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Venkata

Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213



REVIEW ARTICLE

INTERNATIONAL JOURNAL OF RESEARCH IN


PHARMACEUTICAL SCIENCES
Published by Pharmascope Publications Journal Home Page: www.pharmascope.org/ijrps

Phytochemical library of Caralluma genus


Sireesha M1, Venkata Nadh R*2, Suresh Babu K3, Sreenivasulu M1
1Department of Science and Humanities, Vignan’s Foundation for Science, Technology and Research,

Vadlamudi 522 213, India


2GITAM University, Bengaluru Campus, Karnataka – 561203, India
3Department of Chemistry, Mallareddy Engineering College, Hyderabad, India

Article History: ABSTRACT

Received on: 13.07.2018 Caralluma is one of the prominent genus out of 200 genera and 2500 species
Revised on: 19.09.2018 of Asclepiadaceae family. Caralluma genus belongs to Asclepiadaceae and is
Accepted on: 21.09.2018 widely distributed in Asia countries, Africa, Arabian Peninsula, Canary Is-
lands and Southeast Europe. In folkloric medicine, as well as in Unani and
Keywords: Ayurvedic systems of medicine, the plants of Caralluma are being used for the
treatment of diabetic patients and rheumatism. Tribals consider some of
them as food during famines and also as a part of the traditional medicinal
Asclepiadaceae,
system. In India and Pakistan, Caralluma species have been used as
Caralluma,
emergency foods for the last few centuries. As allopathic medicines possess
Medicinal plants,
toxic nature and side effects, the use of plant-based medicine is becoming
Pharmacological
popular. This lead to a sudden enhancement in the production of herbal
activities,
drugs. At present Caralluma is gaining much importance from researchers
Phytochemical library
because it possesses array immunostimulating activities due to presence fla-
vonoids and saponins and pregnane glycosides as active components. The
present article thoroughly reviewed about various phytochemicals present
in different species of Caralluma. Tabulated a list of phytochemicals isolated
by various researchers from different plants of the Caralluma genus. Further,
listed out the species on which enthusiastic researchers of this field can

extend their investigation.

* Corresponding Author a chemical substance found in living organisms viz.,


marine organism, plants and fermentation of mi-
Name: Prof. R. Venkata Nadh
crobes (Baker et al., 2007). Natural products ex-
Phone: +91-9902632733
traction and their uses are well known from an-
Email: doctornadh@yahoo.co.in
cient times since the discovery of fire (Chemat and
ISSN: 0975-7538 Strube, 2015). Natural products are becoming a
significant source for the development of new
DOI: https://doi.org/10.26452/ijrps.v9i4.1655 drugs and new chemical moieties. 60% of pres-
ently using anticancer agents is obtained from the
Production and Hosted by
plants/natural sources (Cragg et al., 2011). All the
Pharmascope.org chemical compounds of any biological system can
© 2018 Pharmascope Publications. All rights reserved. be classified into two broad categories. The first
category is the primary metabolites and the second
INTRODUCTION category is secondary metabolites. The chemical
Nature is the wonderful source of the compounds substances which are meant for growth and devel-
containing medicinal properties. Extraordinary opment of living body are called as primary metab-
chemical diversity can be found in millions of living olites. They include amino acids, carbohydrates, li-
species like animals, marine organisms, microor- pids and proteins. The group of chemical sub-
ganisms and plants (Newman et al., 2003; Bhanot stances other than primary metabolites those ex-
et al., 2011). The term natural product means it is isting in a biological system are called as secondary
metabolites. Presence of secondary metabolites in
© Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1201

Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

living body gives the ability to face the challenges certain sources like fruits (apples and grapes), veg-
in its survival, during the time of its interaction etables (onion and broccoli), spices (turmeric),
with the surroundings (Harborne, 1993). beverages (red wine and green tea), and from
many other sources (Doughari et al., 2009;
Medicinal Plants
Doughari and Obidah, 2008).
According to WHO, the medicinal plant can be de-
Caralluma Genus
fined as a plant in which one or more of its parts
include substances containing therapeutic applica- Caralluma genus belongs to Asclepiadaceae and is
tions or compounds which are responsible for widely distributed in Asia (countries like Afghani-
semi-synthesis of pharmaceuticals. Since olden stan, India, Iran, Pakistan and Sri Lanka), Africa,
days medicinal plants are standing as valuable Arabian Peninsula, Canary Islands and Southeast
sources for therapeutic compounds, many of exist- Europe (Meve et al., 2004; Gilbert 1990). In folk-
ing drugs till today are derived from plant based loric medicine, as well as in Unani and Ayurvedic
natural products or their derivatives (Newman systems of medicine, the plants of Caralluma are
and Cragg, 2012). Use of plants for humankind is being used for the treatment of diabetic patients
older as the begin of mankind. Nowadays medici- and rheumatism (Ramesh et al., 1998). Tribals con-
nal plants are gaining much importance from peo- sider some of them as food during famines (Ahmad
ple who are living in urban areas in treating infec- et al., 1989) and also as a part of the traditional me-
tions like typhoid fever and gonorrhoea. This is due dicinal system (Abdul-Aziz Al-Yahya et al., 2000).
to the inefficiency of modern medicines and in- In India and Pakistan, Caralluma species have been
creased resistance shown by various bacteria to- used as emergency foods for the last few centuries
wards antibiotics, as well as high cost of prescribed (Gandhi, 1999). A spectrum of biological activities
drugs in the maintenance of health (Smolinski et of Caralluma species can be expected due to the ex-
al., 2003; Van den Bogaard and Stobberingh, istence of pregnane glycosides, stigmasterol and
2000). Unfortunately, all over the world modern other phytochemicals in them (Malladi et al., 2017;
health facilities available are not meeting the de- 2018; Suresh Babu et al., 2014). Presently Caral-
mands of the increased human population. There- luma is gaining much importance from researchers
fore it is demanding the further use of natural rem- because it possesses an array of immunostimulat-
edies in maintaining the health of humans. Various ing activities due to the presence of various phyto-
diseases like asthma, constipation, fever and hy- chemicals.
pertension were treated using traditional medici-
Caralluma Adscendens
nal plants (Saganuwan, 2010).
Caralluma adscendens var. gracilis was found to
Phytochemicals
contain a new pregnane glycoside (Figure 1) in di-
The medically active components extracted from ethyl ether fraction of ethanolic extract along with
plants are also known as phytochemicals or phyto- another known pregnane glycoside (Reddy et al.,
constituents and were playing a vital role in pro- 2011).
tecting the plant from various diseases caused by
O
pests and microbes (Doughari et al., 2009; Nweze O
H

et al., 2004). Phytochemical is a Greek word and it O O

means plant-derived chemical. In recent times it is OH

well known that phytochemicals are also playing a OH

vital role in maintaining human health, particularly OH

if they are taken as significant diet (Saxena et al., RO


H

2013). Phytochemicals are widely distributed in R=

O O O O
O

foods like herbs, spices, legumes, vegetables and HO


MeO
O O O O

fungi (Mathai, 2000). Phytochemicals exist in vari- OMe OMe


OMe OH

ous parts of plants like whole grains, seeds, flow- Figure 1: Pregnane glycoside from Caralluma
ers, fruits, stems, bark, leaves and roots (Costa et adscendens var. gracilis
al., 1999). Phytochemistry is one of the branches of
Caralluma Attenuata
chemistry that involves the study of the relation-
ship between organic chemistry and natural prod- A pentacyclic triterpenoid (Figure 2) was isolated
ucts. The studies which are associated with phyto- from the n-hexane extract of roots of Caralluma at-
chemistry are very significant and appropriate as tenuata (Jayalakshmi et al., 2016). Phytochemical
it helps to gain the knowledge on a range of plant- investigation of Caralluma attenuata root extracts
based chemicals those are pharmacologically im- (butanone, ethylene acetate and n-butanol ex-
portant (Temidayo, 2013). A number of phyto- tracts) has shown the presence of saponins, flavo-
chemicals were separated and characterized from noids or flavonoid glycosides and ster-

1202 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences



Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

oids/triterpenoids in Caralluma attenuata and ab-
1R=H

O 2R =
HO O

sence of cardiac glycosides and alkaloids O


OMe

O
(Kiranmayee et al., 2015). 18 3R= HO O
O O
OMe
17 OMe
12
11 13 4R= HO O
O O
19 OH 16 O O
1 OMe
14 OMe OMe
9
2 15
10 8 5R = HO O
O O
OH O
5 OMe
O
O
O
7 OMe
RO 3 OMe OMe
4 6 HO O
O O
H 6R= O O
OMe O O
OMe O O
OMe
OMe OMe

7R= HO O
MeO O O
OAc
OMe

HO
Figure 5a: Pregnane glycosides (5-7) from Car-
alluma adscendens var. fimbriata
Figure 2: Pentacyclic triterpenoid from caral- OR 18 O

luma attenuate 11 12
17

19 13
1 OH 16
Caralluma Dalzielli O
2 10
9
8
14
15

O 5 OH
HO
Five new steroidal glycosides (Figure 3) (Caradal- HO
OH HO
O
O
O
O
O
O 3
4
H
6
7

zieloside A-E) were isolated from CHCl3/MeOH ex- Glucose"" HO


OH MeO OAc OMe
2-Acetyl
tract of Caralluma dalzielii by Oyama et al. (2007). "" Cymarose'
Glucose Thevetose 8 = PhCO
9 = Me2C=C(H)CH2CO

21
H
A= HO
MeO
O
O O
Figure 5b: Pregnane glycosides (8 & 9) from C.
OR2 18
20
OBz
OMe
adscendens var. fimbriata
17 OH OAc 18 O
12
11 13 HO O
19 B= MeO O O 17
1 OH 16 11 12
14 O O RO 19 13
9 OMe 1 OH 16
2 15 OMe 14
10 8
2 9 15
5 OH O 10 8
HO O OH
7 C= O O HO O 5
1
RO 3 4 6 O O O O O 7
OMe OHMeO HO
OH HO O O O 3
4 6
H OMe H
Glucose"" HO OMe
Compound 1- R1= A and R2=Ac OH MeO OR'
Compound 2- R1= Band R2=Ac O Thevetose or Cymarose'
D= HO Glucose"" 2-Acetyl
Compound 3- R1= B and R2=Bz O O
OH Thevetose
Compound 4- R1= C and R2=Ac
Compound 5- R1= D and R2=Bz
OMe MeO
O O
O O
OMe OMe Figure 5c: Pregnane glycosides (10-13) from C.
adscendens var. fimbriata
Figure 3: Steroidal glycosides from Caralluma
Oleic acid (21.08%) and n-hexadecanoic acid
dalzielii
(44.23%) were isolated from a methanolic extract
New pregnane glycosides (27 compounds) (Figure of Caralluma Fimbriata Wall through GC-MS analy-
4) were isolated from a methanolic extract of Car- sis (Priya et al., 2011).
alluma dalzielii (De Leo et al., 2005). High cytotoxic
Caralluma Flava (Desmidorchis Flava)
activities were shown by most of the extracts.
21 O O NH2 Four tetrasaccharide pregnane glycosides (des-
OR1 18 20 OR2 flavasides A-D) (Figure 6) were identified and
11 12
17 OH
Ac = Acetyl
characterized from the sap of Desmidorchis Flava
13
1
19
14
16 Bz = Benzoyl O-NH2-Bz = o-
Aminobenzoyl
(Raees et al., 2016).
8
2 9 15
10 O
O A= O
5 OH O
HO
O O
OH

7 N R1 R2 H MeO OH O O
O
RO 3
21 HO O
18 OMe
4 6 20 OH
H 11 12
17 OMe
Nic = Nicotinoyl Mebu = 2- Methylbutyryl Isoval = Isovaleroyl 1
19
13
16 B= HO O
O
OH
9 14 MeO O
O OH O O
2 15 O
10 8 HO O
H OH Bz = OMe
5 OH
Figure 4: New pregnane glycosides from Caral- RO
3
4
H
6
7
C= HO
MeO
O
O
OH
O
OH
OMe

luma dalzielii Compound 1- R=A, R1= OBz and R3= OBz


HO O
OHHO
O

OH
O O

OMe
Compound 2- R=B, R1= OBz and R3= OBz OH

Caralluma Fimbriata
O
Compound 3- R=C, R1= OBz and R3= OBz D= HO
O
OH
O
Compound 4- R=D, R1= H and R3= OH MeO HO O O
O O
OHHO
OH
Six new pregnane glycosides (2-7) (Figure 5.a-c) OMe

and their aglycon were isolated from ether fraction Figure 6: Tetrasaccharide pregnane glycosides
of ethanolic extract of Caralluma adscendens var. (desflavasides A-D) from Caralluma flava
Fimbriata. Also, another six pregnane glycosides
(8-13) were isolated from the butanolic fraction A new pregnane glycoside (nizwaside) (Figure 7)
(Kunert et al., 2008). was isolated from the sap of Desmidorchis flava and

© Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1203



Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

it was proved as an effective anticancer agent O

against breast cancer cells like MDA, MB231com-


O O
pared to known cancer drug Doxorubicin (Hussain 12
18
17
et al., 2015). However, the antioxidant activity of 19
11 13 16
1 OH
nizwaside was found to be weak. OH
2 9
14
15
O 10 8
O 5 OH
OH O
O O 7
BzO OH O 3
OBz 18 OH OH O O 4 6
O H
Glucose'''' OH OMe
17 OH OMe OAC
12
11 13 Glucose'''' 2 Acetyl- Cymarose'
19 16 Thevetose''
1 14
9
2 15
10
5
H
8
OH
5 - Stalagmoside V
OH
O
O
O
O
O
O 3
4 6
7
Figure 9b: Stalagmoside V from Caralluma stal-
H

OMe OMe
OMe OH
Bz =
agmifera
O

Caralluma Lasiantha/Boucerosia Lasiantha


Caralluma lasiantha (syn. Boucerosia lasiantha) be-
longs to the family Asclepiadaceae and its local
Figure 7: Pregnane glycoside (nizwaside) from name is Kundeti Kommulu (in Telugu)/Siru-
Caralluma flava mankeerai (in Tamil) (Arinathan et al., 2007). Car-
alluma lasiantha is succulent inhabit and is used as
Two new pregnane glycosides (desmiflavasides A
an indoor ornamental plant (Reddy et al., 2012). It
and B) (Figure 8) were isolated from the sap of Des-
grows wild in Anantapur, Chittoor and surround-
midorchis flava and desmiflavasides B proved to
ing places of Andhra Pradesh, India. To reduce the
contain anti-proliferation activity against breast
body heat, fresh rootless Caralluma lasiantha (a
cancer cells at a concentration of 100 mg/mL and
dose of 10 g, twice a day for three days) is used in
75 mg/mL. On the other hand, urease enzyme inhi-
India (Vikneshwaran et al., 2008). Malladi et al.
bition, as well as antioxidant activities for them,
(2017) reviewed the role of Caralluma lasiantha in
were found to be weak (Raees et al., 2015).
traditional Indian medicine. Two new
18 R

12
17 bisdesmosidic C21 pregnane steroidal glycosides
(lasianthosides-A and B) (Figure 10) were isolated
11 13
19 16
1 14 15
9

OH OH
2 10
H
8
OH
from the n-butanol fraction of ethanolic extract of
5

OH
O
O
O
O
O
O 3
4 6
7 OBz
Caralluma lasiantha (Qiu et al., 1999). A flavones
H
HO OH
OH
OH OMe OH
Bz = O
glycoside (luteolin-4-O-neohesperiodoside) (Fig-
21
20 OH ure 11) was isolated from a methanolic extract of
1:R =
Caralluma lasiantha (Ramesh et al., 1999b).
Stigmasterol and C21 Pregnane Steroid (3β,14β-
dihydroxy-14β-pregn-5-en-20-one) were isolated
21 O
20
2:R =

from the less polar solvent extracts (Malladi et al.,



Figure 8: Pregnane glycosides (desmiflavasides 2017 a,b).
A and B) from Caralluma flava OH OH
H H
Caralluma Indica/Boucerosia Indica
H
Kunert et al. (2006) (Figure 9a & b) isolated novel H
OH H
steroidal glycosides Caralluma species. Stalagmo- H O O
side I –V (1-5) are isolated from butanol fraction of H3C
H
O
H

Caralluma stalagmifera and indicoside I and II (7 & HO H O CH3

8) are isolated from the ether fraction of Caralluma H


HO
HO H
OH
indica. H
H
O
H HO H
Me

OR2 HO O
OR'
18 H OH H
H H3C H
11
12
17 OH O H R1
13
1
19
OH
14
16 H R2
OH 9
2 10 8
15 H3CO O
HO
O
O 5 OH H OH
O 7
HO
OH HO
O
O
O
O O 3
4 6 H H
Glucose'''' HO
OH MeO OR OMe
H

Glucose'''' Thevetose'' Cymarose'
Lasianthoside-A –R1, R2 = D14-15, Lasianthoside-B –
1-Stalagmoside I - R = H, R1 = H, R2 = Bz
2-Stalagmoside II - R = H, R1 = Ac, R2 = Bz
3-Stalagmoside III- R = Ac, R1 = Ac, R2 = Bz
R1 = β-OH, R2 = H
4-Stalagmoside IV - R = Ac, R1 = Bz, R2 = Bz
11-Stalagmoside I - R = H R1 = H R2 = H

Figure 10: Lasianthosides A and B from Caral-


Figure 9a: Stalagmoside I–IV from Caralluma luma lasiantha
stalagmifera
1204 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences

Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

OH
CH3
New pregnane glycosides (1-20) (Figure 15a and
O
OH b) were isolated from chloroform and methanol ex-
OH tracts of Caralluma negevensis (Braca et al., 2002).
OH

O
OH
Compounds 1-16 were found to contain bouncer in
O
O
OH
CH2OH aglycon moiety, compounds 17-19 were shown to
contain the calogenin structure and 20th com-
HO O
pound contain 5α-dihydrocalogenin moiety.
OR1 OR2
18
20
17 O
12
11
13
OH O 19 16
1
9 14
Tig =

Figure 11: Luteoline-4-O-neohesperiodoside 2 10


H
8
OH
15

from Caralluma lasiantha 5


7 COO
3
21 29 RO 4 6

28 o-OH-Bz = o-hydroxy benzoyl= Ac= Acetyl


22
OH
20
12 18 H 24 27
23
17
25
Figure 15a: Pregnane glycosides (1-16) from
19 11 13
16 26
Caralluma
1 H 14
9 18 20 OR1 OR1
18 20
2 15 17
10 8 12 17
11 12
H H 13 11 13
19 16 19
1 1 16
7 9 14 9 14
3 5
OH 2 15 15
4 6 10 8 2 10 8
H OH OH
3 5 7 5
7
Figure 12: Stigmasterol RO 4 6 RO
3
4
H
6
21 Compound 17, 18 and 19 Compound 20
20
O
18 Figure 15b: Pregnane glycosides (17-20) from
12
17 Caralluma negevensis
11
19 13 Caralluma Nilagiriana
H 16
1 9 14
Phytochemicals of Caralluma nilagiriana was eval-
2 8 15 uated by using UV-VIS and FTIR spectroscopic
10
H
OH techniques (Renuka et al., 2016). GC-MS analysis
on ethanolic extract of Caralluma nilagiriana
5 7
OH 3 shows the presence of active components like alka-
4 6
loids, flavonoids, phenolic compounds, steroids,

Figure 13: 3β,14β-dihydroxy-14β-pregn-5-en- terpenoids and tannins (Ranganathan et al., 2014).
20-one Rutin, a bioflavonoid present in the ethanolic ex-
tract of shoots of Caralluma nilagiriana was deter-
Caralluma Negevensis mined by high-performance thin layer chromatog-
Two megastigmane glycosides (1 & 2) (Figure 14), raphy (HPTLC) (Renuka et al., 2014).
as well as two new flavone glycosides (3 & 4), were Caralluma Pauciflora
isolated from a methanolic extract of Caralluma
negevensis (Bader et al., 2003). Two pregnanes (Figure 16) were isolated from di-
ethyl ether fraction of ethanolic extract of Caral-
OH
luma pauciflora along with known compounds like
OH
11 11
2 2
O 12
O
1
12
3
1 carumbelloside-III and dihydro russelioside
3

4
6
9 10 4
6
9 10 (Reddy et al., 2011).
8 8
5 5 7
7 O
H H
rha-(1 6)-glc O rha-(1 6)-glc
O 13
13 1 OH OH
2 O OH O 18
18
OR1 17
17 O 12
HO 12
11 13
11 13 19
19 1 16
HO O 1 16
14
14 9
OR2 9
2 15
2 15 10 8
10 8
3-R1=Rha-(1 2)-glc and R2= Glc OH
OH 5
5 7
4-R1= Glc and R2= Glc 7 3
3 RO
RO 4 6
OH O 4 6

2 3
Figure 14: Megastigmane glycosides (1 & 2)
from Caralluma negevensis Caralluma Negeven- Figure 16: Two pregnanes (compound 2 and 3)
sis from Caralluma pauciflora
© Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1205

Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

Caralluma Penicillata 18
20 OH

Four acylated pregnane glycosides (Figure 17) 11


12 17
were identified from the methanolic extract of Car- OH
1
19 13
16
9 H 14
alluma penicillata (Abdallah et al., 2013). O
2 15
HO O 10 H 8
21 5 OH OH
HO O 3
21 7
BzO OBz Bz= O OH O
18 20 4 6
17 BzO OBz
O H
12 18 20
11
13
OH
16 12 17
1 19 11 Me
2 10
9 OH 14
8
15 1 19
13
9 OH 14
16
3 5
H
7
OH OR3 2 10
H
8
15
Figure 20: Polyoxy pregnane glycoside (retro-
OH
OR 4
OH
6
OR
3
4
5
6
7
OR3
spinoside 1) from Caralluma retrospiciens
Compound 4 Compound 1, 2 and 3
Six polyoxy pregnane glycosides (Figure 21a, b)
Figure 17: Four acylated pregnane glycosides were extracted from ether extracts of Caralluma
from Caralluma penicillata retrospiciens and all of them exhibited cytotoxic
property but compound-2 shown high cytotoxic
C15 oxypregnane glycosides (penicillosides A–C) activity (Halaweish et al., 2004).
(Figure 18) were isolated from chloroform fraction 1R= O
O
of ethanol extract of Caralluma penicillata (Abdel-
HO O
O O
OMe OH O
21 OMe OH
Sattar et al., 2001). O
18 O
OH OMe

17 20 2 R = HO O O
O
HO 12 HO O O O
11 OH O
13 OMe OH
Benzoyl= O 1 19 16 OMe OH OMe
R2O H OH 14 OH
O
18 CH3 2 9 15 O O O
10 8 OH 3R= O
20 OH OH
12
17 5 HO
MeO
MeO
OH
11 7 HO
13 RO 3
19 16 4 6 OH O O O
1 O O
9 OH 14 15 O O
O CH3 4R = OH OH OH
2 10 HO MeO
8 HO HO MeO OH
H OH HO
OR3 Isovaleroyl =
3 5
7
CH3

R1O 4
H
6
1- R1= Glc(1-4) Dig, R2= Benzoyl and R3= H Figure 21a: Polyoxy pregnane glycosides (1-4)
2- R1= Glc(1-6) Glc (1-4) Dig, R2= Benzoyl and R3= H
3- R1= Glc(1-6) Glc (1-4), R2= Isovaleroyl and R3= Benzoyl from Caralluma retrospiciens

Figure 18: C15 oxypregnane glycosides (penicil-
losides A–C) from Caralluma penicillata C O
OH
21 O O
O
O
O O O
Caralluma Quadrangular O
12 18 17 20
5R=
HO
OH OH
MeO
CH H2C C O HO MeO OH
11 13
Russelioside B (Figure 19), a pregnane glycoside 1 19 OH 14
16
OH
9
isolated from the n-butanol fraction of methanol 2 10 8 OH
15
6R= HO
HO
O
O O
O
5 O O
extract of Caralluma quadrangular was recom- RO 3
7 OH OMe OH
OMe OH
O
4 6 OMe
mended for managing of diabetes based on its po-
tent antihyperlipidemic effect (Abdel-Sattar et al., Figure 21b: Polyoxy pregnane glycosides (1-4)
2016). from Caralluma retrospiciens
Caralluma Russeliana
18 O-Glc Two triterpenoids (3 and 4), two sterols (5 and 6)
20 and two pregnane glycosides (1 and 2) (Figure
17
12 22.a-c) were isolated from the chloroform extract
11 13
19 16 of Caralluma russeliana (Abdel-Mogib and Raghib,
1 14 15
9
2
2013).
10 8
5 OH 21
3
7 18 20
O
17
4 6 12
11 13
16 OR1
O-Glc(4-1) Glc 1 19 OH 14
9 15
2 10 8
Figure 19: Russelioside B from Caralluma 3 5
OR2
OR3

quadrangular R1O
O
O
O O O
4 6
7

O
MeO
Caralluma Retrospiciens OMe OMe
1- R1 = H, R2 = COC6H5 and R3= COCH2CH(CH3)2
A polyoxy pregnane glycoside (retrospinoside 1) 1a- R1 = Ac, R2 = COC6H5 and R3= COCH2CH(CH3)2
2- R1 = H, R2 =COCH2CH(CH3)2 and R3= COC6H5
(Figure 20) was identified from the n-butanol frac- 2a-R1 = Ac, R2 =COC6H5 and R3= COCH2CH(CH3)2

tion of methanol extract Caralluma retrospections


(Elsebai and Mohamed, 2015). Figure 22a: Pregnane glycosides (1 and 2) from
Caralluma russeliana
1206 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences

Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

O
21
R2 OR1 Tig =
18
20
17
12
11 O
13
19 16
1
9 14
15
Bz =
2 10 8
H OH
HO
3 5
H
7 O
HO
OR
H 4 6
Ac =

3

4

Figure 22b: Pregnane glycosides (1 and 2) Figure 25: Pregnane glycosides, pregnanes and
from Caralluma russeliana flavonoids from Caralluma sinaica
Boucerosia Truncato Coronato/Caralluma
20
12
18
18 20
Truncato-Coronato
11 17
12
13
1
19
9 14
16
19
11
13
17
16
Phytochemical constituents present in ethanolic
1
2 10 8 15
2
9 14
15
extracts of Caralluma truncato coronato were stud-
10 8
3 5
7 3 5
7
ied by GC-MS analysis by Kalimuthu et al. (2013).
OH 4 6
5
OH 4
6
6 The results obtained have shown the presence of
Figure 22c: Sterols (5 and 6) from Caralluma furan, 2-butyltetrahydro- (0.57%), β-sitosterol
russeliana (1.89%), acetic acid, 5-(dimethyle-6-oxocyclo-
hexylidene)-3-methyl-pent-3-enyl ester (3.78%),
Four acylated pregnane glycosides (russeliosides β-tocopherol (4.91%), squalene and lupeol
E–H) (Figure 23) were extracted from chloroform (5.67%), vitamin E (9.45%) and thunbergol
extracts of Caralluma russeliana (Abdel-Sattar et (68.05%).
al., 2007).
Caralluma Tuberculata
OR1
OR2 18 OH

O
Two steroidal glycosides (pregnane glycoside and
12 HO O
11
13
17
OH
HO
OH
O

OMe OH
=A
androstan glycoside) (Figure 26) were found in
19 16
1
9 14 HO O
O O ethyl acetate extract of Caralluma tuberculata and
O
exhibited moderate cytotoxic activity against three
2 15 HO O O =B
10 8 OH OH O
H OMe OH
3 5 OMe
human breast cancer cell lines (Waheed et al.,
OMe
7 OH
OR 4 6
HO O
2011).
O O
HO O
1- R=B, R1=Acetyl, R2= Benzoyl OH
O =C
OMe OH
2- R=C, R1=Acetyl, R2= Benzoyl OMe
3- R=A, R1=Acetyl, R2= Benzoyl
4- R=B, R1=Acetyl, R2= Tigloyl
HO
OH

O
OH

O
C O HO
O
O O
R1 O HO
Figure 23: Acylated pregnane glycosides
OH OH =I
O Glucopyr
OH Glucopyr OMe
O Methoxyribopyr

(russeliosides E–H) from Caralluma russeliana OH


HO
HO
OH
O
O
O

OH
O O
O
O
O O
= II
Glucopyr OH OMe
OH OMe
OMe

A known flavone glycoside and four pregnane gly-


Glucopyr cymaropyr Cym Cym
Sugar O R2
Pregnane Glycoside (1)- R1= H, R2= H and Sugar = I

cosides (Figure 24) were extracted from Caralluma Androstan Glycoside (2) R1= C
H
R2 = C
O
and Sugar = II

russeliana in its n-butanol fraction of ethanol ex-


tract (Abdul-Aziz Al-Yahya et al., 2000). Figure 26: Steroidal glycosides from Caralluma
tuberculata
OH
HO
HO
O Five pregnane glycosides (caratuberside A-E) and HO
OH O
12
18 preganan glycoside-russelioside (Figure 27) were
CH3 18 CH3

11
13 1
19
11
12
13
17 17
16
isolated from chloroform fraction of MeOH extract
1 19 9 16 9 14

2
14
15 OR
2
10 H 8 OH
15 of Caralluma tuberculata. The isolated pregnane
10 8
OR
O O
3 5
H
7
OH
O O
3
4
5
6
7 glycosides exhibited antimalarial, antitrypanoso-
mal and cytotoxic potentials (Abdel-Sattar et al.,
4 6 1 R= H MeO
MeO 2 R= Glc OH 3 R= GLC
OH
4 R= Glc(6''-1'') Glc 2008).
Figure 24: Pregnane glycosides (russeliosides
E–H) from Caralluma russeliana 21
OR
21
OR2 1 OR2 OR1
18 20 18 20
Caralluma Sinaica 11
12
13
17
11
12
13
17
19 16 19 16
1 14 15 1
9 9 14 15
Caralluma sinaica yielded six pregnane glycosides 2 10 8 2 10 8
H OH H OH
along with seven pregnanes and three flavonoids O
3 5 7
R1 O
3 5 7
4 6 4 6
(Figure 25) from its chloroform extract (Al-Massa- Sugar Sugar

rani et al., 2012). Quinone reductase induction was Figure 27: Pregnane glycosides (caratuberside
evaluated for all these isolated compounds. A-E) from Caralluma tuberculata
© Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1207

Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

Caralluma Umbellata Steroidal glycosides were found in different sol-


vent fractions of ethanol extract of Caralluma um-
Kalyani et al. (2013) (Figure 28) isolated a novel
bellata. The isolated steroidal glycosides are
pregnane glycoside from ether eluates of methanol
bourcergenin (new pregnene type steroid) from
and benzene fractions of ethanolic extract of roots
toluene fraction, carumbelloside-VI (bisdesmo-
of Caralluma umbellata.
sidic glycoside) from n-butanol fraction, and car-
O umbellosides I–IV (new tetroxides of boucergenin)
18 from toluene fraction (Kunert et al., 2009). A new
12 O
17 pregnane steroid (Figure 28) containing formyl
11
19 OR
13
16
group was isolated and characterized from Caral-
1
9 14 15 luma umbellata stems along with three known ste-
OH
2 10 8
C CH
roidal compounds (Babu et al., 2008).
3 5 CH3
HO O
O
7
R= CH A C21 steroid (Figure 31) was isolated from the tol-
4 6
HO CH3 uene fraction of ethanol extract of Caralluma um-
OH
bellata from the whole plant (Ramesh et al., 2005).
Figure 28: Pregnane glycoside from Caralluma Caralluma Wissmannii
umbellata
Two pregnane glycosides (5, 6) along with five
Presence of thirty-two compounds was found in a known compounds (viz., β-sitosterol, stigmasterol,
phytochemical analysis of leaves of Caralluma um- luteolin 3',4'–di-O-β-D-glucopyranoside, 3,4-sec-
bellata by Jerome Jeyakumar et al. (2013). The ex- up-20-(29)-en-3-oic acid methyl ester and lupeol)
tracted phytochemical compounds include terpe- (Figure 30.a and b) were isolated in the phyto-
noids, flavonoids, tannins, phenols, glycosides ster- chemical investigation on Caralluma wissmannii
ols and saponins. Two new pregnane compounds (Dawidar et al., 2012).
(CRUR I and CRUR II) (Figure 27) were isolated
from the roots of Caralluma umbellata (Kishore et
al., 2010).
18 21
18 21
20
17 20
12 17
11 12
13
19 11
13
O
16 HO
1 19
9 14 16 O 2
15 1
9 14
15
1
2 10 8
2 10 8 OH
3 5 7
3 5 7 29 29
OH 21 21
4 6 28 22 28
OH
4 6
22 18
18 20 20
CRUR I 12 12 23 24 25 27
CRUR II 23 24 25 27 17
19
11 13
17
16 1
19
11 13
16
Figure 29: Pregnane compounds from Caral- 2
1
9 14 15
26 2
10
9
8
14 15
26
10 8
luma umbellate 3 5 7 HO
3 5 7
4
HO 4 6
4 6
O
3

18 21 Figure 32a: (1) 3,4-seco-lup-20(29)-en-3-oic
12
17
acid methyl ester, (2) lupeol (3) β-sitosterol
11 13
and (4) stigmasterol from Caralluma
1
19 16 wissmannii
9 14 15
2 10 8 O O
H O-Glc
O
3 5 7 O 21
18 20
OH O OH 17 OH HO O
4 6 11 12 13 O-Glc
1 19 9 16
1
2 10
OH 14 15
8 OH
Figure 30: Pregnane steroid from Caralluma 3 5
H
7
OH O

umbellate OR 4 6
7
5
21 R =HO O
20
MeO O O R = HO O
O
18 C OH O O O O
MeO
D-Thevitose and
12 OMe OH
17 OMe D-Thevitose
D-Cymarose D-Cymarose OMe
11
19 13
16 D-Cymarose
1 9 14 6
2
10 8
OH
15
Figure 32b: (5, 6) Pregnane glycosides and (7)
3 5 7 Luteolin 3',4'–di-O-β-D-glucopyranoside from
OH
6 4 Caralluma wissmannii
Figure 31: C21 steroid from Caralluma umbel-
lata
1208 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences

Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

Table 1: A list of phytochemicals isolated from different plants of the Caralluma genus
Name of the phytochemical Name of the plant Reference
Flavone glycoside, Caralluma arabica Kamil et al., 1999
Luteoline-4’-O-neohesperiodo- Caralluma umbellata Ramesh et al., 1999b
side Caralluma lasiantha Ramesh et al., 1999b
Caralluma attenuata Ramesh et al., 1998, 1999b
Caralluma tuberculata Rizwani et al., 1990
Flavones glycosides and Caralluma negevensis Bader et al., 2003
megastigmane glycosides
Pregnane glycosides Caralluma quadrangula Abdel-Sattar et al., 2016
Caralluma flava (Desmidorchis flava) Raees et al., 2015, 2016
Caralluma flava (Desmidorchis flava) Hussain et al., 2015
Caralluma retrospiciens Elsebai and Mohamed, 2015
Caralluma umbellata Kalyani et al., 2013
Caralluma wissmannii Dawidar et al., 2012
Caralluma adscendens var. gracilis Reddy et al., 2011
Caralluma adscendens var.fimbriata Kunert et al., 2008
Caralluma dalzielli De Leo et al., 2005
Caralluma negevensis Braca et al., 2002
Caralluma russeliana Al-Yahya et al., 2000
Caralluma retrospiciens Halim and Khalil., 1996
Caralluma umbellata Lee-Juian et al., 1994
Boucerosia aucheriana Tanaka et al., 1990
Boucerosia aucheriana Hayashi et al., 1988
Caralluma tuberculata Ahmad et al., 1988
Acylated Pregnane glycosides Caralluma quadrangula Abdallah et al., 2013
Caralluma sinaica Al-Massarani et al., 2012
Caralluma tuberculata Abdel-Sattar et al., 2008
Caralluma russeliana Abdel-Sattar et al., 2007
Pregnane glycoside diesters Caralluma russeliana Abdel-Mogib and Raghib,
2013
Oxy Pregnane glycosides Caralluma pencillata Abdel-Sattar et al., 2002
Caralluma pencillata Abdel-Sattar et al., 2001
Polooxy Pregnane glycosides Caralluma retrospiciens Halaweish et al., 2004
Steroidal glycosides Caralluma umbellata Kunert et al., 2009
Caralluma stalagmifera Kunert et al., 2006
Caralluma dalzielii Oyama et al., 2007
Caralluma lasiantha Qiu et al., 1999
Caralluma umbellata Qiu et al., 1997
Caralluma indica Kunert et al., 2006
Acylated steroidal glycosides Caralluma tuberculata Waheed et al., 2011
Pregnane steroids/pregnanes Caralluma umbellata Ramesh et al., 2005
Caralluma pauciflora Reddy et al., 2011
Caralluma umbellata Kishore et al., 2010
Caralluma umbellata Babu et al., 2008
Pregnane ester aglycones Caralluma retrospiciens Khalil, 1995
Triterpenoid Caralluma attenuata Jayalakshmi et al., 2016
Terpenoids Caralluma europaea Formisano et al., 2009
β-sitosterol, lupeol Caralluma wissmannii Dawidar et al., 2012
Caralluma adscendens var. gracilis Reddy et al., 2011
Caralluma truncato-coronata Kalimuthu et al., 2013
Rutin Caralluma nilagiriana Renuka, 2014

In continuation to the above list of phytochemicals CONCLUSION
collection, efforts of various researchers on their
Caralluma is a genus used as traditional medicine
study pertaining to different species of Caralluma
and is a potential source for phytochemicals with
are compiled in Table-1.
medicinal uses. Thorough literature collection
shows few species of Caralluma are explored for
© Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1209

Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213

isolation of phytochemicals from them. nilotica and Papaver somniferum, Pakistan


Enthusiastic researchers in this field can extend Journal Zoology, 1989.
their investigation for further exploration of many
Ahmad VU, Usmanghani K, Rizwani GH. New
other species (like Caralluma acutangula,
pregnane glycosides from Caralluma
Caralluma Arabica, Caralluma cicatricose,
tuberculata, Journal of Natural Products, 51(6),
Caralluma edulis, Caralluma Europaea, Caralluma
1988pp. 1092-1097.
longidens) for phytochemicals present in them.
Al-Massarani SM, Bertrand S, Nievergelt A, El-
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