Skip to main content
Hauptrubriken
CME Facharzt-Training Webinare Zeitschriften Bücher e.Medpedia Podcast
Service
Jobbörse Info & Hilfe
Fachgebiete
Anästhesiologie Allgemeinmedizin Arbeitsmedizin Augenheilkunde Chirurgie Dermatologie Gynäkologie und Geburtshilfe HNO Innere Medizin Kardiologie Neurologie Onkologie und Hämatologie Orthopädie und Unfallchirurgie Pädiatrie Pathologie Psychiatrie Radiologie Rechtsmedizin Urologie Zahnmedizin
Themen
Typ-2-Diabetes und Adipositas Klimawandel und Gesundheit Neues aus dem Markt Praxis und Beruf Seltene Erkrankungen GOÄ & EBM
Sammlungen
Kasuistiken Algorithmen & Infografiken Blickdiagnosen Arthropedia FlapFinder (für Dermatochirurgen) Videos Kongressberichterstattung Medizin für Apothekerinnen und Apotheker Fachpsychotherapie Für Ärztinnen und Ärzte in Weiterbildung Für Medizinstudierende Patientenratgeber
Erweiterte Suche
Anmelden
nach oben
Journal of Natural Medicines
Erschienen in:

12.02.2024 | Original Paper

Vincazalidine A, a unique bisindole alkaloid from Catharanthus roseus

verfasst von: Yusuke Hirasawa, Ayaka Kase, Akie Okamoto, Keigo Suzuki, Mizuki Hiroki, Toshio Kaneda, Nahoko Uchiyama, Hiroshi Morita

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2024

Einloggen, um Zugang zu erhalten

Abstract

A new dimeric indole alkaloid, vincazalidine A consisting of an aspidosperma type and a modified iboga type with 1-azatricyclo ring system consisting of one azepane and two piperidine rings coupled with an oxazolidine ring was isolated from Catharanthus roseus, and the structure including absolute stereochemistry was elucidated on the basis of spectroscopic data as well as DP4 statistical analysis. Vincazalidine A induced G2 arrest and subsequent apoptosis in human lung carcinoma cell line, A549 cells.

Graphical abstract

Anhänge
Nur mit Berechtigung zugänglich
Literatur
1.
Dey A, Mukherjee A, Chaudhury M (2017) Alkaloids from apocynaceae: origin, pharmacotherapeutic properties, and structure-activity studies. Stud Nat Prod Chem 52:373–488CrossRef
2.
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 26:488CrossRefPubMedPubMedCentral
3.
Mayer S, Keglevich P, Keglevich A, Hazai L (2021) New anticancer vinca alkaloids in the last decade-A mini-review. Curr Org Chem 25:1224–1234CrossRef
4.
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 77:610–613CrossRefPubMed
5.
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 77:596–603CrossRefPubMedPubMedCentral
6.
7.
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 76:645–653CrossRefPubMedPubMedCentral
8.
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 76:756–764CrossRefPubMedPubMedCentral
9.
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 76:171–177CrossRefPubMed
10.
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 75:403–407CrossRefPubMed
11.
Nugroho AE, Hirasawa Y, Kaneda T, Shirota O, Matsuno M, Mizukami H, Morita H (2021) Triterpenoids from Walsura trichostemon. J Nat Med 75:415–422CrossRefPubMed
12.
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 73:47–58CrossRefPubMed
13.
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 75:633–642CrossRefPubMedPubMedCentral
14.
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 73:820–825CrossRefPubMed
15.
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 73:627–632CrossRefPubMed
16.
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 83:153423CrossRef
17.
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 81:2600–2604CrossRefPubMed
18.
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 66:350–353CrossRefPubMed
19.
Motegi M, Nugroho AE, Hirasawa Y, Arai T, Hadi AHA, Morita H (2012) Leucomidines A-C, novel alkaloids from Leuconotis griffithii. Tetrahedron Lett 53:1227–1230CrossRef
20.
Nugroho AE, Hirasawa Y, Hosoya T, Awang K, Hadi AHA, Morita H (2010) Bisleucocurine A, a novel bisindole alkaloid from Leuconotis griffithii. Tetrahedron Lett 51:2589–2592CrossRef
21.
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 20:2021–2024CrossRefPubMed
22.
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 73:533–540CrossRefPubMed
23.
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 75:408–414CrossRefPubMed
24.
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 90:601–606CrossRef
25.
26.
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 53:1227–1231CrossRefPubMed
27.
Smith SG, Goodman JM (2010) Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability. J Am Chem Soc 132:12946–12959CrossRefPubMed
28.
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 21:4003–4007CrossRefPubMed
29.
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 63:7421–7427CrossRefPubMed
30.
Dong JG, Bornmann W, Nakanishi K, Berova N (1995) Structural studies of vinblastine alkaloid by exciton coupled circular dichroism. Phytochemistry 40:1821–1824CrossRefPubMed
31.
32.
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 41:1001–1005CrossRefPubMed
33.
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 86:2294–2303CrossRefPubMedPubMedCentral
Metadaten
Titel
Vincazalidine A, a unique bisindole alkaloid from Catharanthus roseus
verfasst von
Yusuke Hirasawa
Ayaka Kase
Akie Okamoto
Keigo Suzuki
Mizuki Hiroki
Toshio Kaneda
Nahoko Uchiyama
Hiroshi Morita
Publikationsdatum
12.02.2024
Verlag
Springer Nature Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 2/2024
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-023-01775-x

Weitere Artikel der Ausgabe 2/2024

Evodiamine inhibits growth of vemurafenib drug-resistant melanoma via suppressing IRS4/PI3K/AKT signaling pathway

  • Original Paper

Upregulation of tumor suppressor PIAS3 by Honokiol promotes tumor cell apoptosis via selective inhibition of STAT3 tyrosine 705 phosphorylation

  • Original Paper

Revision of NMR assignment for Morin-3-O-glucoside and microbial production of Morin-2’-O-glucoside

  • Note

Angelica dahurica extract and its effective component bergapten alleviated hepatic fibrosis by activating FXR signaling pathway

  • Note

Comprehensive study on genetic and chemical diversity of Asian medicinal plants, aimed at sustainable use and standardization of traditional crude drugs

  • Open Access
  • Review

Phytohemagglutinin from Phaseolus vulgaris enhances the lung cancer cell chemotherapy sensitivity by changing cell membrane permeability

  • Original Paper