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Sesquiterpenes from the Marine Algicolous Fungus Drechslera Sp

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Sesquiterpenes from the Marine Algicolous Fungus Drechslera Sp Journal of Saudi Chemical Society (2013) 17, 161–165 King Saud University Journal of Saudi Chemical Society www.ksu.edu.sa www.sciencedirect.com ORIGINAL ARTICLE Sesquiterpenes from the marine algicolous fungus Drechslera sp. Ahmed Abdel-Lateff a,*, Tatsufumi Okino b, Walied M. Alarif c, Sultan S. Al-Lihaibi c a Deptartment of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, P.O. Box 80260, Jeddah 21589, Saudi Arabia b Faculty of Environmental Earth science, Hokkaido University, Sapporo 060-0810, Japan c Marine Chemistry Department, Faculty of Marine Sciences, King AbdulAziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia Received 19 January 2011; accepted 2 March 2011 Available online 16 March 2011 KEYWORDS Abstract A marine fungal isolate, identified as Drechslera sp., was mass cultivated and found to Marine microorganism; produce a new naturally occurring seco-sativene type sesquiterpene helminthosporic acid (1) and Fungi; three known sesquiterpenes, helminthosporol (2), drechslerine A (3) and (+) secolongifolene-diol Sesquiterpenes; (4). The structures of all compounds were determined by interpretation of their spectroscopic data Drechslera sp. 1D (1H and 13C), 2D (COSY, DQF, NOE, HSQC and HMBC) NMR, MS, UV and IR analyses. All compounds have been tested toward antioxidants, antimicrobial and antifouling effects. ª 2011 King Saud University. Production and hosting by Elsevier B.V. All rights reserved. 1. Introduction responsible for production of various secondary metabolites. To date, huge number of compounds have been reported from The genus Drechslera (Helminthosporium) is well known and fungi belonging to this genus, including 6-epi-ophiobolin A widely investigated because many species belonging to it are and 3-anhydro-6-epi-ophiobolin A, 6-epi-3-anhydroophiobo- lin, anhydrocochlioquinone A, 6-epi-ophiobolin, 6-epi-3-anhy- dro-ophiobolin B and eremophilane sesquiterpenes have all * Corresponding author. Tel.: +966 546477175; fax: +966 2 287 been isolated from Drechslera sp. (Shen et al., 1999; Evidente 0104. et al., 2006; Evidente et al., 2005; Osterhage et al., 2002). E-mail address: [email protected] (A. Abdel-Lateff). The main task of the current paper is the continuation of our projects, concentrated on the discovering of new natural 1319-6103 ª 2011 King Saud University. Production and hosting by product with biological activity and/or novel chemical struc- Elsevier B.V. All rights reserved. tures from marine organisms (Gamal-Eldeen et al., 2009; Neu- Peer review under responsibility of King Saud University. mann et al., 2007; Abdel-Lateff, 2008a,b; Alarif et al., 2010; doi:10.1016/j.jscs.2011.03.002 Al-lihaibi et al., 2010). The Drechslera sp. (Phylum: Ascomy- cota; Order: Pleosporales; Family: Pleosporaceae) was ob- tained from the marine green algal material, Ulva sp., Production and hosting by Elsevier (Division: Chlorophycota; Class: Ulvophyceae; Order: Ulva- les, Family Ulvaceae) collected from the To¨nning (North 162 A. Abdel-Lateff et al. Sea). It was cultivated on a semisolid biomalt medium with 2.3. Extraction and isolation added artificial sea salt. Successive fractionation of the EtOAc extract by vacuum liquid chromatography (VLC) over re- Mycelia and medium of the cultivated fungus (5 L) were di- versed phase (RP-18) silica followed by reversed phase (RP- luted with water (100 mL/L), homogenized using Ika Ultra- 18) HPLC yielded four sesquiterpenes, helminthosporic acid turrax at 8000 rpm for 2 min. The resulting mixture was (1), helminthosporol (2)(Tamura et al., 1963), drechslerine A exhaustively extracted with EtOAc (3 · 8 L) and filtered. The (3)(Osterhage et al., 2002) and (+) secolongifolene-diol (4) filtrate was evaporated under reduced pressure to yield (Dorn and Arigoni, 1974; Yadav et al., 1983). (1.1 g) highly viscous dark reddish gum. This extract (1.1 g) In the current paper, compounds 2–4 were identified by was fractionated on NP-Silica (5 · 25 cm, 50 g, Merck 7739), comparison of their spectroscopic data with published values employing gradient elution from n-hexane to EtOAc, to yield (Osterhage et al. 2002; Dorn and Arigoni, 1974; Yadav 6 fractions (F01-F06; n-hexane/EtOAc, 1:0; 8:2; 6:4; 4:6; 2:8; et al., 1983). The complete NMR data of 1 are published for 0:1, each 100 mL) (3.8, 109, 332, 133, 140 and 283 mg), respec- the first time, where compound 1 was semi-prepared syntheti- tively. 1H NMR identified fractions 2 and 3 as promising for cally by Tamura and Sakuri (1964) from the corresponding further fractionation. VLC F02 (109 mg) was fractionated on aldehyde of helminthosporol. NP-Silica (1 · 20 cm, 30 g, Merck 7739), employing gradient elution from n-hexane to EtOAc, to yield 6 fractions (F021- 2. Material and methods F026; n-hexane:EtOAc, 1:0; 98:2.0; 96:4.0; 94:6.0; 92:8.0; 90:10, each 50 mL) (10.5, 17.4, 18.3, 15.2, 20.1, 20.2 mg), 2.1. General respectively. 1H NMR identified fractions F022-F026 as prom- ising for further fractionation. F022 was purified by RP-18 UV spectra were recorded on a Hitachi 300 spectrometer. 1H HPLC (Cosmosil 5C-18 ARII, 250 · 10 mm), using gradient 13 and C NMR spectra were recorded on a JEOL-JNM-EX- elution from 40% H2O/MeCN, to MeCN to yield 1 1 13 400 spectrometer (400 MHz for H and 100 MHz for C, (tR = 12 min, 0.2 mg/L) and 2 (tR = 14 min, 0.2 mg/L). respectively). EI-MS data were obtained with a JEOL JMS- F023 purified by using RP-18 HPLC (Cosmosil 5C18 ARII, 700T mass spectrometer. HPLC was performed on semi-pre- 250 · 10 mm), using gradient elution from 30% H2O/MeCN, parative C-18 column (Cosmosil 5 C18 ARII, 250 · 10 mm) to MeCN to yield 4 and 3. with a UV detector at kmax 220 nm and a flow rate of 2.5 mL/min. Pre-coated Silica Gel 60 F254 plates (E. Merck) 2.4. Biological activities were used for TLC. The compounds were detected by UV absorption at kmax 255 and 366 nm. All solvents were obtained The antimicrobial effects were determined as described by from Merck Company. All solvents were of high grade, except Schulz et al. (1995)). Brine shrimp lethality, a,a-diphenyl-b- for HPLC that was of HPLC-grade. picrylhydrazyl (DPPH) Radical scavenging effects, antifouling assays were measured as reported by (Abdel-Lateff et al., 2003, 2.2. Isolation and taxonomy of the fungal strain 2008a,b, 2009). Antifouling assay was measured as reported by Refaat et al. (2009). Algal material, Ulva sp. (N-4), was collected by divers around the To¨nning (North Sea, 1999). After sterilization with 70% 2.4.1. Helminthosporic acid (1) ethanol algal samples were rinsed with sterile water and 22 Colorless oil; ½aD À25.0 (c 0.05, EtOH); UV (EtOH) kmax pressed onto agar plates to detect any residual fungal spores (log e) 263 (3.72); IR (film) kmax 3384, 2920, 1672, À1 on the surface of algae. Sterilized algae were then cut into 1470 cm ; HREIMS m/z 251.8967 (calcd for C15H24O3, 1 13 pieces and placed on agar plates containing isolation medium: 252.1725); H and C NMR (CDCl3), d (ppm): Table 1. 15 g/L agar, and 1 L seawater from the sample collecting site, plus antibiotics benzyl penicillin and streptomycin sulfate 2.4.2. Helminthosporol (2) (250 mg/L). Fungal colonies growing out of the algal tissue 22 Colorless oil; ½a À25.0 (c 0.08, EtOH); lit. [a]D À28.7 (c were transferred to medium for sporulation (1.0 g glucose, D 1.93, CHCl3); UV (EtOH) kmax (log e) 263 (3.72); lit. UV 0.1 g yeast extract, 0.5 g peptone from meat, enzymatic digest, (EtOH) kmax (log e) 267 (3.99); IR (film) kmax 3420, 2920, 15 g of agar, and 1 L artificial sea water, pH 8) in order to en- 1650, 1470 cmÀ1; EIMS m/z 236 [M+] (72), 218 (38), 205 able taxonomy of the isolates. Fungal strain (N4–6) was iden- (34), 189 (26), 175 (24), 154 (30), 147 (34), 133 (46), 123 tified by Dr. S. Draeger (Institute for Microbiology, Technical (65), 107 (86), 91(100); HREIMS m/z 236.1770 (calcd for University of Braunschweig). 13 C15H24O2, 236.1770); C NMR (CDCl3), d (ppm): 137.0 (s, C-1), 166.0 (s, C-2), 50.8 (s, C-3), 34.3 (t, C-4), 25.3 2.2.1. Cultivation (t, C5), 44.8 (d, C-6), 41.3 (d, C-7), 18.5 (q, C-8), 31.8 Drechslera sp. was cultivated on 5 L of semisolid media, com- (d, C-9), 21.8 (q, C-10), 20.8 (q, C-11), 10.8 (q, C-12), 61.3 posed of biomalt (5 g/L) [Biomalt, Villa Natura Ges- (d, C-13), 62.3 (t, C-14), 188.0 (d, C-15) and 1H NMR undheitsprodukte GmbH, Germany], and artificial seawater (CDCl3): d 1.41 (m, 2H-4), 1.75 (m, H-5a), 0.88 (m, H-5b), contained the following salts (g/L): KBr (0.1), NaCl (23.48), 0.99 (m, H-6), 3.19 (br s, H-7), 1.04 (m, 3H-8), 0.99 (br s, MgCl2Æ6H2O (10.61), CaCl2Æ6H2O (1.47), KCl (0.66), SrCl2Æ6 H-9), 1.08 (d, J = 5.4 Hz, 3H-10), 0.77 (d, J = 5.4 Hz, 3H- H2O (0.04), Na2SO4 (3.92), NaHCO3 (0.19), H3BO3 (0.03), 11), 2.02 (br s, 3H-12), 1.68 (dd, J = 8.7, 5.4 Hz, H-13), for two months, at room temperature with shaking (35 rpm).
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