Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

Isolation and Characterization of Iridoid Glycoside (Gardenoside)

Present in the Leaves of Gardenia jasminoides J.Ellis Cultivated in Iraq
Usama H. Abdul Wahab

*,1
and Zainab J. Awad

*
Department of Pharmacognosy and Medicinal Plants, College of Pharmacy, University of Baghdad, Baghdad,Iraq.

Abstract
Iridoid glycosides are a group of naturally occurring chemical compounds. They are a large family

of compounds biosynthesized by plants, they often have pharmacological effects. The aim of this study

is to isolate and identified iridoid glycoside in a newly studied, cultivated in Iraq named Gardenis

jasminoides. The medicinal importance of iridoid glycoside, on one hand and absence of phytochemical

investigation on leaves of Gardenia on the other hand, acquired this study its importance. Many

compounds were isolated from leaves plant part one of these compounds was identified by different

chemical analysis like: melting point (MP), thin layer chromatography (TLC), Fourier transforms

infrared spectra (FTIR) and high performance liquid chromatography (HPLC).
Keywords: Gardenia jasminoides , Gardenoside,Geniposide,Genipin.

فصل وتوصيف االريدويد كاليكوسايد )الكاردينوسايد( الموجود في اوراق نبات الكاردينيا

المستسرع في العراق
اسامه حسن عبد الوهاب

*،1
و زينة جليل عواد

الخالصة
يٍ قبم انكثيز يٍ انُباجات ٔجهؼب دٔرا يًٓا في يؼانجة ٔجُظيى جصُغ األريذٔيذ كاليكٕسايذ ْي يجًٕػة يٍ انًزكبات انحي

انٓذف يٍ ْذِ انذراسّ ْٕ فصم ٔجشخيص انكاليكٕسايذات انًٕجٕدِ في انُبات انًسحزرع في انؼزاق اسًّ اٌ انكثيز يٍ االيزاض.

(Gardenia.)

انطبية نألريذٔيذ كاليكٕسايذ ٔػذو ٔجٕد دراسّ ػهًيّ جحُأل انًكَٕات انكيًيائية الٔراق َبات انكارديُيا انًسحزرع ٔنالًْية

جى فصم اكثز يٍ يزكب يٍ األريذٔيذ كاليكٕسايذ )انكارديُٕسايذ ٔانجيُيبٕسايذ( يٍ حيث اكحسبث ْذِ انذراسة اًْيحٓا،في انؼزاق

.(M.P, TLC, FTIR and HPLC)انحزكيب انكيًائي نٕاحذ يُٓا بٕاسطة قياس أراق انُبات ٔانحؼزف ػهى
.، جنبين ،الجينيبوسايد الكاردينيا ، الكاردينوسايد :لكلمات المفتاحية ا

Introduction
Rubiaceae are an easily recognizable

family characterized by opposite leaves that

are simple and entire, with interpetiolar

stipules, tubular sympetalous corollas and an

inferior ovary
(1)

. Exceptionally, there are

some plants that have only a single leaf at

each node, alternating from one side to the

other. In these cases, the alternate leaf

arrangement is produced through the

suppression of one leaf at each node
(2)

. A

wide variety of growth forms are present in

the Rubiaceae. While shrubs are most

common, members of the family can also be

trees, lianas or herbs. The flowers, which are

usually bisexual, have a 4–5 lobed calyx and

generally a 4–5 lobed corolla, 4 or 5 stamens

and two carpels
(2)

Gardenia was named by Linnaeus after

Dr. Alexander Garden (1730–1791), a Scottish

physician who immigrated to South Carolina

and corresponded with Linnaeus about

American plants; G. jasminoides is botanical

Latin for ‘jasmine-like'. Gardenias are

evergreen shrubs and small trees growing 1–5

m tall. The leaves are opposite or in whorls of

3 or 4 cm long and 3–25 cm broad, dark green

and glossy with a leathery texture
(3)

. The

flowers are solitary or in small clusters, white,

or pale yellow, with a tubular-based corolla

with 5–12 petals from 5–12 cm in diameter.

Many species are strongly scented. The

flowers are produced on or at the ends of

branches
(4)

. Cultivated forms often have

double rose-like flowers that open from large

buds with a distinctive whorl of petals. Fleshy

or leathery berries then follow. Gardenias will

persist in a wide range of conditions , but if

they are not perfectly content, they will

tend to look quite awful. They seem to do

best in a protected corner of the garden with

some morning sun – they don’t like the full

glare of the afternoon sun
(4)

. There are over
200 species of gardenias, but most of them

are hybrid varieties. Apart from G.

jasminoides, the other most common types of

gardenia are
(5)

 Gardenia augusta;

 Gardenia thunbergia, also known as Star
Gardenia; this can be a shrub or a small tree

and grows to about 1.2–1.5 m tall;
1
Corresponding author E-mail: Usamahasan92@yahoo.com

Received:8 /12/ 2014

Accepted: 28/4/2015

http://en.wikipedia.org/wiki/Rubiaceae#cite_note-Takhtajan-7
http://en.wikipedia.org/wiki/Shrub
http://en.wikipedia.org/wiki/Tree
http://en.wikipedia.org/wiki/Liana
http://en.wikipedia.org/wiki/Herb
http://en.wikipedia.org/wiki/Plant_sexuality#Individual_reproductive_unit_.28a_flower_in_angiosperms.29
http://en.wikipedia.org/wiki/Sepal
http://en.wikipedia.org/wiki/Petal#Corolla
http://en.wikipedia.org/wiki/Stamen
http://en.wikipedia.org/wiki/Gynoecium
http://en.wikipedia.org/wiki/Rubiaceae#cite_note-Takhtajan-7
http://www.anbg.gov.au/biography/linnaeus.html
http://www.somemagneticislandplants.com.au/images/leaves/alternate%20-%20opposite%20leaves.jpg
http://www.somemagneticislandplants.com.au/images/samples/whorl.jpg
http://www.somemagneticislandplants.com.au/images/samples/corolla.jpg
http://www.somemagneticislandplants.com.au/images/samples/berry.jpg
http://www.somemagneticislandplants.com.au/images/samples/hybrid.jpg
http://www.somemagneticislandplants.com.au/index.php/families/11-plants/871-gardenia-augusta
http://www.plantzafrica.com/plantefg/gardenthun.htm

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

 Gardenia nitida, a sturdy plant that can
reach almost 1.5 m when taken care of

properly and well maintained;

 Gardenia radicans, a dwarf variety that
grows to about 45 cm, and produces double

blooms.

Gardenias originated in China and Japan,

and are now found in Africa, Asia and

Australasia. They are attractive landscape

subjects in warm climates, and make good

container plants. The flowers of some species

are used to perfume tea, and others are used to

treat influenza and colds in modern Chinese

herbalism. A yellow dye was made from the

fruits
(5)

Gardenias tend to leach trace elements from

the soil. Patterning yellow of the leaves may

indicate manganese or magnesium

deficiencies, and these can be corrected by the

addition of appropriate trace elements, or using

an enriched fertilizer; but it is quite usual for

the lower leaves of healthy plants to turn

yellow and fall off as new growth is made at

the head of the branches. The root system is

shallow and sensitive, so a thick layer of
mulch to control weeds is better than

cultivating
(5)

G. jasminiodes is a smooth, unarmed

shrub 1 to 2 meters high. Leaves are opposite,

elliptic-ovate, 2 to 6 centimeters long,

narrowed and pointed at both ends, shining

and short petioled, and stipulate. Flowers are

large and very fragrant, occurring singly in the

upper axil of the leaves. Calyx is green, with

funnel-shaped tube and about 1.5 centimeters

long, 5-angled, or winged and divided into

linear lobes about as long as the tube
(6)

Corolla is usually double, white but soon

turning yellowish, and 5 to 8 centimeters
wide. Stamens are as many as the corolla

lobes. Anthers are linear, sessile. Ovary is 1-

celled; style stout, clavate, fusiform, or 2-cleft,

ovules numerous on parietal placentas. Fruits

are ovoid or ellipsoid, 2.5 to 4.5 centimeters

long, 1.5 to 2 centimeters in diameter, yellow,

with 5 to 9 longitudinal ridges
(7)

, as show in

figure (1).

Figure (1):- Photo of Gardenia jasminiodes

G. jasminoides is an evergreen flowering

plant originated in Asia. It is most commonly

found growing wild in Vietnam, Southern

China, Taiwan, Japan, Myanmar and India

distributed in broad-leaved forests at low to

medium elevations
(8)

. With its shiny green

leaves and heavily fragrant white summer

flowers, it is widely used in gardens in warm

temperate and subtropical climates and as a

houseplant in temperate regions
(9)

 Roots used for fever with delirium.

 Decoction of roots used for flatulence,
dyspepsia, and nervous disorders due to

dentition.

 Decoction of leaves and flowers used for
dyspepsia, flatulences, nervous disorders and

abdominal pains.

 Decoction of bark used for menorrhagia
and uterine problems.

 Decoction of flowers used as wash for
inflamed eyes.

 Poultice of leaves for swollen breasts; may
be mixed with violeta and other herbs.

 Antioxidant / Crocin: - Crocin is a water
soluble carotenoid found in the fruits of

gardenia (Gardenia jasminoides) and seems to

possess moderately strong antioxidant activity

(10)
.

 Diabetes / Genipin:- Study discovered
"genipin" from the Gardenia extract. Genipin

blocks the UCP2 enzyme (uncoupling protein

2) that inhibits pancreatic insulin secretion. It

suggests a potential for genipin-related

compounds
(11)

 Antiangiogenic Activity: The n-butanol
fraction of the ethanol extract of gardenia fruit

was found to be most effective in the anti

angiogenic assay
(12)

 Anti-Cerulein Pancreatitis Protective
Activity: A Study showed that Gardenia

jasminoides pretreatment ameliorated the

severity of cerulein-induced acute pancreatitis

in rats
(13)

 Sandostatin and Gardenia Combo /
Pancreatitis: Study showed a combination of
sandostatin and Gardenia jasminoides can

protect pancreatic mitochondria injury in

severe acute pancreatitis
(14)

Iridoids Glycosides
Iridoids are a class of secondary

metabolites found in a wide variety of plants

and in some animals. They are monoterpenes

biosynthesized from isoprene and they are

often intermediates in the biosynthesis

of alkaloids. Chemically, the iridoids usually

consist of acyclopentane ring fused to a six-

membered oxygen heterocycle. The chemical

structure is exemplified by iridomyrmecin, a

defensive chemical produced by

http://www.westafricanplants.senckenberg.de/root/index.php?page_id=14&species=759
http://www.nurseriesonline.com.au/PAGES/Gardenia-Radicans.html
http://en.wikipedia.org/wiki/Secondary_metabolite
http://en.wikipedia.org/wiki/Secondary_metabolite
http://en.wikipedia.org/wiki/Monoterpene
http://en.wikipedia.org/wiki/Isoprene
http://en.wikipedia.org/wiki/Alkaloid
http://en.wikipedia.org/wiki/Cyclopentane
http://en.wikipedia.org/wiki/Iridomyrmecin

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

the Iridomyrmex genus, for which iridoids are
named as show in Figure (1-3).

Chemical structure of iridomyrmecin

Figure (2):- The basic structure of Iridoid

(a glygon of glycoside).

Materials and methods

Plant materials

The leaves of Gardenia jasminoides plant

Family (Rubiaceae) was collected from the

garden of college of pharmacy, Baghdad

University during the November, March and

April (2013-2014). The plant leaves were

cleaned and dried in oven at a temperature (40-

50
0
C) for (15-20) mints then these leaves were

coarsely powered by mechanical grinder and

weight.

Extraction methods of Iridoid glycosides:-

Extraction method NO.1
(15)

A 20gm of the dried powdered leaves of

Gardenia jasminoides was extracted with three

times by reflex with volume (200ml) of 50%

Ethanol for three hours. After filtration the

extract was combined and evaporated to

dryness by rotary evaporator at 60 0C and then
subjected to identification, as shown in figure

(3):-

Dried powder leaves of Gardenia jasminoides (20gm)

Reflex three times with (200ml)

of the 50% Ethanol for 3 hours.

The mixture cool and filter

Filtrate Residue

The extract was combined and evaporated

to dryness (Crude extracts).

Figure (3):- General scheme for method NO.1 for extraction Iridoid glycosides from the leaves of

Gardenia jasminoides
(15)

Extraction method NO.2
(16)

A 20gm of the dried powdered leaves of

Gardenia jasminoides was extracted

(maceration) with (200ml) of the 90% Ethanol

for (3-4) days at room temperature, after

filtration off the solid parts and evaporation the

green solution. The residue is partitioned with

water (50ml) and ether (250ml) and separated

in a funnel. The aqueous extract was

evaporated dryness and then subjected to

identification, as shown in figure (4):-

Dried powder leaves of Gardenia jasminoides (20gm)

Maceration with (200ml)

90% Ethanol for (3-4) days.

Filtration

Filtrate Residue

(Evaporation)

The filtrate is partitioned (water: ether)

(50:250ml) and separated in a funnel.

The aqueous extract was evaporated to dryness (Crude extract).

Figure (4):- General scheme for method NO.2 for extraction Iridoid glycosides from the leaves of

Gardenia jasminoides
(16)

http://en.wikipedia.org/wiki/Iridomyrmex
http://en.wikipedia.org/wiki/Gardenia_jasminoides
http://en.wikipedia.org/wiki/Gardenia_jasminoides
http://en.wikipedia.org/wiki/Gardenia_jasminoides
http://en.wikipedia.org/wiki/Gardenia_jasminoides
http://en.wikipedia.org/wiki/Gardenia_jasminoides

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

Preliminary identification of Iridoid glycosides

The preliminary identification of Iridoid

glycosides of crude extracts of powdered leaves

obtained from the extraction method NO.1 in

result were performed by using thin Layer

chromatography (TLC) was carried out using

the following requirements. Ready made plates

of silica gel GF 254 (20×20 cm) of 0.25 mm

thickness (MERCK) were used, and then the

plates were activated at 110
0
C for 10 min.

before used. Volume of 100 ml of solvent

system was placed in a glass tank (22.5 cm × 22

cm× 7cm), and covered with glass lid and

allowed to stand for 45 min. for saturation

before use different solvent systems were used

for development of Iridoid glycosides

(gardenoside)
(17- 19)

S1= Water: Acetic Acid: N-Butanol

(50:10:40).

S2= Water: N-Propanol: N-Butanol

(60:20:40).

S3= Water: Ethanol: N-Butanol (20:20:80).

S4= Water: N-Butanol (50:50).

Reagent used for detection:-

 Liebermann-Burchard reagentis used in this
study and prepared as follow

(20)
add

carefully 5 ml of acetic anhydride and 5 ml

of concentrated sulfuric acid in to 50 ml of

absolute ethanol, while cooling in ice. Spray

the developed plate and heat it at 100
0

C for

5–10 mints.

 Vanillin-Sulphuric acid reagent (VS)
Solution I: - 5% Ethanolic Sulphuric acid.

Solution II: - 1% Ethanolic Vanillin.

The plate is sprayed vigorously with (10 ml) of

the (Solution I). Followed immediately by (5-

10 ml) of the (Solution II), after heating at 110
0
C for (5-10 min) under observation.

Isolation and purification of Gardenoside
The dry crude extract obtained from

extraction method NO.1 of iridoid glycoside

was used for isolation and purification of

gardenoside and performed as following:

Fractionation by column chromatography
The final residue obtained from the leaves

by extraction method NO.1 was subjected to

column chromatography by using glass

column (100 cm x 5 cm) packed with silica gel

(0.063-0.200 mm) slurry in (250ml)

chloroform, in a ratio of 20 gm of silica gel to

each 1 gm of the residue. A dry loading of the

sample (residue) was used by dissolving it in

small volume of methanol and adsorbing it on

small amount of silica gel of the same grade

used for packing the column, then dried,

grinded and applied to the column in order to

prevent clogging. The column was eluted by

gradient elution technique using (chloroform:

methanol) with an increasing gradually

percentage of methanol from zero to 100% and

the ratios of (chloroform: methanol) was used

(100:0, 90:10, 85:15, 80:20, 70:30, 60:40 and

so on till chloroform: methanol 0:100).The

column developed by adding 50 ml of each

eluent with collecting 5 ml fractions, then

monitored by TLC using S3 as mobile phase.

A total number of 76 fractions were obtained.

Those consecutive fractions, which have the

same number of spots with the same Rf values,

were combined and evaporated to dryness to

get four major fractions.

Table (1): Major fractions obtained from

column chromatography.

Major

fraction

No. of

collections

5ml each

No. of

spots

F1 22–36 1

F2 37–45 2

F3 46–63 3

F4 64–76 3

Preparative TLC plates
Isolation of Iridoid glycosides is carried

out by using preparative TLC which was

performed by using ready made plates of

20x20cm, which are coated by silica gel GF

254 layers of 1mm thickness, (Merck).The

major fraction (F3) obtained by column

chromatography was applied as a concentrated

solution in a row of spots using capillary tube

four times on each plate (the spots should dry

before the next application).The solvent

systems (S1, S2, S3 and S4) was each placed in

a glass tank (22.5 cm X 22 cm X 7 cm), and

covered with a glass lid and allowed to stand

for 45 minutes before use for saturation. The

best solvent used from these four solvent is the

S3 because in S3 separation is better than other

solvent systems (S1,S2 and S4) in preparative

TLC plate. The band corresponding to the

(gardenoside) standard was scraped out and

collected in a beaker, mixed with methanol,

stirred and left a side for one hour, then filtered.

After evaporation of the solvent, the obtained

residue was subjected to chromatography with

the available reference standard of

(gardenoside) using different mobile phases for

identification.

Qualitative and quantitative estimation of

Gardenoside using HPLC analysis
(21)

:-
Qualitative and quantitative estimations of

(gardenoside) component in the crude extract

obtained by all extraction methods was carried

out using high performance liquid

chromatography HPLC) .The identifications

was made by comparism the retention time of

(gardenoside) (obtained from crude extract with

that of authentic standard at identical

chromatographic conditions.

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

HPLC conditions of Gardenoside
(22-24)

1. Mobile phase: Acetonitrile: 0.1% Phosphoric
acid in Water (30:70).

2. Column Type: Thermo BDS Hypersil
[(C18) 2.4μm].

3. Column Dimensions: 100 x 4.6 mm. ID.
4. Column temperature: Ambient.
5. Flow rate: 1.3 ml/min.
6. Injection volume: 20 µL.
7. Injection concentration: 50μg/ml.
8. Detection mode and setting: UV Detector at

λ 238 nm.

Results
Two methods of extraction of iridoids

glycoside (gardenoside) from dried leaves of

G.jasminoides that method NO.1 was better,

because the percentage yield of crude extract

was higher than that obtained from method

NO.2. In addition quantitative examination by

using HPLC analysis showed that the amount

of gardenoside and obtained by method NO.1

was much more compared with that obtained

by method NO.2 as showed in table (2).

Table 2: Percentage yield of crude extracts

obtained from extraction methods NO.1 and

NO.2.

Identification of iridoid glycoside

(Gardenoside) by TLC:-

Gardenoside appeared as a single spot in

different developing solvent systems (S1, S2,

S3, and S4) against gardenoside reference

standard and it has the same color and Rf

values as that of gardenoside reference

standard on the TLC plates after visualization

by Liebermann-Burchard spray reagent, as

shown in figure (5). Results showed that S3 is

the best and more efficient for qualitative and

quantitative analysis.

Identification and characterization of isolated

Gardenoside

Analytical TLC
The TLC plates of the gardenoside

showed that after the initial isolation

purification using silica gel GF254 plate's

detection under UV light at a wave length of

254 or by spraying with reagent gave two spots

using the developing solvent system (S3). The

spots have the color and Rf values to these of

gardenoside.

(s1)

(s2)

(s3)

(s4)

Figure (5):-TLC of gardenoside (ST.) and

the major fraction (F3) was using four

solvent systems (S1, S2, S3 and S4) as

developing solvent systems, visualization

under UV254.

Extraction

method

%yield of

crude

extract

%yield of

Gardenoside

Method

NO.1

6.32 2.75

Method

NO.2

4.91 1.34

ST.

F3 ST.

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

Melting point

The crystals of the isolated samples which

were obtained from methanol showed a

melting point (117-120
0
C) of the isolated

gardenoside compared to melting point of

(118-120
0
C) of the gardenoside standard.

HPLC (high performance liquid

chromatography)

The retention time for the isolated

gardenoside was identical to the main peak of

the crude extract and standard reference; more

over the peaks isolated gardenoside and the

standard reference were super imposable as

shown in figures (6 and 7).

Figure (6):- HPLC analysis of gardenoside

standard

Figure (7):- HPLC analysis of isolated

gardenoside.

FTIR
The FTIR spectrum of the isolated sample

material and its gardenoside standard reference

were identical which confirm that the isolated

compounds are gardenoside as shown in

figures (3-19) to (3-22). The IR spectra of the

isolated gardenoside and its standard reference

material
(25)

, as showed the following

absorption bands at cm
-1

in table (3) and as

shown in figures (8 and 9).

Table (3):- The characteristic IR absorption bands (in cm
-1

) of the isolated gardenoside in

comparison with that of gardenoside as reference standard

Functional

group

Isolated

Gardenoside

standard

Assignment

O-H 3367 3371 Broad O-H stretching band of alcohol indicate

hydrogen bonding

C-H 2908 2909 Stretching of CH3 and CH2 groups

C=O 1689 1688 C=O stretching of lactone (cyclic ester)

C=C 1631 1631 Stretching of C=C bond

C-H 1438,1373 1442,1377 C-H bending of CH2 and CH3, also O-H bending

C-O 1292 1311 C-O stretching of ether

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

Figure (8):- FTIR spectrum of gardenoside standard.

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

Figure (9):- FTIR spectrum of isolated gardenoside.

Iraqi J Pharm Sci, Vol.24(1) 2015 Gardenoside in the leaves of Gardenia jasminoides

Acknowledgment
We acknowledge prof. Dr. Ali Al-

Musawi, University of Baghdad for

taxonomical I identification of Gardenia

jasminoides J.Ellis .

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