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Malyngamide 4, a New Lipopeptide from the Red Sea Marine Cyanobacterium

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Malyngamide 4, a New Lipopeptide from the Red Sea Marine Cyanobacterium Phytochemistry Letters 6 (2013) 183–188 Contents lists available at SciVerse ScienceDirect Phytochemistry Letters jo urnal homepage: www.elsevier.com/locate/phytol Malyngamide 4, a new lipopeptide from the Red Sea marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) a b, c d Lamiaa A. Shaala , Diaa T.A. Youssef *, Kerry L. McPhail , Mohamed Elbandy a Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Saudi Arabia b Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Saudi Arabia c Department of Pharmaceutical Sciences, College of Pharmacy, Oregon State University, Corvallis, OR 97331, United States d Clinical Nutrition Department, Applied Medical Science Faculty, Jazan University, Jazan, Saudi Arabia A R T I C L E I N F O A B S T R A C T Article history: In our continuing effort to discover new drug leads from Red Sea marine organisms, a sample of the Received 19 November 2012 marine cyanobacterium Moorea producens (previously Lyngbya majuscula) was investigated. Bioassay- Received in revised form 28 December 2012 directed purification of a tumor cell-growth inhibitory fraction of the organic extract of the Red Sea Accepted 16 January 2013 cyanobacterium afforded a new compound, malyngamide 4 (1), together with five previously reported Available online 13 February 2013 compounds, malyngamide A (2) and B (3), (S)-7-methoxytetradec-4(E)-enoic acid (lyngbic acid, 4), aplysiatoxin (5) and debromoaplysiatoxin (6). Assignment of the planar structures of these compounds Keywords: was based on extensive analysis of one- and two-dimensional NMR spectra and high-resolution mass Red Sea cyanobacterium spectrometric data. The isolated compounds were evaluated for their inhibitory activity against three Moorea producens cancer cell lines. In addition, the antibacterial activity of the compounds against Mycobacterium Malyngamides 4, A and B and lyngbic acid Aplysiatoxin and debromoaplysiatoxin tuberculosis H37Rv ATCC 27294 (H37Rv) was evaluated. Lyngbic acid (4) was the most active against M. In vitro tumor growth inhibition tuberculosis, while malyngamides 4 (1) and B (3) moderately inhibited the cancer cell lines. The other In vitro inhibition of Mycobacterium compounds were deemed inactive at the test concentrations. tuberculosis ß 2013 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved. 1. Introduction (Appleton et al., 2002; Suntornchashwej et al., 2007). It is believed that these malyngamides come either from cyanobacteria eaten by Marine cyanobacteria are a prolific source of diverse classes of the sea hares (Appleton et al., 2002; Gallimore and Scheuer, 2000; secondary metabolites (Blunt et al., 2012). Marine members of the Suntornchashwej et al., 2007) or from an association of the red alga genus Lyngbya (recently reclassified as Moorea) (Engene et al., 2012) with cyanobacteria (Kan et al., 1998). Two new compounds, continue to provide a structurally diverse array of compounds with malyngamides 2 and 3, were recently reported from the marine different bioactivities including peptides (Balunas et al., 2010; Blunt cyanobacteria Lyngbya sordida (Malloy et al., 2011) and Lyngbya et al., 2012; Gutierrez et al., 2008; Hooper et al., 1998; Nogle et al., majuscula (Gunasekera et al., 2011). 2001; Orjala and Gerwick, 1996; Taniguchi et al., 2010), macrolides Chemically, malyngamides are amide derivatives of a fatty acid (Blunt et al., 2012; Klein et al., 1997, 1999; Luesch et al., 2002; Pereira (mostly, 7-methoxytetradec–4(E)–enoic acid = lyngbic acid) with a et al., 2010; Tan et al., 2002; Teruya et al., 2009) and malyngamides variety of amine-substituted moieties. Members of the malynga- (Blunt et al., 2012; Cardellina et al., 1978, 1979; Gross et al., 2010; mide family display diverse biological activity including cancer cell Gunasekera et al., 2011; Malloy et al., 2011). cytotoxicity (Appleton et al., 2002; Gunasekera et al., 2011; Gross To date, more than 30 malyngamides have been reported with et al., 2010; Kwan et al., 2010; Malloy et al., 2011; Suntornch- the majority from field collections of members of the genus ashwej et al., 2007), anti-inflammatory (Appleton et al., 2002; Lyngbya. However, two malyngamides, M and N, have been Malloy et al., 2011), anti-malarial (Suntornchashwej et al., 2007), reported from the red alga Gracilaria coronopifolia (Kan et al., 1998). anti-tubercular (Suntornchashwej et al., 2007), ichthyotoxic In addition, malyngamides O and P were isolated from the sea hare (Orjala et al., 1995) and nitric oxide-inhibiting activity (Malloy Stylocheilus longicauda (Gallimore and Scheuer, 2000), while the et al., 2011), toxicity to crayfish (Kan et al., 2000) and inhibition of sea hare Bursatella leachii provided malyngamides X and S the MyD88-dependent pathway (Villa et al., 2010). Recently, we reported about the identification of cytotoxic cyclic depsipeptides from Red Sea field collections and laboratory cultures of a marine cyanobacterium Leptolyngbya sp. (Thornburg * Corresponding author. Tel.: +966 548535344; fax: +966 26951696. E-mail addresses: [email protected], [email protected] (Diaa T.A. Youssef). et al., 2011). In continuation of our efforts to identify drug leads 1874-3900/$ – see front matter ß 2013 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved. http://dx.doi.org/10.1016/j.phytol.2013.01.002 184 L.A. Shaala et al. / Phytochemistry Letters 6 (2013) 183–188 O 11' 10' 15 9' O N O O N O O 7' 8' O 5' 6' O O 1 1' 4' 14 N N 3' O O 13' Cl 12' Cl Malyngamide 4 (1) Malyngamide A (2) OH O N O O O N O O O Cl OH Malyngamide B (3) Lyngbic acid (4) HO HO O O O Br O O O O O O O O O O O OH OH OH OH Aplysiatoxin (5) Debromoaplysiatoxin (6) Fig. 1. Structure of Compounds 1–6. from Red Sea cyanobacteria, we have investigated the active experiments delineated an aliphatic chain consistent with a 7– fraction of a lipophilic extract of a new field collection of the methoxytetradec–4(E)-enoic acid (fragment A, Fig. 2) (Cardellina marine cyanobacterium Moorea producens (previously L. majus- et al., 1979; Kwan et al., 2010; Moore, 1981). The E configuration of cula). Bioassay-directed fractionation of the active fractions the C-4/C-5 olefin was assigned based on the large coupling resulted in isolation of a new malyngamide, malyngamide 4 (1), constant value (J4,5 = 15.5 Hz) (Kan et al., 2000). The absolute together with several previously reported compounds including configuration at C-7 in 1 was determined by comparison of the malyngamide A (2) (Cardellina et al., 1979), malyngamide B (3) optical rotation value ([a]D = À12.5) for the hydrolytic product of 1 (Cardellina et al., 1978), lyngbic acid (4) (Cardellina et al., 1978), with that for lyngbic acid (4), suggesting that both compounds aplysiatoxin (5) (Yoshinori and Scheuer, 1974) and debromoaply- have 7S configuration (Gunasekera et al., 2011; Kwan et al., 2010). siatoxin (6) (Yoshinori and Scheuer, 1974) (Fig. 1). In this paper, we The chemical shifts of the signals for the chloromethylene moiety 0 0 report the structure determination of compounds 1–6 and results (C-2 /C-3 ) flanked by two methylenes (fragment B, Fig. 2) are in of assays to test their growth inhibition of three cancer cell lines good agreement with other malyngamides containing this and Mycobacterium tuberculosis H37Rv. structural motif (Cardellina et al., 1979; Kwan et al., 2010; Moore, 1981). Furthermore, chemical shifts for isolated olefinic methine 0 0 2. Results and discussion CH-6 (d 6.87/93.7) and the HMBC-correlated amidic carbon C-7 (164.8, qC), together with chemical shifts for quaternary olefinic C- 0 0 The molecular formula of malyngamide 4 (1) was assigned as 5 (d 173.8) and HMBC-correlated methoxy H3-12 (d 3.76/56.2), + C28H43ClN2O5 from the HRFABMS peak at m/z 523.2947 [M + H] , supported the assignment of fragment C (Fig. 2) and are again in requiring eight degrees of unsaturation. The IR spectrum showed good agreement with literature values (Cardellina et al., 1979; À1 absorptions for the amidic carbonyls at 1660 and 1640 cm and Kwan et al., 2010; Moore, 1981). Finally, the assignment of the N- À1 1 13 for the C-N at 1600 cm . The H and C NMR data for 1 (Table 1) substituted pyrrol-2-one substructure (fragment D, Fig. 2) was 1 13 supported its malyngamide nature with a typical partial structure accomplished by considering HSQC-correlated H/ C chemical of the common 7-methoxytetradec–4(E)–enoic acid (lyngbic acid) shift values, and COSY and HMBC experiments. COSY correlations 0 0 (Cardellina et al., 1979; Kwan et al., 2010; Moore, 1981). Complete between H-9 (d 7.28, 1H) and H-10 (d 6.16, 1H), which in turn 1 1 0 analysis of the 2D NMR experiments including H– H COSY, HSQC couples with H2-11 (d 4.44, 2H) established a spin system that and HMBC established the spin systems within 1 and supported could be placed in a heterocyclic ring based on the presence of two- 1 the presence of four sub-structures including C-1 to C-14 and three-bond HMBC correlations from H signals for all three 0 0 0 0 13 0 (Fragment A), C-1 to C-4 (Fragment B), C-5 to C-7 (fragment C) positions to the C signal for amidic C-8 (dC 170.0, Table 1). Key 0 0 and C-8 to C-11 (fragment D) (Table 1 and Fig. 2). The assignments HMBC correlations (Table 1 and Fig. 3) established the connectivity of the spin-coupling systems and the protonated carbons within 1 of the subunits of 1 (Table 1 and Fig.
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