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

 

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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.

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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 3 Kikuchi T, Matsuda S, Kubo Y, Namba T. New iridoid glucosides from Harpagophytum procumbens DC.  Chem Pharm Bull. 1983;  31 2296-2301
  PubMedGoogle Scholar
• 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
  Article in Thieme ConnectPubMedGoogle Scholar
• 5 El-Naggar L J, Beal J L. Iridoids. A review.  J Nat Prod. 1980;  43 649-707
  CrossrefPubMedGoogle Scholar
• 6 Burger J F W, Brandt E V, Ferreira D. Iridoid and phenolic glycosides from Harpagophytum procumbens.  Phytochemistry. 1987;  26 1453-1457
  CrossrefPubMedGoogle Scholar
• 7 Munkombwe N M. Acetylated phenolic glycosides from Harpagophytum procumbens.  Phytochemistry. 2003;  62 1231-1234
  CrossrefPubMedGoogle Scholar
• 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
  Article in Thieme ConnectPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 10 Kobayashi Y, Ogihara Y. New triterpenoids from the leaves of Bupleurum rotundifolium L.  Chem Pharm Bull. 1981;  29 2230-2236
  PubMedGoogle Scholar
• 11 Kojima H, Tominaga H, Sato S, Ogura H. Pentacyclic triterpenoids from Prunella vulgaris.  Phytochemistry. 1987;  26 1107-1111
  CrossrefPubMedGoogle Scholar
• 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
  Article in Thieme ConnectPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 15 Zhang Y J, Yang C R. Two triterpenoids from Gentiana tibetica.  Phytochemistry. 1994;  36 997-999
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 18 Wang S F, Li S, Li Z G, Li Y. Triterpenoids and other compounds from Salvia roborowskii Maxim.  Pharmazie. 2001;  56 420-422
  PubMedGoogle Scholar
• 19 El Lahlou H, Hirai N, Tsuda M, Ohigashi H. Triterpene phytoalexins from nectarine fruits.  Phytochemistry. 1999;  52 623-629
  CrossrefPubMedGoogle Scholar
• 20 Sridhar C, Rao K V, Subbaraju G V. Flavonoids, triterpenoids and a lignan from Vitex altissima.  Phytochemistry. 2005;  66 1707-1712
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar
• 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
  PubMedGoogle Scholar
• 25 Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.  J Immunol Methods. 1983;  65 55-63
  CrossrefPubMedGoogle Scholar
• 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
  CrossrefPubMedGoogle Scholar

Prof. Bo-Yang Yu

Department of Traditional Chinese Prescription
Key Laboratory of Modern TCM
China Pharmaceutical University

Tongjia Xiang Street 24

Nanjing 210009

People's Republic of China

Phone: + 86 25 83 27 13 21

Fax: + 86 25 83 27 13 21

Email: boyangyu59@163.com

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