ORIGINAL ARTICLES |
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New acetogenin katsuurallene from Laurencia saitoi collected from Katsuura, Japan |
Yu Minamida1,8, Hiroshi Matsuura2, Takahiro Ishii3, Miyu Miyagi3, Yuto Shinjo3, Kosuke Sato4, Takashi Kamada4, Yoshihiro Mihara5, Iwao Togashi2, Keisuke Sugimoto2, Tsuyoshi Abe6, Norio Kikuchi7, Minoru Suzuki7 |
1 Advanced Course of Applied Chemistry, National Institute of Technology, Asahikawa College, Shunkodai 2-2-1-6, Asahikawa, Hokkaido 071-8142, Japan; 2 Department of Materials Chemistry, National Institute of Technology, Asahikawa Collage, Shunkodai 2-2-1-6, Asahikawa, Hokkaido 071-8142, Japan; 3 Department of Biosciences and Biotechnology, Faculty of Agriculture, University of the Ryukyus, 1 Senbaru, Nishihara, Okinawa 903-0213, Japan; 4 Department of Materials and Life Science, Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka 437-8555, Japan; 5 Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hokkaido University of Science, Maeda 7, 15-4-1, Teine-ku, Sapporo, Hokkaido 006-8590, Japan; 6 The Hokkaido University Museum, Hokkaido University, N10 W8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan; 7 Coastal Branch of Natural History Museum and Institute, Chiba,, 123 Yoshio, Katsuura, Chiba 299-5242, Japan; 8 Present Address: Department of Life Science, Graduate School of Engineering Science, Akita University, 1-1 Tegatagakuen-machi, Akita 010-8502, Japan |
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Abstract We examined the chemical constitution of the red alga Laurencia saitoi Perestenko, collected from Katsuura, Boso Peninsula, Chiba Prefecture, Japan. This specimen produced a new polyhalogenated acetogenin, named katsuurallene (1), which structure was determined by the spectral methods, along with known diterpene, deoxyparguerol (2) and triterpene, thyrsiferol (3). In this paper we describe the structural elucidation of katsuurallene together with some biological activities.
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Keywords
Laurencia
Rhodomelaceae
Acetogenin
Triterpene
Diterpene
Biological activity
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Fund:The authors are grateful to Mr. H. Akutsu (Central Laboratory for Research and Education, Center for Advanced Research and Education, Asahikawa Medical University) for the measurement of high resolution mass spectra. This work was supported by JSPS KAKENHI Grant Numbers 18K05799 and 21K14904. |
Corresponding Authors:
Hiroshi Matsuura, E-mail:matsuura@asahikawa-nct.ac.jp
E-mail: matsuura@asahikawa-nct.ac.jp
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Issue Date: 30 May 2022
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1.Wang BG, Gloer JB, Ji NY, Zhao JC.Halogenated organic molecules of rhodomelaceae origin: chemistry and biology.Chem Rev.2013;113:3632–85. 2.Ji NY, Wang BG.Nonhalogenated organic molecules from Laurencia algae.Phytochem Rev.2014;13:653–70. 3.Harizani M, Ioannou E, Roussis V.The Laurencia paradox: an endless source of chemodiversity.In: Kinghorn AD, Falk H, Gibbons S, Kobayashi J, editors.Progress in the chemistry of organic natural products 102.Wien: Springer International Publishing; 2016.p.91–252. 4.M.Suzuki, Database (2021), http:// laure ncia-datab ase.jp.Accessed 29 Aug 2021 5.Koutsaviti A, Daskalaki MG, Agusti S, Kampranis SC, Tsatsanis C, Duarte CM, Roussis V, Ioannou E.Thuwalallenes A–E and Thuwalenynes A–C: new C15 acetogenins with anti-inflammatory activity from a Saudi Arabian Red Sea Laurencia sp.Mar Drugs.2019;17:644. 6.Ghandourah M, Alarif W, Bawakid N.New bioactive C15 acetogenins from the red alga Laurencia obtusa.Pharmacogn Mag.2019;15:199–203. 7.Young DN, Howard BM, Fenical W.Subcellular localization of brominated secondary metabolites in the red alga Laurencia snyderae.J Phycol.1980;16:182–5. 8.Suzuki M, Vairappan CS.Halogenated secondary metabolites from Japanese species of the red algal genus Laurencia (Rhodomelaceae, Ceramiales).Cur Top Phytochemistry.2005;7:1–34. 9.Suzuki M, Kawamoto T, Vairappan CS, Ishii T, Abe T, Masuda M.Halogenated metabolites from Japanese Laurencia spp.Phytochemistry.2005;66:2787–93. 10.Umezawa T, Oguri Y, Matsuura H, Yamazaki S, Suzuki M, Yoshimura E, Furuta T, Nogata Y, Serisawa Y, Matsuyama-Serisawa K, Abe T, Matsuda F, Suzuki M, Okino T.Omaezallene from red alga Laurencia sp.: structure elucidation, total synthesis, and antifouling activity.Angew Chem Int Ed.2014;53:3909–12. 11.Minamida Y, Matsuura H, Ishii T, Sato K, Kamada T, Kato A, Yamagishi Y, Abe T, Kikuchi N, Suzuki M.Chemical composition of Laurencia spp.collected from the Seto Inland Sea of Japan.Biochem Syst Ecol.2021;96:104259. 12.Kikuchi N, Miyata M.Marine Flora at Katsuura-city, Southeastern Part of the Boso Peninsula, Japan (revised edition).J Nat Hist Mus Inst, Chiba, Special Issue.2021;11:9–24. 13.Ishii T, Shinjo Y, Miyagi M, Matsuura H, Abe T, Kikuchi N, Suzuki M.Investigation of insect repellent activity of cyclocolorenone obtained from the red alga Laurencia intricata.Rec Nat Prod.2019;13:81–4. 14.Ishii T, Miyagi M, Shinjo Y, Minamida Y, Matsuura H, Abe T, Kikuchi N, Suzuki M.Two new brominated C15-acetogenins from the red alga Laurencia japonensis.Nat Prod Res.2020;34:2787–93. 15.Suzuki M, Nakano S, Takahashi Y, Abe T, Masuda M.Bisezakyne-A and-B, halogenated C15 acetogenins from a Japanese Laurencia species.Phytochemistry.1999;51:657–62. 16.Lowe G.The absolute configuration of allenes.Chem Commun.1965;411–3. 17.Elsevier CJ, Vermeer P, Gedanken A, Runge W.Synthesis and absolute configurations of halogenoallenes.J Org Chem.1985;50:364–7. 18.Sohn TI, Kim D, Paton RS.Substrate-controlled asymmetric total syntheses of microcladallenes A, B, and C based on the proposed structures.Chem Eur J.2015;21:15988–97. 19.Norte M, Fernandez JJ, Ruano JZ.Three new bromo ethers from the red alga Laurencia obtusa.Tetrahedron.1989;45:5987–94. 20.Imre S, Aydogmus Z, Guner H, Lotter H, Wagner H.Polybrominated non-terpenoid C15 compounds from Laurencia paniculata and Laurencia obtusa.Z Naturforsch.1995;50c:743–7. 21.Esselin H, Sutour S, Liberal J, Cruz MT, Salgueiro L, Siegler B, Freuze I, Castola V, Paoli M, Bighelli A, Tomi F.Chemical composition of Laurencia obtusa extract and isolation of a new C15-acetogenin.Molecules.2017;22:779. 22.Esselin H, Tomi F, Bighelli A, Sutour S.New metabolites isolated from a Laurencia obtusa population collected in Corsica.Molecules.2018;23:720. 23.Suzuki T, Suzuki M, Furusaki A, Matsumoto T, Kato A, Imanaka Y, Kurosawa E.Teurilene and thyrsiferyl 23-acetate, meso and remarkably cytotoxic compounds from the marine red alga Laurencia obtusa (Hudson) Lamouroux.Tetrahedron Lett.1985;26:1329–32. 24.Suzuki T, Takeda S, Suzuki M, Kurosawa E, Kato A, Imanaka Y.Cytotoxic squalene-derived polyethers from the marine red alga Laurencia obtusa (Hudson) Lamouroux.Chem Lett.1987;16:361–4. 25.Suzuki T, Takeda S, Hayama N, Tanaka I, Komiyama K.The structure of brominated diterpene from the marine red alga Laurencia obtusa (Hudson) Lamouroux.Chem Lett.1989;18:969–70. 26.Takeda S, Matsumoto T, Komiyama K, Kurosawa E, Suzuki T.A new cytotoxic diterpene from the marine red alga Laurencia obtusa (Hudson) Lamouroux.Chem Lett.1990;19:277–80. 27.Takeda S, Kurosawa E, Komiyama K, Suzuki T.The structures of cytotoxic diterpenes containing bromine from the marine red alga Laurencia obtusa (Hudson) Lamouroux.Bull Chem Soc Jpn.1990;63:3066–72. 28.Kurata K, Taniguchi K, Agatsuma Y, Suzuki M.Diterpenoid feeding-deterrents from Laurencia saitoi.Phytochemistry.1998;47:363–9. 29.Masuda M, Abe T.The occurrence of Laurencia saitoi Perestenko (L.obtusa auct.japon.) (Ceramiales, Rhodophyta) in Japan.Jpn J Phycol.1993;41:7–18. 30.Ji NY, Li XM, Wang BG.Halogenated terpenes and a C15-acetogenin from the marine red alga Laurencia saitoi.Molecules.2008;13:2894–9. 31.Ji NY, Li XM, Li K, Wang BG.Halogenated sesquiterpenes from the marine red alga Laurencia saitoi (Rhodomelaceae).Helv Chim Acta.2009;92:1873–9. 32.Su H, Yuan ZH, Li J, Guo SJ, Deng LP, Han LJ, Zhu XB, Shi DY.Sesquiterpenes from the marine red alga Laurencia saitoi.Helv Chim Acta.2009;92:1291–7. 33.Schmitz FJ, Michaud DP, Schmidt PG.Marine natural products: parguerol, deoxyparguerol, and isoparguerol.New brominated diterpenes with modified pimarane skeletons from the sea hare Aplysia dactylomela.J Am Chem Soc.1982;104:6415–23. 34.Manzo E, Gavagnin M, Bifulco G, Cimino P, Micco SD, Ciavatta ML, Guo YW, Cimino G.Aplysiols A and B, squalene-derived polyethers from the mantle of the sea hare Aplysia dactylomela.Tetrahedron.2007;63:9970–8. 35.Ishii T, Nagamine T, Nguyen BCQ, Tawata S.Insecticidal and repellent activities of laurinterol from the Okinawan red alga Laurencia nidifica.Rec Nat Prod.2017;11:63–8. 36.Solis PN, Wright CW, Anderson MM, Gupta MP, Phillipson JD.A microwell cytotoxicity assay using Artemia salina (brine shrimp).Planta Med.1993;59:250–2. |
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