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Phytochemical library of caralluma genus
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1201 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 Revised on: 19.09.2018 Accepted on: 21.09.2018 Caralluma is one of the prominent genus out of 200 genera and 2500 species of Asclepiadaceae family. Caralluma genus belongs to Asclepiadaceae and is widely distributed in Asia countries, Africa, Arabian Peninsula, Canary Is- lands and Southeast Europe. In folkloric medicine, as well as in Unani and 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 system. In India and Pakistan, Caralluma species have been used as emergency foods for the last few centuries. As allopathic medicines possess toxic nature and side effects, the use of plant-based medicine is becoming popular. This lead to a sudden enhancement in the production of herbal drugs. At present Caralluma is gaining much importance from researchers 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. Keywords: Asclepiadaceae, Caralluma, Medicinal plants, Pharmacological activities, Phytochemical library * Corresponding Author Name: Prof. R. Venkata Nadh Phone: +91-9902632733 Email: doctornadh@yahoo.co.in ISSN: 0975-7538 DOI: https://doi.org/10.26452/ijrps.v9i4.1655 Production and Hosted by Pharmascope.org © 2018 Pharmascope Publications. All rights reserved. INTRODUCTION Nature is the wonderful source of the compounds containing medicinal properties. Extraordinary chemical diversity can be found in millions of living species like animals, marine organisms, microor- ganisms and plants (Newman et al., 2003; Bhanot et al., 2011). The term natural product means it is a chemical substance found in living organisms viz., marine organism, plants and fermentation of mi- crobes (Baker et al., 2007). Natural products ex- traction and their uses are well known from an- cient times since the discovery of fire (Chemat and Strube, 2015). Natural products are becoming a significant source for the development of new drugs and new chemical moieties. 60% of pres- ently using anticancer agents is obtained from the plants/natural sources (Cragg et al., 2011). All the chemical compounds of any biological system can be classified into two broad categories. The first category is the primary metabolites and the second category is secondary metabolites. The chemical substances which are meant for growth and devel- opment of living body are called as primary metab- olites. They include amino acids, carbohydrates, li- pids and proteins. The group of chemical sub- stances other than primary metabolites those ex- isting in a biological system are called as secondary metabolites. Presence of secondary metabolites in
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 1202 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences living body gives the ability to face the challenges in its
survival, during the time of its interaction with the surroundings (Harborne, 1993). Medicinal Plants According to WHO, the medicinal plant can be de- fined as a plant in which one or more of its parts include substances containing therapeutic applica- tions or compounds which are responsible for semi-synthesis of pharmaceuticals. Since olden days medicinal plants are standing as valuable sources for therapeutic compounds, many of exist- ing drugs till today are derived from plant based natural products or their derivatives (Newman and Cragg, 2012). Use of plants for humankind is older as the begin of mankind. Nowadays medici- nal plants are gaining much importance from peo- ple who are living in urban areas in treating infec- tions like typhoid fever and gonorrhoea. This is due to the inefficiency of modern medicines and in- creased resistance shown by various bacteria to- wards antibiotics, as well as high cost of prescribed drugs in the maintenance of health (Smolinski et al., 2003; Van den Bogaard and Stobberingh, 2000). Unfortunately, all over the world modern health facilities available are not meeting the de- mands of the increased human population. There- fore it is demanding the further use of natural rem- edies in maintaining the health of humans. Various diseases like asthma, constipation, fever and hy- pertension were treated using traditional medici- nal plants (Saganuwan, 2010). Phytochemicals The medically active components extracted from plants are also known as phytochemicals or phyto- constituents and were playing a vital role in pro- tecting the plant from various diseases caused by pests and microbes (Doughari et al., 2009; Nweze et al., 2004). Phytochemical is a Greek word and it means plant-derived chemical. In recent times it is well known that phytochemicals are also playing a vital role in maintaining human health, particularly if they are taken as significant diet (Saxena et al., 2013). Phytochemicals are widely distributed in foods like herbs, spices, legumes, vegetables and fungi (Mathai, 2000). Phytochemicals exist in vari- ous parts of plants like whole grains, seeds, flow- ers, fruits, stems, bark, leaves and roots (Costa et al., 1999). Phytochemistry is one of the branches of chemistry that involves the study of the relation- ship between organic chemistry and natural prod- ucts. The studies which are associated with phyto- chemistry are very significant and appropriate as it helps to gain the knowledge on a range of plant- based chemicals those are pharmacologically im- portant (Temidayo, 2013). A number of phyto- chemicals were separated and characterized from certain sources like fruits (apples and grapes), veg- etables (onion and broccoli), spices (turmeric), beverages (red wine and green tea), and from many other sources (Doughari et al., 2009; Doughari and Obidah, 2008). Caralluma Genus Caralluma genus belongs to Asclepiadaceae and is widely distributed in Asia (countries like Afghani- stan, India, Iran, Pakistan and Sri Lanka), Africa, Arabian Peninsula, Canary Islands and Southeast Europe (Meve et al., 2004; Gilbert 1990). In folk- loric medicine, as well as in Unani and Ayurvedic systems of medicine, the plants of Caralluma are being used for the treatment of diabetic patients and rheumatism (Ramesh et al., 1998). Tribals con- sider some of them as food during famines (Ahmad et al., 1989) and also as a part of the traditional me- dicinal system (Abdul-Aziz Al-Yahya et al., 2000). In India and Pakistan, Caralluma species have been used as emergency foods for the last few centuries (Gandhi, 1999). A spectrum of biological activities of Caralluma species can be expected due to the ex- istence of pregnane glycosides, stigmasterol and other phytochemicals in them (Malladi et al., 2017; 2018; Suresh Babu et al., 2014). Presently Caral- luma is gaining much importance from researchers because it possesses an array of immunostimulat- ing activities due to the presence of various phyto- chemicals. Caralluma Adscendens Caralluma adscendens var. gracilis was found to contain a new pregnane glycoside (Figure 1) in di- ethyl ether fraction of ethanolic extract along with another known pregnane glycoside (Reddy et al., 2011). O RO OH OH OH O O O O O O O O O OO O MeO OMe OH HO OMe OMe R= H H Figure 1: Pregnane glycoside from Caralluma adscendens var. gracilis Caralluma Attenuata A pentacyclic triterpenoid (Figure 2) was isolated from the n-hexane extract of roots of Caralluma at- tenuata (Jayalakshmi et al., 2016). Phytochemical investigation of Caralluma attenuata root extracts (butanone, ethylene acetate and n-butanol ex- tracts) has shown the presence of saponins, flavo- noids or flavonoid glycosides and ster-
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1203 oids/triterpenoids in Caralluma attenuata and ab- sence of
cardiac glycosides and alkaloids (Kiranmayee et al., 2015). HO Figure 2: Pentacyclic triterpenoid from caral- luma attenuate Caralluma Dalzielli Five new steroidal glycosides (Figure 3) (Caradal- zieloside A-E) were isolated from CHCl3/MeOH ex- tract of Caralluma dalzielii by Oyama et al. (2007). OBz 1 RO OH OH OR2 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 H H OH Compound 1- R1= A and R2=Ac Compound 2- R1= Band R2=Ac Compound 3- R1= B and R2=Bz Compound 4- R1= C and R2=Ac Compound 5- R1= D and R2=Bz O OMe O MeO HO O A = O O OMe OMe O O MeO HO OB = O O OMe MeO O O OMe HO O OH C = O O OMeOMe O O MeO O OHO OMe OH O D = Figure 3: Steroidal glycosides from Caralluma dalzielii New pregnane glycosides (27 compounds) (Figure 4) were isolated from a methanolic extract of Car- alluma dalzielii (De Leo et al., 2005). High cytotoxic activities were shown by most of the extracts. OR2 RO OH OH OR1 H 1 2 3 4 5 6 7 8 910 11 12 13 14 15 16 17 18 19 20 21 O O-NH2-Bz = o- Aminobenzoyl O NH2 Bz = Benzoyl N O Nic = Nicotinoyl O Mebu = 2- Methylbutyryl O Isoval = Isovaleroyl Ac = Acetyl Figure 4: New pregnane glycosides from Caral- luma dalzielii Caralluma Fimbriata Six new pregnane glycosides (2-7) (Figure 5.a-c) and their aglycon were isolated from ether fraction of ethanolic extract of Caralluma adscendens var. Fimbriata. Also, another six pregnane glycosides (8-13) were isolated from the butanolic fraction (Kunert et al., 2008). RO OH O 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 H OH O O O OMe HO 2R = O O OMe OMe O HO3 R = O O OMeOMe O O OMe HO O 4 R = O O OMeOMe O O OMe O OHO OMe O 5R = O O OMeOMe O O OMe O O OHO OMe O OMe O O O OMe MeO O HO OAc 6 R = 7 R = 1 R = H Figure 5a: Pregnane glycosides (5-7) from Car- alluma adscendens var. fimbriata O OH OR H 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OH O O O O OHO O OMeOAcMeOOH HO O O OH HO HO Glucose"" Glucose"" 2-Acetyl Thevetose Cymarose' 8 = PhCO 9 = Me2C=C(H)CH2CO Figure 5b: Pregnane glycosides (8 & 9) from C. adscendens var. fimbriata O OH OAc H 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OH O O O O OHO O OMeOR'MeOOH HO O O OH HO HO Glucose"" Glucose"" Thevetose or 2-Acetyl Thevetose Cymarose' RO Figure 5c: Pregnane glycosides (10-13) from C. adscendens var. fimbriata Oleic acid (21.08%) and n-hexadecanoic acid (44.23%) were isolated from a methanolic extract of Caralluma Fimbriata Wall through GC-MS analy- sis (Priya et al., 2011). Caralluma Flava (Desmidorchis Flava) Four tetrasaccharide pregnane glycosides (des- flavasides A-D) (Figure 6) were identified and characterized from the sap of Desmidorchis Flava (Raees et al., 2016). RO OH H 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 R2 H H O Bz = R1 21 20 Compound 1- R=A, R1= OBz and R3= OBz Compound 2- R=B, R1= OBz and R3= OBz Compound 3- R=C, R1= OBz and R3= OBz Compound 4- R=D, R1= H and R3= OH O O OMe O O OMe O OHO MeO O OH OH HO A = OH O O OMe O O OMe O OHO MeO O OH OH HO B = OH O O OMe O OO OHO MeO O OH OH HO C = OH OH HO O O OMe O OO OHO MeO O OH OH HO D = OH OH HO Figure 6: Tetrasaccharide pregnane glycosides (desflavasides A-D) from Caralluma flava A new pregnane glycoside (nizwaside) (Figure 7) was isolated from the sap of Desmidorchis flava and
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 1204 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences it was
proved as an effective anticancer agent against breast cancer cells like MDA, MB231com- pared to known cancer drug Doxorubicin (Hussain et al., 2015). However, the antioxidant activity of nizwaside was found to be weak. O OH OBz H 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 BzO O O O O OOH O OMe H OH OMeOMe OBz = Figure 7: Pregnane glycoside (nizwaside) from Caralluma flava Two new pregnane glycosides (desmiflavasides A and B) (Figure 8) were isolated from the sap of Des- midorchis flava and desmiflavasides B proved to contain anti-proliferation activity against breast cancer cells at a concentration of 100 mg/mL and 75 mg/mL. On the other hand, urease enzyme inhi- bition, as well as antioxidant activities for them, were found to be weak (Raees et al., 2015). O OH H 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O O O OOH O OMe H OH OH O HO OH OH OH OH R OBz Bz = 1:R = OH 2:R = 21 O 20 21 20 Figure 8: Pregnane glycosides (desmiflavasides A and B) from Caralluma flava Caralluma Indica/Boucerosia Indica Kunert et al. (2006) (Figure 9a & b) isolated novel steroidal glycosides Caralluma species. Stalagmo- side I –V (1-5) are isolated from butanol fraction of Caralluma stalagmifera and indicoside I and II (7 & 8) are isolated from the ether fraction of Caralluma indica. O OH H 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OH Me O O O OHO O OMeORMeOOH HO O O OH OH HO HO OR' H OR2 Glucose'''' Glucose'''' Thevetose'' Cymarose' OH 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 4-Stalagmoside IV - R = Ac, R1 = Bz, R2 = Bz 11-Stalagmoside I - R = H R1 = H R2 = H Figure 9a: Stalagmoside I–IV from Caralluma stalagmifera O OH H 1 2 3 4 5 6 7 8 910 11 12 13 14 15 16 17 18 19 OH O O O OOH O OMeOACOMeOH OH O O OH OH OH OH Glucose'''' Glucose'''' 2 Acetyl- Thevetose'' Cymarose' O O O 5 - Stalagmoside V Figure 9b: Stalagmoside V from Caralluma stal- agmifera Caralluma Lasiantha/Boucerosia Lasiantha Caralluma lasiantha (syn. Boucerosia lasiantha) be- longs to the family Asclepiadaceae and its local name is Kundeti Kommulu (in Telugu)/Siru- mankeerai (in Tamil) (Arinathan et al., 2007). Car- alluma lasiantha is succulent inhabit and is used as an indoor ornamental plant (Reddy et al., 2012). It grows wild in Anantapur, Chittoor and surround- ing places of Andhra Pradesh, India. To reduce the body heat, fresh rootless Caralluma lasiantha (a dose of 10 g, twice a day for three days) is used in India (Vikneshwaran et al., 2008). Malladi et al. (2017) reviewed the role of Caralluma lasiantha in traditional Indian medicine. Two new bisdesmosidic C21 pregnane steroidal glycosides (lasianthosides-A and B) (Figure 10) were isolated from the n-butanol fraction of ethanolic extract of Caralluma lasiantha (Qiu et al., 1999). A flavones glycoside (luteolin-4-O-neohesperiodoside) (Fig- ure 11) was isolated from a methanolic extract of Caralluma lasiantha (Ramesh et al., 1999b). Stigmasterol and C21 Pregnane Steroid (3β,14β- dihydroxy-14β-pregn-5-en-20-one) were isolated from the less polar solvent extracts (Malladi et al., 2017 a,b). O O H OHH H3C H3CO H O H H O H OHH HO H H HO H OH O H OH H H O O H H HO H HO HO H H3C H H OHOH H H H O CH3 H R1 R2 Lasianthoside-A –R1, R2 = D14-15, Lasianthoside-B – R1 = β-OH, R2 = H Figure 10: Lasianthosides A and B from Caral- luma lasiantha
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1205 O OH O OH OH CH3 OH OH OH OH CH2OH O O O OHO Figure
11: Luteoline-4-O-neohesperiodoside from Caralluma lasiantha OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 H H H H Figure 12: Stigmasterol O OH OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 H H Figure 13: 3β,14β-dihydroxy-14β-pregn-5-en- 20-one Caralluma Negevensis Two megastigmane glycosides (1 & 2) (Figure 14), as well as two new flavone glycosides (3 & 4), were isolated from a methanolic extract of Caralluma negevensis (Bader et al., 2003). O H O OH 1 2 3 4 5 6 7 8 9 10 11 12 13 rha-(1 6)-glc O H O OH 1 2 3 4 5 6 7 8 9 10 11 12 13 rha-(1 6)-glc O OOH HO OR1 OR2 3-R1=Rha-(1 2)-glc and R2= Glc 4-R1= Glc and R2= Glc 1 2 Figure 14: Megastigmane glycosides (1 & 2) from Caralluma negevensis Caralluma Negeven- sis New pregnane glycosides (1-20) (Figure 15a and b) were isolated from chloroform and methanol ex- tracts of Caralluma negevensis (Braca et al., 2002). Compounds 1-16 were found to contain bouncer in aglycon moiety, compounds 17-19 were shown to contain the calogenin structure and 20th com- pound contain 5α-dihydrocalogenin moiety. RO 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 H OR2 20 OR1 OH O COO OH Tig = o-OH-Bz = o-hydroxy benzoyl= Ac= Acetyl Figure 15a: Pregnane glycosides (1-16) from Caralluma RO 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 H OR1 20 OH Compound 17, 18 and 19 RO 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OR1 20 OH H Compound 20 Figure 15b: Pregnane glycosides (17-20) from Caralluma negevensis Caralluma Nilagiriana Phytochemicals of Caralluma nilagiriana was eval- uated by using UV-VIS and FTIR spectroscopic techniques (Renuka et al., 2016). GC-MS analysis on ethanolic extract of Caralluma nilagiriana shows the presence of active components like alka- loids, flavonoids, phenolic compounds, steroids, terpenoids and tannins (Ranganathan et al., 2014). Rutin, a bioflavonoid present in the ethanolic ex- tract of shoots of Caralluma nilagiriana was deter- mined by high-performance thin layer chromatog- raphy (HPTLC) (Renuka et al., 2014). Caralluma Pauciflora Two pregnanes (Figure 16) were isolated from di- ethyl ether fraction of ethanolic extract of Caral- luma pauciflora along with known compounds like carumbelloside-III and dihydro russelioside (Reddy et al., 2011). RO OH O 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O HO OH RO OH OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O O OH 2 3 Figure 16: Two pregnanes (compound 2 and 3) from Caralluma pauciflora
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 1206 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences Caralluma Penicillata Four acylated
pregnane glycosides (Figure 17) were identified from the methanolic extract of Car- alluma penicillata (Abdallah et al., 2013). OR OH BzO OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 H OOBz 20 OH OR3 Bz= 21 OR OH BzO 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 H OBz 20 OH OR3 21 Compound 4 Compound 1, 2 and 3 Figure 17: Four acylated pregnane glycosides from Caralluma penicillata C15 oxypregnane glycosides (penicillosides A–C) (Figure 18) were isolated from chloroform fraction of ethanol extract of Caralluma penicillata (Abdel- Sattar et al., 2001). R1O OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 H R2O H H O CH3 20 OH OR3 Benzoyl= Isovaleroyl = CH3 CH3O 1- R1= Glc(1-4) Dig, R2= Benzoyl and R3= H 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 Figure 18: C15 oxypregnane glycosides (penicil- losides A–C) from Caralluma penicillata Caralluma Quadrangular Russelioside B (Figure 19), a pregnane glycoside isolated from the n-butanol fraction of methanol extract of Caralluma quadrangular was recom- mended for managing of diabetes based on its po- tent antihyperlipidemic effect (Abdel-Sattar et al., 2016). OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O-Glc 20 O-Glc(4-1) Glc Figure 19: Russelioside B from Caralluma quadrangular Caralluma Retrospiciens A polyoxy pregnane glycoside (retrospinoside 1) (Figure 20) was identified from the n-butanol frac- tion of methanol extract Caralluma retrospections (Elsebai and Mohamed, 2015). O OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OH20 H H H OH O O HO O O OH Me OH HO OH Figure 20: Polyoxy pregnane glycoside (retro- spinoside 1) from Caralluma retrospiciens Six polyoxy pregnane glycosides (Figure 21a, b) were extracted from ether extracts of Caralluma retrospiciens and all of them exhibited cytotoxic property but compound-2 shown high cytotoxic activity (Halaweish et al., 2004). RO OH O 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O HO O OH 20 21 O O HO O O O O O MeO MeOHO HO HO OHOH OH OH OH O O O O O MeO MeOHO HO OH OH OH OH O O HO O O O OMeOMe OMe HO OHOH OH OH O O O O O O OMeOMe OMe OH OH O HO 1 R = 2 R = 3 R = 4R = Figure 21a: Polyoxy pregnane glycosides (1-4) from Caralluma retrospiciens RO OH O 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O O OH 20 21 C O C O H2CCH O O O O O MeO MeOHO HO OH OH OH OH O O HO O O O OMeOMe OMe HO OHOH OH OH O O6 R = 5 R = Figure 21b: Polyoxy pregnane glycosides (1-4) from Caralluma retrospiciens Caralluma Russeliana Two triterpenoids (3 and 4), two sterols (5 and 6) and two pregnane glycosides (1 and 2) (Figure 22.a-c) were isolated from the chloroform extract of Caralluma russeliana (Abdel-Mogib and Raghib, 2013). O OR2 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O OH 20 21 OR3 OR1 O O O O O OMe OMe MeO R1 O 1- R1 = H, R2 = COC6H5 and R3 = COCH2CH(CH3)2 1a- R1 = Ac, R2 = COC6H5 and R3 = COCH2CH(CH3)2 2- R1 = H, R2 =COCH2CH(CH3)2 and R3 = COC6H5 2a-R1 = Ac, R2 =COC6H5 and R3 = COCH2CH(CH3)2 Figure 22a: Pregnane glycosides (1 and 2) from Caralluma russeliana
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1207 HO H HO H 3 4 Figure 22b: Pregnane glycosides (1 and 2) from Caralluma russeliana 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 OH 5 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 OH 6 Figure 22c: Sterols (5 and 6) from Caralluma russeliana Four
acylated pregnane glycosides (russeliosides E–H) (Figure 23) were extracted from chloroform extracts of Caralluma russeliana (Abdel-Sattar et al., 2007). 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OR OR1 OR2 OHH 1- R=B, R1=Acetyl, R2= Benzoyl 2- R=C, R1=Acetyl, R2= Benzoyl 3- R=A, R1=Acetyl, R2= Benzoyl 4- R=B, R1=Acetyl, R2= Tigloyl O O HO O O O OMeOMe OMe HO OH OH OH O O = B OHO O OMe HO OH OH OH O = A OHO O O OMe OMe HO OH OH OH O O = C Figure 23: Acylated pregnane glycosides (russeliosides E–H) from Caralluma russeliana A known flavone glycoside and four pregnane gly- cosides (Figure 24) were extracted from Caralluma russeliana in its n-butanol fraction of ethanol ex- tract (Abdul-Aziz Al-Yahya et al., 2000). 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O CH3 O OHH O OH HO HO OH O MeO OH OR 1 R= H 2 R= Glc 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O CH3 HO OHH O MeO OH OR 3 R= GLC 4 R= Glc(6''-1'') Glc Figure 24: Pregnane glycosides (russeliosides E–H) from Caralluma russeliana Caralluma Sinaica Caralluma sinaica yielded six pregnane glycosides along with seven pregnanes and three flavonoids (Figure 25) from its chloroform extract (Al-Massa- rani et al., 2012). Quinone reductase induction was evaluated for all these isolated compounds. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OR OR1 OHH R2 20 21 O Tig = O Bz = Ac = O Figure 25: Pregnane glycosides, pregnanes and flavonoids from Caralluma sinaica Boucerosia Truncato Coronato/Caralluma Truncato-Coronato Phytochemical constituents present in ethanolic extracts of Caralluma truncato coronato were stud- ied by GC-MS analysis by Kalimuthu et al. (2013). The results obtained have shown the presence of furan, 2-butyltetrahydro- (0.57%), β-sitosterol (1.89%), acetic acid, 5-(dimethyle-6-oxocyclo- hexylidene)-3-methyl-pent-3-enyl ester (3.78%), β-tocopherol (4.91%), squalene and lupeol (5.67%), vitamin E (9.45%) and thunbergol (68.05%). Caralluma Tuberculata Two steroidal glycosides (pregnane glycoside and androstan glycoside) (Figure 26) were found in ethyl acetate extract of Caralluma tuberculata and exhibited moderate cytotoxic activity against three human breast cancer cell lines (Waheed et al., 2011). O OH O O OH C O R1 O R2Sugar OHO HO OH Glucopyr OH OO HO OH Glucopyr OH O OMe Methoxyribopyr O = I OHO HO OH Glucopyr OH O O OH OH Glucopyr O OMe cymaropyr O O OMe Cym O O OMe Cym O = II Pregnane Glycoside (1)- R1= H, R2= H and Sugar = I Androstan Glycoside (2) R1= C H R2 = C O and Sugar = II Figure 26: Steroidal glycosides from Caralluma tuberculata Five pregnane glycosides (caratuberside A-E) and preganan glycoside-russelioside (Figure 27) were isolated from chloroform fraction of MeOH extract of Caralluma tuberculata. The isolated pregnane glycosides exhibited antimalarial, antitrypanoso- mal and cytotoxic potentials (Abdel-Sattar et al., 2008). 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O OR1 OHH OR2 20 21 Sugar R1 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O OR1 OHH OR2 20 21 Sugar Figure 27: Pregnane glycosides (caratuberside A-E) from Caralluma tuberculata
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 1208 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences Caralluma Umbellata Kalyani et al. (2013) (Figure 28) isolated a novel pregnane glycoside from ether eluates of methanol and benzene fractions of ethanolic extract of roots of Caralluma umbellata. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 O O HO OH HO OH
C CH O O OR R = CH CH3 CH3 Figure 28: Pregnane glycoside from Caralluma umbellata Presence of thirty-two compounds was found in a phytochemical analysis of leaves of Caralluma um- bellata by Jerome Jeyakumar et al. (2013). The ex- tracted phytochemical compounds include terpe- noids, flavonoids, tannins, phenols, glycosides ster- ols and saponins. Two new pregnane compounds (CRUR I and CRUR II) (Figure 27) were isolated from the roots of Caralluma umbellata (Kishore et al., 2010). 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OH CRUR I 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OH OH CRUR II 20 21 20 21 Figure 29: Pregnane compounds from Caral- luma umbellate 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OH H 1 21 O O O Figure 30: Pregnane steroid from Caralluma umbellate C O OH OH 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 Figure 31: C21 steroid from Caralluma umbel- lata Steroidal glycosides were found in different sol- vent fractions of ethanol extract of Caralluma um- bellata. The isolated steroidal glycosides are bourcergenin (new pregnene type steroid) from toluene fraction, carumbelloside-VI (bisdesmo- sidic glycoside) from n-butanol fraction, and car- umbellosides I–IV (new tetroxides of boucergenin) from toluene fraction (Kunert et al., 2009). A new pregnane steroid (Figure 28) containing formyl group was isolated and characterized from Caral- luma umbellata stems along with three known ste- roidal compounds (Babu et al., 2008). A C21 steroid (Figure 31) was isolated from the tol- uene fraction of ethanol extract of Caralluma um- bellata from the whole plant (Ramesh et al., 2005). Caralluma Wissmannii Two pregnane glycosides (5, 6) along with five known compounds (viz., β-sitosterol, stigmasterol, luteolin 3',4'–di-O-β-D-glucopyranoside, 3,4-sec- up-20-(29)-en-3-oic acid methyl ester and lupeol) (Figure 30.a and b) were isolated in the phyto- chemical investigation on Caralluma wissmannii (Dawidar et al., 2012). O O 1 HO 2 HO 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 3 HO 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 4 Figure 32a: (1) 3,4-seco-lup-20(29)-en-3-oic acid methyl ester, (2) lupeol (3) β-sitosterol and (4) stigmasterol from Caralluma wissmannii 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 OR H 20 21 OH O OH OH O O OH O O OMe OMe O D-Cymarose O MeO HO D-Thevitose O OH R = D-Cymarose O OMe O MeO HO D-Thevitose O OH R = D-Cymarose 6 5 O OOH HO O-Glc O-Glc 7 and Figure 32b: (5, 6) Pregnane glycosides and (7) Luteolin 3',4'–di-O-β-D-glucopyranoside from Caralluma wissmannii
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Venkata Nadh R et al., Int. J. Res. Pharm. Sci., 9(4), 1201-1213 © Pharmascope Publications | International Journal of Research in Pharmaceutical Sciences 1209 In continuation to the above list of phytochemicals collection, efforts of various researchers on their study pertaining to different species of Caralluma are compiled in Table-1. CONCLUSION Caralluma is a genus used as traditional medicine and is a potential source for phytochemicals with medicinal uses.
Thorough literature collection shows few species of Caralluma are explored for 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, Luteoline-4’-O-neohesperiodo- side Caralluma arabica Kamil et al., 1999 Caralluma umbellata Ramesh et al., 1999b Caralluma lasiantha Ramesh et al., 1999b Caralluma attenuata Ramesh et al., 1998, 1999b Caralluma tuberculata Rizwani et al., 1990 Flavones glycosides and megastigmane glycosides Caralluma negevensis Bader et al., 2003 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
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