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Phenolic constituents from Parakmeria yunnanensis and their anti-HIV-1 activity

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Abstract

Three new phenolic compounds, yunnanensins A–C (1–3), together with fourteen known ones (4–17), were isolated from the leaves and stems of Parakmeria yunnanensis. The structures of new compounds were established on the basis of extensive spectroscopic analyses. Several compounds showed weak anti-HIV-1 activity.

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References

  • Baderschneider, B., and P. Winterhalter. 2001. Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from riesling wine and screening for antioxidant activity. Journal of Agriculture and Food Chemistry 49: 2788–2798.

    Article  CAS  Google Scholar 

  • Bae, E.A., M.J. Han, and D.H. Kim. 1999. In vitro anti-helicobacter pylori activity of some flavonoids and their metabolites. Planta Medica 65: 442–443.

    Article  PubMed  CAS  Google Scholar 

  • Bernini, R., G. Gualandi, C. Crestini, M. Barontini, M.C. Belfiore, S. Willfoer, P. Eklund, and R. Saladino. 2009. A novel and efficient synthesis of highly oxidized lignans by a methyltrioxorhenium/hydrogen peroxide catalytic system. Studies on their apoptogenic and antioxidant activity. Bioorganic & Medicinal Chemistry 17: 5676–5682.

    Article  CAS  Google Scholar 

  • Chang, F.R., Y.C. Chao, C.M. Teng, and Y.C. Wu. 1998. Chemical constituents from Cassytha filiformis II. Journal of Natural Products 61: 863–866.

    Article  PubMed  CAS  Google Scholar 

  • Cheng, Y., J. Zhou, and N. Tan. 2001. Chemical constituent of Parakmeria yunnanensis. Acta Botanica Yunnanica 23: 352–356.

    CAS  Google Scholar 

  • Dhal, R., Y. Landais, A. Lebrun, V. Lenain, and J.P. Robin. 1994. Ruthenium dioxide in fluoro acid medium V. Application to the non-phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins. Tetrahedron 50: 1153–1164.

    Article  CAS  Google Scholar 

  • Fukuyama, Y., Y. Otoshi, K. Miyoshi, K. Nakamura, M. Kodama, M. Nagasawa, T. Hasegawa, H. Okazaki, and M. Sugawara. 1992. Neurotrophic sesquiterpene-neolignans from Magnolia obovata: structure and neurotrophic activity. Tetrahedron 48: 377–392.

    Article  CAS  Google Scholar 

  • Heller, W., and C. Tamm. 1974. Isolierung, Konstitution and synthese der (R)-(−)-eucominsäure. Helvetica Chimica Acta 57: 1766–1784.

    Article  CAS  Google Scholar 

  • Ishii, M., S. Uemoto, K. Fujieda, M. Nonaka, Y. Shoyama, Y. Miyahara, and I. Nishioka. 1979. A new biologically active phenolic from Cattleya trianaei. Phytochemistry 18: 1211–1213.

    Article  CAS  Google Scholar 

  • Jutiviboonsuk, A., H. Zhang, G.T. Tan, C. Ma, N.V. Hung, N.M. Cuong, N. Bunyapraphatsara, D.D. Soejarto, and H.H.S. Fong. 2005. Bioactive constituents from roots of Bursera tonkinensis. Phytochemistry 66: 2745–2751.

    Article  PubMed  CAS  Google Scholar 

  • Kinjo, J., K. Fukui, H. Higuchi, and T. Nohara. 1991. Leguminous plants. 23. The first isolation of lignan tri- and tetra-glycosides. Chemical & Pharmaceutical Bulletin 39: 1623–1625.

    Article  CAS  Google Scholar 

  • Koizumi, T., Y. Isogai, S. Nomoto, K. Shudo, and T. Okamoto. 1976. Isolation of 2-(4-hydroxybenzyl)malic acid from Lycoris radiata. Phytochemistry 15: 342–343.

    Article  CAS  Google Scholar 

  • Kunitomo, J., M. Juichi, Y. Ando, Y. Yoshikawa, S. Nakamura, and T. Shingu. 1975. Alkaloids of berberidaceous plants. 7. Isolation of new base, dehydronantenine and lignan, (−)-episyringaresinol from Nandina domestica. Yakugaku Zasshi 95: 445–447.

    PubMed  CAS  Google Scholar 

  • Lundquist, K., and G.E. Miksche. 1965. A new linkage principle for guaiacylpropane units in spruce lignin. Tetrahedron Letters 6: 2131–2136.

    Article  Google Scholar 

  • Sugiyama, M., and M. Kikuchi. 1993. Characterization of lariciresinol glucosides from Osmanthus asiaticus. Heterocycles 36: 117–121.

    Article  Google Scholar 

  • Nabeta, K., K. Nakahara, J. Yonekubo, H. Okuyama, and T. Sasaya. 1991. Lignan biosynthesis in Larix leptolepis callus. Phytochemistry 30: 3591–3593.

    Article  CAS  Google Scholar 

  • Namba, T., M. Tsunezuka, and M. Hattori. 1982. Dental caries prevention by traditional Chinese medicines. Planta Medica 44: 100–106.

    Article  PubMed  CAS  Google Scholar 

  • Okada, M., S. Park, T. Koshizawa, and M. Ueda. 2009. (R)-eucomic acid, a leaf-opening factor of the model organism, Lotus japonicus. Tetrahedron 65: 2136–2141.

    Article  CAS  Google Scholar 

  • Ono, M., C. Masuoka, Y. Odake, S. Ikegashira, Y. Ito, and T. Nohara. 2000. Antioxidative constituents from Tessaria integrifolia. Food Science and Technology Research 6: 106–114.

    Article  CAS  Google Scholar 

  • Sharp, H., D. Thomas, F. Currie, C. Bright, Z. Latif, S.D. Sarker, and R.J. Nash. 2001. Pinoresinol and syringaresinol: two lignans from Avicennia germinans (Avicenniaceae). Biochemical Systematics and Ecology 29: 325–327.

    Article  PubMed  CAS  Google Scholar 

  • Sohn, E.J., C.S. Kim, Y.S. Kim, D.H. Jung, D.S. Jang, Y.M. Lee, and J.S. Kim. 2007. Effects of magnolol (5,5′-diallyl-2,2′-dihydroxybiphenyl) on diabetic nephropathy in type 2 diabetic Goto-Kakizaki rats. Life Sciences 80: 468–475.

    Article  PubMed  CAS  Google Scholar 

  • Sun, Y.J., Z.L. Li, H. Chen, X.Q. Liu, W. Zhou, and H.M. Hua. 2011. Three new cytotoxic aryltetralin lignans from Sinopodophyllum emodi. Bioorganic & Medicinal Chemistry Letters 21: 3794–3797.

    Article  CAS  Google Scholar 

  • Teng, C.M., S.M. Yu, C.C. Chen, Y.L. Huang, and T.F. Huang. 1990. EDRF-release and Ca+(+)-channel blockade by magnolol, an antiplatelet agent isolated from Chinese herb Magnolia officinalis, in rat thoracic aorta. Life Sciences 47: 1153–1161.

    Article  PubMed  CAS  Google Scholar 

  • Thieme, H., and H.J. Winkler. 1969. Occurrence of lignan glucosides in forsythia. III. Isolation of (+)-epipinoresinol β-D-glucopyranoside. Pharmazie 24: 117.

    PubMed  CAS  Google Scholar 

  • Tovar-Gijón, C.E., B. Hernández-Carlos, E. Burgueño-Tapia, E. Cedillo-Portugal, and P. Joseph-Nathan. 2006. A new C-glycosylflavone from Encyclia michuacana. Journal of Molecular Structure 783: 96–100.

    Article  Google Scholar 

  • Trinh Thi Thanh, V., V. Cuong Pham, H. Doan Thi Mai, M. Litaudon, F. Guéritte, P. Retailleau, V.H. Nguyen, and V.M. Chau. 2012. Cytotoxic lignans from fruits of Cleistanthus indochinensis: synthesis of cleistantoxin derivatives. Journal of Natural Products 75: 1578–1583.

    Article  Google Scholar 

  • Wang, R.R., L.M. Yang, Y.H. Wang, W. Pang, S.C. Tam, P. Tien, and Y.T. Zheng. 2009. Sifuvirtide, a potent HIV fusion inhibitor peptide. Biochemical and Biophysical Research Communications 382: 540–544.

    Article  PubMed  CAS  Google Scholar 

  • Watanabe, K. 1986. Pharmacology of magnolia bark with special reference to gastrointestinal functions. Gendai Toyo Igaku 7: 54–59.

    CAS  Google Scholar 

  • Watanabe, K., H.Y. Watanabe, Y. Goto, N. Yamamoto, and M. Yoshizaki. 1975. Studies on the active principles of magnolia bark. Centrally acting muscle relaxant activity of magnolol and honokiol. Japanese Journal of Pharmacology 25: 605–607.

    Article  PubMed  CAS  Google Scholar 

  • Watanabe, K., H. Watanabe, Y. Goto, M. Yamaguchi, N. Yamamoto, and K. Hagino. 1983. Pharmacological properties of magnolol and honokiol extracted from Magnolia officinalis: central depressant effects. Planta Medica 49: 103–108.

    Article  PubMed  CAS  Google Scholar 

  • Yamamoto, S., A. Otto, and B.R.T. Simoneit. 2004. Lignans in resin of Araucaria angustifolia by gas chromatography/mass spectrometry. Journal of Mass Spectrometry 39: 1337–1347.

    Article  PubMed  CAS  Google Scholar 

  • Youn, U.J., Q.C. Chen, W.Y. Jin, I.S. Lee, H.J. Kim, J.P. Lee, M.J. Chang, B.S. Min, and K.H. Bae. 2007. Cytotoxic lignans from the stem bark of Magnolia officinalis. Journal of Natural Products 70: 1687–1689.

    Article  PubMed  CAS  Google Scholar 

  • Zhao, C., A. Nagatsu, K. Hatano, N. Shirai, S. Kato, and Y. Ogiharac. 2003. New lignan glycosides from Chinese medicinal plant, Sinopodophillum emodi. Chemical and Pharmaceutical Bulletin 51: 255–261.

    Article  PubMed  CAS  Google Scholar 

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Acknowledgments

This project was supported financially by the projects from the Chinese Academy of Sciences (KSCX2-EW-Q-10 and KSCX1-YW-R-24), the NSFC (Nos. 20802082, 81102483 and 30830115), the Major State Basic Research Development Program of China (Nos. 2009CB522300 and 2009CB940900), the Key Scientific and Technological Program of China (2012ZX10001-006), and the project of recruited top talent of sciences and technology of Yunnan Province (2006PY01-47 and 2009C1120).

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Authors and Affiliations

  1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, Yunnan, People’s Republic of China

    Shan-Zhai Shang, Cheng-Qin Liang, Zhong-Hua Gao, Xue Du, Yi-Ming Shi, Wei-Lie Xiao & Han-Dong Sun

  2. Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences and Yunnan province, Kunming Institute of Zoology, Chinese Academy of Sciences, Kunming, 650223, Yunnan, People’s Republic of China

    Huan Chen, Rui-Rui Wang & Yong-Tang Zheng

  3. University of Chinese Academy of Sciences, Beijing, 100039, People’s Republic of China

    Shan-Zhai Shang, Cheng-Qin Liang, Zhong-Hua Gao & Yi-Ming Shi

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  1. Shan-Zhai Shang
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  2. Huan Chen
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  3. Cheng-Qin Liang
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  4. Zhong-Hua Gao
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  5. Xue Du
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  6. Rui-Rui Wang
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  7. Yi-Ming Shi
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  8. Yong-Tang Zheng
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  9. Wei-Lie Xiao
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  10. Han-Dong Sun
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Correspondence to Wei-Lie Xiao or Han-Dong Sun.

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Shang, SZ., Chen, H., Liang, CQ. et al. Phenolic constituents from Parakmeria yunnanensis and their anti-HIV-1 activity. Arch. Pharm. Res. 36, 1223–1230 (2013). https://doi.org/10.1007/s12272-013-0070-1

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  • DOI: https://doi.org/10.1007/s12272-013-0070-1

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