This Issue is Dedicated to the Memory of Professor Ivano Morelli

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1100 Natural Product Communications Vol. 1 (12) 2006 Mavar-Manga et al. [2] Bouquet A, Debray M. (1974) Plantes Médicinales de la Côte d'Ivoire. Travaux et Documents de l'O.R.S.T.O.M. Vol. 32. Paris: O.R.S.T.O.M. 232. [3] Kerharo J, Adam JG. (1974) La Pharmacopée Sénégalaise Traditionnelle: Plantes Médicinales et Toxiques. Paris: Vigots Frères. 1011. [4] Akedengué B. (1992) Medicinal plants used by the Fang traditional healers in Equatorial Guinea. Journal of Ethnopharmacology, 37, 165-173. [5] Neuwinger HD. (2000) African Traditional Medicine: A Dictionary of Plant Use and Applications. Stuttgart: Medpharm, Scientific Publishers. 589. [6] Alves AC, Prista LN. (1962) Gentisic acid as a possible precursor in the biosynthesis of yohimbine. Anais da Faculdade de Farmacia do Porto, 22, 27-33. [7] Muanza DN, Euler KL, Williams L, Newman DJ. (1995) Screening for antitumor and anti-HIV activities of nine medicinal plants from Zaire. International Journal of Pharmacognosy, 33, 98-106. [8] Lamikanra A, Ogundaini AO, Ogungbamila FO. (1990) Antibacterial constituents of Alchornea cordifolia leaves. Phytotherapy Research, 4, 198-200. [9] Ogungbamila FO, Samuelsson G. (1990) Smooth-Muscle Relaxing Flavonoids from Alchornea cordifolia. Acta Pharmaceutica Nordica, 2, 421-422. [10] Hart NK, Johns SR, Lamberton JA, Willing RI. (1970) Alkaloids of Alchornea javanensis: the isolation of hexahydroimidazo [1,2-α] pyrimidines and guanidines. Australian Journal of Chemistry, 23, 1679-1693. [11] Bolzani VDS, Gunatilaka AAL, Kingston DGI. (1995) Bioactive guanidine alkaloids from Pterogyne nitens. Journal of Natural Products, 58, 1683-1688. [12] Conegero LD, Ide RM, Nazari AS, Sarragiotto MH, Dias BP, Nakamura CV, de Carvalho JE, Foglio MA. (2003) Chemical contituents of Alchornea glandulosa (Euphorbiaceae). Quimica Nova, 26, 825-827. [13] Hart NK, Johns SR, Lamberton JA. (1969) Hexahydroimidazopyrimidines, a new class of alkaloids from Alchornea javanensis. 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[19] Delle Monache G, Volpe AR, Delle Monache F, Vitali A, Botta B, Espinal R, De Bonnevaux SC, De Luca C, Botta M, Corelli F, Carmignani M. (1999) Novel hypotensive agents from Verbesina caracasana. 7. Further hypotensive metabolites from Verbesina caracasana. Bioorganic & Medicinal Chemistry Letters, 9, 3249-3254. [20] Honma K, Tsuda M, Mikami Y, Kobayashi J. (1995) Aplysillamides A and B, new antimicrobial guanidine alkaloids from the Okinawan marine sponge Psammaplysilla purea. Tetrahedron, 51, 3745-3748. [21] Ebi GC. (2001) Antimicrobial activities of Alchornea cordifolia. Fitoterapia, 72, 69-72. [22] Tona L, Kambu K, Mesia K, Cimanga K, Apers S, De Bruyne T, Pieters L, Totte J, Vlietinck AJ. (1999) Biological screening of traditional preparations from some medicinal plants used as antidiarrhoeal in Kinshasa, Congo. Phytomedicine, 6, 59-66. [23] Mosmann T. (1983) Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. 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NPC Natural Product Communications Indole Monoterpenes with Antichemotactic Activity from Psychotria myriantha: Chemotaxonomic Significance 2006 Vol. 1 No. 12 1101- 1106 Cláudia A. Simões-Pires a , Fabianne M. Farias b , Andrew Marston a , Emerson F. Queiroz a , Célia G. Chaves b , Amélia T. Henriques b and Kurt Hostettmann a* a Laboratoire de Pharmacognosie et Phytochimie, École de Pharmacie Genève-Lausanne, Université de Genève, Université de Lausanne, CH-1211 Genève 4, Switzerland b Programa de Pós-graduação em Ciências Farmacêuticas, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS, Brazil kurt.hostettmann@pharm.unige.ch Received: June 6 th , 2006; Accepted: August 8 th , 2006 Dedicated to the memory of Professor Ivano Morelli. The alkaloid extract of the aerial parts of Psychotria myriantha (Rubiaceae) displayed antichemotactic activity on polymorphonuclear leukocytes (PMN) assessed by the Boyden chamber assay. On analysis of the crude extract by LC/APCI/MS and LC/UV/DAD, two major constituents could be detected. In order to rapidly identify the active compounds, a microfractionation was conducted during LC/UV/DAD analysis. By this means, both the collected compounds could be assayed separately in the Boyden chamber and were shown to inhibit PMN chemotaxis. Their isolation was performed by semi-preparative HPLC and their structures elucidated by classical spectroscopic methods, including UV, NMR, MS and HRMS. Both compounds showed characteristics of monoterpene indole glucoside alkaloids; one of them was identified as strictosidinic acid and the other was a new natural product, myrianthosine. The antichemotactic activity of the compounds may be related to an antiacute inflammation activity. Keywords: Psychotria myriantha, Rubiaceae, antichemotactic activity, glucoside indole monoterpene alkaloids, myrianthosine, strictosidinic acid. Psychotria myriantha Mull. Arg. is a shrub (up to 2 meters high) occurring in southern Brazil [1]. Up to now, no phytochemical work has been reported on the species. As part of our continuing work on the Rubiaceae [2-5], the alkaloid extract from P. myriantha was tested for antichemotactic activity. From this extract, two active indole monoterpene alkaloid glucosides were isolated. A polar alkaloid-rich extract of P. myriantha aerial parts was prepared as described in the experimental section. In order to identify the constituents, the alkaloid extract was analyzed by LC/UV/MS, with an atmospheric pressure chemical ionization (APCI) interface. Compound 1 gave an ion at m/z 517.1 [M+H] + , while compound 2 gave a molecular ion at m/z 531.0 [M+H] + (Figure 1). The UV spectrum of compound 1 showed absorptions of an indole chromophore (226 and 280 nm), while compound 2 showed three absorptions due to an extended chromophore at 240 (sh), 290 and 350 nm (Figure 1) [4]. LC microfractionation was performed on the extract and the inhibition of polymorphonuclear leukocyte (PMN) chemotaxis by an antichemotactic assay in a modified Boyden chamber was assessed in collected fractions. By this means, inhibition properties could be rapidly linked to two of the LC peaks at retention times of 11.0 and 12.5 min. The migration (μm) of PMN control cells and PMN treated with P. myriantha extract, 1 and 2 are shown in Table 1 as mean ± S.D. For full structure determination, 1 and 2 (Figure 2) were isolated by semi-preparative HPLC. Compound
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