Collection of new natural sources and analysis of their chemical constituents and construction of genetic resource bank

2018 Fiscal Year Annual Research Report

• Project/Area Number: 15H05138
• Research Institution: University of Toyama
• Principal Investigator: 森田 洋行 富山大学, 和漢医薬学総合研究所, 教授 (20416663)
• Co-Investigator(Kenkyū-buntansha): WONG CHINPIOW 富山大学, 和漢医薬学総合研究所, 助教 (10816226)
• Project Period (FY): 2015-04-01 – 2019-03-31
• Keywords: 生物活性 / 植物 / 海綿 / 放線菌

Outline of Annual Research Achievements

昨年度ベトナム・ダナン近海から採集したXestospongia testudinariaの95%メタノール抽出液から1種の新規ステロールを2種の既知ステロールとともに単離した。単離した化合物について細胞毒性と抗菌活性を評価した結果、新規ステロールlangcosterol Aがヒト由来がん細胞に対して細胞毒性を示すことが明らかとなった。さらに、今年度は、ベトナム・フーコック島周辺海域についても海綿調査を行うことで、8種の海綿を採集し、これらの遺伝子を保存した。採集したArenosclera spのメタノール抽出液から新規1種を含む計9種のブロモ化ジフェニルエーテルを得ることができた。これらについて生物活性を評価した結果、新規化合物tribromoiododiphenyl etherと既知類縁体がBacillus subtilisとStaphylococcus aureusに対して強い抗菌活性を示すことが判明した。一方、ベトナム産センダン科植物Chisocheton paniculatusの果実のメタノール抽出液から1種の新規リモノイドを単離し、本化合物が抗炎症活性を有することを明らかにした。さらに、シソ科植物Pogostemom auriculariusの地上部及びヒカゲノカズラ科植物Huperzia phlegmariaの地上部のメタノール抽出液から，3種の新規メロテルペノイドと2種の新規リコポジウムアルカロイドをそれぞれ単離し、前者がヒト由来がん細胞に対して弱いながらも細胞毒性を有すること、一方、後者においては、弱いながらもアセチルコリンエステラーゼ阻害活性を有することを明らかにした。ミャンマー産天然資源については、ベイにてあらたに3種の海綿を、ベイの隣に位置するカレン州にて植物6種を採集し、海綿Clathria proliferaから2種の新規ピロロ-2-アミノイミダゾールを、クマツヅラ科植物Premna serratifolia材のクロロホルム抽出液から、6種の新規テトラヒドロリグナンを含む計18種の化合物の単離・構造決定等に成功した。

Research Progress Status

平成30年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

平成30年度が最終年度であるため、記入しない。

Research Products

• [Int'l Joint Research] University of Yangon/Myeik University(ミャンマー)
  • Country Name: MYANMAR
  • Counterpart Institution: University of Yangon/Myeik University
• [Int'l Joint Research] Hue University/Can Tho University(ベトナム)
  • Country Name: VIET NAM
  • Counterpart Institution: Hue University/Can Tho University
• [Int'l Joint Research] Hasanuddin University(インドネシア)
  • Country Name: INDONESIA
  • Counterpart Institution: Hasanuddin University
• [Journal Article] Lignans with melanogenesis effects from Premna serratifolia wood (2019)
  • Author(s): S. Woo, S. Hoshino, C.P. Wong, N.N. Win, M.D. Awoufack, Prema, H. Ngwe, H. Zhang, F. Hayashi, I. Abe, H. Morita
  • Journal Title: Fitoterapia Volume: 133 Pages: 35~42
  • DOI: 10.1016/j.fitote.2018.12.008
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] A new tetrahydrofuran type lignan from Premna serratifolia wood (2019)
  • Author(s): S. Woo, C.P. Wong, N.N. Win, S. Hoshino, Prema, H. Ngwe, I. Abe, H. Morita
  • Journal Title: Nat Prod Commun Volume: 14 Pages: 113~116
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Bis-iridoid and iridoid glycosides: Viral protein R inhibitors from Picrorhiza kurroa collected in Myanmar (2019)
  • Author(s): N.N. Win, T. Kodama, K.Z.W. Lae, Y.Y. Win, H. Ngwe, I Abe, H. Morita
  • Journal Title: Fitoterapia Volume: 134 Pages: 101~107
  • DOI: 10.1016/j.fitote.2019.02.016
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Brominated diphenyl ethers including a new tribromoiododiphenyl ether from a Vietnamese marine sponge Arenosclera sp. and their antibacterial activities (2019)
  • Author(s): D. Ki, M.D. Awouafack, C.P. Wong, H.M. Nguyen, Q. M. Thai, L.H.T. Nu, H. Morita
  • Journal Title: Chem Biodivers Volume: 16 Pages: e1800593
  • DOI: 10.1002/cbdv.201800593
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Two new pyrrolo-2-aminoimidazoles from a Myanmarese marine sponge, Clathria prolifera (2018)
  • Author(s): S. Woo, N.N. Win, C.P. Wong, T. Ito, S. Hoshino, H. Ngwe, A.A. Aye, N.M. Han, H. Zhang, F. Hayashi, I. Abe, H. Morita
  • Journal Title: J Nat Med Volume: 72 Pages: 803~807
  • DOI: 10.1007/s11418-018-1205-y
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Huperphlegmines A and B, two novel Lycopodium alkaloids with an unprecedented skeleton from Huperzia phlegmaria, and their acetylcholinesterase inhibitory activities (2018)
  • Author(s): H.T. Nguyen, H.T. Doan, D.V. Ho, K. T. Pham, A. Raal, H. Morita
  • Journal Title: Fitoterapia Volume: 129 Pages: 267~271
  • DOI: 10.1016/j.fitote.2018.07.016
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Pogostemins A-C, three new cytotoxic meroterpenoids from Pogostemon auricularius (2018)
  • Author(s): H.T. Nguyen, L.T.T. Tran, D.V. Ho, D.V. Le, A. Raal, H. Morita
  • Journal Title: Fitoterapia Volume: 130 Pages: 100~104
  • DOI: 10.1016/j.fitote.2018.08.015
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] A new Limonoid from Chisocheton paniculatus Fruit collected in Vietnam and its NO production inhibitory activity (2018)
  • Author(s): H.T. Nguyen, H.V. Duc, A. Raal, H. Morita
  • Journal Title: Nat Prod Commn Volume: 13 Pages: 1255~1257
  • Peer Reviewed / Int'l Joint Research
• [Presentation] Synthesis of unnatural compounds by enzyme engineering (2018)
  • Author(s): Morita H.
  • Organizer: 11th International Symposium on Chromatography of Natural Products
  • Int'l Joint Research / Invited
• [Presentation] Synthesis of unnatural compounds by enzyme engineering (2018)
  • Author(s): Morita H.
  • Organizer: Seminar Nasional Kefarmasian Indonesian Pharmaceutical Update
  • Int'l Joint Research / Invited
• [Presentation] Discovery of new lignans from wood of Premna integrifolia collected in Myanmar (2018)
  • Author(s): Woo S., Win N. N., Morita H.
  • Organizer: 第５回富山・バーゼル医薬品研究開発シンポジウム
• [Presentation] Potent HIV-1 Vpr inhibitors from Kaempferia pulchra Rhizomes Collected in Myanmar (2018)
  • Author(s): Win N. N., Morita H.
  • Organizer: 第５回富山・バーゼル医薬品研究開発シンポジウム
• [Presentation] New sesquiterpene quinones from a Vietnamese marine sponge Spongia sp.and their biological activities (2018)
  • Author(s): Nguyen H.M., Morita H.
  • Organizer: 第５回富山・バーゼル医薬品研究開発シンポジウム
• [Presentation] Two new quassinoids isolated from a medicinal plant Picrasma javanica of Myanmar (2018)
  • Author(s): Prema, Wong C. P., Awouafack M. D., Win N. N., Ngwe H., Morita H.
  • Organizer: The 3rd International Symposium on Toyama-Asia-Africa Pharmaceutical Network
  • Int'l Joint Research
• [Presentation] New sesquiterpene aminoquinones from a Vietnamese Spongia sp. and their biological activities (2018)
  • Author(s): Nguyen H. M., Ito T., Morita H.
  • Organizer: 第65回日本生薬学会年会
• [Presentation] Melanogenesis is inhibitor tetrahydrofuran lignans from Premna integrifolia collected in Myanmar (2018)
  • Author(s): Win N. N., Woo S., Prema, Wong C. P., Ito T., Ngwe H., Morita H.
  • Organizer: 第65回日本生薬学会年会
• [Presentation] Synthesis of unnatural compounds by exploiting secondary metabolite enzyme (2018)
  • Author(s): Morita H.
  • Organizer: The 60th Anniversary of School of Chinese Materia Medica Conference
  • Invited
• [Presentation] Anti-melanin deposition activity of a new tetrahydrofuran lignin from Premna serratifolia wood (2018)
  • Author(s): Woo S., Wong C. P., Win N. N., Hoshino S., Prema, Ngwe H., Abe I., Morita H.
  • Organizer: The 10th KSP-JSP-CSP Joint Symposium on Pharmacognosy
• [Remarks] 富山大学和漢医薬学総合研究所 天然物化学分野
  • URL: http://www.inm.u-toyama.ac.jp/napc/index.html