Natural sweeteners: A complete review

Abstract

Two types of sweeteners are available: natural sweeteners of plant origin and artificial or synthetic sweeteners. Sweetening agents either evoke sweet taste or enhance the perception of sweet taste. Natural sweetening agents are preferred over synthetic sweetening agents since they do not have any adverse impact on health. Non-saccharide natural sweetening agents are low calorific, nontoxic and super sweet (100 to 10,000 times sweeter than sugar) in nature and can overcome the problems of sucrose and synthetic sweeteners. Natural sweeteners are useful sugar substitutes for diabetic patients. The active sweet principles stored in plants can be grouped under: terpenoids, steroidal saponins, dihydroisocoumarins, dihydrochalcones, proteins, polyols, volatile oils, etc. in nature. Common and scientific names of these sweeteners along with their properties, chemical structure of sweet principles, pharmaceutical uses have been presented in this paper.

Full text

Journal of Pharmacy Research Vol.4.Issue 7. July 2011
Keerthi Priya et al. / Journal of Pharmacy Research 2011,4(7),2034-2039
2034-2039
Review Article
ISSN: 0974-6943 Available online through
http://jprsolutions.info
*Corresponding author.
Keerthi Priya
Research Scientist- FR&D
Daewoong Pharmaceutical co. Ltd.
Andhraprdesh, India- 502313.
Natural Sweeteners : A Complete Review
Keerthi Priya*, Dr.Vankadari Rama Mohan Gupta, Kalakoti Srikanth
Daewoong Pharmaceutical Co. Ltd. Balanagar,Hyderabad-500 037, Andhraprdesh, India
Received on: 12-04-2011; Revised on: 18-05-2011; Accepted on:21-06-2011
ABSTRACT
Two types of sweeteners are available: natural sweeteners of plant origin and artificial or synthetic sweeteners. Sweetening agents either evoke sweet taste or
enhance the perception of sweet taste. Natural sweetening agents are preferred over synthetic sweetening agents since they do not have any adverse impact
on health. Non-saccharide natural sweetening agents are low calorific, nontoxic and super sweet (100 to 10,000 times sweeter than sugar) in nature and can
overcome the problems of sucrose and synthetic sweeteners. Natural sweeteners are useful sugar substitutes for diabetic patients. The active sweet principles
stored in plants can be grouped under: terpenoids, steroidal saponins, dihydroisocoumarins, dihydrochalcones, proteins, polyols, volatile oils, etc. in nature.
Common and scientific names of these sweeteners along with their properties, chemical structure of sweet principles, pharmaceutical uses have been presented
in this paper.
Key words: Natural sweetening agents, Saccharide sweeteners, Non-saccharide sweeteners. Terpenoids, Polyols
3.Sugar is also employed in the coating of pills and tablets
4.Honey plays an important role in Ayurvedic system of medicine. It is used as
an important vehicle for many preparations
b. Food Industry
Sweetening agents are used to prepare jams, chocolates, sweets, ice-creams,
cakes, candies, juices, soft-drinks, beverages, chewing-gums and many other
food items.
Classification of Natural sweetening agents
The search for sugar substitutes from natural sources has led to the discovery
of several substances that possess an intensely sweet taste or taste-modifying
properties. About 150 plant materials have been found to taste sweet because
they contain large amounts of sugars and/or Polyols or other sweet constitu-
Sweetening Agents
Synthetic Sweetening Agents
Natural Sweetening Agents
Non-sacharides Sweetening Agents
.
Saccharides Sweetening Agents
eg. Sucrose,glucose, honey etc.
Terpenoids
Steroidal saponins
Proteins
Dihydrochalcones
Dihydroisocoumarins
Voletile oils
Polyols
INTRODUCTION
Preference for sweet taste at a range of intensities is characteristic of human
species. In the fetus, taste buds are developed by the 16th week of gestation, and
the new born infant is able to respond favorably to sweetened solutions. Sugar
is a natural sweetener that provides 4 calories per gram. It is acknowledged
that excess sugar ingestion amounts to increased energy intake which, in turn,
can lead to weight gain and chronic diseases associated with obesity and dental
caries. Therefore, there is need for sugar substitutes, which can help reduce
caloric intake, particularly in overweight individuals [1] The demand for new
alternative “low calorie” sweeteners for dietetic and diabetic purposes has
increased worldwide. As of mid-2002, over 100 plant-derived sweet com-
pounds of 20 major structural types had been reported, and were isolated from
more than 25 different families of green plants. Several of these highly sweet
natural products are marketed as sweeteners or flavouring agents in some
countries as pure compounds, compound mixtures, or refined extracts [2].
Many synthetic sweeteners, which are widely used are proved to be carcino-
genic and are non-nutritive. Hence demand greatly increased for natural sweet-
ening agents, especially for non-sacchariferous sweetening agents, because
they are highly potent, useful, safe and low-calorie sugar alternatives. Re-
cently it was found that Himalayan forests are good sources of plants contain-
ing non-saccharide sweetening agents.
Ideal properties of sweetening agents
Sweetening agents should have the following ideal properties
1. They are required to be effective when used in small concentration.
2. They must be stable at a wide range of temperature to which the
formulations are likely to be exposed.
3. Prolonged use of these agents containing preparations should not
produce any carcinogenic effects
4. They should have very low or non-calorific value.
5. They should be compatible with other ingredients in formulations.
6. They should not show batch to batch variations.
They should be readily available and inexpensive.
Uses of Natural Sweetening agents
a. Pharmaceutical uses
1.In pharmaceutical industries these are used in liquid, oral preparations, loz-
enges, pills and tablets.
2.In liquid orals sugar is used to prepare syrup base, to maintain the consis-
tency and viscosity of the preparation and to mask the bitter taste of the drug.
ents [3]. A schematic representation of the types of sweeteners and their origin
is given below.

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Table 1. Various sources for different natural sweetening agents
Plant Family Part Sweetening Principle Chemical Class Times Sweeter
than Sucrose
Abrus Precatoris Leguminosae Leaves,roots Abrusosides & glycyrrhizin Triterpene glycosides 30-100
Achras sapota Sapotaceae Latex and fruit Glycyrrhizin Triterpene glycosides 100
Baccharis gaudichaudiana Aerial parts Gaudichaudioside-A Diterpene Glycosides 100
Beta vulgaris Chenopodiaceae Roots Sucrose Disaccharide -
Cinnamomum osmophloeum Lauraceae Leaves trans-Cinnamaldehyde Aromatic aldehyde 50
Citrus aurantium Rutaceae Peels of the fruits Neohesperidin dihydrochalcone Dihydrochalcone 1000
Citrus limoni Rutaceae Peels of the fruits Hesperidin dihydrochalcone Dihydrochalcone 300
Citrus sinensis Rutaceae Peels of the fruits Hesperidin dihydrochalcone Dihydrochalcone 300
Citrus paradise Rutaceae Peels of the fruits Naringin dihydrochalcone Dihydrochalcone 1000
Cyclocarya palirus -Leaves Cyclocaryoside Steroidal saponins 250
Cynara scolymus Asteraceae Leaves & flowers Cynarin Protein -
Dioscoreophyllum Cuminsii Menispermaceae Fruit pulp Monellin Protein 2500
Eremophila glutinosa -Entire plant -Dihydroflavonols 400
Foeniculum vulgare Umbelliferae Fresh aerial Parts Trans-anethole Phenylpropanoid -
Glycyrrhiza glabra Leguminosae Roots and stolons Glycyrrhizin Triterpene glycosides 100
Hemsleya carnosiflora -Rhizomes Carnosiflosides-V,VI Triterpene glycosides -
Hydrangea macrophylla Saxifragaceae -Phyllodulcin Dihydroisocoumarin 300-400
Illicium verum Illiciceace Dried fruits Trans-anethole Phenyl propanoid -
Lippia dulcis Verbenaceae Herb Hernandulcin Sesquiterpene 1000-1500
Myrrhis odorata Apiaceae Fresh roots trans-Anethole Phenyl propanoid -
Osmorhiza longistylis Apiaceae Fresh roots trans-Anethole Phenyl propanoid -
Perilla frutescens Labiatae Leaves,seeds and Perillartine Monoterpenoid 400-2000
flowering tops
Periandra dulcis -Roots Periandrin VTriterpene glycosides 100-200
Piper marginatum Piperaceae Dried leaves trans-anethole Phenyl propanoid -
Polypodium glycyrrhiza Polypodiaceae Rhizomes Polypodoside Steroidal saponin glycosides 600
Polypodium vulgare Polypodiaceae Rhizomes Osladin Steroidal saponin glycosides 50-100
Pterocarya paliurus -Leaves and stem Pterocaryoside A&B Secodammaranoid saponin 50-100
Rubus suavissimus Rosaceae Leaves Rubusoside & Sauvioside ADiterpene glycosides -
Saccharum officinarum Poaceae Canes Sucrose Disaccharide -
Smilax glycyphylla Liliaceae All parts Glycyphyllin Dihydrochalcone glycosides 100-200
Staurogyne mergunsis -Leaves Strigin Steroidal saponin Glycosides -
Stevia rebaudiana Asteraceae Leaves Steviosides Tricyclicditerpenoid Glycosides 200-300
Siraltia grosvenorii Mogroside VTriterpene glycosides 250
Symplococos paniculata Symplocaceae Leaves Trilobatin Dihydrochalcone Glycosides 400-1000
Synsepalum dulcifucum Sapotaceae Fruits Miraculin Protein
Tessaria dodoneifolia Aerial parts Dihydroquercetin-3-O-Dihydroflavonol
acetate 4-(methyl ether)
Thamatococcus Marantaceae Aril of the fruit Thaumatin Protein 3000
SACCHARIDE SWEETENING AGENTS
Sucrose
The sucrose, derived from Sanskrit word Sarkara, was being extracted from
sugarcane in India, and has been identified about 6000-10,000 BC as mentioned
in Rig and Atharva Vedas. It was introduced in non-Asiatic continents by Alexander
the Great (c.325 BC) [4]. Sucrose is a Disaccharide sugar obtained mainly from
the cane juice of saccharum Officinarum (Graminae) [5] and and from the roots
of Beta Vulgaris (chenopodiaceae) [6]. Sucrose is most often prepared as a fine,
white crystalline powder with a pleasing, sweet taste. It consists of two monosac-
Figure 1. The structural and chemical formula of sucrose
Honey
Honey is a sugar secretion deposited in honeycombs by the bees Apis indica
(Indian Bee), Apis mellifera, Apis dorsata (Rock Bee) and other species of Apis
of family Apidae. Honey is the only sweetener obtained from animal source [8].
The typical composition of honey is: moisture, 17.7%; total sugars, 76.4%;
ash, 0.18%; and total acid (as formic acid), 0.08%. Traditionally its use in
food has been as sweetening agent several aspects of its use indicate that
honey also functions as food preservative [9]. Honey also contains tiny amounts
of several compounds thought to function as antioxidants, including chrysin,
pinobanksin, Vitamin C, catalase, and pinocembrin [10]
Honey is essentially a solution of Leavulose (40-50%), dextrose (32-37%)
and sucrose (0.2%) in water (13-20%). The properties of sugars vary with the
floral source and on the activity of invertase normally present in honey. It is
used as Demulcent, sweetening agents and good nutrient to infant and patients.
It is antiseptic and applied to burns and wounds. It is a common ingredient in
several cough mixtures, Cough drops and used in the preparation of creams,
lotions, soft drinks and candies[11, 12].
Trehalose
Trehalose, also known as mycose or tremalose, is a natural alpha-linked
disaccharide formed by an α,α-1,1-glucoside bond between two a-glucose units.
First it was introduced by H.A.L. Wiggers in 1832. He discovered it in an ergot
of rye. In 1859 Marcellin Berthelot isolated it from trehala manna, a sub-
stance made by weevils, and named it trehalose. Trehalose is also known as
Mycose. It is synthesized by fungi, plants and invertebrate animals. Trehalose
is mainly found in Trehala manna, a common constituent of fungi (Amantia
muscaria)[13].
Trehalose has a solubility and osmotic profile similar to maltose. Above 80ºC
tehalose becomes slightly soluble in water relative to other sugars. Compared
to other sugars, trehalose is more stable to wide ranges of pH and heat, and
does not easily interact with protienaceous molecules. Trehalose was shown to
be homogenously distributed throughout all dietary formulations and was stable
when stored for 7 days at 22ºC and for 6 weeks at 4ºC [14].
As an extension of its natural capability to protect biological structures,
trehalose has been used for the preservation and protection of biologic mate-
rials. It stabilizes bioactive soluble proteins such as monoclonal antibodies and
enzymes for medical use. It is used to preserve blood products for transfusion
and greatly extends shelf life of platelets. It is used to preserve embryos during
freeze-drying where it increases viability [15].Maltose ia also a disaccharide
made by the action of the enzyme Maltase on starch, Lactose occurs in milk
of all mammals and is prepared pure from cows milk.
Saccharide sweetening agents have high calorific values (3600-4000 cal/gm).
These saccharide sweeteners fulfill the most worldwide requirement. But regu-
lar use of sugar can increase prevalence of diseases like dental caries, cardio-
vascular diseases, obesity, diabetes mellitus and micronutrient deficiency. Hence
demand is gradually decreasing for saccharide sweeteners.
NON-SACCHARIDE SWEETENING AGENTS
Non saccahride sweetening agents are those, which contain substances other
than saccharides as sweet principles. They contain Terpenoids, proteins,
dihydrochalcones, steroidal saponins, etc as sweet principles. The non-saccharide
sweeteners posses some advantages over saccharide sweeteners. They are:
Sucrose melts and decomposes at 186ºC to form caramel, and when combusted
produces carbon dioxide, and water [7]. Pharmaceutically sucrose is used for
making syrups, lozenges. It gives viscosity and consistency to fluids. Sucrose is
ubiquitous in food preparations due to both its sweetness and its functional
properties; it is important in the structure of many foods including biscuits and
cookies, candy canes, ice cream, and also assists in the preservation of foods.
The structural and chemical formula is mentioned in Figure 1.
charides, α-glucose and fructose.

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•Non-carcinogenic.
•Potent sweeteners (10,000 times sweeter than sucrose).
•They have very low calorific values, hence useful for diabetic persons.
•They do not have any effect on prevalence of diseases.
TERPENOIDSSteviosides
Stevia is the safest Natural Sweetener and it can substitute sucrose in various
preparations and formulations.[16] Steviosides are obtained from leaves of small
Steviosides
Table2. Components of Stevia
rebaudiana leaf
Component Times sweeter
than sucrose
Stevioside 250-300
Dulcoside 50-120
RebaudiosideB 300-350
RebaudiosideA 250-450
RebaudiosideC 50-150
RebaudiosideD 250-450
RebaudiosideE 150-300
Steiobioside 100-125
Stevioside is the major component (5-15% in the dried leaves) of sweet tasting
leaf extract but has an unpleasant after taste, this problem is solved by blending
it with other compounds or by its conversion into RebaudiosideA, which is
normally present in the leaves in lower content (3-4%), does not have any after
taste and has a sweetening power 1.2 to 1.6 times higher than steviosides.
perennial herb Stevia Rebaudiana
(compositae),a native of Paraguay, South
Brazil and cultivated in Japan, southeast
Asia, USA, etc. Stevioside was first iso-
lated principle of this plant, which is 200-
300 times sweeter principle than sucrose.
In addition to stevioside several other sweet
principles such as steviosides A and B,
Steviobioside, RebaudiosideA, B, C, D, E
and Dulcoside A were isolated from Stevia
rebaudiana leaf. The major components
of the leaf and their sweetness potency
are shown in the table 2 [17].
Table3.Concentrations of rebiana
used in various products
Product Range
(mg/kg or mg/lit)
Carbonated soft drinks 50-600
Still beverages 50-600
Powdered soft drinks 200-200
Chewing gum 300-6000
Dairy products 150-1000
Edible gels 200-1000
Nutraceuticles 200-1000
Pharmaceuticals 50-1000
Rebiana
Rebiana is the common name for
highly-purity rebaudiosideA. It is
sweeter and more delicious than
stevioside [18]. It provides Zero calo-
ries and has a clean, sweet taste with
no significant undesirable taste char-
acteristics. It is also well suited for
blending with other non-caloric or
carbohydrate sweeteners. Rebaudioside
is often 200-300 times sweeter than
that of sucrose. As a dry powder
rebiana is stable for at least 2 years at ambient temperature and under con-
trolled humidity conditions. In solution, it is most stable between pH values 4-
8 noticeably less stable below pH 2. Stability decreases with increase in tem-
perature [19]. Typical rebiana concentrations used to sweeten various foods and
beverages and pharmaceuticals are shown in the table 3. Marketed products are
also available. There is no report on toxicity of Stevia glycosides. In Japan
Stevia sweeteners are used in wide range, in liquid or solid foods, beverages as
a substitute for conventional sugars or artificial diethetics, at present more
than 10 food industries in Japan are undertaking the production of Stevia
glycosides as food additives [20].
Glycyrrhizin
Glycyrrhizin is a pentacyclic triterpenoid saponins glycoside obtained from
the root and stolons of the plant Glycyrrhiza glabra (Leguminosae) com-
monly known as liquorice. Other species of Glycyrrhiza like G.foetida, G.inflata
also contain this sweet principle. Liquorice plant is native of Mediterranean
region and China, cultivated in France, Italy, Spain, USSR, USA, England and
Asia. In India it is found in Srinagar, Jammu, Dehradun, Baramulla, temperate
ammonium chloride, alkali iodides, quinine and cascara. Moreover,various
pharmacological activities of glycyrrhizin, including anti-inflammatory,
immunomodulatory, anti ulcer, and anti allergy activities have been reported.
Glycyrrhizin also has anti viral activity against various DNA and RNA viruses,
including HIV and severe acute respiratory syndrome (SARS) associated
coronavirus. Therefore, a large amount of liquorice and its extracts are on the
world market as sweetening agents and medicinal materials[21].Ammoniated
glycyrrhizin, the fully ammoniated salt of glycyrrhizic acid, is commercially
available and has been found to be 100 times sweeter than sucrose. It is one of
the most efficient substances known for masking bitter taste of quinine. A
Chinese Natural medicine prepared from the dried roots of various glycyrriza
sp. is most frequently prescribed as an important ingredient in many prepara-
tions of traditional Chinese medicine(Kampou medicine) [45].
Fig. Liquorice root
Himalayan regions and south hilly
districts. It is propagated through
division of crown or rooted cut-
tings of underground
stem.Glycyrrhizin is found in the
form of potassium and calcium salt
of glycyrrhizic acid (a trihydroxy
acid, C42H62O; mp 205ºC quick de-
compose) in the roots and stolons
of liquorice plant. Different vari-
eties of liquorice contain varying
amounts of glycyrrhizin (from 6-
14%)[24]. Because of its sweet taste,
glycyrrhizin is used worldwide as a
natural sweetener and flavouring additive. It has been used as expectorant in
cough mixtures and as flavouring agent in formulations of nauseous drugs like
Source Glycyrrhizin content
Persian liquorice 7.5-13 %
(G.glabra var violaceae)
Spanish liquorice 5-10%
(G.glabra var typical)
Russian liquorice 10%
(G.glabra var glandulifera)
Table 4.Glycyrrhizin content in
various spices
Sapodilla (Acharas sapota)
Acharas sapota (sapotaceae) is another
sweet plant, the latex fruits of which
contain glycyrrhizin as sweet principle.
Sapodilla is the medium-sized tree na-
tive to Central America, but it also
grown elsewhere in the tropics. It is best
known source of chicle gum (the co-
agulated latex) which is the basis for
chewing gum manufacture [22]
Polypodium glycyrrhiza
Polypodoside A, a novel intensely sweet constituent of the rhizomes of
polypodium glycyrrhiza. This compound was rated by human taste panel as
exhibiting 600 times sweetness intensity of 6% w/v aqueous sucrose solution
[23].
Abrusosides
These are Triterpene glycoside
sweet principles present in the leaves
of Indian liquorice plant Abrus
precatorius (leguminosae). Like
liquorice, roots of this plant also
contain glycyrrhizin. Abrus
precatorius is a climbing shrub,
indigenously found throughout
India. The plant is propagated
through seeds. Leaves and roots of
this plant contain sweet tasting
Triterpene glycoside principles.
Leaves taste sweeter than roots,
seeds are poisonous and contain
Abrin, a poisonous substance.
Leaves contain Triterpene glycosides Abrusosides, A, B, C, D and E. Roots
contain the sweet oleanane type Triterpene glycoside glycyrrhizin. Hence
this plant is used as substitute for liquorice. Abrusosides are non-toxic.Abrisosides
A, B, C and D are found to be 30, 100, 50, 75 times sweeter than 2% w/v
sucrose, respectively. Abrusoside E is marginally sweet but the monomethyl
ester proved to be more potently sweet [24, 25]. Leaf extract (purified abrusosides
A-D) is commercially used for sweetening foods, beverages and medicines.
Leaves, roots and seed are used for medicinal purposes [26].
Table 5. The botanical name, chemical structure, potency of terpenoid
sweeteners
Botanical name Active sweet Chemical Sweetness Native place
and family principle structure compared of plant species
to sucrose
Perrilla frutescens L Monoterpenoid 400-2000 India
(Labitae) (Perillartine) aSino-Japan
Southeast Asia
Stevia rebaudiana Bertoni Diterpenoid b200-300 Paraguay and
(compositae) (stevioside) South Brazil
Glycyrrhiza glabra Triterpenoid c100 Mediterranean
(Leguminosae) (Glycyrrhizin) Countries & China
Abrus precatorius Triterpenoid -do- India
(Leguminosae) (Glycyrrhizin)
Achras sapota Triterpenoid -do- S.America
(Sapotaceae) (Glycyrrhizin)
a b c

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Perillartine
Perillartine is a monoterpene volatile oil obtained from the leaves, seeds and
flowering tops of the plant perilla frutescens (Labitae).This plant is indigenous
to India and found in Japan and Southeast Asia. Perllartine is 400-2000 times
sweeter than sucrose on a unit weight basis, and 4-8 times sweeter than
saccharine. The volatile oil provides flavours to sauces and confectionary as it
contains the super sweet principle Perillartine [27].
DIHYDRO ISOCOUMARINS
Phyllodulcin
Phyllodulcin is obtained from the plant Hydrangea macrophylla (Saxifragaceae)
commonly known as amacha. This plant is Indigenous to Japan, china and is
found in North and south America, an d temperate hills of India particularly
Assam and in Himalayas. The sweet principle, is 300-400 times sweeter than
sucrose, is shown in table 6. [4]
Table 6. Source, family, chemical structure active principles of
Phyllodulcin
Botanical name Active sweet Chemical Sweetness Native place
And family principle structure compared to sucrose of plant species
Hydrangea Dihydro a300-400 Japan, china,
macrophylla Isocoumarin North & South
(Saxifragaceae) (phyllodulcin) America and India
a
PROTEIN SWEETENERS
Thaumatin
The Thaumatins are a family of very sweet proteins present in the fruits of
the tropical plant Thaumatococcus danielli (marantaceae) a bushy plant that
grows in west Africa[28] All the forms of a Thaumatin are intensely sweet, and
have 207 amino acids. The two predominant forms, Thaumatin I and II differ
by 5 amino acids.Thaumatin elicits a very sweet taste that is rated to be 2000
to 10000 times sweeter than sucrose, depending on purity and concentration.
Thaumatin I and II are soluble in water and dilute alcohol [29]. Their solubility
is maximal at pH 2.7-3. The sweetening power does not disappear on heating.
The sweetness of Thaumatin disappeared on heating at pH above 7 for 15
min, but the sweetness remained even after heating at 80ºC for 4 hr at pH 2.
This indicated that the protein Thaumatin is more thermoresistent under acid
conditions than under neutral or alkaline conditions [30] Thaumatin is effective
at masking bitter notes often associated with pharmaceuticals or vitamins.
Used at 20-400 ppm in pills and tablets, its long lasting effect covers strongly
bitter aftertastes and leaves a pleasant feeling in the mouth. Thaumatin can
also be useful for masking astringency and off-flavors [31]
Miraculin
The taste- modifying protein, miraculin has the unusual property of being able
to modify a sour taste into a sweet taste [32]. Richardella dulcifica (sapotaceae),
a shrub native to tropical West Africa, produces red berries that have an active
ingredient, glycoprotein molecule with some trailing carbohydrate chains called,
miraculin, a taste modifying protein that cause citric acid, ascorbic acid, and
acetic acid, which are normally sour, to perceived as sweet after the berry has
been held in the mouth[32] The maximum sweetness after exposure to 0.4 µm
miraculin induced by 0.02M citric acid was estimated to be around 400000
times that of sucrose on a molar basis [32, 33] The taste modifying effect lasts for
usually 1-2 hr. Miracle fruit is available as freeze dried granules or in tablets –
this form has a longer shelf life than fresh fruit. Tablets are made from
compressed freeze dried fruit which causes the texture to be clearly visible
even in tablet form [34].
Curculin
Curculin isolated from curculigo latifolia, aplant grown in Malaysia, has an
intriguing property of modifying sour taste into sweet taste. In addition to this
taste modifying activity, curculin itself elicits a sweet taste [28] Curculin has a
unique property to exhibit both taste modifying activities. Although curculin
was originally reported to be a homodermic protein, sweet taste of this pro-
tein is actually expressed by its heterodermic isoform (also termed neoculin)
composed of two homologous subunits designated as curculi1, curculin2, which
share 77% identity in the amino acid sequences. The underlying mechanism
for the sweet tasting and taste modifying dual capability of curculin remains
largely a mystery [35].
Monellin
Monellin is present in red berries of West African plant Dioscoreophyllum
cumminsii Diels. This protein is about 3000 times sweeter than sucrose on a
weight basis. Unlike the single chain thaumatin, monellin consists of two
polypeptides of 45 and 50 amino acid residues, respectively that are associ-
ated through non-covalent interactions. Monellin has been shown to lose its
sweetness when heated above 50ºC under acidic pH [28].
Mabinlin
Mabilin the sweet tasting polypeptide exists in the fruits of Chinese plant
capparis masaki. This protein is comprised of two polypeptide chains, of 33
and 72 amino acids respectively, which are tightly associated through non-
covalent interactions. It is about 100 times sweeter than sucrose on a weight
basis [28].
Pentadin
Fruits of the plant penta diplandra brazzeana Ballion, a climbing shrub found
in some countries of tropical Africa(such as Gabon), contain 12-kDa sweet-
tasting protein, first isolated by van der Wel et al (1989). Electrophoretic
studies in the presence and absence of 2-mercaptoethanol suggested that the
mature protein consists of subunits coupled by disulfide bonds. The sweetness
intensity was estimated to be around 500 times that of sucrose on a weight
basis.No further work has been reported towards characterization of this sweet-
tasting protein [36]
Brazzein
Brazzein is also contained in the fruit of P.brazzeana Ballion. It was first
isolated by Mind and Hellekant(1994). The molecular mass of Brazzein is
6473, and its three dimensional structure has been solved, like thaumatin,
brazzein is a single chain protein (54 amino acids). Its sweetness profile
remains even after incubation at 353 K for 4 hrs, probably because of its
compact structure afforded by its four disulfide bridges [28]. Comparision of
thaumatin, monellin, mabinlin, pentadin, brazzein, curculin and miraculin are
shown in the table 7.
Table 7. Composition of protein sweeteners
Protein Source Geographic Sweetness factor Amino acids
Sweetenes Distribution (Weight Basis)
Thaumatin Thaumatococcus danielli Benth West Africa 3,000 207
Monellin Dioscoreophyllum Cumminsii Diels West Africa 3,000 45(A chain)
50(B chain)
Mabinlin Capparis masaki China 100 33(A chain)
72(B chain)
Pentadin Pentadiplandra brazzeana West Africa 500
Brazzein Pentadiplandra brazzeana West Africa 2000 54
Curculin Curculingo latifolia Malaysia 550 114
Miraculin Richadella dulcifica West Africa -191
DIHYDROCHALCONES
Glycyphyllin
The sweet principle glycyphyllin is present in almost all parts of the plant
smilax glycyphylla (liliaceae). Commonly, it is known as barichob-chini. It is
Indigenous to India and found in Himalayas. It is mainly propagated through
Rhizomes and tuberous roots. The sweet principle is a dihydrochalcone gluco-
side, 100-200 times sweeter than sucrose. The extract of shoot or almost all
parts provide sweetening agent [4].
Trilobatin
Trilobatin is obtained from the plants Symplococos paniculata (simplocaceae)
commonly known as sweet leaf, sapphire berry, ludh. This plant is found in India
and is being cultivated on large scale. It is 400-1000 times sweeter than sucrose.
A water soluble fraction from the bark has been reported to exhibit antioxidative
activity. Seeds contain oil. Leaves are used as fodder. Further studies are required
on quantity and distribution of sweet principles in different parts of plant [4].
Neohesperidin Dihydrochalcone
Neohesperidin is obtained from the peels of the fruits of plant citrus aurantium
(Rutaceae), commonly known as Seville orange.The flavonoid compound
neohesperidine is itself bitter but dilute alkali extract gives a sweet compound
called Neohesperidin dihydrochalcone, which is about 1000 times sweeter than
sucrose and has a slow onset and persists for some time.The sweetener is rela-
tively inert to the action of carcinogenic bacteria and is approved in Belgium for
use as a sugar substitute in beverages and chewing gum [37].
Naringin Dihydrochalcone
The sweet principle, Naringin is a type of dihydrochalcone. The flavonoid

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Keerthi Priya et al. / Journal of Pharmacy Research 2011,4(7),2034-2039
2034-2039
parent compound naringin is bitter present in the peels of fruit of the plant
Citrus paradisi (Rutaceae) commonly known as grape fruit. However, the naringin
extract in dilute alkali gives a sweet principle, naringin dihydrochalcone, which
is nearly 1000 times sweeter than sucrose. The plant is indigenous to West
Indies and is cultivated in India. Naringin can be commercialized and could be
used to prepare neohesperidin.
Hesperitin Dihydrochalcone
The parent compound Hesperitin is isolated from the peels of the plant Citrus
sinensis and citrus limoni (Rutaceae). The reduction of hesperidin in dilute alkali
yields hesperidin dihydrochalcone. Partial hydrolysis of this compound, either
by acid or by dissolved or immobilized enzyme, gives rise to sweet hesperetin
dihydrochalcone. This is 300 times sweeter than sucrose [37, 38].Citrus sinensis is
commonly known as betavian, sweet orange. It is native of India and China and
cultivated widely in subtropical regions as most valued commercial citrus of the
world. Citrus limoni is commonly known as lemon and jambira. Wild stock of
this plant is native of Northwest region of India. Both plants are widely culti-
vated in India [24] The botanical name, chemical structure, sweetness potency of
dihydrochalcone sweeteners are given in the table 8.
Table 8. Different dihydrochalcone sweeteners
Botanical name Active sweet Chemical Sweeteness Native place of
and family principle structure compared plant species
to sucrose
Smilax Glycyphylla Dihydro Chalcone a100-200 Temperate hills
(liliaceae) Glycoside (glycyphyllin) of India
Simplococos paniculata Dihydro Chalcone 400-1000 India
(simplocaceae) Glycoside (trilobatin) b
Citrus aurantium Dihydro Chalcone 1000 India
(Rutaceae) Glycoside (Neohesperidin) c
Citrus paradisi DihydroChalcone -do- >1000 West Indies
(Rutaceae) Glycoside(Narigin)
Citrus sinensis Hesperetin 300 India and china
(Rutaceae)
Citrus limoni -do- -do- -do- North west
region of India
a b c
STEROIDAL SAPONINS
Polypodoside A
The sweet principle polypodoside A is obtained from the rhizomes of the North
American plant Polypodium glycyrrhiza (polipodiaceae), commonly known as
liquorice fern, initially, the sweet taste of the rhizomes was attributed to the
presence of a sweet glycoside glycyrrhizin. Later it was found that a novel
intensely sweet compound, polypodosideA, which is 600 times sweeter than 6%
w/v aqueous sucrose solution. This steroidal saponin glycoside on enzymatic
hydrolysis with hesperindinase yields D-glucose, L-rhamnose and aglycone
polypodogenin [39].
Osladin
European polypody fern. Polypodium vulgare (polypodiaceae) rhizomes con-
tain the glycoside Osladin as sweet principle. It is 300-3000 times sweeter than
sucrose [40].
Pterocaryosides A and B
Two novel, potentially sweet 3-4 secodammaranoid saponins, pterocaryoside
Aand B are isolated from the leaves and stems of Chinese tree pterocarya
paliurus. These pterocaryosides are proved as nontoxic, safe and potent sweet-
ening agents. Pterocaryoside A and B are 50and100 times sweeter than 2%
sucrose, respectively.
Strogin
It is isolated from water extract of the leaves of staurogyne mergunsis. This is
a new compound isolated. On the basis of spectral analysis the structure of this
compound was elucidated as 3-O-ß-d-xylopyranosyl-(1or2)-ß-D-glucurono
pyranosyl-3ß, 21ß, 22ß, 23, 29-pentahydroxy olean-12-ene-21-a-(2,3,4-O-
triacetyl)-L-rhamnoside.
Cyclocaryoside
Three intensely sweet cyclocaryosides I, II and III are obtained from the leaves
of cyclocarya paliurus, the structure of cyclocaryoside is elucidated as 20, 24
epoxy- dammaran-(3ß, 12ß, 20S, 24R)-12-ß-D-quinovo pyranosyl-25-hydroxy-
3-O-a-L arabino furanoside. It is the main sweet principle of the plant, possess-
ing about250 times more than the sweetness intensity of sucrose [24].
POLYOL SWEETENERS
Xylitol
Xylitol is apolyol, with a sweetening power similar to sucrose, found in fruits and
vegetables. It has many advantages as a food ingredient. It does not undergo a
Millard reaction, responsible for both darkening and reduction in the nutritional
value of proteins. When continuously supplied in the diet, it limits the tendency
to obesity, and the incorporation of xylitol in food formulations improves the
colour and taste of preparations without causing undesired changes in properties
during storage. A number of studies have shown the beneficial effects of xylitol
as a sweetener when used alone or formulated in combination with other sugars,
provides texture, colour, taste, stable for longer periods than those of products
formulated with conventional sugars such as sucrose [41].With fructose, xylitol is
the sugar recommended for diabetic patients. Because of its negative heat of
dissolution, xylitol produces a feeling of vaporization in the oral and nasal
cavities and is used as a part of the coating of confectionary or pharmaceutical
products such as vitamins or expectorants, and in formulation or dietary comple-
ments such as amino-acids, vitamins, trace elements and non-reducing sugars.
Used in combination with alcohols, sugars and aminoaacids, xylitol has been
used as stabilizing agent for proteins during their extraction from natural mem-
branes thus avoiding denaturation [42].
Erythritol
Erythritol is 1,2,3,4-butanetetrol.It is a white crystalline powder that is odor-
less, with a clean sweet taste that is similar to sucrose. It is approximately 70%
as sweet as sucrose as flows easily because of its non hygroscopic character.
Erythritol is a good tasting bulk sweetener that is suitable for a variety of
reduced-calorie and sugar free foods. Since 1990 erythritol has been commer-
cially produced and added to foods and beverages to provide sweetness as well as
to enhance their taste and texture. Erythritol has a high digestive tolerance, is
safe for people with diabetes, and does not promote tooth decay [43].
CONCLUSIONS
The desire for sweet taste is inborn. Since the ingestion of sugar increases caloric
intake and can lead to obesity, a risk factor for some chronic diseases, this
common sweetener has been restricted in the diet of diabetics. The availability
of natural sweeteners has made it possible to offer consumers sweet taste with-
out the calories that a diet high in sucrose implies.
In India 13 species of plants that accumulate nonsaccharides as the active sweet
principle have been identified. For fast multiplication of these plants, develop-
ments of suitable techniques are required not only to save them from becoming
extinct but also to enable their large scale cultivation. Furthermore, simple
techniques for the extraction of these principles are required which could be
adapted at small-scale level.
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