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Cucurbita-5,23-diene-3β,25-diol from Sicana odorifera
Fitoterapia 75 (2004) 609 – 611 www.elsevier.com/locate/fitote
Phytochemical communication
Cucurbita-5,23-diene-3h,25-diol from Sicana odorifera Sayaka Nakanoa, Yoshinori Fujimotoa,*, Yoshihisa Takaishib, Coralia Osorioc, Carmenza Duquec a
Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan b Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan c Departamento de Quı´mica, Universidad Nacional de Colombia, AA 14490, Bogota´, Colombia Received 4 September 2003; accepted 12 May 2004 Available online 28 July 2004
Abstract The spectral data of a new triterpene, cucurbita-5,23-diene-3h,25-diol, isolated from the seeds of Sicana odorifera, are reported. D 2004 Elsevier B.V. All rights reserved. Keywords: Sicana odorifera; Cucurbita-5,23-diene-3h,25-diol
1. Plant Sicana odorifera (Vell.) Naudin (Cucurbitaceae), popularly known as melo´n de olor in Colombia, seeds obtained from fruits purchased at a local market in Bogota in July 2000, and identified by Prof. Cristina Garzon, Instituto de Ciencias Naturales of Universidad Nacional de Colombia.
* Corresponding author. Tel./fax: +81 3 5734 2241. E-mail address: [email protected] (Y. Fujimoto). 0367-326X/$ - see front matter D 2004 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2004.05.004
610
S. Nakano et al. / Fitoterapia 75 (2004) 609–611
2. Uses in traditional medicine Insect repellent activity [1].
3. Previously isolated classes of constituents Aromatics [2].
4. New isolated constituent Cucurbita-5,23-diene-3h,25-diol (1)(0.004%). m.p.72–73.5 8C (MeOH), C30H50O2; [a]D25+23.58 (c 0.87, CHCl3); 1H NMR (400 MHz, CDCl3): d 0.80 (3H, s, H-30), 0.86 (3H, s, H-18), 0.88 (3H, d, J 6.1 Hz, H-21), 0.92 (3H, s, H-19), 1.02 (3H, s, H-28), 1.14 (3H, s, H-29), 1.31 (6H, s, H-26, H-27), 2.15 (1H, bd, J 13.8 Hz, H-22), 2.26 (1H, bd, J 12.8 Hz, H-10), 2.38 (1H, H-7), 3.47 (1H, t, J 2.4 Hz, H-3), 5.58 (3H, H-6, H-23, H-24); 13 C NMR (100 MHz, CDCl3): d 15.43 (C-18), 17.78 (C-30), 18.69 (C-21), 21.12 (C-1), 24.37 (C-7), 25.44 (C-29), 27.27 (C-28), 27.82 (C-16), 28.03 (C-19), 28.88 (C-2), 29.87 (C-26), 29.96 (C-27), 30.37 (C-12), 32.30 (C-11), 34.48 (C-9), 34.78 (C-15), 36.25 (C20), 37.84 (C-10), 39.14 (C-22), 41.42 (C-4), 43.67 (C-8), 46.28 (C-13), 49.18 (C-14), 50.18 (C-17), 70.73 (C-25), 76.64 (C-3), 121.44 (C-6), 125.48 (C-23), 139.40 (C-24), 141.25 (C-5); HR-EI-MS: m/z 442.3798 [M]+. Calc. for C30H50O2: 442.3811. The structure of (1) was determined on the basis of the spectral data including 1H–1H COSY, HMQC and HMBC NMR spectra and by comparison of NMR data with those reported for a closely related cucurbitane, cucurbita-5,24-diene-3h-ol (boeticol) [3]. In addition, the known triterpene, D:C-friedo-oleana-7,9(11)-diene-3a,29-diol dibenzoate (karounidiol dibenzoate) (0.01%) [4,5] and flavones, (+)-taxifolin (0.007%) [6] and quercetin (0.004%), were isolated.
Acknowledgements This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
S. Nakano et al. / Fitoterapia 75 (2004) 609–611
611
References [1] [2] [3] [4] [5] [6]
Brenesia LR. Mus Nac Costa Rica 1991;35:19. Parada F, Duque C, Fujimoto Y. J Agric Food Chem 2000;48:6200. Nes WD, Wong RY, Benson M, Akihisa T. J Chem Soc Chem Commun 1991:1272. Sekine T, Kurihara H, Waku M, Ikegami F, Ruangrungsi N. Chem Pharm Bull 2002;50:645. Ukiya M, Akihisa T, Tokuda H, Toriumi M, Mukainaka T, Banno N, et al. J Agric Food Chem 2002;50:6710. Nonaka G, Goto Y, Kinjo J, Nohara T, Nishioka I. Chem Pharm Bull 1987;35:1105.
Phytochemical communication
Cucurbita-5,23-diene-3h,25-diol from Sicana odorifera Sayaka Nakanoa, Yoshinori Fujimotoa,*, Yoshihisa Takaishib, Coralia Osorioc, Carmenza Duquec a
Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan b Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi, Tokushima 770-8505, Japan c Departamento de Quı´mica, Universidad Nacional de Colombia, AA 14490, Bogota´, Colombia Received 4 September 2003; accepted 12 May 2004 Available online 28 July 2004
Abstract The spectral data of a new triterpene, cucurbita-5,23-diene-3h,25-diol, isolated from the seeds of Sicana odorifera, are reported. D 2004 Elsevier B.V. All rights reserved. Keywords: Sicana odorifera; Cucurbita-5,23-diene-3h,25-diol
1. Plant Sicana odorifera (Vell.) Naudin (Cucurbitaceae), popularly known as melo´n de olor in Colombia, seeds obtained from fruits purchased at a local market in Bogota in July 2000, and identified by Prof. Cristina Garzon, Instituto de Ciencias Naturales of Universidad Nacional de Colombia.
* Corresponding author. Tel./fax: +81 3 5734 2241. E-mail address: [email protected] (Y. Fujimoto). 0367-326X/$ - see front matter D 2004 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2004.05.004
610
S. Nakano et al. / Fitoterapia 75 (2004) 609–611
2. Uses in traditional medicine Insect repellent activity [1].
3. Previously isolated classes of constituents Aromatics [2].
4. New isolated constituent Cucurbita-5,23-diene-3h,25-diol (1)(0.004%). m.p.72–73.5 8C (MeOH), C30H50O2; [a]D25+23.58 (c 0.87, CHCl3); 1H NMR (400 MHz, CDCl3): d 0.80 (3H, s, H-30), 0.86 (3H, s, H-18), 0.88 (3H, d, J 6.1 Hz, H-21), 0.92 (3H, s, H-19), 1.02 (3H, s, H-28), 1.14 (3H, s, H-29), 1.31 (6H, s, H-26, H-27), 2.15 (1H, bd, J 13.8 Hz, H-22), 2.26 (1H, bd, J 12.8 Hz, H-10), 2.38 (1H, H-7), 3.47 (1H, t, J 2.4 Hz, H-3), 5.58 (3H, H-6, H-23, H-24); 13 C NMR (100 MHz, CDCl3): d 15.43 (C-18), 17.78 (C-30), 18.69 (C-21), 21.12 (C-1), 24.37 (C-7), 25.44 (C-29), 27.27 (C-28), 27.82 (C-16), 28.03 (C-19), 28.88 (C-2), 29.87 (C-26), 29.96 (C-27), 30.37 (C-12), 32.30 (C-11), 34.48 (C-9), 34.78 (C-15), 36.25 (C20), 37.84 (C-10), 39.14 (C-22), 41.42 (C-4), 43.67 (C-8), 46.28 (C-13), 49.18 (C-14), 50.18 (C-17), 70.73 (C-25), 76.64 (C-3), 121.44 (C-6), 125.48 (C-23), 139.40 (C-24), 141.25 (C-5); HR-EI-MS: m/z 442.3798 [M]+. Calc. for C30H50O2: 442.3811. The structure of (1) was determined on the basis of the spectral data including 1H–1H COSY, HMQC and HMBC NMR spectra and by comparison of NMR data with those reported for a closely related cucurbitane, cucurbita-5,24-diene-3h-ol (boeticol) [3]. In addition, the known triterpene, D:C-friedo-oleana-7,9(11)-diene-3a,29-diol dibenzoate (karounidiol dibenzoate) (0.01%) [4,5] and flavones, (+)-taxifolin (0.007%) [6] and quercetin (0.004%), were isolated.
Acknowledgements This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
S. Nakano et al. / Fitoterapia 75 (2004) 609–611
611
References [1] [2] [3] [4] [5] [6]
Brenesia LR. Mus Nac Costa Rica 1991;35:19. Parada F, Duque C, Fujimoto Y. J Agric Food Chem 2000;48:6200. Nes WD, Wong RY, Benson M, Akihisa T. J Chem Soc Chem Commun 1991:1272. Sekine T, Kurihara H, Waku M, Ikegami F, Ruangrungsi N. Chem Pharm Bull 2002;50:645. Ukiya M, Akihisa T, Tokuda H, Toriumi M, Mukainaka T, Banno N, et al. J Agric Food Chem 2002;50:6710. Nonaka G, Goto Y, Kinjo J, Nohara T, Nishioka I. Chem Pharm Bull 1987;35:1105.