Abstract
Two new bisindole alkaloids, leucophyllinines A (1) and B (2) consisting of eburnane and quebrachamine-type skeletons were isolated from the bark of Leuconotis eugeniifolia, and their structures were elucidated on the basis of spectroscopic data. Leucophyllinines A and B showed antiplasmodial activities against Plasmodium falciparum 3D7.
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Nugroho AE, Hashimoto A, Wong CP, Yokoe H, Tsubuki M, Kaneda T, Hadi AHA, Morita H (2018) Ceramicines M-P from Chisocheton ceramicus: isolation and structure–activity relationship study. J Nat Med 72:64–72
Nugroho AE, Inoue D, Wong CP, Hirasawa Y, Kaneda T, Shirota O, Hadi AHA, Morita H (2018) Reinereins A and B, new onocerane triterpenoids from Reinwardtiodendron cinereum. J Nat Med 72:588–592
Nugroho AE, Matsumoto M, Sotozono Y, Kaneda T, Hadi AHA, Morita H (2018) Cycloartane triterpenoids with anti-melanin deposition activity. Nat Prod Commun 13:809–812
Kaneda T, Matsumoto M, Sotozono Y, Fukami S, Nugroho AE, Hirasawa Y, Hamid AHA, Morita H (2019) Cycloartane triterpenoid (23R, 24E)-23-acetoxymangiferonic acid inhibited proliferation and migration in B16-F10 melanoma via MITF downregulation caused by inhibition of both β-catenin and c-Raf–MEK1–ERK signaling axis. J Nat Med 73:47–58
Nugroho AE, Sugai M, Hirasawa Y, Hosoya T, Awang K, Hadi AHA, Ekasari W, Widyawaruyanti A, Morita H (2011) New antiplasmodial indole alkaloids from Hunteria zeylanica. Bioorg Med Chem Lett 21:3417–3419
Hirasawa Y, Hara M, Nugroho AE, Sugai M, Zaima K, Kawahara N, Goda Y, Awang K, Hadi AHA, Litaudon M, Morita H (2010) Bisnicalaterines B and C, atropisomeric bisindole alkaloids from Hunteria zeylanica, showing vasorelaxant activity. J Org Chem 75:4218–4223
Nugroho AE, Hirasawa Y, Kawahara N, Goda Y, Awang K, Hadi AHA, Morita H (2009) Bisnicalaterine A, a vobasine–vobasine bisindole alkaloid from Hunteria zeylanica. J Nat Prod 72:1502–1506
Oshimi S, Deguchi J, Hirasawa Y, Ekasari W, Widyawaruyanti A, Wahyuni TS, Zaini NC, Shirota O, Morita H (2009) Cassiarins C–E, antiplasmodial alkaloids from the flowers of Cassia siamea. J Nat Prod 72:1899–1901
Morita H, Oshimi S, Hirasawa Y, Koyama K, Honda T, Ekasari W, Indrayanto G, Zaini NC (2007) Cassiarins A and B, novel antiplasmodial alkaloids from Cassia siamea. Org Lett 9:3691–3693
Nugroho AE, Zhang W, Hirasawa Y, Tang Y, Wong CP, Kaneda T, Hadi AHA, Morita H (2018) Bisleuconothines B-D, modified eburnane–aspidosperma bisindole alkaloids from Leuconotis griffithii. J Nat Prod 81:2600–2604
Morita H, Nugroho AE, Nagakura Y, Hirasawa Y, Yoshida H, Kaneda T, Shirota O, Ismail IS (2014) Chrotacumines G-J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity. Bioorg Med Chem Lett 24:2437–2439
Nugroho AE, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Shirota O, Ekasari W, Widyawaruyanti A, Morita H (2012) Antiplasmodial indole alkaloids from Leuconotis griffithii. J Nat Med 66:350–353
Motegi M, Nugroho AE, Hirasawa Y, Arai T, Hadi AHA, Morita H (2012) Leucomidines A–C, novel alkaloids from Leuconotis griffithii. Tetrahedron Lett 53:1227–1230
Nugroho AE, Hirasawa Y, Hosoya T, Awang K, Hadi AHA, Morita H (2010) Bisleucocurine A, a novel bisindole alkaloid from Leuconotis griffithii. Tetrahedron Lett 51:2589–2592
Hirasawa Y, Shoji T, Arai T, Nugroho AE, Deguchi J, Hosoya T, Uchiyama N, Goda Y, Awang K, Hadi AHA, Shiro M, Morita H (2010) Bisleuconothine A, an eburnane-aspidosperma bisindole alkaloid from Leuconotis griffithii. Bioorg Med Chem Lett 20:2021–2024
Hirasawa Y, Dai X, Deguchi J, Hatano S, Sasaki T, Ohtsuka R, Nugroho AE, Kaneda T, Morita H (2019) New vasorelaxant indole alkaloids, taberniacins A and B, from Tabernaemontana divaricata. J Nat Med. https://doi.org/10.1007/s11418-019-01293-9
Wong CP, Seki A, Horiguchi K, Shoji T, Arai T, Nugroho AE, Hirasawa Y, Sato F, Kaneda T, Morita H (2015) Bisleuconothine A induces autophagosome formation by interfering with AKT-mTOR signaling pathway. J Nat Prod 78:1656–1662
Deguchi J, Shoji T, Nugroho AE, Hirasawa Y, Hosoya T, Shirota O, Awang K, Hadi AHA, Morita H (2010) Eucophylline, a tetracyclic vinylquinoline alkaloid from Leuconotis eugenifolius. J Nat Prod 73:1727–1729
Goh SH, Mohd Ali AR, Wong WH (1989) Alkaloids of Leuconotis griffithii and L. eugenifolia (Apocynaceae). Tetrahedron 45:7899–7920
Yan KX, Feng XZ (1997) Melaxillarinine, a new bisindole alkaloid from Melodinus axillaris. Chin Chem Lett 8:313–314
Nugroho AE, Morita H (2014) Circular dichroism calculation for natural products. J Nat Med 68:1–10
Trager W, Jensen J (1976) Human malaria parasites in continuous culture. Science 193:673–675
Lambros C, Vanderberg JP (1979) Synchronization of Plasmodium falciparum erythrocytic stages in culture. J Parasitol 65:418–420
Tougan T, Suzuki Y, Itagaki S, Izuka M, Toya Y, Uchihashi K, Horii T (2018) An automated haematology analyzer XN-30 distinguishes developmental stages of falciparum malaria parasite cultured in vitro. Malar J 17:59
Tougan T, Toya Y, Uchihashi K, Horii T (2019) Application of the automated haematology analyzer XN-30 for discovery and development of anti-malarial drugs. Malar J 18:8
Aizawa S, Okamoto T, Sugiyama Y, Kouwaki T, Ito A, Suzuki T, Ono C, Fukuhara T, Yamamoto M, Okochi M, Hiraga N, Imamura M, Chayama K, Suzuki R, Shoji I, Moriishi K, Moriya K, Koike K, Matsuura Y (2016) TRC8-dependent degradation of hepatitis C virus immature core protein regulates viral propagation and pathogenesis. Nat Commun 7:11379–11390
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Tang, Y., Nugroho, A.E., Hirasawa, Y. et al. Leucophyllinines A and B, bisindole alkaloids from Leuconotis eugeniifolia. J Nat Med 73, 533–540 (2019). https://doi.org/10.1007/s11418-019-01297-5
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DOI: https://doi.org/10.1007/s11418-019-01297-5