Indole Alkaloids from Kopsia hainanensis and Evaluation of Their Antimicrobial Activity

Yong Yang; Wen-Jian Zuo; You-Xing Zhao; Wen-Hua Dong; Wen-Li Mei; Hao-Fu Dai

doi:10.1055/s-0032-1315384

Planta Medica, Table of Contents

Planta Med 2012; 78(17): 1881-1884
DOI: 10.1055/s-0032-1315384

Natural Product Chemistry

Letters

Georg Thieme Verlag KG Stuttgart · New York

Indole Alkaloids from Kopsia hainanensis and Evaluation of Their Antimicrobial Activity

Yong Yang

¹Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China

²Horticultural and Garden College, Hainan University, Haikou, Hainan, P. R. China

,

Wen-Jian Zuo

¹Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China

,

You-Xing Zhao

¹Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China

,

Wen-Hua Dong

¹Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China

,

Wen-Li Mei

¹Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China

,

Hao-Fu Dai

¹Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou, Hainan, P. R. China

› Author Affiliations

Abstract

Three new indole alkaloids, named kopsihainin D (1), kopsihainin E (2), and kopsihainin F (3), along with nine known compounds (4–12) were isolated from the twigs of Kopsia hainanensis. The structures of the new compounds were elucidated by spectroscopic methods including HRESIMS, UV, IR, and NMR. Compounds 1 – 3 and 5 showed inhibitory activity against Staphylococcus aureus with an antibacterial circle diameter of 11.2, 9.1, 10.3 and 9.7 mm, respectively.

Key words

Kopsia hainanensis - Apocynaceae - indole alkaloids - antimicrobial activity

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References

References
1 Middleton DJ. A revision of Kopsia (Apocynaceae: Rauvolfioideae). Harvard Pap Bot 2004; 9: 89-142
2 Feng XZ, Kan C, Husson HP, Potier P, Kan SK, Lounasmaa M. Kopsoffine: a new dimeric indole alkaloids of pleiomutine type from Kopsia officinalis . J Nat Prod 1984; 47: 117-122
3 Yun WH, Chen YW, Feng XZ. Studies on chemical constituents from the Kopsia hainanensis isolated and identified the indole alkaloids from the roots. Chin Tradit Herb Drugs 1994; 25: 118-120
4 Yap WS, Gan CY, Low YY, Choo YM, Etoh T, Hayashi M, Komiyama K, Kam TS. Grandilodines A–C, biologically active indole alkaloids from Kopsia grandifolia . J Nat Prod 2011; 74: 1309-1312
5 Tan MJ, Yin C, Tang CP, Ke CQ, Lin G, Ye Y. Antitussive indole alkaloids from Kopsia hainanensis . Planta Med 2011; 77: 939-944
6 Wu YQ, Suehiro M, Kitajima M, Matsuzaki T, Hashimoto S, Nagaoka M, Zhang RP, Takayama H. Rhazinilam and quebrachamine derivatives from Yunnan Kopsia arborea . J Nat Prod 2009; 72: 204-209
7 Low YY, Subramaniam G, Lim KH, Wong R, Robinson WT, Kam TS. Mersiphyllines A and B from Kopsia. Determination of relative configuration at a quaternary center via formation of an alkaloid–borane complex. Tetrahedron 2009; 65: 6873-6876
8 Lim KH, Kam TS. Methyl chanofruticosinate alkaloids from Kopsia arborea . Phytochemistry 2008; 69: 558-561
9 Subramaniam G, Hiraku O, Hayashi M, Koyano T, Komiyama K, Kam TS. Biologically active aspidofractinine alkaloids from Kopsia singapurensis . J Nat Prod 2008; 71: 53-57
10 Wu YQ, Kitajima M, Kogure N, Zhang RP, Takayama H. Two novel indole alkaloids, kopsiyunnannines A and B, from a Yunnan Kopsia . Tetrahedron Lett 2008; 49: 5935-5938
11 Husain K, Jantan I, Kamaruddin N, Said IM, Aimi N, Takayama H. Methyl chanofruticosinates from leaves of Kopsia flavida blume. Phytochemistry 2001; 57: 603-606
12 Kam TS, Sim KM, Koyano T, Komiyama K. Leishmanicidal alkaloids from Kopsia griffithii . Phytochemistry 1999; 50: 75-79
13 Zhu JP, Guggisberg A, Hesse M. Indole alkaloids from Kopsia hannanensis . Planta Med 1986; 52: 63-64
14 Chen J, Chen JJ, Yao XJ, Gao K. Kopsihainanines A and B, two unusual alkaloids from Kopsia hannanensis . Org Biomol Chem 2011; 9: 5334-5336
15 Lim KH, Hiraku O, Komiyama K, Koyano T, Hayashi M, Kam TS. Biologically active indole alkaloids from Kopsia arborea . J Nat Prod 2007; 70: 1302-1307
16 Zhou H, He HP, Luo XD, Wang YH, Yang XW, Di YT, Hao XJ. Three new indole alkaloids from the leaves of Alstonia scholaris . Helv Chim Acta 2005; 88: 2508-2512
17 Kam TS, Subramaniam G, Chen W. Alkaloids from Kopsia dasyrachis . Phytochemistry 1999; 51: 159-169
18 Zhou H, He HP, Kong NC, Wang YH, Liu XD, Hao XJ. Three new indole alkaloids from the leaves of Kopsia officinalis . Helv Chim Acta 2006; 89: 515-519
19 Yagudaew MR. The NMR investigation of alkaloids. VII. ¹³C NMR spectra and structure of kopsanone and kopsinilam. Chem Nat Compd 1984; 20: 320-322
20 Goh SH, Razak Mohd Ali A, Wong WH. Alkaloids of Leuconotis griffithii and L. eugenifolia (Apocynaceae). Tetrahedron 1989; 45: 7899-7920
21 Kam TS, Yoganathan K, Wei C. Paucidactine A and B, new indole akaloids with a novel ring system containing a lactone moiety. Tetrahedron Lett 1996; 37: 3603-3606
22 Lim SH, Sim KM, Abdullah Z, Hiraku O, Hayashi M, Komiyama K, Kam TS. Leuconoxine, kopsinitarine, kopsijasmine, and kopsinone derivatives from Kopsia . J Nat Prod 2007; 70: 1380-1383
23 Kam TS, Yoganathan K. Lahadinines A and B, new cyano-substituted indole alkaloids from Kopsia pauciflora . Phytochemistry 1997; 46: 785-787
24 Xu SY. Methods of pharmacology. Beijing: Peopleʼs Sanitation Press; 2003: 1651
25 Mei WL, Zeng YB, Wu J, Cui HB, Dai HF. Chemical composition and anti-MRSA activity of the essential oil from Chinese eaglewood. J Chin Pharm Sci 2008; 17: 225-229

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