Chemical Characterization of a Commercial Commiphora wightii Resin Sample and Chemical Profiling to Assess for Authenticity

Rida Ahmed; Zulfiqar Ali; Yunshan Wu; Swapnil Kulkarni; Mitchell A. Avery; Muhammed Iqbal Choudhary; Atta-ur-Rahman; Ikhlas A. Khan

doi:10.1055/s-0030-1250674

Planta Medica, Table of Contents

Planta Med 2011; 77(9): 945-950
DOI: 10.1055/s-0030-1250674

Natural Product Chemistry

Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Chemical Characterization of a Commercial Commiphora wightii Resin Sample and Chemical Profiling to Assess for Authenticity

Rida Ahmed¹ ^, ² , Zulfiqar Ali¹ ^, ² , Yunshan Wu³ , Swapnil Kulkarni³ , Mitchell A. Avery³ , Muhammed Iqbal Choudhary² , Atta-ur-Rahman² , Ikhlas A. Khan¹ ^, ⁴

¹National Center for Natural Products Research, School of Pharmacy, University of Mississippi, University, MS, USA
²H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, Pakistan
³Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, University, MS, USA
⁴Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS, USA

Abstract

The gum resin of Commiphora wightii [(Hook. ex Stocks) Engl.] is an ayurvedic medicine for the treatment of arthritis, inflammation, obesity, lipid disorders, and cardiovascular diseases and is known as guggul. Morphologically, it is not easy to distinguish guggul from closely related gum resins of other plants. Reliability of the commercially available guggul is critical due to the high risk of adulteration. To check authenticity, a commercial guggul sample was investigated for its chemical markers and 17 metabolites were identified, including three new, 20(S),21-epoxy-3-oxocholest-4-ene (1), 8β-hydroxy-3,20-dioxopregn-4,6-diene (2), and 5-(13′Z-nonadecenyl)resorcinol (17) from the ethyl acetate soluble part. During the current study, compounds 14–17 were identified as constituents of Mangifera indica gum, as an adulterant in the commercial guggul sample. This discovery highlighted the common malpractices in the trade of medicinal raw material in the developing world. The structures of the compounds were deduced by the spectroscopic technique and chemical methods, as well as by comparison with the reported data. The structure of 20(S),21-epoxy-3-oxocholest-4-ene (1) was also unambiguously deduced by single-crystal X‐ray diffraction technique.

Key words

Commiphora wightii - guggul - Burseraceae - Mangifera indica - single‐crystal X‐ray diffraction

Full Text

References

1 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; 56 723-727
2 Meselhy M R. Inhibition of LPS-induced NO production by the oleogum resin of Commiphora wightii and its constituents. Phytochemistry. 2003; 62 213-218
3 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 1842-1853
4 Benvegnu R, Cimino G, De Rosa S, De Stefano S. Guggulsterol-like steroids from the Mediterranean gorgonian Leptogorgia sarmentosa. Experientia. 1982; 38 1443-1444
5 Migliuolo A, Piccialli V, Sica D. Steroidal ketones from the sponge Geodia cydonium. J Nat Prod. 1990; 53 1262-1266
6 Van Z A, Huis R. Acid-catalyzed isomerization of epoxides to allylic alcohols. J Roy Neth Chem Soc. 1981; 100 425-429
7 Choudhary M I, Azizuddin J S, Musharraf S G, Atta-ur-Rahman. Fungal transformation of dydrogesterone and inhibitory effect of its metabolites on the respiratory burst in human neutrophils. Chem Biodivers. 2008; 5 324-331
8 Gao Z, Ali Z, Khan I A. Glycerogalactolipids from the fruit of Lycium barbarum. Phytochemistry. 2008; 69 2856-2861
9 Barr J R, Scannell R T, Yamaguchi K. Structure elucidation of naturally occurring long-chain mono- and dienes. J Org Chem. 1989; 54 494-496
10 Greger H, Hofer O. New unsymmetrically substituted tetrahydrofurofuran lignans from Artemisia absinthium. Assignment of the relative stereochemistry by lanthanide induced chemical shifts. Tetrahedron. 1980; 36 3551-3558
11 Bultel-Pönce V, Etahiri S, Guyot M. New ketosteroids from the red alga Hypnea musciformis. Bioorg Med Chem Lett. 2002; 12 1715-1718
12 Ahmed A A, Mahmoud A A, Ali E T, Tzakou O, Couladis M, Mabry T J, Gati T, Toth G. Two highly oxygenated eudesmanes and 10 lignans from Achillea holosericea. Phytochemistry. 2002; 59 851-856
13 Patil V D, Nayak U R, Dev S. Chemistry of ayurvedic crude drugs. I. Guggulu (resin from Commiphora mukul). 1. Steroidal constituents. Tetrahedron. 1972; 28 2341-2352
14 Hung T, Stuppner H, Ellmerer-Mueller E P, Scholz D, Eigner D, Manandhar M P. Steroids and terpenoids from the gum resin of Ailanthus grandis. Phytochemistry. 1995; 39 1403-1409
15 Singh C, Dev S. Higher isoprenoids. V. Partial syntheses from cycloartenol, cyclolaudenol. Part 1. Mangiferolic acid, ambolic acid. Tetrahedron. 1977; 33 817-819
16 Sy L-K, Saunders R M K, Brown G D. Phytochemistry of Illicium dunnianum and the systematic position of the Illiciaceae. Phytochemistry. 1997; 44 1099-1108
17 Teresa D P, Urones J G, Marcos I S, Basabe P, Cuadrado M J S, Moro R F. Triterpenes from Euphorbia broteri. Phytochemistry. 1987; 26 1767-1776
18 Knödler M, Conrad J, Wenzig E M, Bauer R, Lacorn M, Beifuss U, Carle R, Schieber A. Anti-inflammatory 5-(11′Z-heptadecenyl)- and 5-(8′Z,11′Z-heptadecadienyl)-resorcinols from mango (Mangifera indica L.) peels. Phytochemistry. 2008; 69 988-993

Prof. Ikhlas A. Khan

National Center for Natural Products Research
School of Pharmacy, University of Mississippi

University, MS 38677

USA

Phone: +1 66 29 15 78 21

Fax: +1 66 29 15 79 89

Email: ikhan@olemiss.edu