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Planta Med 2012; 78(18): 1962-1966
DOI: 10.1055/s-0032-1327895
Natural Product Chemistry
Letters
Georg Thieme Verlag KG Stuttgart · New York

Neuroprotective Lignans from the Stems of Schisandra glaucescens

Heng-Yi Yu
1   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Faculty of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, Wuhan, Peopleʼs Republic of China
,
Cui Hao
1   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Faculty of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, Wuhan, Peopleʼs Republic of China
,
Fan-Yu Meng
1   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Faculty of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, Wuhan, Peopleʼs Republic of China
,
Xue Li
1   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Faculty of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, Wuhan, Peopleʼs Republic of China
,
Zu-Yu Chen
1   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Faculty of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, Wuhan, Peopleʼs Republic of China
,
Xi Liang
1   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Faculty of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, Wuhan, Peopleʼs Republic of China
,
Han-Li Ruan
1   Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Faculty of Pharmacy, Tongji Medical College of Huazhong University of Science and Technology, Wuhan, Peopleʼs Republic of China
› Author Affiliations
Further Information

Publication History

received 08 February 2012
revised 26 July 2012

accepted 08 October 2012

Publication Date:
13 November 2012 (online)

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Abstract

Two new tetrahydrofuran lignans, schiglaucin A and B (1–2), together with eight known analogues (3–10), were isolated from the stems of Schisandra glaucescens Diels. Their structures were elucidated on the basis of spectroscopic techniques (HRESIMS, UV, IR, NMR, and CD experiments). All of the compounds were tested for their neuroprotective activities against H2O2- and CoCl2-induced cell injuries in SH-SY5Y cells, respectively. Compounds 1–10 showed significant neuroprotective effects against H2O2-induced SH-SY5Y cell death, while compounds 1–5 and 8–10 exhibited significant neuroprotective effects against CoCl2-induced SH-SY5Y cell injury.

Key words

Schisandra glaucescens Diels. - Schisandraceae - lignans - schiglaucin A - schiglaucin B - neuroprotective

Supporting Information

 

  • References

  • 1 Kuo YH, Li SY, Wu MD, Huang RL, Yang Kuo LM, Chen CF. A new anti-HBeAg lignan, kadsumarin A, from Kadsura matsudai and Schizandra arisanensis . Chem Pharm Bull 1999; 47: 1047-1048
    CrossrefPubMedGoogle Scholar
  • 2 Chen M, Kilgore N, Lee KH, Chen DF. Rubrisandrins A and B, lignans and related anti-HIV compounds from Schisandra rubriflora . J Nat Prod 2006; 69: 1697-1701
    CrossrefPubMedGoogle Scholar
  • 3 Li RT, Han QB, Zheng YT, Wang RR, Yang LM, Lu Y, Sang SQ, Zheng QT, Zhao QS, Sun HD. Structure and anti-HIV activity of micrandilactones B and C, new nortriterpenoids possessing a unique skeleton from Schisandra micrantha . Chem Commun 2005; 23: 2936-2938
    PubMedGoogle Scholar
  • 4 Xiao WL, Li RT, Li SH, Li XL, Sun HD, Zheng YT, Wang RR, Lu Y, Wang C, Zheng QT. Lancifodilactone F: a novel nortriterpenoid possessing a unique skeleton from Schisandra lancifolia and its anti-HIV activity. Org Lett 2005; 7: 1263-1266
    CrossrefPubMedGoogle Scholar
  • 5 Li LN, Xue H, Ge DL, Kunio K, Toshio M, Sadafumi O. Isolation and structure elucidation of seco-neokadsuranic acid A and 3,4-seco-(24Z)-lanosta-4(30),8,24-triene-3,26-dioic acid. Planta Med 1989; 55: 300-302
    Article in Thieme ConnectPubMedGoogle Scholar
  • 6 Ma WH, Lu Y, Huang H, Zhou P, Chen DF. Schisanwilsonins A–G and related anti-HBV lignans from the fruits of Schisandra wilsoniana . Bioorg Med Chem Lett 2009; 19: 4958-4962
    CrossrefPubMedGoogle Scholar
  • 7 Xue JJ, Cao JL, Yang GY, Pu JX, Sun HD, Hu QF, Xiao WL. Lignans from Schisandra lancifolia . J Asian Nat Prod Res 2011; 13: 492-497
    CrossrefPubMedGoogle Scholar
  • 8 Giridharan VV, Thandavarayan RA, Sato S, Ko KM, Konishi T. Prevention of scopolamine-induced memory deficits by schisandrin B, an antioxidant lignan from Schisandra chinensis in mice. Free Radic Res 2011; 45: 950-958
    CrossrefPubMedGoogle Scholar
  • 9 Song JX, Lin X, Wong RN, Sze SC, Tong Y, Shaw PC, Zhang YB. Protective effects of dibenzocyclooctadiene lignans from Schisandra chinensis against beta-amyloid and homocysteine neurotoxicity in PC12 cells. Phytother Res 2011; 25: 435-443
    PubMedGoogle Scholar
  • 10 Zhan YH. Traditional Chinese medicine resources in Shennongjia. Wuhan: Hubei Science & Technology Press; 1994: 93
    Google Scholar
  • 11 Meng FY, Sun JX, Li X, Yu HY, Li SM, Ruan HL. Schiglautone A, a new tricyclic triterpenoid with a unique 6/7/9-fused skeleton from the stems of Schisandra glaucescens . Org Lett 2011; 13: 1502-1505
    CrossrefPubMedGoogle Scholar
  • 12 Meng FY, Sun JX, Li X, Pi HF, Zhang P, Ruan HL. Triterpenoids from the stems of Schisandra glaucescens . Helv Chim Acta 2011; 94: 1778-1785
    CrossrefPubMedGoogle Scholar
  • 13 Zou J, Yang LB, Jiang J, Diao YY, Li XN, Huang J, Yang JH, Li HL, Xiao WL, Du X, Shang SZ, Pu JX, Sun HD. Lanostane triterpenoids from the stems of Schisandra glaucescens . Planta Med 2012; 78: 472-479
    Article in Thieme ConnectPubMedGoogle Scholar
  • 14 Zou J, Jiang J, Diao YY, Yang LB, Huang J, Li HL, Du X, Xiao WL, Pu JX, Sun HD. Cycloartane triterpenoids from the stems of Schisandra glaucescens and their bioactivity. Fitoterapia 2012; 83: 926-931
    CrossrefPubMedGoogle Scholar
  • 15 Lee CL. Studies on the components of Formosan lauraceous plants. I. Four lignans from the bark of Machilus zuihoensis forma longipaniculata . Natl Sci Counc Monthly 1981; 9: 578-583
    PubMedGoogle Scholar
  • 16 Liu HT, Xu LJ, Peng Y, Yang XW, Xiao PG. Two new lignans from Schisandra henryi . Chem Pharm Bull 2009; 57: 405-407
    CrossrefPubMedGoogle Scholar
  • 17 Liu JS, Huang MF. Constituents of Schisandra sphenanthera Rehd. et Wils. IV. Structures of anwuweizic acid and dl-anwulignan, and the absolute configurations of d-epigalbacin. Acta Chem Sin 1984; 42: 264-270
    PubMedGoogle Scholar
  • 18 Abou-Gazar H, Bedir E, Takamatsu S, Ferreira D, Khan IA. Antioxidant lignans from Larrea tridentate . Phytochemistry 2004; 65: 2499-2505
    CrossrefPubMedGoogle Scholar
  • 19 Shen YC, Hsieh PW, Kuo YH. Neolignan glucosides from Jasminum Urophyllum . Phytochemistry 1998; 48: 719-723
    CrossrefPubMedGoogle Scholar
  • 20 Zhang YL, Gan ML, Li S, Wang SJ, Zhu CG, Yang YC, Hu JF, Chen NH, Shi JG. Chemical constituents of stems and branches of Adina polycephala . Chin J Chin Mater Med 2010; 35: 1261-1271
    PubMedGoogle Scholar
  • 21 Yin HQ, Fu HW, Hua HM, Pei YH. Chemical constituents of Saussurea lappa C.B Clarke. J Shenyang Pharm Univ 2006; 23: 641-643
    PubMedGoogle Scholar
  • 22 Yi JH, Zhang GL, Li BG, Chen YZ. Two glycosides from the stem bark of Tetracentron sinense . Phytochemistry 2000; 53: 1001-1003
    CrossrefPubMedGoogle Scholar
  • 23 Wang YH, Zhang ZK, He H, Gao S, Kong NC, Ding M, Hao XJ. Lignans and triterpenoids from Cissus repens (Vitaceae). Acta Botanica Yunnanica 2006; 28: 433-437
    PubMedGoogle Scholar
  • 24 Ma CJ, Lee MK, Kim YC. meso-Dihydroguaiaretic acid attenuates the neurotoxic effect of staurosporine in primary rat cortical cultures. Neuropharmacology 2006; 50: 733-740
    CrossrefPubMedGoogle Scholar
  • 25 Zhai H, Inoue T, Moriyama M, Esumi T, Mitsumoto Y, Fukuyama Y. Neuroprotective effects of 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans. Biol Pharm Bull 2005; 28: 289-293
    CrossrefPubMedGoogle Scholar