Generic placeholder image

Mini-Reviews in Organic Chemistry


ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Review Article

Phytochemical Constituents of Guggul and their Biological Qualities

Author(s): Vijay Kumar*, Simranjeet Singh and Ravindra Singh

Volume 17, Issue 3, 2020

Page: [277 - 288] Pages: 12

DOI: 10.2174/1570193X16666190129161757

Price: $65


In the herbal drug pharmaceutical industry, guggul is enjoying emergent consumer acceptance around the world. In the Indian market, more than fifty formulations of guggul have been introduced by well-known brands including Himalaya, Patanjali and Baidyanath Pharmaceuticals. Basically, guggul is the gum resin from Commiphora wightii (syn. Commiphora Mukul). It has been used to treat various ailments including obesity, osteoarthritis, arthritis, constipation, liver disorders, inflammation, anemia, diabetes, etc. Including medicinal properties, it is used as a good binding agent and mixed in various herbal formulations. To review the major phytochemical, medicinal properties and analytical methods involved in the detection of guggul by using the exhaustive bibliographic research by means of various scientific engines and databases. Guggul contained approximately 66 phytochemical including gallic acid, quercetin, and guggulsterones E and Z. These phytochemicals have a wide range of pharmacological activities such as antioxidant, antibacterial, antimutagenic, antivenom and antitumor. It has been noticed that the mode of action of guggulsterone has not been fully explored. Pharmacology and toxicological studies are very few. These works have shown huge literature gap, which is to be fulfilled through the detailed in-vivo and in-vitro studies.

Keywords: Cholesterol, commiphora mukul, guggulusterone, obesity, sterols, terpenoids.

Graphical Abstract
Newman, D.J.; Cragg, G.M. Natural products as sources of new drugs from 1981 to 2014. J. Nat. Prod., 2016, 79(3), 629-661.
[] [PMID: 26852623]
Kulhari, A.; Sheorayan, A.; Kalia, S.; Chaudhury, A.; Kalia, R.K. Problems, progress and future prospects of improvement of Commiphora wightii (Arn) Bhandari, an endangered herbal magic, through modern biotechnological tools: A review. Genet. Resour. Crop Evol., 2012, 59, 1223-1254.
Satyavati, G.V. Guggulipid: A promising hypolipidaemic agent from gum guggul (Commiphora mukul). Economic and Medicinal Plant Research. Wagner, H; Farnsworth, N.R., Ed.; New York: Academic Press, 1991, pp. 47-48.
Satyavati, G.V.; Dwarakanath, C.; Tripathi, S.N. Experimental studies on the hypocholesterolemic effect of Commiphora mukul. Engl. (Guggul). Indian J. Med. Res., 1969, 57(10), 1950-1962.
[PMID: 5372181]
Deng, R. Therapeutic effects of guggul and its constituent guggulsterone: cardiovascular benefits. Cardiovasc. Drug Rev., 2007, 25(4), 375-390.
[] [PMID: 18078436]
Shen, T.; Li, G.H.; Wang, X.N.; Lou, H.X. The genus Commiphora: a review of its traditional uses, phytochemistry and pharmacology. J. Ethnopharmacol., 2012, 142(2), 319-330.
[] [PMID: 22626923]
Yousefi, M.; Hoseini, S.M.; Salari, R. Evaluating the clinical efficacy of Guggulu resin on constipation, A randomized clinical trial. Adv. Integr. Med., 2016, 3(3), 98-102.
Singh, S.K.; Rajoria, K. Ayurvedic management of spondyloepiphyseal dysplasia tarda, a rare hereditary disorder. J. Ayurveda Integr. Med., 2016, 7(4), 249-254.
[] [PMID: 27890699]
Bhatia, A.; Bharti, S.K.; Tripathi, T.; Mishra, A.; Sidhu, O.P.; Roy, R.; Nautiyal, C.S. Metabolic profiling of Commiphora wightii (guggul) reveals a potential source for pharmaceuticals and nutraceuticals. Phytochemistry, 2015, 110, 29-36.
[] [PMID: 25561401]
Matsuda, H.; Morikawa, T.; Ando, S.; Oominami, H.; Murakami, T.; Kimura, I.; Yoshikawa, M. Absolute stereostructures of polypodane- and octanordammarane-type triterpenes with nitric oxide production inhibitory activity from guggul-gum resins. Bioorg. Med. Chem., 2004, 12(11), 3037-3046.
[] [PMID: 15142562]
Prasad, K.R.; Chandrakumar, A. Stereoselective syntheses of γ-alkyl (aryl)-α.;β-dihydroxy-gbutyrolactones and naturally occurring lipid guggultetrol. Tetrahedron, 2007, 63, 1798-1805.
Zhu, N.; Rafi, M.M.; DiPaola, R.S.; Xin, J.; Chin, C.K.; Badmaev, V.; Ghai, G.; Rosen, R.T.; Ho, C.T. Bioactive constituents from gum guggul (Commiphora wightii). Phytochemistry, 2001, 56(7), 723-727.
[] [PMID: 11314959]
Lalla, J.; Hamrapurkar, P.; Sacket, S. Estimation of guggulsterones E and Z in solid dosage forms containing Commiphora mukul. Hook. J. Planar Chromatogr. Mod. TLC, 2007, 20, 197-202.
Roy, S.K.; Pal, R.; Sarin, J.P.S. TLC separation and quantitative determination of guggulsterones. Indian J. Pharm., 1989, 51, 251-253.
Agrawal, H.; Kaul, N.; Paradkar, A.R.; Mahadik, K.R. HPTLC method for guggulsterone. I. Quantitative determination of E- and Z-guggulsterone in herbal extract and pharmaceutical dosage form. J. Pharm. Biomed. Anal., 2004, 36(1), 33-41.
[] [PMID: 15351045]
Singh, S.K.; Verma, N.; Gupta, R.C. Sensitive high-performance liquid chromatographic assay method for the determination of guggulsterone in serum. J. Chromatogr. B Biomed. Appl., 1995, 670(1), 173-176.
[] [PMID: 7493077]
Verma, N.; Singh, S.K.; Gupta, R.C. Simultaneous determination of the stereoisomers of guggulsterone in serum by high-performance liquid chromatography. J. Chromatogr. B Biomed. Sci. Appl., 1998, 708(1-2), 243-248.
[] [PMID: 9653969]
Nagrajan, M.; Waszkuc, T.W.; Sun, J. Simultaneous determination of E- and Zguggulsterones in dietary supplements containing Commiphora mukul extract (guggulipid) by liquid chromatography. J. AOAC Int., 2001, 1, 24-28.
Mesrob, B.; Nesbitt, C.; Misra, R.; Pandey, R.C. High-performance liquid chromatographic method for fingerprinting and quantitative determination of E- and Z-guggulsterones in Commiphora mukul resin and its products. J. Chromatogr. B Biomed. Sci. Appl., 1998, 720(1-2), 189-196.
[] [PMID: 9892081]
Gottumukkala, A.L.; Ramakrishna, T.; Babu, S.K.; Subbaraju, G.V. Determination of E- and Z-guggul formulations by high-performance liquid chromatography. Asian J. Chem., 2005, 17, 1789-1793.
Haque, I.; Kumar, M.; Mukhopadhyay, K.A. Rapid and simple UPLC-MS-MS based simultaneous determination of the medicinally important E- and Z-guggulsterone from Oleogum-resins of naturally occurring Commiphora wightii plants. Chromatographia, 2009, 70, 1613-1618.
Musharraf, S.G.; Iqbal, N.; Gulzar, U.; Ali, A.; Choudhary, M.I.; Atta-Ur-Rahman, Effective separation and analysis of E- and Z-guggulsterones in Commiphora mukul resin, guggulipid and their pharmaceutical product by high performance thin-layer chromatography-densitometric method. J. Pharm. Biomed. Anal., 2011, 56(2), 240-245.
[] [PMID: 21676570]
Musharraf, S.G.; Iqbal, N.; Gulzar, U.; Ali, A.; Choudhary, M.I. Atta-ur-Rahman. Screening of E- and Z-guggulsterones in the gum-resin exudates of some common plants and method validation in raw, extracted, and pharmaceutical formulations of Commiphora mukul by HPLC. J. Liq. Chromatogr. Relat. Technol., 2011, 34, 2103-2117.
Shelke, N.; Kuber, V.K.; Bhope, S.; Jadhav, R. Simultaneous HPTLC analysis of E-guggulsterone; Z-guggulsterone; 11-keto-β-boswellic acid and 3-acetyl-11-keto-β-boswellic acid in an anti-arthritic formulation. J. Planar Chromatogr. Mod. TLC, 2011, 24, 242-247.
Vyas, J.; Itankar, P.; Tauqeer, M.; Kelkar, A.; Agrawal, M. Development of HPTLC method for estimation of piperine; guggulsterone E and Z in polyherbal formulation. Pharmacogn. J., 2013, 5, 259-264.
Khanna, N.; Arora, D.; Halder, S.; Mehta, A.K.; Garg, G.R.; Sharma, S.B.; Mahajan, P. Comparative effect of Ocimum sanctum, Commiphora mukul, folic acid and ramipril on lipid peroxidation in experimentally-induced hyperlipidemia. Indian J. Exp. Biol., 2010, 48(3), 299-305.
[PMID: 21046985]
Singh, R.B.; Niaz, M.A.; Ghosh, S. Hypolipidemic Commiphora Mukul therapy in patients and antioxidant effects of as an adjunct to dietary with hyperch-olesterolemia. Cardiovasc. Drugs Ther., 1994, 8, 659-664.
[] [PMID: 7848901]
Nohr, L.A.; Rasmussen, L.B.; Straand, J. Resin from the mukul myrrh tree, guggul, can it be used for treating hypercholesterolemia? A randomized, controlled study. Complement. Ther. Med., 2009, 17(1), 16-22.
[] [PMID: 19114224]
Szapary, P.O.; Wolfe, M.L.; Bloedon, L.T.; Cucchiara, A.J.; DerMarderosian, A.H.; Cirigliano, M.D.; Rader, D.J. Guggulipid for the treatment of hypercholesterolemia: a randomized controlled trial. JAMA, 2003, 290(6), 765-772.
[] [PMID: 12915429]
Ulbricht, C.; Basch, E.; Szapary, P.; Hammerness, P.; Axentsev, S.; Boon, H.; Kroll, D.; Garraway, L.; Vora, M.; Woods, J. Guggul for hyperlipidemia, a review by the natural standard research collaboration. Complement. Ther. Med., 2005, 13(4), 279-290.
[] [PMID: 16338199]
Wang, X.L.; Kong, F.; Shen, T.; Young, C.Y.F.; Yuan, H.Q.; Lou, H.X. Sesquiterpenoids from myrrh inhibit expression and function of the androgen receptor in human prostate cancer cells. Acta Pharmacol. Sin., 2011, 32, 338-344.
[] [PMID: 21372825]
Ramawat, K.G.; Merillon, J.M. Bioactive Molecules and Medicinal Plants Springer; Heidelberg, 2008, p. 101.
Urizar, N.L.; Liverman, A.B.; Dodds, D.T.; Silva, F.V.; Ordentlich, P.; Yan, Y.; Gonzalez, F.J.; Heyman, R.A.; Mangelsdorf, D.J.; Moore, D.D. A natural product that lowers cholesterol as an antagonist ligand for FXR. Science, 2002, 296(5573), 1703-1706.
[] [PMID: 11988537]
Yu, B.Z.; Kaimal, R.; Bai, S.; El Sayed, K.A.; Tatulian, S.A.; Apitz, R.J.; Jain, M.K.; Deng, R.; Berg, O.G. Effect of guggulsterone and cembranoids of Commiphora mukul on pancreatic phospholipase A(2): role in hypocholesterolemia. J. Nat. Prod., 2009, 72(1), 24-28.
[] [PMID: 19102680]
Bellamkonda, R.; Rasineni, K.; Singareddy, S.R.; Kasetti, R.B.; Pasurla, R.; Chippada, A.R.; Desireddy, S. Antihyperglycemic and antioxidant activities of alcoholic extract of Commiphora mukul gum resin in streptozotocin induced diabetic rats. Pathophysiology, 2011, 18(4), 255-261.
[] [PMID: 21767936]
Lv, N.; Song, M.Y.; Kim, E.K.; Park, J.W.; Kwon, K.B.; Park, B.H. Guggulsterone, a plant sterol, inhibits NF-kappaB activation and protects pancreatic beta cells from cytokine toxicity. Mol. Cell. Endocrinol., 2008, 289(1-2), 49-59.
[] [PMID: 18343024]
Sharma, B.; Salunke, R.; Srivastava, S.; Majumder, C.; Roy, P. Effects of guggulsterone isolated from Commiphora mukul in high fat diet induced diabetic rats. Food Chem. Toxicol., 2009, 47(10), 2631-2639.
[] [PMID: 19635521]
Singh, B.B.; Mishra, L.C.; Vinjamury, S.P.; Aquilina, N.; Singh, V.J.; Shepard, N. The effectiveness of Commiphora mukul for osteoarthritis of the knee: an outcomes study. Altern. Ther. Health Med., 2003, 9(3), 74-79.
[PMID: 12776478]
Duwiejua, M.; Zeitlin, I.J.; Waterman, P.G.; Chapman, J.; Mhango, G.J.; Provan, G.J. Anti-inflammatory activity of resins from some species of the plant family Burseraceae. Planta Med., 1993, 59(1), 12-16.
[] [PMID: 8441773]
Meselhy, M.R. Inhibition of LPS-induced NO production by the oleogum resin of Commiphora wightii and its constituents. Phytochemistry, 2003, 62(2), 213-218.
[] [PMID: 12482459]
Cheng, Y.W.; Cheah, K.P.; Lin, C.W.; Li, J.S.; Yu, W.Y.; Chang, M.L.; Yeh, G.C.; Chen, S.H.; Choy, C.S.; Hu, C.M. Myrrh mediates haem oxygenase-1 expression to suppress the lipopolysaccharide-induced inflammatory response in RAW264.7 macrophages. J. Pharm. Pharmacol., 2011, 63(9), 1211-1218.
[] [PMID: 21827494]
Shishodia, S.; Aggarwal, B.B. Guggulsterone inhibits NF-kappaB and IkappaBalpha kinase activation, suppresses expression of anti-apoptotic gene products, and enhances apoptosis. J. Biol. Chem., 2004, 279(45), 47148-47158.
[] [PMID: 15322087]
Francis, J.A.; Raja, S.N.; Nair, M.G. Bioactive terpenoids and guggulusteroids from Commiphora mukul gum resin of potential anti-inflammatory interest. Chem. Biodivers., 2004, 1(11), 1842-1853.
[] [PMID: 17191820]
Kalariya, N.M.; Shoeb, M.; Reddy, A.B.; Zhang, M.; van Kuijk, F.J.; Ramana, K.V. Prevention of endotoxin-induced uveitis in rats by plant sterol guggulsterone. Invest. Ophthalmol. Vis. Sci., 2010, 51(10), 5105-5113.
[] [PMID: 20435582]
Kimura, I.; Yoshikawa, M.; Kobayashi, S.; Sugihara, Y.; Suzuki, M.; Oominami, H.; Murakami, T.; Matsuda, H.; Doiphode, V.V. New triterpenes, myrrhanol A and myrrhanone A, from guggul-gum resins, and their potent anti-inflammatory effect on adjuvant-induced air-pouch granuloma of mice. Bioorg. Med. Chem. Lett., 2001, 11(8), 985-989.
[] [PMID: 11327606]
Niranjan, R.; Kamat, P.K.; Nath, C.; Shukla, R. Evaluation of guggulipid and nimesulide on production of inflammatory mediators and GFAP expression in LPS stimulated rat astrocytoma, cell line (C6). J. Ethnopharmacol., 2010, 127(3), 625-630.
[] [PMID: 20018235]
Manjula, N.; Gayathri, B.; Vinaykumar, K.S.; Shankernarayanan, N.P.; Vishwakarma, R.A.; Balakrishnan, A. Inhibition of MAP kinases by crude extract and pure compound isolated from Commiphora mukul leads to down regulation of TNF-alpha, IL-1beta and IL-2. Int. Immunopharmacol., 2006, 6(2), 122-132.
[] [PMID: 16399617]
Fraternale, D.; Sosa, S.; Ricci, D.; Genovese, S.; Messina, F.; Tomasini, S.; Montanari, F.; Marcotullio, M.C. Anti-inflammatory, antioxidant and antifungal furanosesquiterpenoids isolated from Commiphora erythraea (Ehrenb.) Engl. resin. Fitoterapia, 2011, 82(4), 654-661.
[] [PMID: 21316424]
Shen, T.; Wan, W.; Yuan, H.; Kong, F.; Guo, H.; Fan, P.; Lou, H. Secondary metabolites from Commiphora opobalsamum and their antiproliferative effect on human prostate cancer cells. Phytochemistry, 2007, 68(9), 1331-1337.
[] [PMID: 17343886]
Shishodia, S.; Sethi, G.; Ahn, K.S.; Aggarwal, B.B. Guggulsterone inhibits tumor cell proliferation, induces S-phase arrest, and promotes apoptosis through activation of c-Jun N-terminal kinase, suppression of Akt pathway, and downregulation of antiapoptotic gene products. Biochem. Pharmacol., 2007, 74(1), 118-130.
[] [PMID: 17475222]
Tripathi, Y.B.; Malhotra, O.P.; Tripathi, S.N. Thyroid stimulating action of Z-guggulsterone obtained from Commiphora mukul. Planta Med., 1984, 50, 78-80.
Andersson, M.; Bergendorff, O.; Shan, R.; Zygmunt, P.; Sterner, O. Minor components with smooth muscle relaxing properties from scented myrrh (Commiphora guidotti). Planta Med., 1997, 63(3), 251-254.
[] [PMID: 9225607]
Dolara, P.; Corte, B.; Ghelardini, C.; Pugliese, A.M.; Cerbai, E.; Menichetti, S.; Lo Nostro, A. Local anaesthetic, antibacterial and antifungal properties of sesquiterpenes from myrrh. Planta Med., 2000, 66(4), 356-358.
[] [PMID: 10865454]
Koch, A.; Tamez, P.; Pezzuto, J.; Soejarto, D. Evaluation of plants used for antimalarial treatment by the Maasai of Kenya. J. Ethnopharmacol., 2005, 101(1-3), 95-99.
[] [PMID: 15878245]
Omer, S.A.; Adam, S.E.; Mohammed, O.B. Antimicrobial activity of Commiphora myrrha against some bacteria and Candida albicans Isolated from Gazelles at King Khalid Wildlife Research Centre. Res. J. Med. Plant, 2011, 5, 65-71.
Rahman, M.M.; Garvey, M.; Piddock, L.J.; Gibbons, S. Antibacterial terpenes from the oleo-resin of Commiphora molmol (Engl.). Phytother. Res., 2008, 22(10), 1356-1360.
[] [PMID: 18570217]
Annu, W.; Latha, P.G.; Shaji, J.; Anuja, G.I.; Sujia, S.R.; Sini, S.; Shyamal, S.; Shine, V.J.; Shikha, P.; Rajiasekharan, S. Anti-inflammatory analgesic and anti-lipid peroxidation studies onleaves of Commiphora caudata (Wight & Arn). Engl. J. Ind. Nat. Prod. Res., 2004, 1, 44-48.
Hariprasad, K.; Prabhu, N.; Acharya, S.; Nagappa, A.N.; Naik, V. A Comparative Clinical Evaluation of Trayodashanga Guggulu and Mustadiyapana Yoga Basti in Gridhrasi. Value Health, 2014, 17(7), A771.
[] [PMID: 27202843]
Suvarna, H.P.; Acharya, S.; Nagappa, A.N. clinical evaluation of shuddha guggulu in hypothyroidism patients. Value Health, 2015, 18, A301-A307.
Acharya, S.; Singh, R.; Nagappa, A.N.; Mateti, U.V. Clinical evaluation of amritadi guggulu and mandoora bhasma in osteoarthritis patients. Value Health, 2015, 18, A335-A766.
Patel, M.G.; Pundarikakshudu, K. Anti-arthritic activity of a classical Ayurvedic formulation Vatari Guggulu in rats. J. Tradit. Complement. Med., 2015, 6(4), 389-394.
[] [PMID: 27774424]
Kuvettu, H.; Acharya, S.; Nagappa, A.N. Clinical evaluation of amritha guggulu in the management of gout. Value Health, 2016, 19, A807-A918.
Venkataramasubramanian, V.; Kumar, B.S.; Sudalai, A. Enantioselective synthesis of guggultetrol and D-ribo-phytosphingosine tetraacetate via L-proline catalyzed sequential a-aminooxy-lation/Horner-Wardsworth-Emmons olefination-sharpless asymmetric dihydroxylation strategy. Tetrahedron, 2015, 26, 571-576.
Ahmad, M.U.; Ali, S.M.; Ahmad, A.; Sheikh, S.; Ahmad, I. Guggullipid derivatives: synthesis and applications. Chem. Phys. Lipids, 2010, 163(4-5), 362-366.
[] [PMID: 20188717]
Li, L.; Qu, C.; Zhou, K. Toxicity and side effects of frankincense and myrrh. J. Toxicol., 2008, 22, 496-497.
Omer, S.A.; Adam, S.E. Toxicity of Commiphora myrrha to goats. Vet. Hum. Toxicol., 1999, 41(5), 299-301.
[PMID: 10509432]
Rao, R.M.; Khan, Z.A.; Shah, A.H. Toxicity studies in mice of Commiphora molmol oleo-gum-resin. J. Ethnopharmacol., 2001, 76(2), 151-154.
[] [PMID: 11390128]
Ghatak, A.; Asthana, O.P. Recent trends in hyperlipoproteinemias and its pharmacotherapy. Indian J. Pharmacol., 1995, 27, 14-29.
Karuparthy, V.R.; Vepachedu, S. Guggulipid and cholesterol levels. JAMA, 2003, 290(21), 2800-2801.
[] [PMID: 14657060]
Ikhlas, S.; Ahmad, M. Binding studies of guggulsterone-E to calf thymus DNA by multi-spectroscopic, calorimetric and molecular docking studies. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2018, 190, 402-408.
[] [PMID: 28954252]

Rights & Permissions Print Export Cite as
© 2022 Bentham Science Publishers | Privacy Policy