Dey A, Mukherjee A, Chaudhury M (2017) Alkaloids from apocynaceae: origin, pharmacotherapeutic properties, and structure-activity studies. Stud Nat Prod Chem 52:373–488

Article  CAS  Google Scholar 

Mohammed AE, Abdul-Hameed ZH, Alotaibi MO, Bawakid NO, Sobahi TR, Abdel-Lateff A, Alarif WM (2021) Chemical diversity and bioactivities of monoterpene indole alkaloids (MIAs) from Six apocynaceae genera. Molecules 26:488

Article  CAS  PubMed  PubMed Central  Google Scholar 

Mayer S, Keglevich P, Keglevich A, Hazai L (2021) New anticancer vinca alkaloids in the last decade-A mini-review. Curr Org Chem 25:1224–1234

Article  CAS  Google Scholar 

Hirasawa Y, Hattori R, Ohtani M, Uchiyama N, Hakamatsuka T, Morita H (2023) Cryptadine C, a new C27N3-type Lycopodium alkaloid from Lycopodium cryptomerinum. J Nat Med 77:610–613

Article  CAS  PubMed  Google Scholar 

Nugroho AE, Wong CP, Hirasawa Y, Kaneda T, Tougan T, Horii T, Hadi AHA, Morita H (2023) Ceramicines Q-T from Chisocheton ceramicus. J Nat Med 77:596–603

Article  CAS  PubMed  PubMed Central  Google Scholar 

Nugroho AE, Komuro T, Kawaguchi T, Shindo Y, Wong CP, Hirasawa Y, Kaneda T, Tougan T, Horii T, Hadi AHA, Morita H (2024) Ceramicines U–Z from Chisocheton ceramicus and structure–antimalarial activity relationship study. J Nat Med. https://doi.org/10.1007/s11418-023-01746-2

Article  PubMed  Google Scholar 

Ogasawara A, Noguchi R, Shigi T, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Hadi AHA, Morita H (2022) Caloforines A-G, coumarins from the bark of Calophyllum scriblitifolium. J Nat Med 76:645–653

Article  CAS  PubMed  PubMed Central  Google Scholar 

Nugroho AE, Tange M, Kusakabe S, Hirasawa Y, Shirota O, Michiyo M, Mizukami H, Tougan T, Horii T, Morita H (2022) Chukranoids A-I, isopimarane diterpenoids from Chukrasia velutina. J Nat Med 76:756–764

Article  CAS  PubMed  PubMed Central  Google Scholar 

Hirasawa Y, Tanaka T, Hirasawa S, Wong DP, Uchiyama N, Kaneda T, Goda Y, Morita H (2022) Cliniatines A-C, new amaryllidaceae alkaloids from Clivia miniata, inhibiting acetylcholinesterase. J Nat Med 76:171–177

Article  CAS  PubMed  Google Scholar 

Hirasawa Y, Agawa-kakimoto M, Zaima K, Uchiyama N, Goda Y, Morita H (2021) Complanadine F, a novel dimeric alkaloid from Lycopodium complanatum. J Nat Med 75:403–407

Article  CAS  PubMed  Google Scholar 

Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Matsuno M, Mizukami H, Morita H (2021) Triterpenoids from Walsura trichostemon. J Nat Med 75:415–422

Article  CAS  PubMed  Google Scholar 

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

Article  CAS  PubMed  Google Scholar 

Amelia P, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Morita H (2021) Two new bisindole alkaloids from Tabernaemontana macrocarpa Jack. J Nat Med 75:633–642

Article  CAS  PubMed  PubMed Central  Google Scholar 

Amelia P, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Morita H (2019) Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med 73:820–825

Article  CAS  PubMed  Google Scholar 

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 73:627–632

Article  CAS  PubMed  Google Scholar 

Hirasawa Y, Yasuda R, Minami W, Hirata M, Nugroho AE, Tougan T, Uchiyama N, Hakamatsuka T, Horii T, Morita H (2021) Divaricamine A, a new anti-malarial trimeric monoterpenoid indole alkaloid from Tabernaemontana divaricata. Tetrahedron Lett 83:153423

Article  CAS  Google Scholar 

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

Article  CAS  PubMed  Google Scholar 

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

Article  CAS  PubMed  Google Scholar 

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

Article  CAS  Google Scholar 

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

Article  CAS  Google Scholar 

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

Article  CAS  PubMed  Google Scholar 

Tang Y, Nugroho AE, Hirasawa Y, Tougan T, Horii T, Hadi AHA, Morita H (2019) Leucophyllinines A and B, bisindole alkaloids from Leuconotis eugeniifolia. J Nat Med 73:533–540

Article  CAS  PubMed  Google Scholar 

Nugroho AE, Ono Y, Jin E, Hirasawa Y, Kaneda T, Rahman A, Kusumawati I, Tougan T, Horii T, Zaini NC, Morita H (2021) Bisindole alkaloids from Voacanga grandifolia Leaves. J Nat Med 75:408–414

Article  CAS  PubMed  Google Scholar 

Morita H, Haseo A, Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Rahman A, Kusumawati I, Cholies Zaini N (2015) A new indole alkaloid from Voacanga grandifolia. Heterocycles 90:601–606

Article  Google Scholar 

Hiroki M, Abulikemu A, Totsuka C, Hirasawa Y, Kaneda T, Morita H (2024) Isovincathicine from Catharanthus roseus induces apoptosis in A549 cells. J Nat Med. https://doi.org/10.1007/s11418-023-01740-8

Article  PubMed  Google Scholar 

Svoboda GH, Barnes AJ Jr (1964) Alkaloids of Vinca rosea Linn. (Catharantbus roseus G. Don) XXIV. Vinaspine, vincathicine, rovidine, desacetyl VLB, and vinaphamine. J Pharm Sci 53:1227–1231

Article  CAS  PubMed  Google Scholar 

Smith SG, Goodman JM (2010) Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability. J Am Chem Soc 132:12946–12959

Article  CAS  PubMed  Google Scholar 

Grimblat N, Gavín J, Hernández DA, Sarotti AM (2019) Combining the power of j coupling and DP4 Analysis on stereochemical assignments: the J-DP4 methods. Org Lett 21:4003–4007

Article  CAS  PubMed  Google Scholar 

Cairns E, Hashmi MA, Singh AJ, Eakins G, Lein M, Keyzers R (2015) Structure of echivulgarine, a pyrrolizidine alkaloid isolated from the pollen of Echium vulgare. J Agric Food Chem 63:7421–7427

Article  CAS  PubMed  Google Scholar 

Dong JG, Bornmann W, Nakanishi K, Berova N (1995) Structural studies of vinblastine alkaloid by exciton coupled circular dichroism. Phytochemistry 40:1821–1824

Article  CAS  PubMed  Google Scholar 

TURBOMOLE GmBH (2019) TURBOMOLE V7.0, a development of University of Karlsruhe and Forschungszentrum karlsruhe GmbH, 1989-2007. https://www.turbomole.org/

Tafur SS, Occolowitz JL, Elzey TK, Paschal JW, Dorman DE (1976) Alkaloids of Vinca rosea. (Catharanthus roseus G. Don). XXXVII. Structure of vincathicine. J Org Chem 41:1001–1005

Article  CAS  PubMed  Google Scholar 

Sánchez-Martínez HA, Morán-Pinzón JA, del Olmo Fernández E, López ED, Adserias Vistué JF, López-Pérez JL, Guerrero De León E (2023) Synergistic combination of NAPROC-13 and NMR 13C DFT calculations: a powerful approach for revising the structure of natural products. J Nat Prod 86:2294–2303

Article  PubMed  PubMed Central  Google Scholar