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Erschienen in: Journal of Natural Medicines 3/2015

01.07.2015 | Note

Dysosesquiflorins A and B, sesquiterpenoids from Dysoxylum densiflorum

verfasst von: Alfarius E. Nugroho, Rio Sugiura, Takanori Momota, Yusuke Hirasawa, Chin Piow Wong, Toshio Kaneda, A. Hamid A. Hadi, Hiroshi Morita

Erschienen in: Journal of Natural Medicines | Ausgabe 3/2015

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Abstract

Two new aromadendrane sesquiterpenoids, dysosesquiflorins A and B (1 and 2), were isolated from Dysoxylum densiflorum bark, and their structures were elucidated on the basis of NMR spectroscopic data. These dysosesquiflorins showed in vitro cytotoxic activity against several cancer cell lines.
Literatur
1.
Zurück zum Zitat Mabberley DJ (2011) Meliaceae. In: Kubitzki K (ed) Flowering plants. Eudicots. Sapindales, Cucurbitales, Myrtaceae. Springer, Berlin, pp 185–211 Mabberley DJ (2011) Meliaceae. In: Kubitzki K (ed) Flowering plants. Eudicots. Sapindales, Cucurbitales, Myrtaceae. Springer, Berlin, pp 185–211
2.
Zurück zum Zitat Xie B-J, Yang S-P, Yue J-M (2008) Terpenoids from Dysoxylum densiflorum. Phytochemistry 69:2993–2997PubMedCrossRef Xie B-J, Yang S-P, Yue J-M (2008) Terpenoids from Dysoxylum densiflorum. Phytochemistry 69:2993–2997PubMedCrossRef
3.
Zurück zum Zitat Duh C-Y, Wang S-K, Chen I-S (2000) Cytotoxic prenyleudesmane diterpenes from the fruits of Dysoxylum kuskusense. J Nat Prod 63:1546–1547PubMedCrossRef Duh C-Y, Wang S-K, Chen I-S (2000) Cytotoxic prenyleudesmane diterpenes from the fruits of Dysoxylum kuskusense. J Nat Prod 63:1546–1547PubMedCrossRef
4.
Zurück zum Zitat Chen JL, Kernan MR, Jolad SD, Stoddart CA, Bogan M, Cooper R (2007) Dysoxylins A–D, tetranortriterpenoids with potent anti-RSV activity from Dysoxylum gaudichaudianum. J Nat Prod 70:312–315 Chen JL, Kernan MR, Jolad SD, Stoddart CA, Bogan M, Cooper R (2007) Dysoxylins A–D, tetranortriterpenoids with potent anti-RSV activity from Dysoxylum gaudichaudianum. J Nat Prod 70:312–315
5.
Zurück zum Zitat Adesanya SA, Païs M, Sévenet T, Cosson JP (1991) Apotirucallane triterpenes from Dysoxylum roseum. J Nat Prod 54:1588–1594CrossRef Adesanya SA, Païs M, Sévenet T, Cosson JP (1991) Apotirucallane triterpenes from Dysoxylum roseum. J Nat Prod 54:1588–1594CrossRef
6.
Zurück zum Zitat Liu H, Heilmann J, Rali T, Sticher O (2001) New tirucallane-type triterpenes from Dysoxylum variabile. J Nat Prod 64:159–163PubMedCrossRef Liu H, Heilmann J, Rali T, Sticher O (2001) New tirucallane-type triterpenes from Dysoxylum variabile. J Nat Prod 64:159–163PubMedCrossRef
7.
Zurück zum Zitat Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MIM, Lajis NH, Morita H (2009) Acutaxylines A and B, two novel triterpenes from Dysoxylum acutangulum. Tetrahedron Lett 50:4830–4832CrossRef Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MIM, Lajis NH, Morita H (2009) Acutaxylines A and B, two novel triterpenes from Dysoxylum acutangulum. Tetrahedron Lett 50:4830–4832CrossRef
8.
Zurück zum Zitat Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MIM, Lajis NH, Shiro M, Morita H (2009) Chrotacumines A–D, chromone alkaloids from Dysoxylum acutangulum. J Nat Prod 72:1879–1883PubMedCrossRef Ismail IS, Nagakura Y, Hirasawa Y, Hosoya T, Lazim MIM, Lajis NH, Shiro M, Morita H (2009) Chrotacumines A–D, chromone alkaloids from Dysoxylum acutangulum. J Nat Prod 72:1879–1883PubMedCrossRef
9.
Zurück zum Zitat 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 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
10.
Zurück zum Zitat Li C-S, Yu H-W, Li G-Y, Zhang G-L (2010) Chemical constituents from the roots of Dysoxylum densiflorum. Zhongguo Tianran Yaowu 8:270–273 Li C-S, Yu H-W, Li G-Y, Zhang G-L (2010) Chemical constituents from the roots of Dysoxylum densiflorum. Zhongguo Tianran Yaowu 8:270–273
11.
Zurück zum Zitat Gu J, Qian S-Y, Zhao Y-L, Cheng G-G, Hu D-B, Zhang B-H, Li Y, Liu Y-P, Luo X-D (2014) Prenyleudesmanes, rare natural diterpenoids from Dysoxylum densiflorum. Tetrahedron 70:1375–1382CrossRef Gu J, Qian S-Y, Zhao Y-L, Cheng G-G, Hu D-B, Zhang B-H, Li Y, Liu Y-P, Luo X-D (2014) Prenyleudesmanes, rare natural diterpenoids from Dysoxylum densiflorum. Tetrahedron 70:1375–1382CrossRef
12.
Zurück zum Zitat Gu J, Qian S-Y, Cheng G-G, Li Y, Liu Y-P, Luo X-D (2013) Chemical components of Dysoxylum densiflorum. Nat Prod Bioprospect 3:66–69PubMedCentralCrossRef Gu J, Qian S-Y, Cheng G-G, Li Y, Liu Y-P, Luo X-D (2013) Chemical components of Dysoxylum densiflorum. Nat Prod Bioprospect 3:66–69PubMedCentralCrossRef
13.
Zurück zum Zitat 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 68:186–191 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 68:186–191
14.
Zurück zum Zitat Wong CP, Kaneda T, Hadi AHA, Morita H (2014) Ceramicine B, a limonoid with anti-lipid droplets accumulation activity from Chisocheton ceramicus. J Nat Med 68:22–30PubMedCrossRef Wong CP, Kaneda T, Hadi AHA, Morita H (2014) Ceramicine B, a limonoid with anti-lipid droplets accumulation activity from Chisocheton ceramicus. J Nat Med 68:22–30PubMedCrossRef
15.
Zurück zum Zitat 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 67:381–385PubMedCrossRef 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 67:381–385PubMedCrossRef
16.
Zurück zum Zitat 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 66:350–353PubMedCrossRef 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 66:350–353PubMedCrossRef
17.
Zurück zum Zitat Zaima K, Koga I, Iwasawa N, Hosoya T, Hirasawa Y, Kaneda T, Ismail I, Lajis N, Morita H (2013) Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med 67:9–16PubMedCrossRef Zaima K, Koga I, Iwasawa N, Hosoya T, Hirasawa Y, Kaneda T, Ismail I, Lajis N, Morita H (2013) Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med 67:9–16PubMedCrossRef
18.
Zurück zum Zitat 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 66:566–570 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 66:566–570
19.
Zurück zum Zitat Nugroho AE, Momota T, Sugiura R, Hanzawa M, Yajima E, Nagakura Y, Yasuda N, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Fukaya H, Morita H (2014) Dysotriflorins A–M, triterpenoids from Dysoxylum densiflorum. Tetrahedron 70:9661–9667 Nugroho AE, Momota T, Sugiura R, Hanzawa M, Yajima E, Nagakura Y, Yasuda N, Hirasawa Y, Wong CP, Kaneda T, Hadi AHA, Fukaya H, Morita H (2014) Dysotriflorins A–M, triterpenoids from Dysoxylum densiflorum. Tetrahedron 70:9661–9667
20.
Zurück zum Zitat Rios MY, Estrada-Soto S, Flores-Morales V, Aguilar MI (2013) Chemical constituents from Flourensia resinosa S.F. Blake (Asteraceae). Biochem Syst Ecol 51:240–242CrossRef Rios MY, Estrada-Soto S, Flores-Morales V, Aguilar MI (2013) Chemical constituents from Flourensia resinosa S.F. Blake (Asteraceae). Biochem Syst Ecol 51:240–242CrossRef
21.
Zurück zum Zitat Mata R, Bye R, Linares E, Macias M, Rivero-Cruz I, Perez O, Timmermann BN (2003) Phytotoxic compounds from Flourensia cernua. Phytochemistry 64:285–291PubMedCrossRef Mata R, Bye R, Linares E, Macias M, Rivero-Cruz I, Perez O, Timmermann BN (2003) Phytotoxic compounds from Flourensia cernua. Phytochemistry 64:285–291PubMedCrossRef
22.
Zurück zum Zitat Fan W-W, Xu F-Q, Dong F-W, Li X-N, Wei X-Y, Zhou J, Hu J-M (2013) Dendrowardols A and B, two new sesquiterpenoids from Dendrobium wardianum Warner. Tetrahedron Lett 54:1928–1930CrossRef Fan W-W, Xu F-Q, Dong F-W, Li X-N, Wei X-Y, Zhou J, Hu J-M (2013) Dendrowardols A and B, two new sesquiterpenoids from Dendrobium wardianum Warner. Tetrahedron Lett 54:1928–1930CrossRef
23.
Zurück zum Zitat Zhang X, Gao H, Han H, Liu H, Wang N, Yao X, Wang Z (2007) Sesquiterpenes from Dendrobium nobile. Zhongcaoyao 38:1771–1774 Zhang X, Gao H, Han H, Liu H, Wang N, Yao X, Wang Z (2007) Sesquiterpenes from Dendrobium nobile. Zhongcaoyao 38:1771–1774
24.
Zurück zum Zitat Zhang G, Bi Z, Wang Z, Xu L, Xu G (2003) Advances in studies on chemical constituents from plants of Dendrobium Sw. Zhongcaoyao 34:s5–s8 Zhang G, Bi Z, Wang Z, Xu L, Xu G (2003) Advances in studies on chemical constituents from plants of Dendrobium Sw. Zhongcaoyao 34:s5–s8
25.
Zurück zum Zitat Phongmaykin J, Kumamoto T, Ishikawa T, Suttisri R, Saifah E (2008) A new sesquiterpene and other terpenoid constituents of Chisocheton penduliflorus. Arch Pharmacal Res 31:21–27CrossRef Phongmaykin J, Kumamoto T, Ishikawa T, Suttisri R, Saifah E (2008) A new sesquiterpene and other terpenoid constituents of Chisocheton penduliflorus. Arch Pharmacal Res 31:21–27CrossRef
26.
Zurück zum Zitat de Rijke D, Traas PC, ter Heide R, Boelens H, Takken HJ (1978) Acidic components in essential oils of costus root, patchouli and olibanum. Phytochemistry 17:1664–1666CrossRef de Rijke D, Traas PC, ter Heide R, Boelens H, Takken HJ (1978) Acidic components in essential oils of costus root, patchouli and olibanum. Phytochemistry 17:1664–1666CrossRef
Metadaten
Titel
Dysosesquiflorins A and B, sesquiterpenoids from Dysoxylum densiflorum
verfasst von
Alfarius E. Nugroho
Rio Sugiura
Takanori Momota
Yusuke Hirasawa
Chin Piow Wong
Toshio Kaneda
A. Hamid A. Hadi
Hiroshi Morita
Publikationsdatum
01.07.2015
Verlag
Springer Japan
Erschienen in
Journal of Natural Medicines / Ausgabe 3/2015
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-015-0888-6

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