This Issue is Dedicated to the Memory of Professor Ivano Morelli

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1106 Natural Product Communications Vol. 1 (12) 2006 Simões-Pires et al. [14] Libot F, Miet C, Kunesch N, Poisson JE, Pusset J, Sevenet T. (1987) Plants of New-Caledonia. 110. Rubiaceae of Oceania - Alkaloids from Psychotria oleoides of New-Caledonia and from Calycodendron-Milnei of Vanuatu (New-Hebrides). Journal of Natural Products, 50, 468-473. [15] Roth A, Kuballa B, Cabalion P, Anton R. (1985) Preliminary study of the alkaloids of Psychotria forsteriana. Planta Medica, 5, 289-289. [16] Solis PN, Ravelo AG, Palenzuela JA, Gupta MP, Gonzalez A, Phillipson JD. (1997) Quinoline alkaloids from Psychotria glomerulata. Phytochemistry, 44, 963-969. [17] Achenbach H, Lottes M, Waibel R, Karikas GA, Correa MD, Gupta MP. (1995) Constituents of tropical medicinal plants. 66. Alkaloids and other compounds from Psychotria correae. Phytochemistry, 38, 1537-1545. [18] Lopes S, Von Poser GL, Kerber VA, Farias FM, Konrath EL, Moreno P, Sobral ME, Zuanazzi JAS, Henriques AT. (2004) Taxonomic significance of alkaloids and iridoid glucosides in the tribe Psychotrieae (Rubiaceae). Biochemical Systematics and Ecology, 32, 1187-1195. [19] Solis PN, Wright CW, Gupta MP, Phillipson JD. (1993) Alkaloids from Cephaelis dichroa. Phytochemistry, 33, 1117-1119. [20] Uesato S, Matsuda S, Inouye H. (1984) Mechanism for iridane skeleton formation from acyclic monoterpenes in the biosynthesis of secologanin and vindoline in Catharanthus roseus and Lonicera morrowii. Chemical & Pharmaceutical Bulletin, 32, 1671-1674. [21] Reanmongkol W, Subhadhirasakul S, Kongsang J, Tanchong M, Kitti J. (2000) Analgesic and antipyretic activities of n-butanol alkaloids extracted from the stem bark of Hunteria zeylanica and its major constituent, strictosidinic acid, in mice. Pharmaceutical Biology, 38, 68-73. [22] Turner RA, Johnson JA, Semble EL. (1983) Anti-rheumatic drug effects on neutrophil response to chemotactic factors - A comparison of analytical techniques. Proceedings of the Society for Experimental Biology and Medicine, 173, 200-204. [23] Both FL, Misturini J, Henriques AT, Elisabetsky E. (2002) Avaliação da atividade analgésica de extratos alcaloídicos de espécies de Psychotria. Revista Brasileira de Plantas Medicinais, 5, 41-45. [24] Zigmond SH, Hirsch JG. (1973) Leukocyte locomotion and chemotaxis - New methods for evaluation and demonstration of a cell-derived chemotactic factor. Journal of Experimental Medicine, 137, 387-410.
NPC Natural Product Communications HPLC Based Activity Profiling for Inhibitors of Human Neutrophil Elastase in Isatis tinctoria Leaf Extracts 2006 Vol. 1 No. 12 1107 - 1110 Matthias Hamburger a,b , Georg-Ulrich Rüster b and Matthias F. Melzig c a Institute of Pharmaceutical Biology, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland b Institute of Pharmacy, University of Jena, Semmelweisstrasse 10, D-07743 Jena, Germany c Institute of Pharmacy, Free University Berlin, Königin-Luise-Stasse 2 u. 4, D-14195 Berlin, Germany matthias.hamburger@unibas.ch Received: June 7 th , 2006; Accepted: August 5 th , 2006 Dedicated to the memory of Professor Ivano Morelli. In continuation of our search for anti-inflammatory constituents in lipophilic extracts of Isatis tinctoria, an HPLC-based profiling for inhibitors of human neutrophil elastase was performed. Using a linear gradient profile, fractions with significant activity (>50%) appeared in the second half of the chromatogram and corresponded to moderately to highly lipophilic constituents. The active fractions of intermediate polarity were further analyzed by HPLC, TLC and GC. They contained mainly α-linolenic, linoleic, cis-11-octadecenoic acid, oleic and palmitic acids. Keywords: Isatis tinctoria, anti-inflammatory, human neutrophil elastase, α-linolenic acid, linoleic acid, activity profiling. The woad plant (Isatis tinctoria L, Brassicaceae) is an old indigo dye and medicinal plant of temperate climate zones. The plant was used for the treatment of wounds, ulcers, snakebites, and various inflammatory afflictions, but fell into oblivion with the disappearance of woad cultivation [1]. In contrast, the related I. indigotica is a widely used plant in traditional Chinese Medicine up to now [2, 3]. Our interest in woad was spurred by its purported anti-inflammatory properties for which we obtained first, in vitro evidence in a broad-based pharmacological screening involving more than 20 clinically relevant targets [4]. Subsequently, we identified the alkaloid tryptanthrin as a potent inhibitor of COX-2 and 5-LOX catalyzed eicosanoid synthesis [5, 6], and an indolin-2-one derivative as inhibitor of histamine release from mast cells [7]. We found that the major inhibitor of 5-LOX in woad extracts was γ-linoleic acid [8]. Further anti-inflammatory activities of Isatis constituents have been reported by other groups, for example, inhibition of the expression of inducible NO synthase [9] by tryptanthrin, and inhibition of IL-6 release and TNFα by indirubin [10]. Lipophilic Isatis extracts displayed activity in various in vivo models of inflammation, cutaneous allergy and arthritis [11, 12]. In a clinical pilot study, the same extracts reduced inflammation and water loss in a cutaneous irritation model [13]. A significant inhibition of leucocytic elastase from neutrophils had been observed in our initial in vitro screening [4]. This enzyme is one of two main proteinases of neutrophils released in connection with inflammation. It cleaves fibrous elastin, collagens, cartilage proteoglycans, and other matrix proteins. Elevated plasma levels of neutrophil elastase are a characteristic feature of an active inflammation [14, 15]. We, therefore, decided to identify the inhibitors of human neutrophil elastase in woad extracts with the aid of HPLC-based activity profiling using an established bioassay [16]. We had previously used the approach of HPLC profiling for
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