Chemical components of Dysoxylum densiflorum

doi:10.1007/s13659-013-0025-8

Natural Products and Bioprospecting ›› 2013, Vol. 3 ›› Issue (2): 66-69.DOI: 10.1007/s13659-013-0025-8

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Chemical components of Dysoxylum densiflorum

Ji GU^a,b, Sheng-Yan QIAN^a,b, Gui-Guang CHENG^a,b, Yan LI^a, Ya-Ping LIU^a, Xiao-Dong LUO^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

Received:2013-03-18 Revised:2013-04-06 Online:2018-02-11 Published:2013-04-24
Supported by:
This work was supported by the NSFC 21002105, the 973 Program of Ministry of Science and Technology of China (2011CB915503), the Fourteenth Batch Candidates of the Young Academic Leaders of Yunnan Province (Min XU, 2011CI044) and by West Light Foundation of the Chinese Academy of Sciences.

Chemical components of Dysoxylum densiflorum

Ji GU^a,b, Sheng-Yan QIAN^a,b, Gui-Guang CHENG^a,b, Yan LI^a, Ya-Ping LIU^a, Xiao-Dong LUO^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China

通讯作者: Xiao-Dong LUO,E-mail:xdluo@mail.kib.ac.cn
基金资助:
This work was supported by the NSFC 21002105, the 973 Program of Ministry of Science and Technology of China (2011CB915503), the Fourteenth Batch Candidates of the Young Academic Leaders of Yunnan Province (Min XU, 2011CI044) and by West Light Foundation of the Chinese Academy of Sciences.

Abstract

Abstract: Three new diterpenoids, including two halimanes, 5(10),13E-halimadiene-3α,15-diol (1), and 5(10),14-halimadiene-3α,13ξ-diol (2), one labdane, 12-(3-methyl-furan)-labd-8(17)-en-19-oic acid (3), together with sixteen known compounds were isolated from the barks of Dysoxylum densiflorum. All compounds were elucidated by extensive spectroscopic analysis.

Key words: halimane, labdane, Dysoxylum densiflorum

摘要： Three new diterpenoids, including two halimanes, 5(10),13E-halimadiene-3α,15-diol (1), and 5(10),14-halimadiene-3α,13ξ-diol (2), one labdane, 12-(3-methyl-furan)-labd-8(17)-en-19-oic acid (3), together with sixteen known compounds were isolated from the barks of Dysoxylum densiflorum. All compounds were elucidated by extensive spectroscopic analysis.

关键词: halimane, labdane, Dysoxylum densiflorum

Ji GU, Sheng-Yan QIAN, Gui-Guang CHENG, Yan LI, Ya-Ping LIU, Xiao-Dong LUO. Chemical components of Dysoxylum densiflorum[J]. Natural Products and Bioprospecting, 2013, 3(2): 66-69.

Ji GU, Sheng-Yan QIAN, Gui-Guang CHENG, Yan LI, Ya-Ping LIU, Xiao-Dong LUO. Chemical components of Dysoxylum densiflorum[J]. 应用天然产物, 2013, 3(2): 66-69.

References

[1] Luo, X. D.; Wu, S. H.; Wu, D. G.; Ma, Y. B.; Qi, S. H., Tetrahedron 2002, 58, 7797-7804.
[2] (a) Qi, S. H.; Wu, D. G.; Zhang, S.; Luo, X. D., Z. Naturforsch. B:Chem. Sci. 2003, 58, 1128-1132; (b) Nagakura, Y.; Yamanaka, R.; Hirasawa, Y.; Hosoya, T.; Rahman, A.; Kusumawati, I.; Zaini, N. C.; Morita, H., Heterocycles 2010, 80, 1471-1477; (c) Tan, Q. G.; Luo, X. D. Chem. Rev. 2011, 111, 7437-7522; (d) Liu, W. X.; Tang, G. H.; He, H. P.; Zhang, Y.; Li, S. L.; Hao, X. J. Nat. Prod. Bioprospect. 2012, 2, 29-34.
[3] (a) Govindachari, T. R.; Kumari, G. N. K.; Suresh, G. Phytochemistry 1996, 44, 153-155; (b) Wah, L. K.; Abas, F.; Cordell, G. A.; Ito, H.; Ismail, I. S. Steroids 2012, 78, 210-219.
[4] Mulholland, D. A.; Iourine, S.; Taylor, D. A. H. Phytochemistry 1998, 47, 1421-1422.
[5] (a) Fujioka, T.; Yamamoto, M.; Kashiwada, Y.; Fujii, H.; Mihashi, K.; Ikeshiro, Y.; Chen, I. S.; Lee, K. H., Bioorg. Med. Chem. Lett. 1998, 8, 3479-3482; (b) Duh, C. Y.; Wang, S. K.; Chen, I. S. J. Nat. Prod. 2000, 63, 1546-1547.
[6] (a) Mohamad, K.; Martin, M. T.; Litaudon, M.; Gaspard, C.; Sevenet, T.; Pais, M. Phytochemistry 1999, 52, 1461-1468; (b) Luo, X. D.; Wu, S. H.; Ma, Y. B.; Wu, D. G. Phytochemistry 2000, 54, 801-805; (c) Liu, H.; Heilmann, J.; Rali, T.; Sticher, O. J. Nat. Prod. 2001, 64, 159-163; (d) Kurimoto, S. I.; Kashiwada, Y.; Lee, K. H.; Takaishi, Y. Phytochemistry 2011, 72, 2205-2211; (e)Wang, F.; Guan, Y. Fitoterapia 2012, 83, 13-17.
[7] Yang, D. H.; Cai, S. Q.; Zhao, Y. Y.; Liang, H. J. Asian Nat. Prod. Res. 2004, 6, 233-236.
[8] Aalbersberg, W.; Singh, Y. Phytochemistry 1991, 30, 921-926.
[9] (a) Xie, B. J.; Yang, S. P.; Yue, J. M. Phytochemistry 2008, 69, 2993-2997; (b) Li, C. S.; Yu, H. W.; Li, G. Y.; Zhang, G. L., Zhongguo Tianran Yaowu 2010, 8, 270-273.
[10] (a) Luo, X.; Wu, S.; Ma, Y.; Wu, D. Yunnan Zhiwu Yanjiu 2001, 23, 368-372; (b) Luo, X. D.; Wu, S. H.; Ma, Y. B.; Wu, D. G., Phytochemistry 2001, 57, 131-134; (c) Zhang, X. Y.; Li, Y.; Wang, Y. Y.; Cai, X. H.; Feng, T.; Luo, X. D. J. Nat. Prod. 2010, 73, 1385-1388.
[11] (a) Hara, N.; Asaki, H.; Fujimoto, Y.; Gupta, Y. K.; Singh, A. K.; Sahai, M. Phytochemistry 1995, 38, 189-194; (b) Nagashima, F.; Tanaka, H.; Kan, Y.; Huneck, S.; Asakawa, Y. Phytochemistry 1995, 40, 209-212; (c) Ono, M.; Ito, Y.; Nohara, T. Chem. Pharm. Bull. 2001, 49, 1220-1222; (d) Nagashima, F.; Suzuki, M.; Takaoka, S.; Asakawa, Y. J. Nat. Prod. 2001, 64, 1309-1317; (e) Appendino, G.; Borrelli, F.; Capasso, R.; Campagnuolo, C.; Fattorusso, E.; Petrucci, F.; Taglialatela-Scafati, O. J. Agric. Food Chem. 2003, 51, 6970-6974; (f) Meragelman, T. L.; Pedrosa, D. S.; Gil, R. R. Biochem. Syst. Ecol. 2004, 32, 45-53; (g) Kanlayavattanakul, M.; Ruangrungsi, N.; Watanabe, T.; Kawahata, M.; Therrien, B.; Yamaguchi, K.; Ishikawa, T. J. Nat. Prod. 2005, 68, 7-10; (h) Ono, M.; Yamasaki, T.; Konoshita, M.; Ikeda, T.; Okawa, M.; Kinjo, J.; Yoshimitsu, H.; Nohara, T. Chem. Pharm. Bull. 2008, 56, 1621-1624; (i) Ono, M.; Eguchi, K.; Konoshita, M.; Furusawa, C.; Sakamoto, J.; Yasuda, S.; Ikeda, T.; Okawa, M.; Kinjo, J.; Yoshimitsu, H.; Nohara, T. Chem. Pharm. Bull. 2011, 59, 392-396; (j) Kubota, T.; Iwai, T.; Takahashi-Nakaguchi, A.; Fromont, J.; Gonoi, T.; Kobayashi, J. Tetrahedron 2012, 68, 9738-9744.
[12] McChesney, J. D.; Dou, J.; Sindelar, R. D.; Goins, D. K.; Walker, L. A.; Rogers, R. D. J. Chem. Crystallogr. 1997, 27, 283-290.
[13] Kumar, V.; Niyaz, N. M. M.; Wickramaratne, D. B. M.; Balasubramaniam, S. Phytochemistry 1991, 30, 1231-1233.
[14] Kim, D. S. H. L.; Chen, Z.; Van, T. N.; Pezzuto, J. M.; Qiu, S.; Lu, Z. Z. Synth. Commun. 1997, 27, 1607-1612.
[15] Fang, J. M.; Chen, Y. C.; Wang, B. W.; Cheng, Y. S. Phytochemistry 1996, 41, 1361-1365.
[16] Li, C. J.; Zhang, D. M.; Luo, Y. M.; Yu, S. S.; Li, Y.; Lu, Y. Phytochemistry 2008, 69, 2867-2874.
[17] Ren, X. Y.; Ye, Y. J. Asian Nat. Prod. Res. 2006, 8, 677-682.
[18] Hsieh, Y. L.; Fang, J. M.; Cheng, Y. S. Phytochemistry 1998, 47, 845-850.
[19] Muhammad, I.; Mossa, J. S.; El-Feraly, F. S. Phytother. Res. 1996, 10, 604-607.
[20] Rodrigues-Filho, E.; Magnani, R. F.; Xie, W.; Mirocha, C. J.; Pathre, S. V. J. Braz. Chem. Soc. 2002, 13, 266-269.
[21] Villamizar, J.; Pittelaud, J. P.; Rodrigues, J. R.; Gamboa, N.; Canudas, N.; Tropper, E.; Salazar, F.; Fuentes, J. Nat. Prod. Res. 2009, 23, 891-902.
[22] Anjaneyulu, A. S. R.; Krishnamurthy, M. V. R.; Rao, G. V. Tetrahedron 1997, 53, 9301-9312.
[23] Sun, Z.; Chen, B.; Zhang, S.; Hu, C. J. Nat. Prod. 2004, 67, 1975-1979.
[24] Cui, E. J.; Park, J. H.; Park, H. J.; Chung, I. S.; Kim, J. Y.; Yeon, S. W.; Baek, N. I. J. Korean Soc. Appl. Biol. Chem. 2011, 54, 362-366.
[25] Venkateswarlu, S.; Ramachandra, M. S.; Krishnaraju, A. V.; Trimurtulu, G.; Subbaraju, G. V. Indian J. Chem., Sect. B:Org. Chem. Incl. Med. Chem. 2006, 45, 252-257.
[26] Liang, X. T.; Yu, D. Q.; Wu, W. L.; Deng, H. C. Hua Hsueh Hsueh Pao 1979, 37, 215-230.
[27] (a) Lin, S. J.; Rosazza, J. P. N. J. Nat. Prod. 1998, 61, 922-926; (b) Iwamoto, M.; Ohtsu, H.; Matsunaga, S.; Tanaka, R. J. Nat. Prod. 2000, 63, 1381-1383; (c) Li, Y. C.; Kuo, Y. H., Chem. Pharm. Bull. 2002, 50, 498-500; (d) Minami, T.; Wada, S. I.; Tokuda, H.; Tanabe, G.; Muraoka, O.; Tanaka, R. J. Nat. Prod. 2002, 65, 1921-1923; (e) Wang, Y. Z.; Tang, C. P.; Ke, C. Q.; Weiss, H. C.; Gesing, E. R.; Ye, Y. Phytochemistry 2007, 69, 518-526.

Chemical components of Dysoxylum densiflorum

Chemical components of Dysoxylum densiflorum

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