Isolation and Anti-Inflammatory Activity Evaluation of Triterpenoids and a Monoterpenoid Glycoside from Harpagophytum procumbens

Abstract

A new triterpenoid glycoside, designated harproside (1), and a new iridoid glycoside, named pagide (2), along with six known triterpenoids (3-8), were obtained from the tubers of Harpagophytum procumbens D. C. (devil's claw), and their structures were established through chemical methods and spectroscopic analyses. In an in vitro assay, the six triterpenoids showed anti-inflammatory activity. Compounds 3, 7, and 8 showed significant inhibitory activity against neutrophil respiratory burst stimulated by PMA, while compounds 4, 5, and 6 showed marginal inhibitory activity.

Key words

Pedaliaceae - Harpagophytum procumbens (Burch.) D. C. ex Meissner subsp. procumbens - devil's claw - terpenoids - monoterpenoid glycoside - neutrophil respiratory burst

References

• 1 Stewart K M, Cole D. The commercial harvest of devil's claw (Harpagophytum spp.) in southern Africa: the devil's in the details.  J Ethnopharmacol. 2005;  100 225-236
• 2 McGregor G, Fiebich B, Wartenberg A, Brien S, Lewith G, Wegener T. Devil's claw (Harpagophytum procumbens): an anti-inflammatory herb with therapeutic potential.  Phytochem Rev. 2005;  4 47-53
• 3 Kikuchi T, Matsuda S, Kubo Y, Namba T. New iridoid glucosides from Harpagophytum procumbens DC.  Chem Pharm Bull. 1983;  31 2296-2301
• 4 Boje K, Lechtenberg M, Nahrstedt A. New and known iridoid- and pheny lethanoid glycosides from Harpagophytum procumbens and their in vitro inhibition of human leukocyte elastase.  Planta Med. 2003;  69 820-825
• 5 El-Naggar L J, Beal J L. Iridoids. A review.  J Nat Prod. 1980;  43 649-707
• 6 Burger J F W, Brandt E V, Ferreira D. Iridoid and phenolic glycosides from Harpagophytum procumbens.  Phytochemistry. 1987;  26 1453-1457
• 7 Munkombwe N M. Acetylated phenolic glycosides from Harpagophytum procumbens.  Phytochemistry. 2003;  62 1231-1234
• 8 Clarkson C, Campbell W E, Smith P. In vitro antiplasmodial activity of abietane and totarane diterpenes isolated from Harpagophytum procumbens (devil's claw).  Planta Med. 2003;  69 720-724
• 9 Qi J, Chen J J, Cheng Z H, Zhou J H, Yu B Y, Qiu S X. Iridoid glycosides from Harpagophytum procumbens D.C. (devil's claw).  Phytochemistry. 2006;  67 1372-1377
• 10 Kobayashi Y, Ogihara Y. New triterpenoids from the leaves of Bupleurum rotundifolium L.  Chem Pharm Bull. 1981;  29 2230-2236
• 11 Kojima H, Tominaga H, Sato S, Ogura H. Pentacyclic triterpenoids from Prunella vulgaris.  Phytochemistry. 1987;  26 1107-1111
• 12 Ryu S Y, Oak M H, Yoon S K, Cho D I, Yoo G S, Kim T S, Kim K M. Anti-allergic and anti-inflammatory triterpenes from the herb of Prunella vulgaris.  Planta Med. 2000;  66 358-360
• 13 Wang Z J, Zhao Y Y, Tu G Z, Hong S L, Chen Y Y. Studies on chemical constituents from Prunella vulgaris.  Acta Pharm Sin. 1999;  34 679-681
• 14 Sashida Y, Ogawa K, Yamanouchi T, Tanaka H, Shoyama Y, Nishioka I. Triterpenoids from callus tissue of Actinidia polygama.  Phytochemistry. 1994;  35 377-380
• 15 Zhang Y J, Yang C R. Two triterpenoids from Gentiana tibetica.  Phytochemistry. 1994;  36 997-999
• 16 Ma C M, Cai S Q, Cui J R, Wang R Q, Tu P F, Hattori M, Daneshtalab M. The cytotoxic activity of ursolic acid derivatives.  Eur J Med Chem. 2005;  40 582-589
• 17 Ikuta A, Tomiyasu H, Morita Y, Yoshimura K. Ursane- and oleanane-type triterpenes from Ternstroemia gymnanthera callus tissues.  J Nat Prod. 2003;  66 1051-1054
• 18 Wang S F, Li S, Li Z G, Li Y. Triterpenoids and other compounds from Salvia roborowskii Maxim.  Pharmazie. 2001;  56 420-422
• 19 El Lahlou H, Hirai N, Tsuda M, Ohigashi H. Triterpene phytoalexins from nectarine fruits.  Phytochemistry. 1999;  52 623-629
• 20 Sridhar C, Rao K V, Subbaraju G V. Flavonoids, triterpenoids and a lignan from Vitex altissima.  Phytochemistry. 2005;  66 1707-1712
• 21 Lahlou E H, Hirai N, Kamo T, Tsuda M, Ohigashi H. Actinidic acid, a new triterpene phytoalexin from unripe kiwi fruit.  Biosci Biotechnol Biochem. 2001;  65 480-483
• 22 Wang J P, Raung S L, Kuo Y H, Teng C M. Daphnoretin-induced respiratory burst in rat neutrophils is, probably, mainly through protein kinase C activation.  Eur J Pharmacol. 1995;  288 341-348
• 23 Chadfield M, Olsen J. Determination of the oxidative burst chemiluminescent response of avian and murine-derived macrophages versus corresponding cell lines in relation to stimulation with Salmonella serotypes.  Vet Immunol Immunopathol. 2001;  80 289-308
• 24 Mu L L, Kou J P, Zhu D N, Yu B Y. Antioxidant activities of the chemical constituents isolated from the leaves of Ginkgo biloba.  Chin J Nat Med. 2008;  6 26-29
• 25 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
• 26 Nakamura Y, Takahashi K, Satoh K, Shimetani A, Sakagami H, Nishikawa H. Role of free radicals and metal ions in direct current-induced cytotoxicity.  J Endod. 2006;  32 442-446