloids, Glycoside, flavanoids, triterpinoides,
steroids.
INTRODUCTION
The subject of Phytochemistry
or plant chemistry has undergone the significant development in recent year as
distinct discipline is concerned with the enormous verity of substances that
are synthesis and accumulated by plant and structural elucidation of substance.
The technology involves extraction isolation purification and characterization
of phytoconstetuent1. The observation of visible effect of plant
extract on intact animal can gives information of their pharmacological
activity and possible uses is called Phyto-pharmacological
study. As result of rapid development of phytochemistry
and pharmacology listing method in recent year, new plant drugs are finding
their way into medicine as purified phytochemicals
rather than in the form of traditional and galanical
preparation, the knowledge of Phytochemistry and pharmacology is very important
to understand the action of plant constituent on animal and human system2.
Zizyphus mauritiniana Lamk (syn; Z. jujuba (L.) Lam.Z. jujuba (L.) Gaertn.
(including var. stenocarpa Kuntze and forma aequilatrifolia
Engl.) Z. tomentosa Poir.Z. rotundata D.C.
Z. aucheri Boiss.
Z. insularis Smith Z. sororia Roem. and Schult. Z. orthocantha D.C.)
The species has a wide range of morphologies from
shrubs to small or mediumsized trees which might be
erect, semi-erect or spreading. Height can vary from 3-4 to 10-16 m or more
although trees of 20 m are rare. Trees are semi-deciduous and much branched.
The bark has deep longitudinal furrows and is greyish
brown or reddish in colour. Usually the shrub or tree
is spinous, but occasionally unarmed.
Branchlets are densely white pubescent, especially when young and
tend to be zig-zag. Branches erect and spreading,
becoming flexuous and dull browngrey. Fruiting
branches are not deciduous.
Leaf laminae are elliptic to ovate or nearly
orbicular, (1.3-)3-8(-12) cm long and (0.4-)1.5-5(-6.5) cm at the widest point.
The apex is rounded, obtuse or subacute to
emarginated, the base rounded, sometimes cuneate, mostly
symmetrical or nearly so.
Margins are
minutely serrulate. There are 3 marked nerves almost
to the apex, the nerves being depressed in the upper, light or dark green,
glabrous surface. Lower surface is whitish due to persistent dense hairs but
may be buff coloured. Occasionally the lower surface
is glabrous.
Leaves are petiolate 1.1-5.8 mm long and stipules are mostly spines,
in each pair one hooked and one straight, or both hooked, or more rarely
neither developed into a spine.
Flowers have
sepals which are dorsally tomentose, a disk about 3
mm in diameter and a 2-celled ovary, immersed in the disk. Styles are 2, 1 mm
long and connate for half their length. Flowers tend to have an acrid smell.
Flowers are borne
in cymes or small axillary clusters. Cymes can be
sessile or shortly pedunculate, peduncles 1-4 mm tomentose. Pedicels are also tomentose
and are 2-4 mm at flowering and 3-6 mm at fruiting.
Fruit is a
glabrous globose or oval edible drupe varying greatly
in size from (1-) 1.5 (-2) cm diameter but some oval varieties can reach 5 x 3
cm. The pulp is acidic and sweet, the fruit greenish, yellow or sometimes
reddish.
The species is
distributed throughout the warm subtropics and tropics of
The intraspecific taxa described are
not very meaningful in view of this tendency to naturalise
and produce wild heterogeneous populations. Several varietal names have been
given to wild morphotypes. One variety, Z. mauritiana var. orthocantha
(D.C.) A. Cher. is found south of the western Sahara and in
Phytochemistry:
The fruit pulp of ziziphus mauritiana lamk was reach in
nutrients4,5 The
richness of the pulp in nutritive compounds has been widely recognized. Nonetheless there are no definitive values
for pulp composition. However ber is richer than apple in protein,
phosphorus, calcium, carotene and Vitamin C6 and oranges in
phosphorus, iron, vitamin C and carbohydrates
and exceeds them in calorific value. Ripe fruits provide 20.9 Calories per 100
g of pulp7 (Singh et al., 1973a). In terms of carbohydrates,
pulp contains 12.8 – 13.6 % of which 5.6 % is sucrose, 1.5 % glucose, 2.1 %
fructose and 1 % starch. Total sugars content is markedly different according
to cultivar8,9,10. The amino acids asparagine,
aspartic acid, glycine, glutamic
acid, serine, áserine and threonine,
are found in the pulp11 but not many analyses or comparisons have been made. Major interest has focused on
Vitamin C content and ber pulp is considered a rich
source. Content ranges from 70-165 mg/100 g12 . The FAO and WHO recommendation13that
the daily intake for an adult man should be 30 mg, illustrates the value of ber pulp in the diet. Pulp contains about 70 IU Vitamin A
/100 g and the ß-carotene content ranges from 75 to more than 80 mg/100 g14.
Ascorbic acid,
thiamine, riboflavin and bioflavonoids:
Ziziphus jujuba fruits are very rich in vitamins C and B1
(thiamine) and B2 (riboflavin)15,16.
Compared with ber, one fruit per day would meet the diet requirements for
Vitamin C and Vitamin B complex of an adult man recommended by FAO/WHO. It is
also known to have a high Vitamin P (bioflavonoid) content. In some fruits17
Baratov et al., (1975) reported 188 to 544 mg
Vitamin C and 354 to 888 mg Vitamin P per 100 g pulp. It was also reported that even higher contents of Vitamin
C (up to 811 mg/100 g) and vitamin P (up to 1230 mg/100 g). Vitamin P (bioflavonoids) enhances the action of Vitamin C. Vitamin C
and Vitamin P also act together to help maintain the thin walls of capillaries18,19.
Vitamin P also has antibacterial, anti inflammatory and antioxidant properties,
and is known to stimulate bile production, promote circulation and prevent
allergies20.
Pectin A:
Pectin A was
isolated21 from Z. jujuba fruit.
Pectin A was found to contain 2,3,6-tri-o-acetyl D lactose units. Pectin has a
number of pharmaceutical properties such as binding bile acid, lowering plasma
cholesterol and anti diarrhoeal properties22
.
Alkaloids:
Stem bark of Ziziphus species contain alkaloids23.
A sapogenin, zizogenin has
been isolated from Z. mauritiana stems24.
The cyclic peptide alkaloids, mauritine-A, mucronine-D, amphibine-H, nummularine-A and –B25(Tschesche
et al., 1976), sativanine-A and sativanine-B, frangulanine, nummularine-B and mucronine were isolated
from the bark of Z. jujuba 26. Also
some cyclic peptide alkaloids are
isolated that are sativanine-C, sativanine-G,
sativanine-E, sativanine-H,
sativanine-F, sativanine-D
and sativanine-K from Z. jujuba
stem bark. The alkaloids coclaurine, isoboldine, norisoboldine27,other constituent
like asimilobine, iusiphine
and iusirine were isolated from Z. jujuba leaves28. Cyclopeptide
and peptide alkaloids from Z. jujuba were
found to show sedative effects29. The seeds of Z. jujuba var. spinosa
also contain cyclic peptide alkaloids sanjoinenine,
franguloine and amphibine-D
and four peptide alkaloids; sanjoinine-B-D-F and -G230.
The seeds are used in Chinese medicine as a sedative. Chemical studies of Z.
mauritiana led to the isolation of the cyclopeptide alkaloids, mauritines
A and B; C-F, G and H, frangufoline; amphibines D, E, B and F; hysodricanin-A,
scutianin-F and aralionin-C31. The cyclopeptide alkaloid, mauritine
J, was isolated from the root bark of Z. mauritiana32.
Glycosides:
Flavonoid
glycosides/spinosins:
The new spinosin (2”-O- beta
–glucosylswertisin) extracted from Z. jujuba var. spinosa
seed. and later it cne be presented as three acylated flavone-C-glycosides
(6’’’-sinapoylspinosin, 6’’’-feruloylspinosin and 6’’’-p-coumaroylspinosin)33.
All showed mild sedative activity in pharmacological tests discovered a new flavonoid, named zivulgarin,
compound (4-beta-D-glycopyranosyl swetisin)34.
Structure of isolated
constituents of Zizyphus mauritiana Lamk
Glycosides/saponins:
The glycoside saponin is found in the seeds, leaf and stem of Z.
jujube35. Saponins are part of sugar chains which attach themselves
to a sterol or triterpene. They are known to bind
with cholesterol preventing it from being reabsorbed into the system.
They are being widely researched for cancer prevention and cholesterol
control.. The saponins isolated from
the seeds of Z .jujuba include jujubosides A, B,A1 B1 and C and acetyljujuboside
B36 and the protojujubosides A, B and B137.extracted
the saponin, ziziphin, from
the dried leaves of Z. jujuba. It has a
structure, 3-O-a-L-rhamnopyranosyl
(1-2)-a-Larabinopyranosyl-20-O-(2,3)-di-O-acetyl-a-L-rhamnopyranosyl38
jujubogenin.
Triterpenoic
acids:
The following triterpenoic acids have been isolated from the fruits of Z.
jujuba: colubrinic
acid, alphitolic acid, 3-O-cis-p-coumaroylalphitolic
acid, 3-O-transp- coumaroylalphitolic acid,
3-O-cis-p-coumaroylmaslinic acid, 3-O-trans-pcoumaroylmaslinic acid, oleanolic acid, betulonic acid, oleanonic acid, zizyberenalic
acid and betulinic acid39. Triterpenoic acids has been extracted from roots of Z. mauritiana shown cytotoxic
effects40 .
Betulinic
acid:
Betulinic acid is a naturally occurring pentacyclic triterpenoid which
has demonstrated selective cytotoxicity against a
number of specific tumour types. It has been found to
selectively kill human melanoma cells while leaving healthy cells alive41
,
Lipids:
Both the pericarp and the seeds of Z. jujuba
contain two main classes of phospholipids: phosphatidylcholines
and phosphatidylglycerols. Oleic acid is present in
the fatty oil of the seeds42. Bioactivity guided fractionation of
petroleum ether- EtOAc- and soluble extracts of the
seeds of Z. jujuba indicated that the
triglyceride, 1,3-di-O-[9(Z)-octadecenoyl]-
2-O-[9(Z),12(Z)-octadecadienoyl] glycerol, and a
fatty acid mixture of linoleic, oleic and stearic acids, were the major active components of the seed
oil43.
Pharmacology:
Although Zizyphus mauritiana Lamk has been prescribed in various complication including haemoptysis, menstruarl and other
vaginal disorders, diuretic stomachic ,laxative. In folklore system of medicine
but scientific profile of efficacy is still lacking.
Neurological
properties:
Hypnotic-sedative
and anxiolytic effect:
The seeds and
leaves of many Ziziphus species have
been found to have anxiolytic and hypnotic-sedative
effects. They are known to depress activity of the central nervous system which
reduces anxiety and induces sleep. Saponins and flavonoids from Z. jujuba seeds
were examined for sedative activity. All compounds tested showed sedative and
hypnotic effects. Swertisin, the most potent compound
was tested for type of action. It was found that it produced sleep, but was not
anticonvulsant or muscle relaxant44. Alkaloids from Z. jujuba were also found to show sedative activity. Both sanjoinine A and nuciferine
prolonged the sleeping time produced by hexobarbital.
When sanjoinine was heated it was found to produce an
isomer of even greater sedative effect45.
2.4.4.2
Cognitive activities:
The oleamide, a component of Z. jujuba
extract, could be a useful chemo-preventative agent against Alzheimer’s
disease. They found that methanolic Z. jujuba showed 34.1 % activation effect on choline acetyltransferase in
vitro, an enzyme that controls the production of acetylcholine which
appears to be depleted in the brains of Alzheimer patients. Using
sequential fractionation the active ingredient was found to be
cis-9-octadecenoamide (oleamide) which showed 65%
activation effect. Administration of oleamide to mice
significantly reversed the scopolamineinduced memory
and/or cognitive impairment in the passive avoidance test and Y maze test. Mice
treated with oleamide before scopolamine injections
were protected from the effects46.
Antidiabetic:
Extract of Z. mauritiana was found to have anti-diabetic activity in Wistar rats47
Antioxidant
effects:
Z. jujuba extract
showed a relatively strong antioxidative activity48.
Antiinflammatory effect:
The constituent
present in the fruit of Z. jujuba showed marked anti-inflammatory effect49.
Z. mauritiana leaf extracts were found to
possess significant anti-inflammatory activity against carrageenan-induced rat paw oedema50.
Antifertility/contraception:
The ethyl acetate
extract of Z. jujuba bark was found to effect antisteroidogenic activity and hence fertility in adult
female mice. It was found to arrest the normal oestrus
cycle of adult female mice at diestrus stage and
reduced the wet weight of ovaries significantly. Haematological
profiles, biochemical estimations of whole blood and serum remained unaltered
in extract-treated mice. Normal oestrus cycle and
ovarian steroidogenisis were restored after
withdrawal of treatment. Antifertility activities of
crude extracts were found to be reversible51.
Hypotensive
and antinephritic effect:
Ziziphus jujuba has
been found to stimulate nitric oxide release in vitro, in cultured
endothelial cells and in vivo, in the kidney tissues of rats53.
The effects of Z. jujuba on nitric oxide
release in the kidney may contribute to its hypotensive
(reduction of blood pressure) and antinephritic
(reduction of inflammation of the kidney) action, possibly by increasing renal
blood flow.
2.4.7
Cardiovascular activity:
A neo-lignan isolated from Z. mauritiana leaves was found to increase the release of
endogenous prostaglandin I2 (the most potent natural inhibitor of platelet
aggregation yet discovered and a powerful vasodilator) from the rat aorta by up
to 25.3 % at 3 micro g/ml54.
2.4.8 Immunostimulant effects:
The leaf extract
of Z. jujuba was found to stimulate chemotactic, phagocytic and
intracellular killing potency of human neutrophils
(infection fighting white blood cells) at 5-50 micro g/ml55.
2.4.9 Antifungal
activity:
Z. jujuba has
been found to show antifungal effects. Ethanol extract from the root showed
significant inhibitory activity on the fungi Candida albicans,
C. tropicalis, Aspergillus
flavus, A.
CONCLUSION:
For centuries, indigenous drugs
either alone or in combination have been advocated in the traditional system of
medicine for the treatment of various ailments.
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Accepted on 10.11.2008
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