Abstract
A chemical investigation of the ethyl acetate extract of the fermentation broth of Alternaria tenuissima EN-192, an endophytic fungus obtained from the stems of the marine mangrove plant Rhizophora stylosa, resulted in the isolation of nine known secondary metabolites, including four indole-diterpenoids: penijanthine A (1), paspaline (2), paspalinine (3), and penitrem A (4); three tricycloalternarene derivatives: tricycloalternarene 3a (5), tricycloalternarene 1b (6), and tricycloalternarene 2b (7); and two alternariol congeners: djalonensone (8) and alternariol (9). The chemical structures of these metabolites were characterized through a combination of detailed spectroscopic analyses and their comparison with reports from the literature. The inhibitory activities of each isolated compound against four bacteria were evaluated and compounds 5 and 8 displayed moderate activity against the aquaculture pathogenic bacterium Vibrio anguillarum, with inhibition zone diameters of 8 and 9 mm, respectively, at 100 μg/disk. To the best of our knowledge, this is the first report on the secondary metabolites of mangrove-derived A lternaria tenuissima and also the first report of the isolation of indole-diterpenoids from fungal genus A lternaria.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Al-Burtamani S K, Fatope M O, Marwah R G, Onifade A K, Al-Saidi S H. 2005. Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. Journal of Ethnopharmacology, 96(1–2): 107–112.
Aly A H, Edrada-Ebel R, Indriani I D, Wray V, Muller W E G, Totzke F, Zirrgiebel U, Schachtele C, Kubbutat M H G, Lin W H, Proksch P, Ebel R. 2008. Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. Journal of Natural Products, 71(6): 972–980.
Colwell R R, Grimes D J. 1984. Vibrio diseases of marine fish populations. Helgoland Marine Research, 37(1–4): 265–287.
Cui C M, Li X M, Li C S, Proksch P, Wang B G. 2010a. Cytoglobosins A-G, cytochalasans from a marine-derived endophytic fungus, Chaetomium globosum QEN-14. Journal of Natural Products, 73(4): 729–733.
Cui C M, Li X M, Meng L, Li C S, Huang C G, Wang B G. 2010b. 7-Nor-ergosterolide, a pentalactone-containing norsteroid and related steroids from the marine-derived endophytic Aspergillus ochraceus EN-31. Journal of Natural Products, 73(11): 1 780–1 784.
de Jesus A E, Gorst-Allman C P, Steyn P S, van Heerden F R, Vleggaar R, Wessels P L, Hull W E. 1983. Tremorgenic mycotoxins from Penicillium crustosum. Biosynthesis of penitrem A. Journal of the Chemical Society, Perkin Transactions 1: 1 863–1 868.
Demircan D, Candan A. 2006. Identification of Vibrio anguillarum by PCR (rpo N gene) associated with vibriosis in marine fish in Turkey. Turkish Journal of Veterinary & Animal Sciences, 30(3): 305–310.
Evelyn T P T. 1971. First records of vibriosis in Pacific salmon cultured in Canada, and taxonomic status of the responsible bacterium, Vibrio anguillarum. Journal of the Fisheries Research Board of Canada, 28(4): 517–525.
Gallagher R T, Finer J, Clardy J, Leutwiler A, Weibel F, Acklin W, Arigoni D. 1980. Paspalinine, a Tremorgenic Metabolite from Claviceps p aspali Stevens Et Hall. Tetrahedron Letters, 21(3): 235–238.
Gao S S. 2011a. Secondary Metabolites of Four Marinederived Fungi and Their Bioactivities. Institute of Oceanology, Chinese Academy of Sciences. PhD Thesis. p.49–62.
Gao S S, Li X M, Li C S, Proksch P, Wang B G. 2011b. Penicisteroids A and B, antifungal and cytotoxic polyoxygenated steroids from the marine alga-derived endophytic fungus Penicillium chrysogenum QEN-24S. Bioorganic & Medicinal Chemistry Letters, 21(10): 2 894–2 897.
Itabashi T, Hosoe T, Wakana D, Fukushima K, Takizawa K, Yaguchi T, Okada K, de Campos Takaki G M, Kawai K. 2009. A new indoloditerpene derivative, penijanthine A, isolated from Penicillium janthinellum. Journal of Natural medicine, 63(1): 96–99.
Kono Y, Gardner J M, Suzuki Y, Takeuchi S. 1986. Studies on host-selective toxins produced by a pathotype of Alternaria -citri causing brown spot disease of mandarins. Agricultural and Biological Chemistry, 50(6): 1 597–1 606.
Li D L, Li X M, Proksch P, Wang B G. 2010. 7-O-methylvariecolortide A, a new spirocyclic diketopiperazine alkaloid from a marine mangrove derived endophytic fungus, Eurotium rubrum. Natural Product Communications, 5(10): 1 583–1 586.
Li D L, Li X M, Wang B G. 2009. Natural anthraquinone derivatives from a marine mangrove plant-derived endophytic fungus Eurotium rubrum: structural elucidation and DPPH radical scavenging activity. Journal of Microbiology and Biotechnology, 19(7): 675–680.
Liebermann B, Elliger R, Gunther W, Ihn W, Gallander H. 1997. Tricycloalternarenes produced by Alternaria alternata related to ACTG-toxins. Phytochemistry, 46(2): 297–303.
Liu D, Li X M, Meng L, Li C S, Gao S S, Shang Z, Proksch P, Huang C G, Wang B G. 2011. Nigerapyrones A-H, alphapyrone derivatives from the marine mangrove-derived endophytic fungus Aspergillus niger MA-132. Journal of Natural Products, 74(8): 1 787–1 791.
Mantle P G, Weedon C M. 1994. Biosynthesis and transformation of tremorgenic indole-diterpenoids by Penicillium p axilli and Acremonium l olii. Phytochemistry, 36(5): 1 209–1 217.
Munday-Finch S C, Wilkins A L, Miles C O. 1996. Isolation of paspaline B, an indole-diterpenoid from Penicillium paxilli. Phytochemistry, 41(1): 327–332.
Onocha P A, Okorie D A, Connolly J D, Roycroft D S. 1995. Monoterpene diol, iridoid glucoside and dibenzo-alphapyrone from Anthocleista d jalonensis. Phytochemistry, 40(4): 1 183–1 189.
Strobel G A. 2002. Rainforest endophytes and bioactive products. Critical Reviews in Biotechnology, 22(4): 315–333.
Wang B G, Ebel R, Wang C Y, Wray V, Proksch P. 2002. New methoxylated aryltetrahydronaphthalene lignans and a norlignan from Aglaia cordata. Tetrahedron Letters, 43(33): 5 783–5 787.
Wang S, Li X M, Teuscher F, Li D L, Diesel A, Ebel R, Proksch P, Wang B G. 2006. Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. Journal of Natural Products, 69(11): 1 622–1 625.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supported by the National Natural Science Foundation of China (Nos. 30910103914, 31270403) and the Ministry of Science and Technology (No. 2010CB833802)
Rights and permissions
About this article
Cite this article
Sun, H., Gao, S., Li, X. et al. Chemical constituents of marine mangrove-derived endophytic fungus Alternaria tenuissima EN-192. Chin. J. Ocean. Limnol. 31, 464–470 (2013). https://doi.org/10.1007/s00343-013-2106-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00343-013-2106-2