海洋真菌来源吲哚生物碱类化合物的结构和活性研究

doi:10.11978/j.issn.1009-5470.2013.01.005

Abstract

Abstract: In recent years, marine natural products of fungal origin have gained considerable recognition, as many of them possess novel structures and interesting biological and pharmacological properties. This review includes 134 indole alkaloids of marine-derived fungi with their structures and activities published during 1991-2010. Of the indole alkaloids, there were 19 fumitremorgins, 22 notoamides, 18 cytochalasans, 9 fumiquinazolines, 11 indole terpenes, 21 peptides and other single indole alkaloids, and 34 bisindole alkaloids. These indole alkaloids showed not only unique structures but also a variety of important biological activities and had potential values in application.

Key words: marine fungi, indole alkaloids, structure, activity

CLC Number:

O629.3

LI Qing-xin, SHI Xue-feng, HUANG Zhi, TIAN Xin-peng, WANG Fa-zuo. Indole alkaloids from marine-derived fungi: structures and activities[J].Journal of Tropical Oceanography, 2013, 32(1): 35-47.

References

[1] BLUNT J W, COPP B R, MUNRO M H G,et al. Marine natural products[J]. Nat Prod Rep, 2011,282:196-268.
[2] RATEB M E, EBEL R. Secondary metabolites of fungi from marine habitats[J]. Nat Prod Rep, 2011,282:290-344.
[3] BUGNI T S, IRELAND C M. Marine-derived fungi: A chemically and biologically diverse group of microorganisms [J]. Nat Prod Rep, 2004,211:143-163.
[4] SALEEM M, ALI M S, HUSSAIN S,et al. Marine natural products of fungal origin[J]. Nat Prod Rep, 2007,245:1142.
[5] KOCHANOWSKA-KARAMYAN A J, HAMANN M T. Marine indole alkaloids: Potential new drug leads for the control of depression and anxiety[J]. Chem Rev, 2010,1108:4489-4497.
[6] GUL W, HAMANN M T. Indole alkaloid marine natural products: An established source of cancer drug leads with considerable promise for the control of parasitic, neurological and other diseases[J]. Life Sci, 2005,785:442-453.
[7] LI SHUMING. Genome mining and biosynthesis of fumitremorgin-type alkaloids in ascomycetes[J]. J Antibiot, 2011,641:45-49.
[8] YAMAZAKI M, SUZUKI S, MIYAKI K. Tremorgenic toxins from Aspergillus fumigatus Fres[J]. Chem Pharm Bull, 1971,198:1739-1740.
[9] WANG FAZUO, FANG YUCHUN, ZHU TIANJIAO,et al. Seven new prenylated indole diketopiperazine alkaloids from holothurian-derived fungus Aspergillus fumigatus [J]. Tetrahedron, 2008,6434:7986-7991.
[10] ZHANG MIN, WANG WENLIANG, FANG YUCHUN,et al. Cytotoxic alkaloids and antibiotic nordammarane triterpenoids from the marine-derived fungus Aspergillus sydowi [J]. J Nat Prod, 2008,716:985-989.
[11] CUI CHENGBIN, KAKEYA H, OKADA G,et al. Tryprostatin A and tryprostatin B, novel mammalian-cell cycle inhibitors produced by Aspergillus fumigatus [J]. J Antibiot, 1995,4811:1382-1384.
[12] CUI CHENGBIN, KAKEYA H, OKADA G,et al. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. 1. Taxonomy, fermentation, isolation and biological properties[J]. J Antibiot, 1996,496:527-533.
[13] CUI CHENGBIN, KAKEYA H, OSADA H. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. 2. Physico-chemical properties and structures[J]. J Antibiot, 1996,496:534-540.
[14] CUI CHENGBIN, KAKEYA H, OSADA H. Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus , which inhibit mammalian cell cycle at G2/M phase[J]. Tetrahedron, 1996,5239:12651-12666.
[15] CUI CHENGBIN, KAKEYA, H, OSADA, H. Spirotryprostatin B, a novel mammalian cell cycle inhibitor produced by Aspergillus fumigatus [J]. J Antibiot, 1996,498:832-835.
[16] CUI CHENGBIN, KAKEYA H, OSADA H. Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus , which inhibit mammalian cell cycle at G2/M phase[J]. Tetrahedron, 1997,531:59-72.
[17] KATO H, YOSHIDA T, TOKUE T,et al. Notoamides A-D: Prenylated indole alkaloids isolated from a marine-derived fungus, Aspergillus sp. [J]. Angew Chem Int Edit, 2007,4613:2254-2256.
[18] TSUKAMOTO S, KATO H, SAMIZO M,et al. Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp. [J]. J Nat Prod, 2008,7112:2064-2067.
[19] GRUBBS A W, ARTMAN G D, TSUKAMOTO S,et al. A concise total synthesis of the notoamides C and D[J]. Angew Chem Int Edit, 2007,4613:2257-2261.
[20] TSUKAMOTO S, KATO H, GRESHOCK T J,et al. Isolation of Notoamide E, a key precursor in the biosynthesis of prenylated indole alkaloids in a marine-derived fungus, Aspergillus sp. [J]. J Am Chem Soc, 2009,13111:3834-3835.
[21] TSUKAMOTO S, KAWABATA T, KATO H,et al. Isolation of antipodal --versicolamide B and notoamides L-N from a marine-derived Aspergillus sp. [J]. Org Lett, 2009,116:1297-1300.
[22] TSUKAMOTO S, UMAOKA H, YOSHIKAWA K,et al. Notoamide O, a Structurally unprecedented prenylated indole alkaloid, and notoamides P-R from a marine-derived fungus, Aspergillus sp. [J]. J Nat Prod, 2010,738:1438-1440.
[23] KITO K, OOKURA R, KUSUMI T,et al. X-ray structures of two stephacidins, heptacyclic alkaloids from the marine-derived fungus Aspergillus ostianus [J]. Heterocycles, 2009,788:2101-2106.
[24] CARTER S B. Effects of cytochalasins on mammalian cells[J]. Nature, 1967,2135073:261-264.
[25] LIN ZHENJIAN, ZHU TIANJIAO, CHEN LI,et al. Three new aspochalasin derivatives from the marine-derived fungus Spicaria elegans [J]. Chin Chem Lett, 2010,217:824-826.
[26] LIN ZHENJIAN, ZHU TIANJIAO, WEI HONGJUAN,et al. Spicochalasin A and new aspochalasins from the marine-derived fungus Spicaria elegans [J]. Eur J Org Chem, 2009,18:3045-3051.
[27] LIU RUI, LIN ZHENJIAN, ZHU TIANJIAO,et al. Novel open-chain cytochalsins from the marine-derived fungus Spicaria elegans [J]. J Nat Prod, 2008,717:1127-1132.
[28] NUMATA A, TAKAHASHI C, ITO Y,et al. Penochalasins, a novel class of cytotoxic cytochalasans from a Penicillium species separated from a marine alga: Structure determination and solution conformation[J]. J Chem Soc, Perkin Trans 1, 1996,3:239-245.
[29] IWAMOTO C, YAMADA T, ITO Y,et al. Cytotoxic cytochalasans from a Penicillium species separated from a marine alga[J]. Tetrahedron, 2001,5715:2997-3004.
[30] CHRISTIAN O E, COMPTON J, CHRISTIAN K R,et al. Using jasplakinolide to turn on pathways that enable the isolation of new chaetoglobosins from Phomospis asparagi [J]. J Nat Prod, 2005,6811:1592-1597.
[31] CUI CHUANMING, LI XIAOMING, LI CHUNSHUN,et al. Cytoglobosins A-G, cytochalasans from a marine-derived endophytic fungus, Chaetomium globosum QEN-14[J]. J Nat Prod, 2010,734:729-733.
[32] SCHUMANN J, HERTWECK C. Molecular basis of cytochalasan biosynthesis in fungi: Gene cluster analysis and evidence for the involvement of a PKS-NRPS hybrid synthase by RNA silencing[J]. J Am Chem Soc, 2007,12931:9564-9565.
[33] NUMATA A, TAKAHASHI C, MATSUSHITA T,et al. Fumiquinazolines, novel metabolites of a fungus isolated from a saltfish[J]. Tetrahedron Lett, 1992,3312:1621-1624.
[34] TAKAHASHI C, MATSUSHITA T, DOI M,et al. Fumiquinazolines A-G, novel metabolites of a fungus separated from a Pseudolabrus marine fish[J]. J Chem Soc, Perkin Trans 1, 1995,18:2345-2353.
[35] BELOFSKY G N, ANGUERA M, JENSEN P R,et al. Oxepinamides A-C and fumiquinazolines H-I: Bioactive metabolites from a marine isolate of a fungus of the genus Acremonium [J]. Chem-Eur J, 2000,68:1355-1360.
[36] SNIDER B B, ZENG HONGBO. Total syntheses of --fumiquinazolines A, B, and I[J]. Org Lett, 2000,225:4103-4106.
[37] WANG HAISHAN, GANESAN A. Total synthesis of the fumiquinazoline alkaloids: solution-phase studies[J]. J Org Chem, 2000,654:1022-1030.
[38] XU MINJUAN, GESSNER G, GROTH I,et al. Shearinines D-K, new indole triterpenoids from an endophytic Penicillium sp. strain HKI 0459with blocking activity on large-conductance calcium-activated potassium channels[J]. Tetrahedron, 2007, 632:435-444.
[39] SMETANINA O F, KALINOVSKY A I, KHUDYAKOVA Y V,et al. Indole alkaloids produced by a marine fungus isolate of Penicillium janthinellum Biourge[J]. J Nat Prod, 2007,706:906-909.
[40] SMETANINA O F, KALINOVSKY A I, KHUDYAKOVA Y V,et al. Indole alkaloids produced by a marine fungus isolate of Penicillium janthinellum biourge [J]. J Nat Prod, 2007,7012:2054-2054.
[41] TSUDA M, KASAI Y, KOMATSU K,et al. Citrinadin A, a novel pentacyclic alkaloid from marine-derived fungus Penicillium citrinum [J]. Org Lett, 2004,618:3087-3089.
[42] MUGISHIMA T, TSUDA M, KASAI Y,et al. Absolute stereochemistry of citrinadins A and B from marine-derived fungus[J]. J Org Chem, 2005,7023:9430-9435.
[43] SCHLINGMANN G, MILNE L, WILLIAMS D R,et al. Cell wall active antifungal compounds produced by the marine fungus Hypoxylon oceanicum LL-15G256 - II. Isolation and structure determination[J]. J Antibiot, 1998,513:303-316.
[44] MALMSTROM J. Unguisins A and B: New cyclic peptides from the marine-derived fungus Emericella unguis [J]. J Nat Prod, 1999,625:787-789.
[45] ZHENG JINKAI, ZHU HUAJIE, HONG KUI,et al. Novel cyclic hexapeptides from marine-derived fungus, Aspergillus sclerotiorum PT06-1[J]. Org Lett, 2009,1122:5262-5265.
[46] TOSKE S G, JENSEN P R, KAUFFMAN C A,et al. Aspergillamides A and B: Modified cytotoxic tripeptides produced by a marine fungus of the genus Aspergillus [J]. Tetrahedron, 1998,5444:13459-13466.
[47] DU LIN, LI DEHAI, ZHU TIANJIAO,et al. New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. [J]. Tetrahedron, 2009,655:1033-1039.
[48] NUMATA A, TAKAHASHI C, ITO Y,et al. Communesins, cytotoxic metabolites of a fungus isolated from a marine alga[J]. Tetrahedron Lett, 1993,3414:2355-2358.
[49] WIGLEY L J, MANTLE P G, PERRY D A. Natural and directed biosynthesis of communesin alkaloids[J]. Phytochemistry, 2006,676:561-569.
[50] JADULCO R, EDRADA R A, EBEL R,et al. New communesin derivatives from the fungus Penicillium sp. derived from the Mediterranean sponge Axinella verrucosa [J]. J Nat Prod, 2004, 671: 78-81.
[51] TSUDA M, MUGISHIMA T, KOMATSU K,et al. Speradine A, a new pentacyclic oxindole alkaloid from a marine-derived fungus Aspergillus tamarii [J]. Tetrahedron, 2003,5918:3227-3230.
[52] LIN AIQUN, DU LIN, FANG YUCHUN,et al. Iso-alpha-cyclopiazonic acid, a new natural product isolated from the marine-derived fungus Aspergillus flavus C-F-3[J]. Chem Nat Compd, 2009,455:677-680.
[53] WU QUANXIANG, CREWS M S, DRASKOVIC M,et al. Azonazine, a novel dipeptide from a hawaiian marine sediment-derived fungus, Aspergillus insulicola [J]. Org Lett, 2010,1220:4458-4461.
[54] USAMI Y, YAMAGUCHI J, NUMATA A. Gliocladins A-C and glioperazine:Cytotoxic dioxo- or trioxopiperazine metabolites from a Gliocladium sp. separated from a sea hare[J]. Heterocycles, 2004,635:1123-1129.
[55] SUGIYAMA Y, ITO Y, SUZUKI M,et al. Indole derivatives from a marine sponge-derived yeast as DPPH radical scavengers[J]. J Nat Prod, 2009,7211:2069-2071.
[56] TAKAHASHI C, NUMATA A, ITO Y,et al. Leptosins, antitumor metabolites of a fungus isolated from a marine alga[J]. J Chem Soc Perkin Trans 1, 1994,13:1859-1864.
[57] TAKAHASHI C, NUMATA A, MATSUMURA E,et al. Leptosins I and J, cytotoxic substances produced by a Leptosphaeria sp. Physico-chemical properties and structures[J]. J Antibiot, 1994,4711:1242-1249.
[58] TAKAHASHI C, TAKAI Y, KIMURA Y,et al. Cytotoxic metabolites from a fungal adherent of a marine alga[J]. Phytochemistry, 1995,381:155-158.
[59] TAKAHASHI C, MINOURA K, YAMADA T,et al. Potent cytotoxic metabolites from a leptosphaeria species - structure determination and conformational-analysis[J]. Tetrahedron, 1995,5112:3483-3498.
[60] YAMADA T, IWAMOTO C, YAMAGAKI N,et al. Leptosins M-N1, cytotoxic metabolites from a Leptosphaeria species separated from a marine alga. Structure determination and biological activities[J]. Tetrahedron, 2002,583:479-487.
[61] YAMADA T, IWAMOTO C, YAMAGAKI N,et al. Leptosins O-S, cytotoxic metabolites of a strain of Leptosphaeria sp isolated from a marine alga[J]. Heterocycles, 2004,633:641-653.
[62] VAROGLU M, CORBETT T H, VALERIOTE F A,et al. Asperazine, a selective cytotoxic alkaloid from a sponge-derived culture of Aspergillus niger [J]. J Org Chem, 1997,6221:7078-7079.
[63] SON B W, JENSEN P R, KAUFFMAN C A,et al. New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium [J]. Nat Prod Lett, 1999,133:213-222.
[64] OVENDEN S P, SBERNA G, TAIT R M,et al. A diketopiperazine dimer from a marine-derived isolate of Aspergillus niger [J]. J Nat Prod, 2004,6712:2093-2095.
[65] CARR G, TAY W, BOTTRIELL H,et al. Plectosphaeroic acids A, B, and C, indoleamine 2,3-dioxygenase inhibitors produced in culture by a marine isolate of the fungus Plectosphaerella cucumerina [J]. Org Lett, 2009,1114:2996-2999.

Indole alkaloids from marine-derived fungi: structures and activities

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