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ISSN 2278- 4136

ZDB-Number: 2668735-5
IC Journal No: 8192
Volume 2 Issue 1
Online Available at www.phytojournal.com

Journal of Pharmacognosy and Phytochemistry

Carotenoids
Omayma A. Eldahshan1 and Abdel Nasser B. Singab1*

1. Pharmacognosy Department, Faculty of Pharmacy, Ain Shams University, Cairo, Egypt.


[E-mail: dean@pharma.asu.edu.eg]

Carotenoids form one of the most important classes of plant pigments and play a crucial role in defining the quality
parameters of fruit and vegetables. Carotenoids are of great interest due to their essential biological functions in
both plants and animals. Herein, the review article discuss how carotenoids synthesised in plants leading to different
types, their role in plants and biological activities to human and all details concerning the most important
carotenoids in our life
Keyword: Carotenoids, Classification, Biosynthesis, Function, -Carotene

1. Introduction in human health. Plant pigments are obviously


Without pigments were nothing. Life presents physiologically important, and recent research
us with a kaleidoscope of colors. From the green suggests novel protective mechanisms, both
grass of home to a forest's ruddy autumn hues, we photo-protective and anti-oxidative. Plant
are surrounded by living color. Living things pigments are economically important, in
obtain their colors, with few exceptions, from determining the colours and patterns of attractive
natural pigments. In addition to their role in flowers and valuable fruits. They are also
coloration, natural pigments carry out a variety of important nutritionally, with an understanding of
important biological functions[1]. emerging new roles in nutrition and in aiding
Plants play an important aesthetic function by health[3]. All of these reasons were a motivation
providing flowers with a broad spectrum of for production a review about one of the most
colors[2]. Plant pigments are important in important plant pigments; carotenoids.
signalling, as in attracting pollinating and
dispersal agents, and repelling herbivores. They 1.1Carotenoids
are also important for humans, attracting our Carotenoids form one of the most important
attention and providing us with nutrients. Plant classes of plant pigments and play a crucial role
pigments are important clues to humans and other in defining the quality parameters of fruit and
herbivorous animals in helping identify plants vegetables [4].
find plant parts such as fruit, leaves, stems, roots, They are found principally in plants, algae, and
or tubers and determine stages of plant photosynthetic bacteria, where they play a critical
development such as ripeness or overall role in the photosynthetic process. They also
senescence. It was realized early in this century occur in some non-photosynthetic bacteria,
that many of these pigments play a positive role yeasts, and molds, where they may carry out a

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Journal of Pharmacognosy and Phytochemistry

protective function against damage by light and compounds are a zeaxanthin and lutein
oxygen[1,5]. (hydroxy), spirilloxanthin (methoxy),
Carotenoids are responsible for many of the red, echinenone (oxo), and antheraxanthin
orange, and yellow hues of plant leaves, fruits, (epoxy)[10].
and flowers, as well as the colors of some birds,
insects, fish, and crustaceans. Some familiar 1.3 Structure
examples of carotenoid coloration are the oranges Carotenoids are lipid-soluble C40 tetraterpenoids.
of carrots and citrus fruits, the reds of peppers The majority carotenoids are derived from a 40-
and tomatoes, and the pinks of flamingos and carbon polyene chain, which could be considered
salmon[6]. Some 600 different carotenoids are the backbone of the molecule. This chain may be
known to occur naturally, and new carotenoids terminated by cyclic end-groups (rings) and may
continue to be identified[1,7]. They are partially be complemented with oxygen-containing
responsible for fall coloration after the leaf functional groups.
chlorophyll has been destroyed[8]. In nature, carotenoids are predominantly present
Animals are unable to synthesise carotenoids de in the all-trans configuration. However,
novo, and rely upon the diet as a source of these processing fruits and vegetables produces a 10%
compounds[9]. to 39% increase in cis-isomers. [11] The degree of
isomerisation is directly correlated with the
intensity and duration of the heating process.
1.2 Classification
However, when Rock et al. fed processed
Carotenoids are classified according to the
vegetables to subjects, no increase in 9-cis-b-
structure as follows:
carotene plasma concentrations was observed.
1. The hydrocarbon carotenoids which are
Rather, the plasma response was characterized by
known as carotenes example -carotene
an increase of all trans-carotene, due to
2. The oxygenated carotenoids which are
derivatives of these hydrocarbons known isomerization of cis-isomers to all trans--
as xanthophylls, examples of these carotene or a rapid tissue uptake[12].

Astaxanthin

Antheraxanthin

Present in: salmon, shrimp, lobster, and flamingo


Present in many plants, especially maize

Capsanthin

Canthaxanthin

Present in: salmon, shrimp, flamingo feathers Present in: peppers, paprika

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Journal of Pharmacognosy and Phytochemistry

-Carotene

-Carotene

Present in carrots, most green plants Present in carrots and most other plants

-Carotene
-Carotene

Present in most green plants Present in many plants, often with -carotene

-Cryptoxanthin

-Carotene

Present in many plants Present in many coloured plants as maize and papaya

7,8-Didehydroastaxanthin
Diatoxanthin

Present in: salmon and crustaceans


Present in algae and corals

Lactucaxanthin
Fucoxanthinol

Present in algae
Present in many algae and seaweed

Lycopene
Lutein

Present in many green plants Present in many plants, especially in tomato

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Journal of Pharmacognosy and Phytochemistry

Zeaxanthin
Neoxanthin

Present in the chloroplasts of most plants Present in many plants, especially in maize

Peridinin
Neurosporene

Present in many plants, intermediate between carotene and Present in the chloroplasts (green particles) of compound
lycopene most plants

1.4 Biosynthesis tomato, one specific to green


In the plastids, where carotenoid biosynthesis tissues (LCY-B) and the other to
takes place, IPP is synthesized through the chromoplasts (CYC-B), first
plastid-specific DOXP (1-deoxyxylulose 5- produces -carotene containing
phosphate) pathway. one -ring which is subsequently
converted to -carotene by the
1. The carotenoid pathway is catalyzed by same enzyme.
phytoene synthase (PSY), resulting in the b. On the other hand, lycopene -
condensation of two C-20 geranylgeranyl cyclase (LCY-E) produces -
diphosphate (GGPP) molecules to form carotene. The formation of -
phytoene. carotene, the precursor for lutein,
2. Four desaturation reactions, two each involves formation of a -ring on
catalyzed by the membrane associated -carotene by lycopene -cyclase.
phytoene desaturase (PDS) and -carotene
desaturase (ZDS), result in the formation 4. The - and -carotenes are the precursors
of the pink lycopene from the colorless for the xanthophylls, which are
phytoene. oxygenated carotenoids generated by -
3. The cyclization of lycopene represents a and -ring specific hydroxylases.
branch point in the pathway, and two 5. -carotene is converted to zeaxanthin by
products can be formed depending on the the carotenoid -ring hydroxylases (HYD-
position of the double bond on the B), encoding a nonheme diiron enzyme
cyclohexane ring. for which there are two genes in
Arabidopsis. The hydroxylation of the -
a. On one hand, lycopene -cyclase, ring is carried out by the carotenoid -ring
for which there are two forms in hydroxylase (HYD-E), a cytochrome

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Journal of Pharmacognosy and Phytochemistry

P450 enzyme, CYP97C1, encoded by the number of conjugated double bonds of the
Arabidopsis LUT1 locus. molecule and is influenced to a lesser extent by
6. In addition to displaying activity toward carotenoid end groups (cyclic or acyclic) or the
the -ring, LUT1 can also hydroxylate the nature of substituents in carotenoids containing
-ring. Hydroxylation of the -ring of - cyclic end groups[17]. It has been known for many
carotene is also mediated by a P450 years that carotenoids bleach i.e., lose their
enzyme (E. Wurtzel, personal color, when exposed to radicals or to oxidizing
communication). Lutein is the main species. This process involves interruption of the
carotenoid present in the petals of conjugated double bond system either by
marigold, and the broad range of colors cleavage or by addition to one of the double
that characterize marigold flowers is due bonds. Cleavage can be detected by
to the very different levels of this characterizing the products that are formed,
xanthophyll. which frequently are carbonyls [18] or epoxides[19].
7. The formation of ketocarotenoids, such Because of their role as antioxidants, carotenoids
as, for example, astaxanthin, requires the have been suggested to be protective against
addition of keto groups in each -ring of coronary vascular disease. One contributor to the
zeaxanthin[13]. development of coronary vascular disease is the
oxidation of low-density lipoproteins (LDL).
1.5 Function When LDL is oxidized it is readily taken up by
1. For plant life: carotenoids are essential for foam cells in the vascular endothelium where it
plant life, providing important photoprotective contributes to the development of atherosclerotic
functions during photosynthesis; light harvesting lesion[20,21].
and prevention of photo-oxidative damage, and This hypothesis is supported by the observational
serving as precursors for the biosynthesis of the epidemiological studies that report that foods rich
phytohormone abscisic acid (ABA). They have a in carotenoids and antioxidant vitamins are
role in attraction of pollinators[4,14]. associated with reduced risk of cardiovascular
disease[22]. Many epidemiologic studies have
2. For human: of the over 600 carotenoids found associated high carotenoid intake with a decrease
in nature, about 40 are present in a typical human in the incidence of chronic disease. However, the
diet. Of these carotenoids, only 14 and some of biological mechanisms for such protection are
their metabolites have been identified in blood currently unclear. Multiple possibilities exist:
and tissues[15]. certain carotenoids

Their function as antioxidants in the plant shows 1) Can be converted to retinoids (i.e. have pro-
interesting parallels with their potential role as vitamin A activity).
antioxidants in foods and humans[4]. The 2) Can modulate the enzymatic activities of
antioxidant actions of carotenoids are based on lipoxygenases (proinflammatory and
their singlet oxygen quenching properties and immunomodulatory molecules).
their ability to trap peroxyl radicals[16]. The best 3) Can have antioxidants properties which are
documented antioxidant action of carotenoids is well above what is seen with vitamin A,
their ability to quench singlet oxygen. This results 4) Can activate the expression of genes which
in an excited carotenoid, which has the ability to encode the message for production of a
dissipate newly acquired energy through a series protein, connexin[43], which is an integral
of rotational and vibrational interactions with the component of the gap junctions required for
solvent, thus regenerating the original unexcited cell to cell communication. Such gene
carotenoid, which can be reused for further cycles activation is not associated with antioxidant
of singlet oxygen quenching. The quenching capacity and is independent of pro-vitamin A
activity of a carotenoid mainly depends on the activity[23].

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Journal of Pharmacognosy and Phytochemistry

Other health benefits of carotenoids that may be of fiber or protein must first be broken down by
related to their antioxidative potential include mastication, gastric acid, pancreatic enzymes, and
enhancement of immune system function[24], bile acids[34].
protection from sunburn[25], and inhibition of the In the small intestinal enterocyte, -carotene can
development of certain types of cancers[26]. be transformed into vitamin A mainly as retinyl
In summary, carotenoids may act as antioxidants ester (20-75%) through cleavage of the -
and may exhibit chemopreventive anti- carotene molecule. The majority of conversion to
atherosclerotic effects and anticancer effects in vitamin A takes place, not in the liver, but in the
some specific animal models, using specific intestinal mucosa[35]. This cleavage depends on
carcinogens. the vitamin A content of the meal and the vitamin
A status of the individual[36]. In vitamin A-
-Carotene depleted subjects, synthetic -carotene had 50%
of the potency of retinol; in other words, 2 mg -
carotene was equivalent to 1 mg vitamin A[37].
However, -carotene has not been shown to
precipitate vitamin A toxicity, and it has been
-Carotene: ,-Carotene
demonstrated in several species that, when
dietary -carotene increases, the regulatory
-carotene is the most widely studied carotenoid
mechanisms limit vitamin A production from
and is one of the major carotenoids in our diet
carotenoids[18]. -carotene not converted to
and in human blood and tissues[27].
vitamin A is absorbed by the lymphatics, having
been incorporated into chylomicrons as intact -
Colour: yellow to orange.
carotene or other non-vitamin A products of -
Source: Beet root, apricots, cantaloupe, carrots,
carotene cleavage[38].
pumpkin, sweet potato, pink grapefruit, tomatoes,
watermelon, mango, papaya, peaches, prunes,
squash and oranges whereas green fruits and Immune response
vegetables such as green beans, broccoli, brussel There is growing evidence from in vitro and in
sprouts, cabbage, kale, kiwi, lettuce, peas and vivo laboratory animal studies that -carotene can
spinach[28] Capsicum annuum var. protect phagocytic cells from autooxidative
lycopersiciforme rubrum[29], rosa mosqueta hips damage, enhance T and B lymphocyte
(Rosa rubiginosa, Rosa eglanteria)[30]. proliferative responses, stimulate effector T cell
functions, and enhance macrophage, cytotoxic T
Medicinal uses cell and natural killer cell tumoricidal capacities,
as well as increase the production of certain
Vitamin A
interleukins[39]. A recent study in HIV-infected
Beta-carotene is a pro-vitamin which the body
women reported lower serum concentrations of
converts into vitamin A[31]. -Carotene is the
lycopene, -carotene, and -carotene, especially
most abundant form of vitamin A in fruits and
in those with low counts of CD-4 helper cells[40].
vegetables[32]. The other two carotenoids with
Both -carotene and selenium are deficient in a
vitamin A activity, -carotene and -
significant percentage of both HIV and AIDS
cryptoxanthin are not prevelant in food.
patients. Their roles as antioxidants in HIV/AIDS
carotene is an effective source of vitamin A in
appear to be related to both direct immune
both conventional food and dietary
modulation and inhibition of cytokine and NF-kB
supplements[33].
activation, inhibiting HIV replication. Beta
Absorption of -carotene and other carotenoids
carotene has been shown to act directly as an
from vegetables is usually (5-30%) of the
immunomodulator by increasing natural killer
absorption from synthetic supplements, due to the
cell function and improving CD4 count. As an
food matrix surrounding -carotene. This matrix
antioxidant, beta carotene appears to support

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Journal of Pharmacognosy and Phytochemistry

enzymatic defence systems involved in that beneficial effects of -carotene occur at


minimizing oxidative damage. physiologic or dietary levels of intake, whereas
harmful effects in some subpopulations can be
Antioxidant seen if pharmacologic levels are given.
The fact that LDL is a major transporter of - Proponents believe that beta-carotene helps to
carotene and lycopene in the circulation[41] and neutralize free radicals, which are believed to
that these carotenoids have the capacity to trap lead to cancer[31]. A diet rich in beta-carotene-
peroxyl radicals and quench singlet oxygen lends rich fruits and vegetables or high blood levels of
support to this hypothesis. beta-carotene are associated with a reduced risk
-Carotene is a scavenger of peroxyl radicals, of cancer at a number of common sites, such as
especially at low oxygen tension. This activity lung and stomach[49]. Animal studies have
may be also exhibited by others carotenoids. The indicated that beta-carotene can delay or prevent
interaction of carotenoids with peroxyl radicals induction of sarcomas and skin cancer in mice
may proceed via an unstable -carotene radical exposed to carcinogens[50].
adduct [42, 43]. Carotenoid adduct radicals have been The inhibitory effects of the newly-developed
shown to be highly resonance stabilized and are forms of beta-carotene - water-soluble and
predicted to be relatively unreactive. They may liposomal-have been studied in rats and mice
further undergo decay to generate non radical bearing tumors induced in 4 models of
products and may terminate radical reactions by carcinogenesis. Water-soluble beta-carotene
binding to the attacking free radicals[43]. failed to influence the carcinogenesis in the
Carotenoids act as antioxidants by reacting more mammary gland and esophagus in rats; however,
rapidly with peroxyl radicals than do unsaturated it significantly inhibited carcinoma development
acyl chains. In this process, carotenoids are in murine vagina and cervix uteri (47%).
destroyed[44]. Liposomal beta-carotene significantly inhibited
Carotenoids partially or completely protect intact lung adenomas (46.4%) and mammary
cells (e.g. human liver cell line HepG2) against carcinomas (55.6%) in the urethane-treated
oxidant-induced lipid peroxidation, and the mice[51]. In a conducted double-blind placebo-
protective effect is independent of provitamin A controlled trial to evaluate the chemopreventive
activity[45]. Further, in both normal and potential of either vitamin
transformed thymocytes, -carotene acted as an Four studies in the USA, Canada, and Italy have
antioxidant at 150 mm Hg pO2, inhibiting shown that beta-carotene, as a single agent,
radical-induced lipid peroxidation. However, completely or partially reduces oral leukoplakia
upon increasing the pO2 to 760 mmHg, b- in 44-71% of patients. Another study, in India,
carotene lost its antioxidant activity in normal reported that 14% of patients responded
thymocytes and actually exhibited a dose- completely to beta-carotene; the percentage with
dependent prooxidant effect in the tumor partial improvement was not given. The extent to
thymocytes[46]. These data point out a key role of which a reduction in oral leukoplakia will lead to
the oxygen tension on the antioxidant/prooxidant a reduction in the incidence of oral cancer is
effects of beta-carotene[49]. High carotenoid unknown[52].
concentrations may also result in a prooxidative Numerous studies have shown that a high intake
effect, which may be modified by interactions of carotenoid rich fruit and vegetables is
with other nutrients[47]. associated with a decreased risk of cancer[53].
A large study examining the effects of beta-
Cancer carotene and alpha-tocopherol on prostate cancer
Research emphasizing the biology of carotenoids revealed that "beta-carotene apparently increased
was initiated after Peto et al. suggested that - the risk of clinically evident prostate cancer only
carotene might be the primary anticancer agent in in drinkers, and that the increase was dose related
fruits and vegetables[48]. It could be hypothesized to alcohol intake[55].

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Journal of Pharmacognosy and Phytochemistry

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