CHAPTER ONE
INTRODUCTION AND LITERATURE REVIEW
1.1 INTRODUCTION
Early man had to rely directly on nature for all his needs because he had no other means to cater
for these needs. His food, shelter, clothing, weapons for defence were all provided for by nature.
In addition, he got his health and cure needs from nature –this marked the beginning of medicine.
Primitive man had used materials from plants, animals and minerals to cater for his health,
however, plant materials have been used the most. Although, many of the earliest practices of
medicine have been found to be inappropriate (for example, the use of Catharanthus roseus in
the treatment of diabetes), many others have been proven to be appropriate and are still used in
modern medicine. Examples include the use of Digitalis leaves for the treatment of heart failure,
leaves of Ocimum gratissimum for its anti-diarrhoeal property, barks of Cinchona and leaves of
Artemisia annua for the treatment of malaria. How primitive man got to know what plants could
be used for particular conditions is not sure, but it is not unlikely that he got the knowledge by
intuition, trial and error or observing other animals that had consumed these plants (Sofowora,
2008).
1.1.1MEDICINAL PLANTS
A medicinal plant is any plant which, in one or more of its organs, contains substances that can
be used for therapeutic purposes or which are precursors for the synthesis of useful drugs. A
good number of drugs prescribed by orthodox medical practitioners were first isolated from plant
1
and many of these drugs are still obtained from their natural sources. Examples include: dtubocurarine, obtained from Chondrodendron sp.; vinblastine and vincristine from Catharanthus
roseus; atropine and hyoscine from Atropa belladonna leaves; ergot alkaloids from Claviceps
purpurea; digoxin and digitoxin from Digitalis purpurea L. leaves; reserpine from Rauwolfia
vomitoria or R. serpentina root. However, some are now prepared synthetically for commercial
purpose. An example is papaverine, formerly obtained from Papaver somniferum poppy
(Sofowora, 2008). Due to the enormous number of drug that have been discovered from plant,
and the current upsurge in drug resistant diseases, the search for novel bioactive compounds and
alternative sources of known medicinally useful compounds continues.
1.1.2 THE NEED FOR STANDARDIZATION AND QUALITY CONTROL
Of the major criticism levied against the use of herbal medicines, the most important are
standardization and quality control (Sofowora, 2008). It is already known and well accepted that
both standardization and quality control begins from collection of the raw materials. Various
factors can affect the composition and proportion of active principles in plant materials. These
factors include the species, the geographical location, climatic conditions/seasonal variations,
age of the plant and time of collection, hence, the need for standardization and quality control.
According to regulatory guidelines and pharmacopoeias; macroscopic and microscopic
evaluation, chemical profiling as well as selection of chemical markers are important for quality
control and standardization of botanicals.
1.1.2.1 CHEMICAL PROFILING
Chemical profiling is the first task in the standardization of traditional medicines in China (Liang
et al., 2014). This can be adopted worldwide. The existence and variability of the constituents of
2
botanicals makes it difficult to evaluate their safety and efficacy by measuring the amount of a
particular constituent(s). A chemical profile or fingerprint of such a product is most reliable. This
is because a chemical profile evaluates the product as a whole and indicates the presence of
multiple chemical markers, other constituents and impurities that maybe present within a sample
(Liang et al., 2014). The most commonly used techniques in profiling of botanicals are
chromatographic techniques. Chromatographic techniques often used include TLC, HPTLC,
HPLC and GC – this is known as chromatographic fingerprinting. Chromatographic
fingerprinting has been demonstrated to be a powerful technique for the quality control of herbal
medicines, and according to WHO guidelines, it is one of the parameters required for quality
evaluation of these drugs (Rasheed, et al., 2012).
1.1.2.2 CHEMICAL MARKERS
Chemical markers are chemically-defined constituents of a herbal drug which are of interest for
quality control purposes independent of whether they have any therapeutic activity or not.
Ideally, chemical markers should be components that contribute to the therapeutic effect(s) of
herbal medicines, as their measurement could also serve as a means of measuring the potency of
the drug; other chemical components are used as markers. This is because only small amounts of
active principles are usually produced and these amounts are affected by various extrinsic factors
such as changes in climatic conditions. However, any compound(s) selected as markers should
be neutral to environmental changes (Li, et al., 2008; Kushwaha, et al., 2010; Rasheed, et al.,
2012). Therefore, the process of identifying and selecting of chemical markers should be a highly
validated process; plant materials should be collected from different geographical location, at
different seasons, at different times of the day and at different ages. All these samples should be
3
analyzed separately before a conclusive decision can be made regarding the constituents to be
selected as markers.
1.2 LITERATURE REVIEW
1.2.1 THE GENUS: Ixora
Ixora is a genus belonging to the family Rubiaceae. Plants of this genus are evergreen, flowering
shrubs or trees. The genus holds around 500 species, the most common being Ixora coccinea,
commonly known as “Flame of the Woods” or “Burning Love”. The name “Ixora” is derived
from an Indian deity. The flowers are reputed to be part of Hindu worship offerings at statues of
incarnations of Paramathma and are commonly used as well in Indian folk medicine. The genus
is widely distributed in the tropics; from Africa to Southeast Asia and through Oceania and
Australia, with a few found in tropical America and is mostly cultivated for ornamental purposes.
Ixora also grows commonly in subtropical climates in the United States, such as Florida
(Radhakrishnan, 2002; Idowu, et al., 2010; Kharat, et al., 2013).
There are numerous species, differing in leaf size, flower colour and size, and/or plant height.
There are also numerous named cultivars, most of which can be distinguished by the size of the
leaves and flowers as well and the colour of the flowers. The colour of the flowers vary widely.
The flower could be red, orange, yellow, pink, or purple in colour, again differing according to
species or cultivar (Kharat, et al., 2013; Rockledge Gardens).
1.2.2 DESCRIPTION
4
Plants of this genus are densely branched; leaves are coriaceous, up to 10 cm long, sessile, subsessile, oblong or obtuse. Flowers are numerous; they grow in clusters in a corymb manner. The
colour of flowers varies, depending on the species or variety. Fruits are globose, fleshy, 2-seeded
and are pea-sized. Several popular cultivars are dwarfs, usually staying under 3feet (1 meter) in
height. The plant usually flowers in April - May and fruits in May–June (Kharat, et al., 2013).
The following are photographs of some species of Ixora.
5
1.2.3 TAXONOMY (Kharat, et al., 2013)
Kingdom: Plantae
Division: Angiosperms
Class: Eudicots
Subclass: Asterids
Order: Gentianales
Family: Rubiaceae
Subfamily: Ixoroideae
Tribe: Ixoreae
Genus: Ixora
Some of the species include (Idowu, et al., 2010; GRIN)
Ixora abyssinica (Fresen.) Oliv.
Ixora acuminata Roxb.
Ixora aggregata Hutch.
6
Ixora albersii K.Schum.
Ixora amoena Wall. exG. Don
Ixora aneimenodesma K.Schum.
Ixora arborea Roxb. ex Sm.
Ixora assimilis (Sond.) Kuntze
Ixora asteriscus K.Schum.
Ixora atrata Stapf
Ixora baldwinii Keay
Ixora barbata Roxb.
Ixora batesii Wernham
Ixora bauchiensis Hutch. & Dalziel
Ixora brachycalyx (Hiern) Kuntze
Ixora brachypoda DC.
Ixora carniflora K.Krause
Ixora casei Hance
Ixora chinensis Lam.
Ixora coccinea L.
Ixora congesta Stapf
Ixora crebrifolia (Hiern) Kuntze
Ixora delicatula Keay
Ixora edentula (Sond.) Kuntze
Ixora fastigiata (R.D.Good) Bremek.
Ixora finlaysoniana Wall. ex G.Don
7
Ixora foliosa Hiern
Ixora gardeniifolia (A.Rich.) Kuntze
Ixora gerrardii (Harv.) Kuntze
Ixora guineensis Benth.
Ixora hookeri (Oudem.) Bremek.
Ixora incana (Klotzsch) Kuntze
Ixora javanica (Blume) DC.
Ixora kavalliana K.Schum.
Ixora laxiflora Sm.
Ixora lutea Hutch.
Ixora macrothyrsa
Ixora mannii (Hiern) Kuntze
Ixora nigerica Keay
Ixora nitida Schumach. & Thonn.
Ixora pavetta Andrews
Ixora radiata Hiern
Ixora rhodesiaca Bremek.
Ixora rosea K.Schum.
Ixora siamensis G.Don
Ixora stricta Roxb.
Ixora thomsonii Hiern
Ixora villosa (Vahl) Poir.
Ixora viridiflora K.Schum.
8
1.2.4 CHEMICAL CONSTITUENTS
Several chemical constituents have been reportedly isolated and identified from different parts of
the plant species belonging to the Ixora genus, ranging from flowers, seed oil, fruits, leaves or
aerial part and root. This study has reported the names and structures of virtually all chemical
compounds that have been isolated from the genus and they are shown both in table and figures
below:
9
Table 1. Folkloric uses, pharmacological activities and reported isolated chemical constituents of Ixora species
Ixora species
Plant Part Folkloric use
Reported
Used
activities/properties
I. acuminata Leaves and Fresh leaves (3-4 at a time) are eaten
Roxb.
roots
(raw/ boiled) thrice daily as a remedy
for headache and cooling of forehead.
The infusion of the leaves is taken
orally in the treatment of jaundice
(Purkayastha et al., 2005; Laloo et al.,
2006; Srivastava & Nyishi 2010).
Ixora alba
Leaves and It has been reported to used in the
stem-bark
treatment of whooping cough, anemia,
highly coloured urine and general
debility ( Talpade & Chachad, 2016).
I.
Stems
amplexicaulis
I. arborea
Flowers
Fruit
Root
Its flowers are used in pulmonary
troubles and whooping cough (Aktar et
al., 2009).
& Fruits and roots are given to females
when urine is highly coloured (Aktar et
al., 2009).
10
biological Reported isolated chemical
constituents
The stems of I. amplexicaulis
afforded
6α,16α-dihyroxyent-kaurane(1),
(24R)-6βhydroxy-24-ethyl-cholest-4en-3-one(2),
7βhydroxysitosterol(3), maslinic
acid(4), 3,3'-bis(3,4-dihydro4-hydroxy-6-methoxy-2H-1benzopyran)(5)
and
protocatechuic acid(6) (Chen
et al., 2016).
Leaf
stem
I. brachiata Leaf
Roxb (Rasna) Root
The decoction of bark is used for
anaemia and general debility and
remedy for urinary diseases (Aktar et
al., 2009).
and The root is medically important in the
treatment of skin diseases (SadeghiNejad et al., 2014)
Antispasmodic effect on isolated Betulin(7),
erythrodiol(8),
guinea pig ileum, hypotension in lupeol(9), and stigmasterol
cat/dog and CNS depressant effect in (10)(Aktar et al., 2009).
mice. Antioxidant (free radical
scavenging) activity (Aktar et al.,
2009; Usha et al., 2016).
Chrysin-5-O-β-Dxylopyranoside (11) (Chauhan
et al., 1984; Darwish and
Ibraheim, 2003)
The ethanolic extracts of the leaf and
the root have been reported to possess
antifungalactivity against
tested
dermatophytic species. According to
Siddha literature, I. brachaita Roxb
have been reported to possess antiinflamatory, aromatic and antipyretic
properties
(Sadeghi-Nejad
and
Deokule, 2009).
The ethanolic and methanolic root
extracts has been reported to have
anti-Leishmania effect (SadeghiNejad et al., 2014)
11
Flowers
The methanolic extract of the flowers
was found to possess significant antiinflammatory activity against cotton
pellet induced subacute inflammation
in rats (Vimala et al., 1997;
Dahanukar et al., 2000).
Ixora
chinensis
Lamk
Flowers
Infusion of the fresh flowers drunk ad
libitum is said to be good as a remedy
against
incipient
tuberculosis,
haemorrhage and headache, and for
contusion (Batugal et al., 2004;
Kharat, et al., 2013).
Seeds
Leaves
Palmitic acid(12), stearic
acid(13), oleaic acid(14),
linoleic acid(15), crepenynic
acid (octadec-cis-9-en- 1 2ynoic acid) (16),
cis,cis,cis, trans-8,10,12,14octadecatetraenoic acid
(ixoric acid) (17)(Minquan,
1990; Johnson and wyatt,
2004; Kharat, et al., 2013)
I. chinensis leaves have beenused to
treat headache and stomachache and
Ixoroside (18) and ixoside
(7,8-dehydroforsythide) (19)
12
as a remedy for incipient tuberculosis
(Kharat, et al., 2013).
Root
Ixora
coccinea L.
Flowers
In Malaysia, the root decoction is given
after birth (parturition) and are also use
for urinary trouble.
In Indonesia, the decoction of roots is
used for bronchial disorders (Kharat, et
al., 2013)
Decoction of the flowers is given for
thetreatment of cancer, leucorrhoea,
dysentery, diarrhoea, dysentery,
catarrhal bronchitis, dysmenorrhoea,
haemoptysis, andhypertension,
amenorrhea and irregular
menstruation(Maniyar, et al., 2010;
Kharat, et al., 2013; Rajeevand
Rajamanoharan,2014).
Decoctionof flowers or bark is used as
a lotion for eyetroublesand eruptions in
children (Joshi,et al., 2013;
Ratnasooriya et al., 2005; Batugal et
al., 2004; Ghani, 2003; Annapurna et
al., 2003 Saha et al., 2008, Latha et al.,
1995) and healing of ulcers (Nayak et
al., 1999).
The flowers are used externally in the
treatment sores,chronic ulcer, scabies,
and some type of dermatitis and also
human internally for cholera,
leucorrhoea, antitumor and gonorrhea
(Arunachalam et al., 2009).
The fresh juice of flower have
along with known geniposidic
acid (20) (Takeda et al., 1975)
Pharmacological investigations of the
flower had revealed: analgesic and
anti-inflammatory activities (Nayak
et al., 1999; Aher et al., 2013);
antioxidant (Saha et al.,
2008)antidiarrheal activity (Maniyar,
et al., 2010); antileucoderma activity
(Joy et al., 1998); cytotoxic and
antitumour activities (Annapurna et
al., 2003, Latha and Panikkar, 1998;
Ratnasooriya et al., 2005);
chemoprotective effects of the
flowers on cisplatin-induced toxicity
in mice (Latha and Panikkar, 2001);
modulatory effects of the flowers on
cyclophosphamide-induced toxicity
in mice (Latha and Panikkar, 1999,
Latha et al., 2004) as well as
hepatoprotective effects of the
flowers against paracetamol
overdose-induced hepatotoxicity in
rats (Latha et al., 2003).
Aqueous ethanolic extracts of I.
coccinea dry flowers have also been
13
Cycloartenol 3-palmitate(21),
Cycloartenol
3myristate(22),lupeol
(23),
oleanolic acid (24), sitosterol
(25), lupeol 3-palmitate (26),
and ursolic acid (27) (Ragasa
et al., 2004; Latha and
Panikkar, 1999; Latha et al.,
2001;Reena et al., 1994).
Biochin A, Myricetin(28),
Quercetin(29),
Rutin(30),
Ursolic
acid(27),
Diadzein(31)
and
formononetin(32),
cyanadin-3-Rutinoside(33)
and
delphinidin
3-Oglucoside(34). (Sumathy et
al., 2011; Joshi et al., 2013;
Kharat, et al., 2013)
21,23-Epoxy-tirucall-7-en-3βol (Ixoroid)(35), stigmast-5en-3-O-β-D-glucoside (36), 5O-caffeoylquinic acid (37)
and D-mannitol (38) (Versiani
protective action against
electroconvulsions
Flower paste is applied daily once on
cuts and wounds till it cures
(Policepatel and Manikrao, 2013).
reported to possess antimicrobial
activity (Latha et al., 1995). The
hexane fraction of the flowers has
been reported to show significant
antigenotoxic properties
(Ratnasooriya et al., 2005, Latha et
al., 2001).
The wound healing activity of the
flowers has been reported (Nayak et
al., 1999).
Cardioprotective effect of methanolic
extract of Ixora coccinea flowers on
doxorubicin induced cardiac
Ixora flower has traditionally been myopathy has been reported (Momin
associated with enhanced sexuality and et al., 2011).
the re-kindling of passion.
Decoction of roots used as sedative in
the treatment of nausea, hiccups and
loss of appetite and fever. Flowers are
used to treat diarrhea, dysentery,
leucorrhoea,
dysmenorrhea,
haemoptysis and catarrhal bronchitis.
Leaves are used for treating sores,
ulcers, and skin disease.
In tropical Asia, infusion of flowers
and bark are used for blood-shot eyes,
leaves for sores and ulcers.
Fruits
The fruits, when fully ripe, are used as
a dietary source (Naskar et al., 2013;
Dontha et al., 2015)
Aerial part The decoction and poultice fresh leaves Amptothecin isolated from the leaves
14
et al., 2012)
Amptothecin(39) (Saravanan
(Leaves
and stem)
and stems are used in folk medicine for
the treatment of sprains, eczema, boils
and contusions, wounds / sores, ulcers,
eye troubles and diarrhoea(Ghani,
2003, Annapurna et al., 2003,
Ratnasooriya et al., 2005, Latha et al.,
1995).
The leaves are also used to pacify
vitiated pitta, skin diseases, colic,
flatulence, diarrhea,indigestion, ulcers,
wounds, and used as antiseptic (Kharat,
et al., 2013).
of I. coccinea has been reported to
demonstrate strong anticancer
activity (Saravanan and Boopalan,
2011).
Using in vitro HIV-1 replication
assays with a CD4+ T cellline and
peripheral blood mononuclear cells,
pure ixoratannin A-2 isolated from
the leaves of I. coccinea has been
confirmed to have antiviral activity
and minimal cytotoxicity activity
(Tietjen et al., 2015).
Peptide I (1) exhibited selective
potency against Hep3B liver cancer
while compound II (2)and compound
2 did not show notable cytotoxicity
toward cancercell lines but peptide
2showed
significant
antiinflammatory effects on neutrophils
(Lee, et al., 2010).
The cardioprotectiveeffect of the
leaves on doxorubicin induced
cardiac myopathy and have proved
effective in maintaining the
hemodynamic, electrocardiographic,
biochemicaland histopathological
parameters close to normal, by
boosting the endogenous
antioxidantstores and blunting the
oxidative stress (Dontha et al., 2015)
Antiulcer,
Anti-inflammatory,
antimitotic
and
antimicrobial
activities have been reported for the
15
and Boopalan, 2011).
17β-dammara-12,20-diene3β-ol (Ixorene) (40), βsitosterol (25), lupeol(23)and
D-mannitol (38). (Ikram, et
al., 2013; Dontha et al., 2015).
Ixorapeptide I (41) and
Ixorapeptide II (42) (Lee, et
al., 2010).
Epicatechin(43), procyanidin
A-2(44), ixoratannin A-2
(45),
cinnamtannin
B1(46),kaempferol
7-O-α-Lrhamnoside(47), kaempferol
3-O-α-L-rhamnoside(48),
quercetin-3-O-α-Lrhamnopyranoside(49),
kaempferol 3, 7-O- α-Ldirhamnoside
(kaempferitrin)(50) ( Idowu,
et al., 2010).
GC-MS analysis of the leaves
extract of Ixora coccinea
afforded the following:
3, 7, 11, 15- Tetramethyl
2hexadecen-1-ol(51); Ethyl
15-methyl-hexa
decanoate(52);
Z,Z-6,28Heptatriacontadien-2-one(53);
Ethyl
9,cis,11,transoctadecadienoate
(54);
Ethyl
9,12,15,octadecatrienoate(55);
leaves (Arunachalam et al., 2009;
Kharat, et al., 2013; Dontha et al.,
2015)
Hypoglycaemic
and
the
hypolipidemic activity of the aqueous
extract of the leaves of Ixora
coccinea Linn in alloxan induced
diabetic albino rats have also been
reported (Neelima et al., 2011;
Maniyar and Bhixavatimath, 2011;
Kharat, et al., 2013; Dontha et al.,
2015).
Report have shown the antidiarrhoeal activity of aqueous extract
of the leaves and flowers of I.
coccinea against a castor oil induced
diarrhoea model in rats (Dontha et al.,
2015; Prabhu et al., 2010; Maniyar et
al., 2010).
Anti-inflammatory, antimitotic and
antimicrobial activities have been
reported for the leaves while CNS
depressant, hypothermic and semen
coagulant activities for the aerial
parts have also been reported
(Annapurna et al., 2003; Latha and
Panikkar, 1999).The leaves have also
been found to be active against a
plant pathogenic fungus, Drechslera
oryzae(Annapurna et al., 2003) as
well as possessing antinociceptive /
anti-inflammatory, antihistamine and
antioxidant activities (Bose et al.,
16
Bi cyclo (5.1.0)octane,8methylene(56);
Methyl
6,9,12,15,18
heneicosapentaenoate(57);
Squalene(58);
Dodecane,1fluoro
(59);
Trans-2,4Dimethylthiane S,S- Dioxide
(60);
Z,Z-6,28
Heptatriactontadien
(61);
Methyl
2-HydroxyPentadicanoate (62); Methyl
17-Methyl-Octadecanoate
(63);
Ethyl
9,12Hexadecadienoate (64); Ethyl
9,12,15
Octadecatrienoate
(65); Bicyclo [5.1.0]octane,8methyl (66); 1,3-Di methyl 3-isobutyldiaziridine(67);
Cyclohexane, hexyl (68);
1,2,4,5 –cyclo hexanetetrol
(69);
Trans-2-Methyl-4-NPentylthiane S,S-dioxide(70);
Chloroacetic acid,tetradecyl
ester (71); Heptasanoic acid,
25-methyl, methyl ester(72)
(Shyam and Suresh, 2013)
2011; Ratnasooriya et al., 2005, Saha
et al., 2008). Lupeol, isolated from
the petroleum ether fraction of the
ethanol extract of the leaves of Ixora
coccinea, showed anti-inflammatory
activity in the carrageenan-induced
paw edema test in rats (Reena et al.,
1994, Ratnasooriya et al., 2005).
Ixora coccinea extracts have also
been reported to possess wound
healing properties (Saifuddin et al.,
2006)
The in vitro antileishmanial activity
of the leaves extract has also been
reported (Naskar et al., 2013; Dontha
et al., 2015).
Evaluation of anti-asthmatic activity
of the leave extract has also been
reported(Missebukpo et al., 2011;
Kharat, et al., 2013)
Root
Diluted tincture and decoction of the
roots are used for mouthwash and as
gargles for sore throat, nausea, loss of
appetite (anorexia), fever, hiccups,
diarrhea, dysentery, sores, chronic
ulcers and skin diseases, gonorrhea
(Batugal et al., 2004; Annapurna et al.,
2003, Ratnasooriya et al., 2005;
Arunachalam et al., 2009;Joshi,et al.,
2013)
The anthelmintic activity of the roots
in different extracts against Indian
earthworm, Pherituma posthuma has
been as reported ( Surana et al., 2011;
Dontha et al., 2015).
Antileucoderma activity for the root
has also been reported (Joy et al.,
1998)
The roots of I. coccinea showed
wound healing and antimicrobial
17
Palmitic acid methyl ester,
PME (73), stearic acid methyl
ester (74), oleic acid methyl
ester (75) and linoleic acid
methyl ester (76), cis Δ9, trans
Δ11-octadecadienoic acid (77)
Palmitic acid(12),stearic
acid(13), oleic acid(14),
linoleic acid (15) (Annapurna
et al., 2003; Kharat, et al.,
Roots ground into pulp, mixed with
activity (Kharat, et al., 2013).
water and as tincter are used for
.
diarrhea and dysentery (Maniyar, et al.,
2010; Vadivu et al., 2010).
The root is alsoused as astringent and
antiseptic against scabies and other skin
diseases (Kharat, et al., 2013).
Ixora
congesta
Roxb.
Ixora
cuneifolia
(GRIN)
Ixora elliptica
R.Br et Ridl
Ixora ferrea
(Jacq.) Benth
Ixora
finlaysoniana
Remedy for fevers, toothache, measles, Anti-inflammatory (Iwu, 1993).
and bronchial infections (Iwu, 1993).
Root and stem are used to cure nervous
disorders and fever (De Block, 1998;
Johnson and Wyatt, 2004).
Leaf and root, mixed with root of
Badaduk or Decaspermum fruticosum
or root of Biliusa or Arytera sp. Is
boiled and the infusion, about 150ml
two times daily is taken, to treat warm
body and fatigue. The decoction is also
used for bath (Kulip and Majawat,
2000).
Useful in the treatment of Stomachic
(Johnson and Wyatt, 2004).
I. finlaysoniana flowers has been
scientificallydocumented to possess
estrogenic,abortifacient and antiimplantation properties (Kharat, et al.,
2013)
Anti-gestagenic activity (oral
administration of extract to adult
female rats at 250mg/kg dose on days
1-5 or 1-7 post-coitum prevented
pregnancy in 100% rats) (Kharat, et
al., 2013).
18
2013).
9, 12-Octadecadienoic(78),
di-n-octyl phthalate(79), βAmyrin(80), Kaempferol-7O-glucoside(81),
Kaempferitrin(50)
and
Quercitrin(49) (Joshi,et al.,
2013; Dontha et al., 2015)
Leaves
Ixora fulgens
Roxb.
Ixora
Roots
grandifolia
Leaves
Ixora
javanica
(Blume) DC.
Flowers
Root
I.finlaysoniana leaves showed
antigestagenicactivity.
Used in treatment of toothache(Johnson
and Wyatt, 2004)
Thea root is used in delivery and
Stomachache (Kharat, et al., 2013;
Johnson and Wyatt, 2004)
The leaves of I. grandiflora are used as
poultice in fresh form for treatment of
sprain,eczema, boils and concussions.
The decoctionof the leaves is also used
in treatment of wounds and skin ulcer
(Kharat, et al., 2013).
Flower eaten as vegetable. Leaf and I. javanica flower extract have been
flower are used in a cure-all infusion
reported to demonstrate anti-tumours
activity (Nair et al., 1991; Kharat, et
al., 2013)
Root crush with lime water/poultice for
19
n-nonacosanol(82),
αamyrin(83), β-sitosterol(25),
3-hydroxyhexan-5-olide(84),
sitosterol -3-O- β –Dglucoside(36), protocatechuic
acid(6), and Gallic acid(85),
(3R, 5R)-3-(βglucopyranosyloxy)-5hexanolide
(parasorboside)(86), D-1-Omethyl-myo-inositol(87) and
Galactitol (88)
Unny et al., 2003; Singh,
1993, Darwish and Ibraheim,
2003; Kharat, et al., 2013
.
Ferulic
acid(89),
protocatechuic
acid(6)and caffeic acid(90).
Nair and Panikkar, 1990; Nair
et al., 1991; Kharat, et al.,
2013
Ixora laxifora
Ixora
macrophylla
Barth.
I.
macrothyrsa
Methanol
flower
extract
Flowers
I. nigricans
R. Br. ex
Wight & Arn
Ixora pavetta Flowers
Stem-bark
Roots and
snake bite (Johnson and Wyatt, 2004)
Used in the treatment of inflammation Anti-nociceptive
and
antiand painful conditions such as inflammatory ((Iyadi, et al., 2005))
rheumatic arthritis, sprains, spasmodic
colics (Iyadi, et al., 2005)
Used to treat headache and puerperium
Johnson and Wyatt, 2004.
I. macrothyrsa pacifies vitiated
kapha, pitta, burning sensations,
eczema,
ringworm
other
skin
diseases
menorrhagia,leucorrhea and general
weakness.
The flowers of I. macrothyrsa are used
toimpart color to herbal preparation
(Kharat, et al., 2013).
Used to treat dysentery and root crush
with lime water/poultice for snake bite
(Johnson and Wyatt, 2004).
Traditionally the plant is used for the
treatment of diarrhoea, dysentery,
urinary disorders, leucorrhoea, veneral
diseases and sedative(Srinivas, K.;
Celestin Baboo, 2011).
Anti-bacterial (including Methicillin Wahab, et al., 2012; Kharat,
Resistant Staphylococcus aureus et al., 2013
MRSA
and
Acinetobacter
baunmannii)
.
The flowers of I. pavetta have been
extracted by ethanol and evaluated
for theantiulcer activity by Aspirin
induced and pylorus ligation of rats
(Kharat, et al., 2013).
Two spoonfuls of stem bark extract is
administered daily twice for 9 days in
the treatment of jaundice(Bapuji &
Ratnam, 2009)
Theroots are reported for its use in
20
3-butyn-2-ol(91), 3-butyn-1ol(92), amyl nitrite(93), 2octyn-1-ol(94),
1,
9decadiyne(95) and glyoxylic
acid (96) from the flowers of
I. pavetta Vahl. (Srinivas, K.;
Celestin Baboo, 2011).
I.
Fruits
philippinensis
I. parviflora Root
Vahl
Bark
Leaves
Flowers
Ixora pendula
Jack
Ixora
rhodesiaca
Bremek
Ixora stricta
Roxb
I. undulata
Leaves
urinary diseases (Talpade & Chachad,
2016)
The fruits are edible
Root used in treatment of dysuria and
Antioxidant activity (Wen et al.,
Menorrhagia ( Kharat, et al., 2013)
2011)
The fruits and roots are used as antidote
(Bachheti et al., 2011).
The decoction of bark is used for
anemia and debility (Bachheti et al.,
2011).
Antioxidant (Bose et al., 2011)
β-sitosterol(25),
The leaf extract of I. parviflora
kaempferol(97), β-sitosterolshowed antiviral, hypotensive and
3-O- β -D-glycoside (36),
spasmolytic activity (Kharat, et al., kaempferol-7-O-methyl
ether(98)
2013).
(Bachheti et al., 2011; Kharat,
et al., 2013)
The flowers of I. parviflora are
pounded in milk and given for relieving
whooping cough and in treatment of
ulcers (Bachheti et al., 2011; Kharat, et
al., 2013).
Used to treat rhinosis and sore
(Johnson and Wyatt, 2004).
Remedy for measles, cold, skin Anti-microbial (Iwu, 1993).
diseases (Iwu, 1993).
Remedy for nervous disorders and also Whitening activity (Johnson and
to treat stomach ache (Johnson and Wyatt, 2004, Kuo-Ching, 2004).
Wyatt, 2004, Kuo-Ching, 2004).
Rubiothiazepine isolated from the root Rubiothiazepine(99).
21
has been reported to show cytotoxic (Mohammed et al. 2014).
activity
against
EL4 (Murine
Leukemia) and also showed cytotoxic
and HIV-1 activity against MT-4 and
HIV-1IIIB with (Mohammed et al.
2014)
22
1-(R)-phenylethanol
βgentiobioside(100), 2-methylphenylmethanol
βgentiobioside(101),
3,4dimethylphenol
βgentiobioside(102),
(5R,6R,Z)-5,6-dihydroxy-5,6dihydro-2H-thiopyran-2oneO-methyloxime
β-Dglucopyranoside(103),
(5R,6R,Z)-5,6-dihydroxy-5,6dihydro-2H-thiopyran-2-one
O-methyl
oxime
βgentiobioside(104),
kaempferol
3-O-α-Lrhamnopyranosyl-(1→6)-(4"trans-p-coumaroyl)-β-Dgalactopyranoside7-O-α-Lrhamnopyranoside(105),corch
oionoside C(106), icariside
B1(107),
3-methoxy-4hydroxyphenol
1-O-β-Dglucopyranoside(108),
kaempferol
3-Orobinobioside(109), quercetin
3-O-robinobioside(110),
variabiloside E(111), and
acteoside(112)(Sugimoto et
al., 2014; Ragasa et al., 2015).
D-mannitol(38) (Mohammed
et al. 2014)
CH3
CH3
H 3C
H 3C
CH3
H
CH3
CH3
CH3
H
H
OH
O
HO
6,16-dihyroxy-ent-kaurane (1)
OH
OH
7-hydroxysitosterol (3)
(24R)-6-hydroxy-24-ethyl-cholest-4-en-3-one (2)
CH3
H3C
COOH
OH
OH
O
CH3
CH3
HO
H
HO
H 3C
O
OH
H
O
O
CH3
OH
O
3,3'-bis(3,4-dihydro-4-hydroxy-6-methoxy-2H-1-benzopyran)(5)
CH2
H
H
CH2OH
CH3
OH
CH3
H
H3C
CH3
CH3
H3C
H3C
H3C
H
C
H2
CH3
CH3
CH3
Betulin (7)
HO
H
H3C
Erythrodiol (8)
CH3
H3 C
CH3
CH3
CH3
CH3
HO
H3C
stigmasterol (10)
HO
CH3
OH
Protocatechuic acid (6)
Maslinic acid (4)
CH3 H
FIG. 1 Chemical constituents from the stem of Ixora amplexicaulis
HO
CH3
CH3
CH3
H
CH3
H3C
CH3
OH
H3C
CH3
Lupeol (9)
FIG. 2 Chemical constituents from the leaves of Ixora arborea
23
HO
O
O
HO
O
O
HO
OH
Chrysin-5-O- -D-xylopyranoside (11)
FIG. 3 Chemical constituents from the stem of Ixora arborea
O
O
OH
OH
Stearic acid (13)
Palmitic acid (12)
OH
OH
O
Oleic acid (14)
O
Linoleic acid (15)
OH
OH
O
O
cis,cis,cis, trans-8,10,12,14- octadecatetraenoic acid
(ixoric acid) (17)
crepenynic acid
(octadec-cis-9-en- 1 2-ynoic acid) (16)
FIG. 4 Chemical constituents from the seed oil of Ixora chinensis
HO
O
HO
O
H
H
H
HO
O
O
OH
O
OH
O
H
OH
O
CH3
O
OH
H
HO
O
HO
H
HO
H
OH
O
O
HO
O
HO
Ixoroside (18)
HO
O
HO
HO
Ixoside (7,8-dehydroforsythide) (19)
FIG. 5 Chemical constituents from the leaves of Ixora chinensis
24
HO
Geniposidic acid (20)
CH2
H3 C
H3C
H3C
H3C
H 3C
H
OH
O
OH
H3C
O
CH3
O
CH3
CH3
O
H3 C
CH3
H 3C
H
CH3
CH3
HO
H3C
H
CH3
Cycloartenol 3-palmitate (21) Cycloartenol 3-myristate (22)
H 3C
CH3
H
Lupeol (23)
CH2
H3C
CH3
H
H3C
H3C
CH3
H3C
CH3
CH3
COOH
O
H3C
H 3C
H
CH3
CH3
O
HO
H3C
HO
CH3
H
CH3
Sitosterol (25)
Oleanolic acid (24)
CH3
Lupeol 3-palmitate (26)
H3 C
CH3
CH3
COOH
CH3
HO
H3 C
CH3
H
Ursolic acid (27)
FIG. 6 Chemical constituents from the flowers of Ixora coccinea
25
CH3
OH
HO
O
OH
OH
OH
HO
HO
O
O
OH
OH
O
Myricetin (28)
O
OH
OH
OH
OH
OH
OH
OH
HO
OH
O
O
O
O
Rutin (30)
Quercetin (29)
H 3C
O
HO
HO
HO
O
OH
OH
OH
HO
O
O
+
OH
O
O
CH3
Formononetin (32)
HO
OH
O
OH
O
H3C
OH
OH
HO
O
HO
+
OH
O
OH
O
HO
Cyanadin-3-rutinoside (33)
OH
HO
OH
O
O
OH
Delphinidin 3-O-glucoside (34).
FIG. 7 Chemical constituents from the flowers of Ixora coccinea
CH3
O
CH3
H3C
CH3
H3C
CH3
H
H
CH3
H
H
H3C
CH3
O
H
H
O
HO
HO
OH
CH3
21,23-Epoxy-tirucall-7-en-3ol (35)
(Ixoroid )
CH3
CH3 H
OH
H
H
HO
OH
Stigmast-5-en-3-O--D-glucoside (36)
(Sitosterol-3-O--D-glucoside)
OH
OH
OH
HO
OH
OH
D-mannitol (38)
26
CH3
FIG. 8 Chemical constituents from the flowers of Ixora coccinea
H2C
CH3
CH2
CH3
CH3
CH3
H3C
H
CH3
H3C
H3C
CH3
CH3
H
CH3
H 3C
H
CH3
17-dammara-12,20-diene-3-ol (40)
(Ixorene)
HO
H3C
H
CH3
Lupeol (23)
H3C
H3C
OH
OH
H 3C
OH
HO
OH
HO
Sitosterol (25)
OH
D-mannitol (38)
CH3
O
OH
O
O
O
N
H
O
NH
O
HN
N
N
H
H3CO
N
O
Ixorapeptide II (42)
Ixorapeptide I (41)
FIG. 9 Chemical constituents from the leaves of Ixora coccinea
27
OH
OH
OH
OH
HO
OH
HO
O
O
OH
OH
OH
HO
O
O
OH
OH
HO
OH
OH
O
HO
O
OH
O
O
HO
O
HO
OH
HO
OH
OH
Epicatechin (43)
Procyanidin A-2 (44)
OH
HO
OH
Ixoratannin A-2 (45)
OH
OH
HO
O
OH
OH
OH
O
H3C
HO
OH
O
HO
O
OH O
O
HO
OH
OH
O
HO
OH O
OH
kaempferol 7-O--L-rhamnoside (47)
HO
HO
OH
O
HO
Kaempferol 3-O--L-rhamnoside (48)
OH
OH
H3C
HO
HO
HO
HO
O
OH
OH
O
O
O
OH
HO
OH
HO
OH
Cinnamtannin B-1 (46)
O
OH
O
HO
CH3
OH
O
O
O
OH
CH3
O
Kaempferol 3, 7-O- -L-dirhamnoside (kaempferitrin) (50)
OH
O
O
HO
CH3
OH
O
HO
Quercetin-3-O--L-rhamnopyranoside (49)
(Quercetrin)
FIG. 10 Chemical constituents from the leaves of Ixora coccinea
28
HO
O
O
Ethyl 15-methyl-hexa decanoate (52)
O
3, 7, 11, 15- Tetramethyl 2 hexadecen-1-ol (51)
O
O
Ethyl 9,cis,11,trans octadecadienoate (54)
Z,Z-6,28-Heptatriacontadien-2-one (53)
OR
(6Z,28Z)-heptatriaconta-6,28-dien-2-one
Bi cyclo (5.1.0) octane,8-methylene (56)
O
O
Ethyl 9,12,15,octadecatrienoate (55)
F
O
Dodecane,1-fluoro (59)
O
Methyl 6,9,12,15,18 heneicosapentaenoate (57)
O
S
O
Trans-2,4-Dimethylthiane S,S- Dioxide (60)
Squalene (58)
O
HO
O
Methyl 2-Hydroxy-Pentadicanoate (62)
Z,Z-6,28 Heptatriactontadien (61)
O
O
O
O
Ethyl 9,12-Hexadecadienoate (64)
Methyl 17-Methyl-Octadecanoate (63)
FIG. 11 Chemical constituents through GC-MS from the leaves of Ixora coccinea
29
HO
OH
HO
OH
O
O
Ethyl 9,12,15 Octadecatrienoate (65);
1,2,4,5 -cyclo hexanetetrol (69)
O
S
O
Bicyclo [5.1.0]octane,8-methyl (66)
Trans-2-Methyl-4-N-Pentylthiane S,S-dioxide (70)
N
O
NH
O
1,3-Di methyl -3-isobutyldiaziridine (67)
Cl
Chloroacetic acid,tetradecyl ester (71)
O
Cyclohexane, hexyl (68)
O
Heptasanoic acid, 25-methyl, methyl ester (72)
FIG. 12 Chemical constituents through GC-MS from the leaves of Ixora coccinea contd.
O
O
O
O
Palmitic acid methyl ester, PME (73)
Stearic acid methyl ester (74)
O
Oleic acid methyl ester (75)
O
Linoleic acid methyl ester (76)
O
O
O
COOH
OH
cis, trans-9, 11-octadecadienoic acid (77)
Palmitic acid (12)
O
OH
OH
Stearic acid (13)
Oleic acid (14)
OH
Linoleic acid (15)
O
FIG. 13 Chemical constituents from the root of Ixora coccinea
30
O
H3C
O
CH3
O
OH
CH3 H3C
O
CH3
O
CH3
9, 12-Octadecadienoic (78)
O
HO
Di-n-octyl phthalate (79)
CH3
H3C
-amyrin (80)
OH
HO
HO
OH
O
OH
OH
H 3C
HO
O
O
OH
HO
O
O
O
OH
HO
O
OH
OH
OH
O
O
OH
CH3
O
Kaempferol 3, 7-O- -L-dirhamnoside (kaempferitrin) (50)
Kaempferol-7-O-glucoside (81)
OH
OH
O
HO
OH
O
HO
O
O
CH3
OH
HO
Quercetin-3-O--L-rhamnopyranoside (49)
(Quercetrin)
FIG. 14 Chemical constituents from the root of Ixora coccinea contd.
31
CH3
H 3C
H 3C
H 3C
OH
CH3
CH3
CH3
nonacosanol (82)
CH3
CH3
HO
HO
CH3
COOH
HO
H3C
Sitosterol (25)
-amyrin (83)
CH3
H 3C
H 3C
CH3
CH3
H
O
OH
O
OH
Protocatechuic acid (6)
3-Hydroxyhexan-5-olide (84)
COOH
H
O
HO
HO
OH
H
CH3 H
OH
O
CH3
Stigmast-5-en-3-O--D-glucoside (36)
(Sitosterol-3-O--D-glucoside)
OH
HO
HO
HO
O
O
CH3
OH
Parasorboside (86)
OH
OH
OH
O
OH
HO
HO
HO
O
O
CH3
D-1-O-methyl-myo-inositol (87)
Gallic acid (85)
HO
HO
OH
HO
OH
HO
Galactitol (88)
FIG. 15 Chemical constituents from the leaves of Ixora finlaysoniana
COOH
HO
O
OH
HO
O
O
OH
OH
OH
Ferulic acid (89)
caffeic acid (90)
OH
(4-hydroxy-3-methoxy cinnamic acid)
Protocatechuic acid (6)
OR
[(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid]
FIG. 16 Chemical constituents from the flowers of Ixora javanica
32
CH3
OH
OH
O
O
N
amyl nitrite (93)
3-butyn-1-ol (92)
3-butyn-2-ol (91)
O
O
OH
OH
1, 9-decadiyne (95)
Glyoxylic acid (96)
2-octyn-1-ol (94)
FIG. 17 Chemical constituents from the flowers of Ixora pavetta
CH3
H3C
H 3C
CH3
H 3C
H
O
Sitosterol (25)
HO
OH
H3C
O
O
OH
OH O
Kaempferol (97)
H
Stigmast-5-en-3-O--D-glucoside (36)
(Sitosterol-3-O--D-glucoside)
OH
OH
O
CH3
O
HO
HO
HO
H
CH3 H
OH
H 3C
CH3
OH
OH O
Kaempferol-3-O-methyl ether (98)
FIG. 18 Chemical constituents from the leaves of Ixora parviflora
33
HO
OH
O
HO
O
HO
S
OH
N
O
CH3
Rubiothiazepine (99)
7-[(-D-glucopyranosyl)oxy]-6- hydroxy-2-methoxy-4,5-dihydro-1,3-thiazepine
Glc
Glc 6' GlcO
1-(R)-phenylethanol -gentiobioside (100)
6'
GlcO
2-methylphenylmethanol-gentiobioside (101)
HO
Glc
6'
GlcO
GlcO
S
3,4-dimethylphenol -gentiobioside (102)
N
HO
O
Glc
6'
GlcO
(5R,6R,Z)-5,6-dihydroxy-5,6-dihydro-2H-thiopyran-2one O-methyl oxime 6-O--D-glucopyranoside (103)
S
OH
N
O
RhaO
O
(5R,6R,Z)-5,6-dihydroxy-5,6–2H-thiopyran2-one O-methyl oxime-gentiobioside (104)
OH
O
4''
OGal
E-p-coumarate
6''
Rha
kaempferol 3-O--L-rhamnopyranosyl-(1 6)-(4"-trans-pcoumaroyl)--D-galactopyranoside 7-O--L-rhamnopyranoside (105)
FIG. 19 Chemical constituents from the leaves of Ixora undulata
34
H
C
OH
OH
OH
OH
OH
O
O
HO
HO
HO
O
O
O
O
OH
OH
Corchoionoside C (106)
Icariside B1 (107)
OH
OH
HO
OH
O
OH
O
O
HO
HO
OCH3
OH
O
OH
OH
OH
O
O
O
3-methoxy-4-hydroxyphenol-1-O--D-glucopyranoside (108)
H 3C
O
HO
OH
HO
OH
kaempferol 3-O-robinobioside (109)
O
HO
OH
OH
OH
OH
O
OH
OH
O
O
HO
O
O
O
OH
H 3C
O
OH
HO
OH
quercetin 3-O-robinobioside (110
O
variabiloside E (111)
OH
O
HO
OH
OH
OH
Rha (6'')--D-Gal (4'-E-coumarate)
O
O
HO
H 3C
HO
Rha (3')-Glu (4'-E-caffeate)
O
O
O
O
O
OH
OH
O
OH
H3C
OH
HO
O
HO
HO
OH
OH
O
HO
HO
OH
OH
acetoside (112)
OH
OH
D-mannitol (38)
NOTE: Robinobioside: [ -D-(6'-O--L-rhamnopyranosyl)galactopyranoside]
FIG. 20 Chemical constituents from the leaves of Ixora undulatacontd
35
CHAPTER TWO
METHODOLOGY
2.1 COLLECTION
The leaves of five different species of Ixora were collected from different locations at Obafemi
Awolowo University, Ile-Ife (pictures of the aerial parts of these species are shown in Figure 21
below). Voucher specimens have been deposited at the department of Botany, Obafemi Awolowo
University, for proper identification. For the purpose of this study, these plants are known as small
red (SR) – having small leaves and red flowers; small yellow (SY) – having small leaves and yellow
flowers; medium red (MR) – having medium-sized leaves and red flowers; medium yellow (MY) –
having medium-sized leaves and yellow flowers; and big red (BR) – having big leaves and red
flowers.
36
aghgh
SMALL YELLOW (SY)
SMALL RED (SR)
MEDIUM YELLOW (MY)
MEDIUM RED (MR)
BIG RED (BR)
37
2.2 EXTRACTION
The leaves from each plant were separately air-dried at ambient temperature and labeled. The dried
leaves were then size-reduced and extracted with methanol by percolation. The filtrates form each
plant material was concentrated using a rotary evaporator.
2.3 FRACTIONATION
About 2g of each crude extract was dissolved using small volumes of methanol, adsorbed unto
silica gel with the aid of a mortar and pestle, and then, it was left to dry. The dried silica gel was
packed into a column that had been laid with cotton wool, and after packing, the column was
overlaid with cotton wool. The adsorbed extract was then eluted with n-hexane, ethyl acetate,
acetone and methanol (in order of increasing polarity). The eluate of each solvent were combined,
concentrated to dryness and then reconstituted using the same solvent. This yielded the following
fractions:
n-Hexane fractions,
Ethyl acetate fractions,
Acetone fractions,
Methanol fractions and
Crude extracts each of SR, SY, MR, MY, and BR.
Partition was not done because the crude extracts were not soluble in water.
2.4 THIN LAYER CHROMATOGRAPHY (TLC)
Each fraction (i.e. n-hexane, ethyl acetate, acetone and methanol) and the crude extracts from all the
species were analyzed using silica gel pre-coated on alumina plates. All TLC analyses were carried
38
out at ambient temperature, in a 10ml chromatographic tank. Different solvent systems were tried
before the reported solvent systems were used.
Fractions
Solvent system used
n-Hexane
Ethyl acetate
EtOAc (100%)
EtOAc:n-Hex (1:1)
EtOAc:n-HEx(7:3)
Acetone
MeOH:EtOAc:AcOH (1:10:0.5)
Methanol
MeOH:EtOAc:AcOH (3:7:0.5)
Crude
n-Hex:EtOAc:AcOH (1:10:0.5)
39
CHAPTER THREE
RESULT
EtOAc fractions
Solvent system: EtOAc 100%
EtOAc fractions
Solvent system: EtOAC:n-Hex
1:1
EtOAc fractions
Solvent system: n-Hex:EtOAc 3:7
Acetone fractions
Solvent system:
MeOH:EtOAc:AcOH 1:10:0.5
40
MeOH fractions
Solvent system:
MeOH:EtOAc:AcOH 3:7:0.5
Crude extract
Solvent system:
n-Hex:EtOAc:AcOH 1:10:0.5
41
CHAPTER FOUR
DISCUSSION AND CONCLUSION
The extensive literature survey revealed that Ixora species have different important medicinal
properties with diverse pharmacological spectrum. This study reviews the various chemical
constituents, pharmacological, therapeutic applications and traditional knowledge of the genera
Ixora. The ethno-pharmacological uses and biological activities attributed to species of Ixora
suggest that this genus is a rich source of medicinally useful phytochemicals. This study has
revealed that most of the compounds that have been reported from this genus were isolated form
Ixora coccinea, followed by Ixora undulata. It is also clear from the study that only few of these
compounds exist in other species as well.
The chemical profiling of five different species (SR, SY, MR, MY and BR) in our laboratory using
TLC revealed that less than 40% of the chemical constituents are the same which further proved
that there are significant differences in their chemical constituents as shown in the discussion of
results below.
ETHYL ACETATE FRACTION (EtOAc fr)
Solvent system: EtOAc:Hex 7:3
The constituent at Rf-0.839 is present in both MR and MY, but absent in all others. Likewise, the
constituent at Rf-0.805 is present in both SR and SY, but absent in others. The constituent at Rf0.782 is only present in MR, it is absent in others, while the constituent at Rf-0.736 is present in all
except BR, but is lightly expressed. The constituent at Rf-0.701 is only present in MR and MY.
Two different bands (having different colours) appear at Rf-0.609. One is present in SR and SY,
while the other is only present in MR. The constituent at Rf-0.471 is only present in SR and SY. A
constituent appears at Rf-0.437, which is only present in MR. The constituent at Rf-0.425 is present
in MY, and it seems to be present in BR. The constituent at Rf-0.345 is present in SR and SY, but
absent in others. Two different bands appear at Rf-0.287, one is only present in BR, while the other
42
is present in SR, SY and MY. Two different bands appear at 0.253, one is present in MR, while the
other in MY. Two different constituents appear at Rf-0.218 and 0.138, both are present only in MR.
The constituent at Rf-0.23 is only present in SR and SY. The constituent at Rf-0.195 is only present
in BR. Two different constituents appear at Rf-0.184, one is present only in MY, while the other is
present only in SR and SY. The constituent at Rf-0.172 is present in all. The constituent at Rf-0.161
is only present in BR.The constituent at Rf-0.115 is present only in SR, SY and MR. The
constituent at Rf-0.080 is only present in SR, SY and MY.
ACETONE FRACTION
Solvent system: MeOH:EtOAc:AcOH 1:10:0.5
The constituent at Rf-0.651 is present in SR, SY and MR, but not conspicuous in others. The
constituents at Rf-0.535 is again present in SR, SY and MR, but not obvious in others. The
constituent at Rf-0.151 is present in all except MY.
METHANOL FRACTION (MeOH fr)
Solvent system: MeOH:EtOAc:AcOH 3:7:0.5
The constituents at Rf-0.391 and 0.092 are present in all.
CRUDE EXTRACT
Solvent system: n-Hex:EtOAc:AcOH 1:10:0.5
The constituent at Rf-0.860 is present in BR and MY, but is absent in MR. The constituent at Rf0.849 is only conspicuous in MR. The constituent at Rf-0.814 is present in BR and MY. The
constituents at Rf-0.709, 0.663, 0.360 and 0.058 are present in all extracts. The constituent at Rf0.628 is present in all except BR, but is lightly expressed in MR. The constituent at Rf-0.198 is
present in all except in BR.
The review also revealed that many of the isolated chemical compounds from the various species
possess good anti-oxidant, anti-cancer, anti-inflammatory, anti-HIV or antiviral etc activities.
43
The systematically analyzed batteries of in-vitro assays and various chemical constituents isolated
from these genus has in no doubt provided insight into the factors contributing to their bioactivity
and hence, their various important medicinal uses. However, despite the fact that different species
had been extensively used traditionally, various pharmacological activities of isolated chemical
compounds have not extensively tested. There is need for further evaluation of the pharmacological
potency of the various compounds isolated from Ixora species in order to make them useful in
formulations for their practical clinical applications, which can be used for the welfare of mankind.
This is an attempt to compile and document the information on different aspects of Ixora species
and highlight the needs for research and development in future.
44
REFERENCES
Aher, A.N.; Pal, S. C. and Muke, S.A. (2013). Analgesic and anti-inflammatory activities of Ixora
coccinea flower. Indian Drugs, 50 (01): 64-67
Aktar, F.; Kaisar, Md.A.; Kabir, A. N. M. H.; Hasan, C.M. and Rashid, M.A. (2009).
Phytochemical and Biological Investigations of Ixora arborea Roxb. Dhaka University
Journal of Pharmaceutical Sciences, 8 (2): 161-166.
Arunachalam, G.; Subramanian, N.; Pazhani, G. P.; Karunanithi, M. and Ravichandran, V. (2009).
Phytochemical and anti-ulcer investigation of the fresh leaf extract of I.coccinea Linn
(Rubiaceae) in albino rat model, Int. J. Pharm. Sci. 1, 26-31.
Bachheti, R. K.; Pandey, D.P.; Joshi, A.; Rana, V. and Rai, I. (2011). Phytochemical analysis of
aerial Parts of Ixora parviflora. International Journal of ChemTech Research, 3 (3): 10281032.
Bapuji, J.L and Ratnam, S.V (2009). Traditional Uses of Some Medicinal Plants by tribals of
Gangaraju Madugula Mandal of Visakhapatnam District, Andhra Pradesh. Ethnobotanical
Leaflets 13: 388-398.
Batugal, Pons A; Jayashree Kanniah; Lee Sok Young and Jeffrey T Oliver (2004). Medicinal
Plants Research in Asia. The Framework and Project Workplans, 1: 164
Bose, S.; Maji, S. and Chakraborty, P. (2011). Comparative study of In Vitro and In Vivo
antioxidant property of different Ixora species. Journal of Advanced Pharmacy Education &
Research, 2: 90-103
Chauhan, J.S.; Kumar, S. and Chaturvedi, R. (1984). A flavone glycoside from the stem of Ixora
arborea. Phytochemistry, 23(10): 2404-2405
Chen, L.; Zhan, R.; Jiang, J.; Zhang, Y.; Dong, Y. and Chen, Y. (2016). A new ent-kaurane
45
diterpenoid from Ixora amplexicaulis. Nat Prod Res., 30(1):105-109
Darwish, F.M.M. and Ibraheim, Z.Z. (2003). Phytochemical Study of Ixora finlaysoniana Wall.
Ex.G.Don growing in Egypt. Bull Pharm Sci. 26(1):91-96.
Dontha, S., Kamurthy, H. and Mantripragada, B. (2015). Phytochemical and Pharmacological
Profile of Ixora: A Review. International Journal of Pharmaceutical Sciences and Research,
6(2): 567-584.
Idowu, T. O.; Ogundaini, A. O.; Salau, A. O.; Obuotor, E. M.; Bezabih; M. and Abegas, B. M.
(2010). Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora
coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry; 71 (17-18).
Ikram, A.; Versiani, M. A.; Shamshad, S.; Ahmed, S. K.; Ali, S. T. and Faizi, S. (2013). Ixorene, a
New Dammarane Triterpene from the Leaves of Ixora coccinea Linn. Rec. Nat. Prod., 7 (4):
302-306
Iyadi, K. C., Antai, A.B., Nia, R. and Okokon, J.E. (2005). Anti-inflammatory and Antinociceptive
Activity of Methanol extract from Ixora laxifora flower. African Journal of Biomedical
Research, 8: 47 – 50.
Joshi, A.B.,
Surlikar, P.M. and Bhobe, M. (2013).
Ixora coccinea Linn: Phytochemical
Investigation. International Journal of Research in Pharmacy and Chemistry, 3 (3): 691-696
Joy, P. P.; Thomas, T.; Mathew, S. and Skaria, B.P. (1998). Medicinal Plants: Aromatic and
Medicinal Plants Research Station Kerala Agricultural UniversityPublisher, Kerala, India,
p193
Kharat, A. R. Nambiar, V. V.; Tarkasband, Y. S And Pujari, R.R (2013).
Phytochemical and Pharmacological Activity of Genus Ixora.
A Review on
International Journal of
Research in Pharmacy and Chemistry; 3 (3): 628-635
Laloo, R; Kharlukhi, CL; Jeeva, S and Mishra, BP (2006). Status of medicinal plants in the
disturbed and the undisturbed sacred forests of Meghalaya, northeast India: population
46
structure and regeneration efficacy of some important species. Current Science, 90(2):225232.
Lee, C.L.; Liao, Y.C.; Hwang, T.L.; Wu, C.C.; Chang, F.R. and Wu, Y.C. (2010). Ixorapeptide I
and ixorapeptide II, bioactive peptides isolated from Ixora coccinea. Bioorganic & Medicinal
Chemistry Letters, 20: 7354–7357
Liang, Juanjuan; Gao, Huimin; Chen, Liangmian; Xiao, Wei; Wang, Zhenzhong; Wang, Yongyan
and Wang, Zhimin (2014). Chemical Profiling of an Antimigraine Herbal Preparation,
Tianshu Capsule, Based on the Combination of HPLC, LC-DAD-MSn, and LC-DAD-ESI-ITTOF/MS Analyses. Evidence-Based Complementary and Alternative Medicine; pp 11
Maniyar, Y. and Bhixavatimath, P. (2011). Evaluation of the Hypoglycaemic and Hypolipidaemic
activities of the aqueous extract of the leaves of I. coccinea Linn. in Diabetic Rats. Journal of
Clinical and Diagnostic Research, 5(7): 1381-1384.
Maniyar, Y.; Bhixavatimath, P. and Agashikar, N.V. (2010). Anti-diarrhoeal activity of flowers of
Ixora coccinea Linn. in rats. J Ayurveda Integr Med., 1(4): 287-291.
Minquan, H. (1990). A C18 conjugated tetraenoic acid from Ixora chinensis seed oil.
Phytochemistry, 29 (4): 1317-1319
Missebukpo A; Metwogo K; Agobon A; Eklu Gadegbeku K; Akilikoku K and Gbeassor M (2011):
Evaluation of anti-asthmatic activity of Ixora coccinea. Journal of pharmacology and
toxicology; 6(6): 559-570.
Mohammed MMD, Ibrahim NA, Chen M, Zhai L (2014) Rubiothiazepine a Novel Unusual
Cytotoxic Alkaloid from Ixora undulata Roxb. Leaves. Nat Prod Chem Res., 2 (2): 1-4
Momin, F.; Shaikh, S.; Khan, N.; Joshi, R.; Shikalgar, T. and Naikwade, N. (2011).
Cardioprotective effect of Ixora coccinea Linn. flower extract on Doxorubicin induced
Cardiomyopathy in Rats. Pharmacologyonline 3: 1145-1158
Nair, SC; Panikkar, B; Akamanchi, K. G.; Panikkar, K. R. (1991). Inhibitory effects of Ixora
47
javanica extract on skin chemical carcinogenesis in mice and its antitumour activity. Cancer
Letters, 60(3):253-258.
Naskar, M.; Bhattacharya, S. and Biswas, M. (2013). Antileishmanial effect of Ixora coccinea leaf
extracts on the in vitro growth of Leishmania donovani promastigotes. J. Adv. Pharm. Edu. &
Res. 3(4).
Neelima, N.; Sudhakar, M.; Patil, M. B.; and Lakshmi, B. V. S. (2011). Hypolipidemic activity and
HPTLC analysis of Ixora coccinea L. Leaves. Journal of Applied Pharmaceutical Science, 01
(10): 172-175
Policepatel, S.S. and Manikrao, V.G. (2013). Ethnomedicinal plants used in the treatment of skin
diseases in Hyderabad Karnataka region, Karnataka, India. Asian Pac J Trop Biomed, 3(11):
882-886
Prabhu, B., Yasmeen, M. and Agashikar, N.V (2010). Evaluation of the Anti-diarrhoeal Activity
of the Leaves of Ixora coccinea Linn. in rats. Journal of Clinical and Diagnostic Research, 4:
3298-3303.
Purkayastha, J.; Nath, S.C. and Islam, M. (2005). Ethnobotany of medicinal plants from DibruSaikhowa Biosphere Reserve of Northeast India. Fitoterapia, 76: 121– 127
Radhakrishnan, C (2002). The red bloom, The Hindu Online edition of India's National Newspaper
Tuesday, Dec 10, 2002.
Ragasa, C.Y., Tan, M.C.S., Fortin, D.R., Shen, C-C. (2015).
Chemical Constituents of Ixora
philippinensis Merr. Journal of Applied Pharmaceutical Science, 5 (09): 062-067
Ragasa, CY; Tiu, F and Rideout, JA (2004). New cycloartenol esters from Ixora coccinea.
Natural Product Research, 18(4):319-323
Rajeev, P. and Rajamanoharan, S. (2014). An ethno botanical survey of medicinal plants in
Sillalai, Jaffna, Northern Province, Sri Lanka. International Journal of Herbal Medicine; 1
(6): 22-30
48
Rasheed, N. M. A.; Nagaiah, K.; Goud, P. R. and Sharma V. U. M. (2012). Chemical marker
compounds and their essential role in quality control of herbal medicines; Annals of
Phytomedicine 1(1): 1-8,
Ratnasooriya W. D.; Deraniyagala, S.A.; Bathige, S. D. N. K.; Goonasekara, C.L. and Jayakody,
J. R. A. C. (2005a). Antinociceptive action of aqueous extract of the leaves of Ixora
coccinea. Acta Biologica Hungarica, 56 (1–2): 21–34
Ratnasooriya, W. D.; Deraniyagala, S.A.; Galhena, G; Liyanage, S. S. P.; Bathige, S. D. N. K. and
Jayakody, J. R. A. C. (2005b) Anti-inflammatory activity of the aqueous leaf extract of Ixora
coccinea. Pharmaceutical Biology, 43(2):147-152.
Sadeghi-Nejad, B. and Deokule, S.S. (2009). Antidermatophytic activities of Ixora brachiate
Roxb. African Journal of Biochemistry Research, 3 (10):344-348
Sadeghi-Nejad, B., Saki, J. and
Azish, M. (2014). Effect of Aqueous Allium cepa and Ixora
brachiata Root Extract on Leishmania major Promastigotes. Jundishapur J Nat Pharm Prod.,
9(2): 1-3
Saha, R.; Alam, Md. A.; Akter, R. and Jahangir, R. (2008). In vitro free radical scavenging
activity of Ixora coccinea L. Bangladesh J Pharmacol., 3: 90-96
Saravanan, P. and Boopalan, E. (2011). Occurrence of Camptothecin an Anticancer Drug from
Ixora coccinea Linn. Intl. J. Appl. Biol,. 2 (2): 30-34
Sharma, J.; Gairola, S.; Gaur, R.D. and Painuli, R.M. (2012). The treatment of jaundice with
medicinal plants in indigenous communities of the Sub-Himalayan region of Uttarakhand,
India. Journal of Ethnopharmacology 143 (1): 262–291
Shyam, P. and Suresh, P.K. (2013). Comparative analysis of three leaf extracts of Ixora coccinea
Linn. for their protective and antioxidant potentials and correlation with analytical data.
International Journal of Pharma and Bio Sciences, 4(4): 937 – 949
Sofowora, A (2008) Medicinal plants and traditional medicine in Africa. John Wiley and Sons,
49
New York.
Songlin Li, Quanbin Han, Chunfeng Qiao, Jingzheng Song, Chuen Lung Cheng, and Hongxi Xu
(2008). Chemical markers for the quality control of herbal medicines: an overview. Chinese
Medicine v.3
Srinivas K, Celestin Baboo RV. (2011). GC-MS study of Ixora pavetta Vahl. International J
Pharm Sci Res, 2(8):2100-2102.
Srivastava, R.C. and Nyishi Community (2010). Traditional Knowledge of Nyishi (Daffla) Tribe
of Arunachal Pradesh. Indian Journal of Traditional Knowledge, 9 (1):26-37
Sugimoto, S.; Matsunami, K.; Wanas, A. S.; Mizuta, T.; Kamel, M. S. and Otsuka, H. (2014).
Structure elucidation of secondary metabolites isolated from the leaves of Ixora undulata and
their inhibitory activity toward advanced glycation end-products formation. Phytochemistry,
108:189-95.
Sumathy H.; Sangeetha J. and Vijayalakshmi, K. (2011). Chromatographic Fingerprint Analysis
of Ixora coccinea Methanolic Flower Extract.
International Journal of Pharmaceutical
Sciences and Drug Research. 3(4): 327-330
Surana, A. R.; Aher, A. N.; Pal, S. C. and Deore (2011). Evaluation of anthelmintic activity of
Ixora coccinea. J. of Pharm. & Life Sci., 2(6): 813-814.
Swatantra K. S. Kushwaha, Neelottama Kushwaha, Neeleshwar Maurya, A. K. Rai (2010). Role of
Markers in the Standardization of Herbal Drugs: A Review. Archives of Applied Science
Research, , 2 (1) 225-229
Takeda, Y.; Nishimura, H. and Inouye, H. (1975). Two new iridoid glucosides from Ixora
chinensis. Phytochemistry, 14(12): 2647-2650
Talpade, M. B. and Chachad, D. P. (2016). Pharmacognostic & Phytochemical Characterization of
Ixora alba L. World Journal of Pharmaceutical Research; 5 (3): 1015-1022
50
Usha, M. L.; Reginald, A.M. and Immanuel, G. (2016). .Ixora L. - An Overview. European
Journal of Pharmaceutical and Medical Research, 3(2), 146-154
Vadivu, R.; Jayshree, N.; Kasthuri, C.; Rubhini, K. and Rukmankathan, G. (2009).
Pharmacognostical standardization of leaves of Ixora coccinea Linn. J. Pharm. Sci. & Res.,
1(4): 151-157
Versiani, M. A.; Ikram, A.; Khalid, S.; Faizi, S. and Tahiri, I.A. (2012).
Ixoroid: A New
Triterpenoid from the Flowers of Ixora coccinea. Natural Product Communication, 7 (7):
831-834.
Wen, K. C.; Chiu, H. H.; Fan, P. C.; Chen, C. W.; Wu, S. M.; Chang, J.H. and Chiang, H. M.
(2011). Antioxidant activity of Ixora parviflora in a cell/cell-free system and in UV-exposed
human fibroblasts. Molecules, 16(7):5735-52
Yadava R.N. (1989). Analysis of Fixed Oils from the roots of I. Coccinea. Asian Journal of
Chemistry, 1 (3): 307-308.
51