Chukranoids A-I, isopimarane diterpenoids from Chukrasia velutina.
Antimalarial activity
Chukranoids A–I
Chukrasia velutina
Isopimarane diterpenoid
Meliaceae
Journal
Journal of natural medicines
ISSN: 1861-0293
Titre abrégé: J Nat Med
Pays: Japan
ID NLM: 101518405
Informations de publication
Date de publication:
Sep 2022
Sep 2022
Historique:
received:
10
02
2022
accepted:
19
03
2022
pubmed:
6
5
2022
medline:
30
8
2022
entrez:
5
5
2022
Statut:
ppublish
Résumé
Bioactivity guided separation of Chukrasia velutina root methanolic extract led to the isolation of nine new isopimarane diterpenoids, chukranoids A-I (1-9). The absolute configuration was then assigned by comparing the experimental CD spectra and the calculated CD spectra. Chukranoids A-I (1-9) showed moderate antimalarial activity against Plasmodium falciparum 3D7 strain. It seems that conjugate system in the isopimarane skeleton may influence their antimalarial activity.
Identifiants
pubmed: 35511335
doi: 10.1007/s11418-022-01623-4
pii: 10.1007/s11418-022-01623-4
pmc: PMC9069220
doi:
Substances chimiques
Abietanes
0
Antimalarials
0
Diterpenes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
756-764Informations de copyright
© 2022. The Author(s) under exclusive licence to The Japanese Society of Pharmacognosy.
Références
Mabberley DJ (2011) Meliaceae. Flowering Plants Eudicots: Sapindales, Cucurbitales, Myrtaceae. Kubitzki K, Springer: 185–211
Ragettli T, Tamm C (1978) The Chukrasines A, B, C, D and E, five new tetranortriterpenes from Chukrasia tabularis A. JUSS Helv Chim Acta 61:1814–1831
doi: 10.1002/hlca.19780610527
Luo J, Li Y, Wang JS, Kong LY (2011) D-Ring-opened phragmalin-type limonoids from Chukrasia tabularis var. velutina. Chem Biodivers 8:2261–2269
doi: 10.1002/cbdv.201000285
Luo J, Li Y, Wang JS, Lu J, Kong LY (2012) Three new C-15-isobutyryl 16-norphragmalin-type limonoids from Chukrasia tabularis var. velutina. Phytochem Lett 5:249–252
doi: 10.1016/j.phytol.2012.01.005
Luo J, Wang JS, Luo JG, Wang XB, Kong LY (2011) Velutabularins A-J, phragmalin-type limonoids with novel cyclic moiety from Chukrasia tabularis var. velutina. Tetrahedron 67:2942–2948
doi: 10.1016/j.tet.2011.02.049
Luo J, Li Y, Wang JS, Wang XB, Luo JG, Kong LY (2011) Phragmalin-type limonoid orthoesters from Chukrasia tabularis var. velutina. Chem Pharm Bull 59:225–230
doi: 10.1248/cpb.59.225
Prema, Wong CP, Kodama T, Nugroho AE, El-Desoky AH, Awouafack MD, Win YY, Ngwe H, Abe I, Morita H, Morita H (2020) Three new quassinoids isolated from the wood of Picrasma javanica and their anti-Vpr activities. J Nat Med 74:571–578
doi: 10.1007/s11418-020-01411-y
Prema, Wong CP, Awouafack MD, Nugroho AE, Win YY, Win NN, Ngwe H, Morita H, Morita H (2019) Two new quassinoids and other constituents from the Picrasma javanica wood and their biological activities. J Nat Med 73:589–596
doi: 10.1007/s11418-018-01279-z
Kaneda T, Matsumoto M, Sotozono Y, Fukami S, Nugroho AE, Hirasawa Y, Hadi 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
doi: 10.1007/s11418-018-1233-7
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
doi: 10.1007/s11418-019-01297-5
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
doi: 10.1007/s11418-019-01293-9
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
doi: 10.1007/s11418-019-01317-4
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
doi: 10.1007/s11418-017-1109-2
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
doi: 10.1007/s11418-018-1188-8
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
doi: 10.1021/acs.jnatprod.8b00749
Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Morita H (2021) Triterpenoids from Walsura trichostemon. J Nat Med 75: 415–422
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
doi: 10.1007/s11418-020-01476-9
Nugroho AE, Ono Y, Jin E, Hirasawa Y, Kaneda T, Rahman A, Kusumawati I, Tougan T, Horii T, Zaini NC, Morita H, Tang Y, Nugroho AE, Hirasawa Y, Tougan T, Morita H (2021) Bisindole alkaloids from Voacanga grandifolia leaves. J Nat Med 75:408–414
doi: 10.1007/s11418-020-01475-w
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
doi: 10.1007/s11418-021-01510-4
Spartan Software https://www.wavefun.com/products/spartan.html
TURBOMOLE GmbH (2019) TURBOMOLE V7.0, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989–2007. https://www.turbomole.org/
Asili J, Lambert M, Ziegler HL, Stærk D, Sairafianpour M, Witt M, Asghari G, Ibrahimi IS, Jaroszewski JW (2004) Labdanes and isopimaranes from Platycladus orientalis and their effects on erythrocyte membrane and on Plasmodium falciparum growth in the erythrocyte host cells. J Nat Prod 67:631–637
doi: 10.1021/np034033e
Trager W, Jensen JB (1976) Human malaria parasites in continuous culture. Science (80- ) 193:673 LP – 675. https://doi.org/10.1126/science.781840
Lambros C, Vanderberg JP (1979) Synchronization of Plasmodium falciparum erythrocytic stages in culture. J Parasitol 65:418–420
doi: 10.2307/3280287
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. https://doi.org/10.1186/s12936-018-2208-6
doi: 10.1186/s12936-018-2208-6
pubmed: 29391022
pmcid: 5796453
Toya Y, Tougan T, Horii T, Uchihashi K (2021) Lysercell M enhances the detection of stage-specific Plasmodium-infected red blood cells in the automated hematology analyzer XN-31 prototype. Parasitol Int 80:102206. https://doi.org/10.1016/j.parint.2020.102206
doi: 10.1016/j.parint.2020.102206
pubmed: 33049417
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. https://doi.org/10.1186/s12936-019-2642-0
doi: 10.1186/s12936-019-2642-0
pubmed: 30642330
pmcid: 6332852