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The Chemical Investigations of the Mangrove Plant Avicennia Marina

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The Chemical Investigations of the Mangrove Plant Avicennia Marina 24 The Open Natural Products Journal, 2009, 2, 24-32 Open Access The Chemical Investigations of the Mangrove Plant Avicennia marina and its Endophytes Feng Zhu*,1, Xin Chen1, Yihua Yuan1, Meizhen Huang1, Huili Sun2 and Wenzhou Xiang2 1Department of Chemistry & Chemical Engineering, Foshan Universtiy, Foshan 528000, P. R. China and 2LMB, LAMB and LMM, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, P. R. China Abstract: A diverse array of bioactive compounds have been isolated and characterized from the mangrove plant Avicen- nia marina and its endophytes. Extensive chemical investigations of the different parts (barks, leaves, twigs, etc.) of the mangrove plant A. marina and its endophytes (mainly endophytic fungi) resulted in the reporting of the isolation of 123 compounds, and most of them are new or novel compounds. Most of compounds produced by the endophytes were differ- ent from the chemical components of the host A. marina, but it can still be found that some metabolites of the endophytes and some chemical components of the host possess the same structure unit. It suggested that there exist some biogenetic relationships between the endophytes and its host. Their biological activities, structural and stereochemical assignments are reported. Keywords: Avicennia marina, mangrove, chemical component, endophyte, metabolite. INTRODUCTION Recently, Han et al. [11] reported that the twigs of A. marina growing at Xiamen, P. R. China yielded two new Recently, it was found that the mangrove plants and its abietane diterpenoids, a pair of inseparable epimers 6H- endophytes can produce lots of significant natural structures 11,12,16-trihydroxy-6,7-secoabieta-8,11,13-triene-6,7-dial [1]. As a pioneer tree species of mangrove forest ecosystems, 11,6-hemiacetal (6) and 6H-11,12,16-trihydroxy-6,7- Avicennia marina belonging to the family Verbenaceae, is a secoabieta-8,11,13-triene-6,7-dial 11,6-hemiacetal (7), as cosmopolitan species widely distributed along tropical and well as 6,11,12,16-tetrahydroxy-5,8,11,13-abitetetraen-7-one subtropical coastlines. The barks, leaves, and fruits of this (8). Compounds 6-8 showed moderate cytotoxic and antimi- species have been used as traditional medicine in Egypt to crobial activities. treat skin diseases [2]. A. marina contains abundant chemical components. Since Bell et al. [3] reported the bark of A. ma- Naphthalene Derivatives rina contains triterpenoids (betulic acid 0.3%, taraxerol Sutton et al. [12] reported that infection of wound tissue 0.06% and taraxerone 0.05%), and traces of hydrocarbon, of A. marina seedlings by a fungus belonging to the genus lots of chemical components were isolated from the different Phytophthora induced the production of three chemically- parts of A. marina by natural chemists, especially it was related naphthofuranone phytoalexins. One was identified as found that lots of significant metabolites can be produced by its endophytes recently, which laid foundation for the exploi- naphtha[1,2-b]furan-4,5-dione (9), and the other two tenta- tively as 3-hydroxy-naphtha[1,2-b]furan- 4,5-dione (10) and tation of A. marina. Here, the chemical components isolated 2-[2-(2-hydroxy)propyl]-naphtha[1,2-b]furan-4,5-dione (11). from the plant and the metabolites produced by its endo- These components present in the extract of the inoculated phytes were reviewed. tissue were found to be inhibitory to the growth of Phyto- CHEMICAL INVESTIGATIONS OF AVICENNIA MA- phthrora sp. in vitro bioassay, and accounted for nearly all of RINA the activity of the extract. Terpenoids and Steroids From the leaves of A. marina collected in Beihai, Guangxi province, Jia et al. [9] also isolated two naphtho- Many terpenoids and steroids exist in the barks [3], quinone derivatives identified as avicequinone B (12) and leaves [4-6], flowers [7], fruits [8] of A. marina were identi- avicequinone C (13). In 2007, Han et al. [13] reported seven fied by HPLC, GC or GC-MS technique. Jia et al. [9] re- unusual naphthoquinone derivatives were isolated from the ported the isolation of lupeol (1), betulin (2), -sitosterol (3) twigs of A. marina collected in Xiamen province, namely, and ergost-6,22-diene-5,8-epidioxy-3-ol (4), from the avicennone A-G (14-20), along with the known compounds leaves of A. marina collected in Beihai, Guangxi province, avicequinone A (21), stenocarproquinone B (22), avicequi- P. R. China. From the leaves collected in Hainan province, none C (13), avicenol A (23), and avicenol C (24). Com- Feng et al. [10] also isolated lupeol and betulin, and another pounds 13, 21, 22 and a mixture of 17 and 18, which contain terpenoid, betutinic acid (5). a 4,9-dione group, showed strong antiproliferative and mod- erate cytotoxic activities, as well as antibacterial effects. The *Address correspondence to this author at the Department of Chemistry & new ligan, (7S, 8R)-4,4,9-trihydroxy-3,3,5,5- tetrameth- Chemical Engineering, Foshan University, Foshan 528000, P. R. China; oxy-7,8-dehydro-9-al-2,7-cycloligan (25), together with the E-mail: [email protected] 1874-8481/09 2009 Bentham Open The Chemical Investigations of the Mangrove Plant Avicennia marina The Open Natural Products Journal, 2009, Volume 2 25 CH2 Et Me Me H Me Me Me Me Me Me H R Me H H Me H H H Me O HH H HO O H 1 R = -Me Me Me HO 3 HO 4 2 R = -CH2OH 5 R = -COOH Me OH Me OHC HO CHO OH Me Me OH 6 O 6 6R O H OH 7 6S Me Me OH Me Me 8 Fig. (1). Terpenoids and steroids from Avicennia marina. R O O R1 OMe R1 R R O R2 O OH O O O 12 R1 = R2 = R = H O OMe 9 R = H, R1 = OH 13 R1 = R2 = H, R = -C(CH3)2OH 10 R = H, R = H 17 R1 = OH, R2 = R = H 1 14 R = H 18 R = R = H, R = OH 11 R = -C(CH3)2OH, R1 = H 1 2 15 R = OH O R O O R OH O O OH H O OH OH O 19 R = H 21 R = OH 16 20 R = OH 22 R = H OH OH OMe OMe R MeO MeO OMe OH OMe OMe O OH OH HO HO OMe HO 23 R = OH OHC OMe OMe 24 R = H 25 26 Fig. (2). Naphthalene derivatives from Avicennia marina. known compound, lyoniresinol (26), were also isolated by and found it showed moderate cytotoxity against BT-20 hu- Han et al. [11] from the twigs. man carcinoma cells with ED50 of 18 μg/mL. Flavones Jia et al. [9] also obtained three flavones from the leaves, and identified them as 5-hydroxy-4, 7-dimethoxyflavone Sharaf et al. [14] isolated a flavone, luteolin 7-O- (28), quercetin (29) and kaempferol (30). Four known methylether (27), from A. marina aerial parts collected from flavones including 4,5-dihydroxy-3,7-dimethoxyflavone Abu-Ramad, 500 km south of Hurghada (Red Sea shore), (31), 4,5-dihydroxy-3,5,7-trimethoxyflavone (32), 4,5,7- 26 The Open Natural Products Journal, 2009, Volume 2 Zhu et al. trihydroxyflavone (33), and 3,4,5-trihydroxy-7- Sun et al. [19] reported that the isolation and characterization methoxyflavone (namely 27) were isolated by Feng et al. of five new iridoid glucosides, marinoids A - E ( 48 - 52 ), [15] from the aerial parts of A. marina collected in Hainan along with the known iridoid glucosides 36, 46 and 47 from island of South China Sea. The scavenging activity of them the leaves of A. marina collected in the coast of Xiamen, was evaluated using the ,-diphenyl--picrylhydrazyl Southern China. They pointed out that the iridoid glucosides (DPPH) radical-scavenging assay. Compounds 31 and 32 in the leaves of plant A. marina may play a role for chemical showed only weak activities, while compounds 33 and 27 defense against ecological invasion. showed moderate activities, with IC50 of 52.0 and 37.0 COOR1 μg/mL, respectively. Another flavone, 5,7-dihydroxy- H 3,4,5-trimethoxyflavone (34), was also isolated by them [10] later. O R 3 H HO R2 O OR2 OO R 4 OH HO OH R 35 R1 = R2 = H 1 R5 37 R1 = Me, R2 = H OH O 40 R1 = Me, R2 = (2E,4E)-5-phenyl-2,4-pentadienoyl 42 R1 = H, R2 = (E)-cinnamoyl 27 R1 = R5 = H, R2 = OMe, R3 = R4 = OH 43 R1 = H, R2 = (E)-p-coumaroyl 28 R1 = R3 = R5 = H, R2 = R4 = OMe 44 R1 = H, R2 = (E)-caffeoyl 29 R1 = R2 = R3 = R4 = OH, R5 = H 51 R1 = H, R2 = 4-hydroxy-3,5-dimethoxybenzoyl 30 R1 = R2 = R4 =OH, R3 = R5 = H 52 R1 = H, R2 = 3(R)-hydroxy-5-phenyl-4(E)-pentenoyl 31 R1 = R5 = H, R2 = R3 = OMe, R4 = OH COOR1 32 R1 = H, R2 = R3 = R5 = OMe, R4 = OH H 33 R1 = R3 = R5 = H, R2 = R4 = OH 34 R1 = H, R2 = OH, R3 = R4 = R5 = OMe R2 O Fig. (3). Flavones from Avicennia marina. R3 H HO Me O 10 O OH Glucosides OH R4O 1. Iridoid Glucosides 36 R1 = R2 = H, R3 = OH, R4= (E)-cinnamoyl, Me-10alpha It has been reported that there is no general agreement on 38 R1 = Me, R2 = R4 = H, R3 = OH, Me-10alpha the taxonomy of the mangrove plant genus Avicennia. The 39 R1 = Me, R2 = H, R3 = OH, R4 = (E)-cinnamoyl, Me-10alpha genus is considered either as a member of the family Ver- 41 R1 = Me, R3 = R4 = H, R2 = (2E,4E)-5-phenyl-2,4-pentadienoyl, Me-10alpha 45 R = R = H, R = OH, R = (2E,4E)-5-phenyl-2,4-pentadienoyl, Me-10alpha benaceae or the family Avicenniaceae.
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