nach oben

Erschienen in:

16.02.2018 | Note

Reinereins A and B, new onocerane triterpenoids from Reinwardtiodendron cinereum

verfasst von: Alfarius Eko Nugroho, Daisuke Inoue, Chin Piow Wong, Yusuke Hirasawa, Toshio Kaneda, Osamu Shirota, A. Hamid A. Hadi, Hiroshi Morita

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2018

Einloggen, um Zugang zu erhalten

Abstract

Bioactivity guided separation of Reinwardtiodendron cinereum barks methanol extract led to the isolation of two new onocerane triterpenoids, reinereins A and B (1 and 2), together with three known onocerane triterpenoids. Their structures were elucidated on the basis of NMR spectroscopic data. In vitro cytotoxic activities of the isolated compounds against several type of cancer cells were evaluated.

Mabberley DJ (2011) Meliaceae Flowering plants Eudicots: Sapindales, Cucurbitales, Myrtaceae. Kubitzki K., Springer, p 185-211

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

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 20:2021–2024CrossRef

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 75:4218–4223CrossRef

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 66:350–353CrossRef

Nagakura Y, Nugroho AE, Hirasawa Y, Hosoya T, Rahman A, Kusumawati I, Zaini NC, Morita H (2013) Sanjecumins A and B: new limonoids from Sandoricum koetjape. J Nat Med 67:381–385CrossRef

Wong CP, Deguchi J, Nugroho AE, Kaneda T, Hadi AHA, Morita H (2013) Ceramicines from Chisocheton ceramicus as lipid-droplets accumulation inhibitors. Bioorg Med Chem Lett 23:1786–1788CrossRef

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 24:2437–2439CrossRef

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 78:1656–1662CrossRef

10.

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 72:64–72CrossRef

11.

Nugroho AE, Sugiura R, Momota T, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Morita H (2015) Dysosesquiflorins A and B, sesquiterpenoids from Dysoxylum densiflorum. J Nat Med 69:411–415CrossRef

12.

Mori R, Nugroho AE, Hirasawa Y, Wong CP, Kaneda T, Shirota O, Hadi AHA, Morita H (2014) Opaciniols A-C, new terpenoids from Garcinia opaca. J Nat Med 68:186–191CrossRef

13.

Wong C, Shimada M, Nugroho AE, Hirasawa Y, Kaneda T, Hadi AHA, Osamu S, Morita H (2012) Ceramicines J-L, new limonoids from Chisocheton ceramicus. J Nat Med 66:566–570CrossRef

14.

Kiang AK, Tan EL, Lim FY, Habaguchi K, Nakanishi K, Fachan L, Ourisson G (1967) Lansic acid, a bicyclic triterpene. Tetrahedron Lett 8:3571–3574CrossRef

15.

Nishizawa M, Nishide H, Kosela S, Hayashi Y (1983) Structure of lansiosides: biologically active new triterpene glycosides from Lansium domesticum. J Org Chem 48:4462–4466CrossRef

16.

Tanaka T, Ishibashi M, Fujimoto H, Okuyama E, Koyano T, Kowithayakorn T, Hayashi M, Komiyama K (2002) New onoceranoid triterpene constituents from Lansium domesticum. J Nat Prod 65:1709–1711CrossRef

17.

Habaguchi K, Watanabe M, Nakadaira Y, Nakanishi K, Kiang AK, Lim FY (1968) The full structures of lansic acid and its minor congener, an unsymmetric onoceradienedione. Tetrahedron Lett 9:3731–3734CrossRef

18.

Alexandra NM, Samuel R, Chase MW, Caroline MP, Greger H (2005) Aglaia (Meliaceae): an evaluation of taxonomic concepts based on DNA data and secondary metabolites. Am J Bot 92:534–543CrossRef

19.

Dong S-H, Zhang C-R, Dong L, Wu Y, Yue J-M (2011) Onoceranoid-Type triterpenoids from Lansium domesticum. J Nat Prod 74:1042–1048CrossRef

20.

Tilaar M, Wih WL, Ranti AS, Wasitaatmadja SM, Suryaningsih Junardy FD, Maily (2008) Review of Lansium domesticum correa and its use in cosmetics. Bol Latinoam Caribe Plant Med Aromat 7:183–189

Titel: Reinereins A and B, new onocerane triterpenoids from Reinwardtiodendron cinereum
verfasst von: Alfarius Eko Nugroho
Daisuke Inoue
Chin Piow Wong
Yusuke Hirasawa
Toshio Kaneda
Osamu Shirota
A. Hamid A. Hadi
Hiroshi Morita
Publikationsdatum: 16.02.2018
Verlag: Springer Singapore
Erschienen in: Journal of Natural Medicines / Ausgabe 2/2018
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-018-1188-8

Springer Medizin

Abstract

Bitte loggen Sie sich ein, um Zugang zu diesem Inhalt zu erhalten

Weitere Artikel der Ausgabe 2/2018

Discrimination of Schisandrae Chinensis Fructus and Schisandrae Sphenantherae Fructus based on fingerprint profiles of hydrophilic components by high-performance liquid chromatography with ultraviolet detection

Lanostane triterpenoids from Fomitopsis officinalis and their trypanocidal activity

Oxyresveratrol prevents murine H22 hepatocellular carcinoma growth and lymph node metastasis via inhibiting tumor angiogenesis and lymphangiogenesis

Structure–activity relationships of flavanones, flavanone glycosides, and flavones in anti-degranulation activity in rat basophilic leukemia RBL-2H3 cells

New diterpenes from Nigella damascena seeds and their antiviral activities against herpes simplex virus type-1

Lignosulfonic acid attenuates NF-κB activation and intestinal epithelial barrier dysfunction induced by TNF-α/IFN-γ in Caco-2 cells