Investigation of practical calculation protocols in the reproduction of spectra of natural products.

• Project/Area Number: 26660093
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Bioorganic chemistry
• Research Institution: Hirosaki University
• Principal Investigator: Hashimoto Masaru 弘前大学, 農学生命科学部, 教授 (40212138)
• Co-Investigator(Kenkyū-buntansha): NEHIRA Tatsuo 広島大学, 大学院総合科学研究科, 准教授 (60321692)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000); Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 天然物構造決定 / スペクトル解析 / 分子起動計算予測 / 天然物 / 分子起動計算 / NMR化学シフト予想 / 密度汎関数分子軌道法 / 化学シフト計算 / 電子円二色性スペクトル計算

Outline of Final Research Achievements

Spectral analyses are indispensable in structural determination of natural products. Usually those have required empirical databases. Thus, the reliability decreases in the cases of determinations of structurally unique natural products. On the other hand, remarkable progress of computer technologies enabled us to perform the spectral reproduction based on the non-empirical manner. But this methodology is now insufficient in natural product chemistry due to only a few examples existing. Thus the present study performs the scope and limitation of spectral calculations by investigating the suitable combinations of method of calculations, basis sets, and optimization algorism.

Research Products

• [Journal Article] Homopetasinic acid isolated from Diaporthe sp. strain 1308-05 (2016)
  • Author(s): A Ito, I Kumagai, M Maruyama, H Maeda, A Tonouchi, T Nehira, K Kimura, M Hashimoto
  • Journal Title: Tetrahedron Letters Volume: 57(10) Issue: 10 Pages: 1117-1119
  • DOI: 10.1016/j.tetlet.2016.01.095
  • Peer Reviewed / Open Access
• [Journal Article] Isolation, absolute structures, and biological properties of cyclohelminthols I-IV from Helminthosporium velutinum yone96 (2016)
  • Author(s): Yuna Honmura, Shota Uesugi, Hayato Maeda, Kazuaki Tanaka, Tatsuo Nehira, Ken-ichi Kimura, Masaaki Okazaki, Masaru Hashimot
  • Journal Title: Tetrahedron Volume: 72 Issue: 10 Pages: 1400-1405
  • DOI: 10.1016/j.tet.2016.01.036
  • Peer Reviewed
• [Journal Article] Homojesterones: vinylogous analogues of jesterone from Helminthosporium velutinum TS28 (2016)
  • Author(s): M Arayama, S Uesugi, K Tanaka, H Maeda, T Nehira, K Kimura, M Hashimoto
  • Journal Title: Tetrahedron Volume: 72(7) Issue: 7 Pages: 1031-1035
  • DOI: 10.1016/j.tet.2015.12.077
  • Peer Reviewed / Open Access
• [Journal Article] Cassane diterpenoids from the roots of Caesalpinia decapetala var. japonica and structure revision of caesaljapin (2016)
  • Author(s): S. Kamikawa, S. Oshimo, E. Ohta, T. Nehira, H. Omura, and S. Ohta
  • Journal Title: Phytochemistry Volume: 121 Pages: 50-57
  • DOI: 10.1016/j.phytochem.2015.10.001
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Structure Revision of Caesalpinista A and Caesalpinista B and Isolation of a New Furanoditerpenoid from the Cotyledons of Caesalpinia decapetala var. japonica (2016)
  • Author(s): S. Kamikawa, E. Ohta, T. Nehira, H. Omura, and S. Ohta
  • Journal Title: Helvetica Chimca Acta Volume: 99 Issue: 2 Pages: 133-137
  • DOI: 10.1002/hlca.201500171
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Computation-Assisted Structural Elucidation of Epoxyroussoeone and Epoxyroussoedione Isolated from Roussoella japanensis KT1651 (2015)
  • Author(s): Y Honmura, H Takekawa, K Tanaka, H Maeda, T Nehira, W Hehre, M Hashimoto
  • Journal Title: Journal of natural products Volume: 78(7) Issue: 7 Pages: 1505-1510
  • DOI: 10.1021/np500924n
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Isolation, ECD assisted structural analyses, biosynthetic discussions, and biological activities of epi-cochlioquinones D and its derivatives (2015)
  • Author(s): M Arayama, T Nehira, H Maeda, K Tanaka, H Miyagawa, T Ueno, S Hosokawa, M Hashimoto
  • Journal Title: Tetrahedron Volume: 71(29) Issue: 29 Pages: 4788-4794
  • DOI: 10.1016/j.tet.2015.05.044
  • Peer Reviewed / Open Access
• [Journal Article] Achaetolide-II isolated from Helminthosporium velutinum TS28 (2015)
  • Author(s): M Arayama, H Maeda, K Tanaka, N Takada, T Nehira, M Hashimoto
  • Journal Title: Tetrahedron Volume: 71(41) Issue: 41 Pages: 7900-7905
  • DOI: 10.1016/j.tet.2015.08.013
  • Peer Reviewed / Open Access
• [Journal Article] Novel himachalene-type sesquiterpenes from male adults of Chinese Windmill butterfly, Byasa alcinous alcinous (2015)
  • Author(s): Hisashi Omura, Taro Noguchi, Tatsuo Nehira
  • Journal Title: Natural Products Researches Volume: 29 Issue: 4 Pages: 1-6
  • DOI: 10.1080/14786419.2015.1019352
  • Peer Reviewed
• [Journal Article] Niphateolide A: isolation from the marine sponge Niphates olemda and determination of its absolute configuration by an ECD analysis (2015)
  • Author(s): H. Kato, T. Nehira, K. Matsuo, T. Kawabata, Y. Kobashigawa, H. Morioka, F. Losung, R. E. P. Mangindaan, N. J. de Voogd, H. Yokosawa, S. Tsukamoto
  • Journal Title: Tetrahedron Volume: 71 Issue: 38 Pages: 6956-6960
  • DOI: 10.1016/j.tet.2015.07.009
  • NAID: 120006897988
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Taichunamides: Unprecedented Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404) (2015)
  • Author(s): 9.Ippei Kagiyama, Hikaru Kato, Tatsuo Nehira, Jens C. Frisvad, David H. Sharman, Robert M, Williams, Sachiko Tsukamoto
  • Journal Title: Angewandte Chemie International Edition Volume: 55 Issue: 3 Pages: 1128-1132
  • DOI: 10.1002/anie.201509462
• [Journal Article] Isotopic Differentiation Protocol, a Selective Extraction of C- and N-Terminal Ions in ESI-Ms/Ms De Novo Peptide Sequencing (2015)
  • Author(s): .Fujii, M.; Chiba, H.; Tamayama, N.; Kanamaru, S.; Hashimoto, M.
  • Journal Title: Nat. Prod. Chem. Res. Volume: 3 Issue: 1 Pages: 164-164
  • DOI: 10.4172/2329-6836.1000164
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Relative and absolute structure of phomolide C (2015)
  • Author(s): Ito, A.; Maeda, H.; Tonouchi, A.; Hashimoto, M
  • Journal Title: Biosci. Biotech. Biochem Volume: 79 Issue: 7 Pages: 1-3
  • DOI: 10.1080/09168451.2015.1015953
  • Peer Reviewed / Open Access
• [Journal Article] Isolation and structure elucidation of potential anti-dengue metabolites from tawa-tawa (Euphorbia hirta Linn.) (2014)
  • Author(s): Tayone, W. C.; Tayone, J. C.; Hashimoto, M
  • Journal Title: Walailak Journal of Science and Technology Volume: 11 Pages: 825-832
  • DOI: 10.14456/wjst.2014.65
  • Peer Reviewed / Open Access
• [Journal Article] Neomacrophorin I, II, and III, novel drimenyl cyclohexanes with hydroxylated butanoates from Trichoderma sp. 1212-03 (2014)
  • Author(s): 3. Hirose, A.; Maeda, H.; Tonouchi, A.; Nehira, T.; Hashimoto, M.
  • Journal Title: Tetrahedron Volume: 70 Issue: 7 Pages: 1458-1463
  • DOI: 10.1016/j.tet.2013.12.087
  • Peer Reviewed / Open Access
• [Journal Article] リンゴ果実におけるマイコパラサイト現象の生物有機化学的研究 (2014)
  • Author(s): 橋本勝
  • Journal Title: 日本化学会生体機能関連部会ニュースレター Volume: 28 Pages: 3-6
  • Peer Reviewed / Open Access
• [Journal Article] Lambertellin system, the mechanism for fungal replacement of Monilinia fructigena with Lambertella corni-maris without competitive inhibition on agar media (2014)
  • Author(s): 1.Hirose, A.; Kudo, S.; Murakami, T.; Tanaka, K.; Harada, K.; Hashimoto, M
  • Journal Title: Bioorg. Med. Chem. Volume: 22 Issue: 8 Pages: 2489-2495
  • DOI: 10.1016/j.bmc.2014.02.051
  • Peer Reviewed
• [Journal Article] absolute configuration determination via comparison of experimental and theoretical electronic circular dichroic spectra (2014)
  • Author(s): Tetsuro Ito, Tatsuo Nehira, Dehydroxylation of stilbenoid oligomers
  • Journal Title: Tetrahedron Letters Volume: 55 Issue: 2 Pages: 314-318
  • DOI: 10.1016/j.tetlet.2013.10.106
  • Peer Reviewed
• [Journal Article] Dehydroxylation of stilbenoid oligomers: absolute configuration determination via comparison of experimental and theoretical electronic circular dichroic spectra (2014)
  • Author(s): Tetsuro Ito, Tatsuo Nehira
  • Journal Title: Tetrahedron Letters Volume: 55 Issue: 35 Pages: 314-318
  • DOI: 10.1016/j.tet.2014.06.074
  • Peer Reviewed
• [Journal Article] Chiroptical molecular propeller based on hexakis(phenylethyl)benzene through the complexation-induced intramolecular transmission of local point chirality (2014)
  • Author(s): Ryo Katoono, Keiichi Kusaka, Shunsuke Kawai, Yuki Tanaka, Keisuke Hanada, Tatsuo Nehira, Kenshu Fujiwara, Takanori Suzuki
  • Journal Title: Prganic and Biomolecular Chemistry Volume: 12 Issue: 47 Pages: 9532-9538
  • DOI: 10.1039/c4ob01601g
  • Peer Reviewed
• [Journal Article] Acanthomanzamines A-E with new manzamine frameworks from the marine sponge Acanthostrongylophora ingens. (2014)
  • Author(s): A. Furusato, H. Kato, T. Nehira, K. Eguchi, T. Kawabata, Y. Fujiwara, F. Losung, R. E. P. Mangindaan, N. J. de Voogd, M. Takeya, H. Yokosawa, S. Tsukamoto
  • Journal Title: Org. Lett. Volume: 16 Issue: 15 Pages: 3888-3891
  • DOI: 10.1021/ol5015569
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Presentation] Cochlioquinone 化学の新展開―ECD の徹底活用と新たな生物活性考察 (2015)
  • Author(s): 荒山美紀、前多隼人、田中和明、根平達夫、宮川恒、上野民夫、細川誠二郎、橋本勝
  • Organizer: University of Saskatchewan Special Simminor
  • Place of Presentation: yokohama
  • Year and Date: 2015-09-10
• [Presentation] Isolation, ECD Assisted Structural Analyses, Biosynthetic Discussions, and Biological activities of epi-Cochlioquinones D and its Derivatives (2015)
  • Author(s): M. Arayama, T. Nehira, H. Maeda, K. Tanaka, H. Miyagawa, T. Ueno, S. Hosokawa, M. Hashimoto
  • Organizer: 15th International Conference on Chiral Spectroscopy
  • Place of Presentation: 札幌
  • Year and Date: 2015-08-31
  • Int'l Joint Research / Invited
• [Presentation] Bioorganic Studies on Mycoparasitism on Apple Fruites (2015)
  • Author(s): Masaru Hashimoto
  • Organizer: University of Saskatchewan Special Simminor
  • Place of Presentation: サスカチュワン
  • Year and Date: 2015-08-19
• [Presentation] Phomolide Cの相対及び絶対配置の決定 (2015)
  • Author(s): 伊藤厚、殿内暁夫、橋本勝
  • Organizer: 第10回化学生態学研究会
  • Place of Presentation: 函館
  • Year and Date: 2015-06-13
• [Presentation] 分子軌道計算支援による新規マクロフォリンの構造決定 (2015)
  • Author(s): 橋本勝, 本村優奈, 根平達夫
  • Organizer: 第10回化学生態学研究会
  • Place of Presentation: 函館
  • Year and Date: 2015-06-13
• [Presentation] Spiroleptospholの全合成研究 (2015)
  • Author(s): 高橋萌子、橋本勝
  • Organizer: 日本農芸化学会2015年度大会
  • Place of Presentation: 岡山
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] Phomolide Cの相対及び絶対配置の決定 (2015)
  • Author(s): 伊藤厚・殿内暁夫・橋本勝
  • Organizer: 日本農芸化学会2015年度大会
  • Place of Presentation: 岡山
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] 新規epi-cochlioquinone誘導体と その生合成前駆体の単離と構造 (2015)
  • Author(s): 荒山美紀、田中和明、前多隼人、根平達夫、橋本勝
  • Organizer: 日本農芸化学会2015年度大会
  • Place of Presentation: 岡山
  • Year and Date: 2015-03-26 – 2015-03-29
• [Presentation] Bioorganic Studies on Mycoparasitism on Apple Fruites (2014)
  • Author(s): Masaru Hashimoto
  • Organizer: Michigan State Univesity Department of Chemistry Seminor
  • Place of Presentation: Michigan State University
  • Year and Date: 2014-12-05
  • Invited
• [Presentation] 量子化学計算支援によるEpoxyroussoeone 類の構造決定 (2014)
  • Author(s): 本村優奈、狩原恭平、田中和明、前多隼人、根平達夫、Warren J. Hehrec、橋本勝
  • Organizer: 第56回天然有機化合物討論会
  • Place of Presentation: 高知
  • Year and Date: 2014-10-15 – 2014-10-17
• [Presentation] リンゴ果実におけるマイコパラサイト現象の生物有機化学的研究 (2014)
  • Author(s): 橋本勝
  • Organizer: 日本化学会東北支部、青森地区講演会
  • Place of Presentation: 弘前
  • Year and Date: 2014-10-03
  • Invited
• [Presentation] Helminthosporium velutinum TS28が生産する新規epi-cochlioquinone誘導体 (2014)
  • Author(s): 荒山美紀、田中和明、橋本勝
  • Organizer: 平成26年度 日本農芸化学会北海道支部・東北支部 合同支部大会
  • Place of Presentation: 札幌
  • Year and Date: 2014-09-22
• [Presentation] Phomolide Cの相対及び絶対配置の決定 (2014)
  • Author(s): 伊藤厚、殿内暁夫、橋本勝
  • Organizer: 平成26年度 日本農芸化学会北海道支部・東北支部 合同支部大会
  • Place of Presentation: 札幌
  • Year and Date: 2014-09-22
• [Presentation] MS/MSペプチド配列解析における簡便なイオン識別法の開発 (2014)
  • Author(s): 橋本勝、藤井眞、千葉洋、玉山方子
  • Organizer: 平成26年度 日本農芸化学会北海道支部・東北支部 合同支部大会
  • Place of Presentation: 札幌
  • Year and Date: 2014-09-22
• [Presentation] リンゴ果実におけるマイコパラサイト現象の生物有機化学的研究 (2014)
  • Author(s): 橋本勝
  • Organizer: 北海道大学理学部化学科講演会
  • Place of Presentation: 札幌
  • Year and Date: 2014-09-12
• [Presentation] Neomacrophorin類の構造決定 (2014)
  • Author(s): 橋本勝, 廣瀬あかね, 殿内暁夫, 前多隼人, 根平達夫
  • Organizer: 第9回化学生態学研究会
  • Place of Presentation: 函館
  • Year and Date: 2014-06-28
• [Presentation] 量子化学計算支援によるEpoxyrousseone類の構造決定 (2014)
  • Author(s): 本村優奈, 狩原恭平, 田中和明, 前多隼人, 根平達夫, Warren Hehre, 橋本勝
  • Organizer: 第9回化学生態学研究会
  • Place of Presentation: 函館
  • Year and Date: 2014-06-28
• [Presentation] 計算機支援による天然物の構造決定 (2014)
  • Author(s): 橋本勝
  • Organizer: 理研シンポジウム物質構造解析2014：MS とNMR の基礎と実践
  • Place of Presentation: 理化学研究所
  • Year and Date: 2014-06-20
  • Invited
• [Remarks] 有機実験室
  • URL: http://nature.cc.hirosaki-u.ac.jp/lab/2/biochem/yuki/