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Phytol and Glycerol Derivatives from the Marine Green Alga Codium

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Phytol and Glycerol Derivatives from the Marine Green Alga Codium Phytol and Glycerol Derivatives from the Marine Green Alga Codium iyengarii of the Karachi Coast (Arabian Sea) Muhammad Shaiq Ali*, Muhammad Saleem, Viqar Uddin Ahmad and Simin Shameel H. E. J. Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan * Reprint requests to Dr. M. S. Ali. E-mail: [email protected] Z. Naturforsch. 56b, 837-841 (2001); received March 3, 2001 Codium iyengarii , Chlorophyceae, Codiosides The ethyl acetate soluble part of a methanolic extract of the marine green alga Codium iyengarii, collected from the Karachi coast of the Arabian Sea, afforded four new derivatives of glycerol named : codioside A,B,C,D (1-4), a new derivative of frans-phytol named codio- ester (5) and rrans-phytol (6). The structures of 1-5 were elucidated with the aid of acid hydrolysis, methylation, GC-MS, and spectroscopy. The structure of 1 was confirmed through the HMBC NMR technique and the structures of compounds 2 -4 were based on the assign­ ments made for 1. Introduction H- jC?—R* A number of fatty acids (saturated and unsatu­ rated), sterols, terpenoids, and sugars of various classes have been already detected from seaweeds [1-2]. A wide range of these marine natural pro­ ducts showed biological activities [3]. The mem­ bers of the genus Codium are known for their anti­ cancer activity [4]. Rl R2 R3 The marine alga Codium iyengarii ia a member of Chlorophyceae (green algae) found in bulk Codioside A 1 palmitate" OH H around Karachi and adjacent coastal areas of the Codioside B 2 oleate" OH H Arabian Sea. The results of a previous study pub­ Codioside C 3 oleate/palmitate" palrrdtate/oleate" " gals lished by Usmanghani and Shameel showed that Codioside D 4 palmitate" palmitate'" H water extract of C. iyengarii is capable to inhibit the growth of gram-positive bacteria [5]. The pre­ Fig. 1. Palmitic acid: CH 3(CH2)i4COOH; oleic acid: sent paper describes the results of an attempt CH3(CH2)7CH=CH(CH2)7COOH. made to investigate the chemical constituents of C. iyengarii. As a result of this study, five new com­ enough to allow some chemical reactions and pounds were isolated and characterized. They in- therefore, their structures were elucidated with the clulde: four glyco-fatty acid derivatives of glycerol aid of a combination of chemical reaction as well (1-4, codioside A to D) and a fatty acid derivative as physical data including the HMBC NMR tech­ of mms-phytol (5, codio-ester). nique together with the comparison of literature values. As the skeleta of 1 -4 are rather similar Results and Discussion they are discussed here together. The fatty acids The methanol soluble part of C. iyengarii af­ attached to the glycerol (1-4) and rrans-phytol (5) forded four new glycoglycerides named codiosides were identified by treating 1 -5 with sodium meth- A -D (1-4) (Fig. 1) and a new fatty ester of trans- oxide and the resulting methyl esters of fatty acids phytol named codioester (5). The quantities of iso­ were analyzed by GC-MS using known reference lated constituents 1 -5 (average 20 mg) were compounds. Similarly, after the detachment of the 0932-0776/2001/0800-0837 $ 06.00 © 2001 Verlag der Zeitschrift für Naturforschung, Tübingen • www.znaturforsch.com D Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung This work has been digitalized and published in 2013 by Verlag Zeitschrift in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der für Naturforschung in cooperation with the Max Planck Society for the Wissenschaften e.V. digitalisiert und unter folgender Lizenz veröffentlicht: Advancement of Science under a Creative Commons Attribution Creative Commons Namensnennung 4.0 Lizenz. 4.0 International License. 838 M. S. Ali et al. • Phytol and Glycerol Derivatives from Marine Green Alga Codium ivengarii J ff NaOMe ff H2C — O j-C — CH2— (CH2)13 CH3 --------------- ► MeO— C— CH2— (CH2) i3 CT13 H2C — OH OC-MS with Standard fatty acid methyl «ster Hj:— OH H2 C .OH *+ O— C OH Scheme 1. fatty moieties, the sugar units in 1 -4 were iden­ tified by acid hydrolysis to liberate the free glyco- units and then they were compared by TLC with the authentic sugar samples. The whole methodol­ ogy is explained for 1 in Scheme 1. Palmitic acid occurs very commonly in the green seaweed of the Karachi coast and is usually found in largest proportion, whereas oleic acid is the OH most commonly occurring unsaturated fatty acid Fig. 2. Selective HMBC connectivities in 1. [6 ]. Various phycochemical studies revealed that the main algal fatty acids are either saturated or ds-unsaturated with a 1 2 - 2 0 carbon chain and up sible to study the HMBC spectrum and establish to six double bonds [7]. Most of the fatty acids the structure of 1. However, the 13C NMR spectra are found as complex esters in marine algae or helped to establish the structures of 1-4. Based terrestrial plants. Glycerol can accommodate 1-3 on the information obtained from the HMBC molecules of fatty acids producing mono- to tri­ spectrum of 1, the structures of 2 -4 could easily glycerides. be established. The structures of 1 -4 were elucidated further The *H NMR spectrum of 1 displayed the anom­ by positive FAB-MS and NMR spectroscopy. The eric proton at <5 = 4.12 as a doublet (J = 7.5 Hz) positive FAB mass spectra of 1 -4 and their corre­ which showed HMBC interactions (Fig. 2) with sponding high resolution spectra gave the formu­ the methylene at d = 67.6 which in turn showed lae C2 5 H 4 9 O 9 , C2 7 H 5 1 O 9 , C4 9 H 5 1 O 1 5 and interactions with the anomeric carbon at d = 103.7. C4 1 H 7 9 O10, respectively. The IR spectra of all four Two more significant triplets resonating at (3 = 2.19 glycerides showed the absorptions of ester car­ (2 H, J = 7.1 Hz) and 0.81 (3H,/ = 7.0 Hz) were bonyl and hydroxyl function. Compound 3 attributed to 2"-H and 16"-H. A signal of two pro­ showed in addition an olefinic absorption at 1605 tons appeared at <5 = 4.32 as a doublet (/ = 6.2 Hz) cm-1. Most of the oxygenated methines and and was assigned to 1-H. The downfield chemical methylenes appeared in the XH NMR spectra as shift of this methylene group revealed that an het­ complex multiplets. Only anomeric and olefinic eroatom was attached to it which was proved methines, ester substituted methylenes, and through HMBC experiments (Fig. 2). Other oxy­ methyl signals could be detected in the XH NMR genated methines and methylenes were found to spectra. In addition, the methylene protons resonate at d = 3.80-3.22 as complex multiplets. (C3 H2) in 1 could also be traced in the spectrum The downfield carbon signals at (5 = 103.7 and by means of a selective decoupling experiment at 173.8 were assigned to anomeric and ester car­ d = 3.17 as a broad doublet and thus it was pos- bonyl carbons, respectively. The confirmation of M. S. Ali et al. ■ Phytol and Glycerol Derivatives from Marine Green Alga Codium ivengarii 839 palmitic acid [ 8 ] and glucose was performed as de­ An acyclic diterpenoidal fatty ester was also ob­ scribed in the experimental section and in tained from the same source and assigned as 5. The Scheme 1. Finally, the structure of 1 was elucidated molecular formula was depicted through HRMS as as 1-palmitate 3-gluco propanetriol and named C3 6 H 7 o 0 2 showing the presence of two double codioside A. bonds in the molecule. IR absorptions were found The *H NMR spectrum of 2 was highly similar to at 1725 (ester, C = 0) and 1610 cm “ 1 (C=C). The XH/ that of 1 except the presence of two olefinic signals 13C NMR signals and mass fragmentation pattern as doublet of triplets at <3 = 5.16 (J = 5.5,1.6 Hz) and provided strong evidence for the presence of a phy­ 5.04 (J = 5.6, 1.6 Hz) and their corresponding car­ tol type skeleton [11], A comparison of XH and 13C bons resonated in the 13C NMR spectrum at d - data of 5 with the data of cis- and rrans-phytols re­ 129.4 and 129.6 and were assigned to C-9" and C- vealed that 5 was the ester of fraws-phytol [12-13]. 10", respectively. The GC-MS experiments with 2 In case of fram-phytol, the oxygenated methylene indicated the presence of oleic acid [9-10] and thus group (1-H) appears at <5 = 4.1, whereas in c/s-phy- 2 was characterized as 1-oleate 3-gluco propanet­ tol it shifts downfield by 0.3-0.4ppm. Moreover, riol and named codioside B. the literature shows that in ?ram,-phytol, oxy-meth- The *H NMR spectrum of 3, which showed two ylenic carbon (C-l) appears at d - 59.4 and olefinic triplets at d = 2.19 (/ = 7.0 Hz) for four protons and carbons at <5 = 123.1(C-2) and 140.0 (C-3), [13] at (5 0.82 (J - 6 . 8 Hz) for six protons, suggested two whereas in the c/s-isomer they appear at (3 = 61.9, fatty acid units in the molecule. This was further 118.2 and 142.5, respectively [11]. The palmitate supported by the 13C NMR spectrum which dis­ moiety was confirmed through the GC-MS tech­ played two carbonyl resonances at <5 = 173.7 and nique.
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