Natural Products and Bioprospecting    2022, Vol. 12 Issue (3) : 19-19     DOI: 10.1007/s13659-022-00342-3
ORIGINAL ARTICLE |
Lignans and sesquiterpenoids from the stems of Schisandra bicolor var. tuberculata
Shui-Mei Zhang1,2, Kun Hu1, Xiao-Nian Li1, Han-Dong Sun1, Pema-Tenzin Puno1
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing, 10039, People's Republic of China
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Abstract  A pair of new tetrahydrofuran lignan enantiomers, (±)-schibiculatin A [(±)-1], a new enedione lignan, schibiculatin B (2), two new cadinane-type sesquiterpenoids, schibiculatins C (3) and D (4), along with two known seco-cadinane-type sesquiterpenoids (5 and 6) and seven known miscellaneous lignans (713) were isolated from the stems of Schisandra bicolor var. tuberculata. The structures of 14 were elucidated by comprehensive analysis of their spectroscopic data, quantum chemical calculations, as well as single-crystal X-ray diffraction. A few isolated compounds were tested for their protective activities against corticosterone-induced apoptosis in PC12 cells. Among them, compounds 5 and 6 showed moderate activities.
Keywords Schisandra bicolor var. tuberculata      Cadinane-type sesquiterpenoids      Lignans      Quantum chemical calculation     
Fund:We thank Service Center for Bioactivity Screening, State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany for bioactivity screening. This project was supported financially by the National Natural Science Foundation of China (No. 81903520).
Corresponding Authors: Kun Hu,E-mail:hukun@mail.kib.ac.cn;Pema-Tenzin Puno,E-mail:punopematenzin@mail.kib.ac.cn     E-mail: hukun@mail.kib.ac.cn;punopematenzin@mail.kib.ac.cn
Issue Date: 24 June 2022
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Shui-Mei Zhang,Kun Hu,Xiao-Nian Li, et al. Lignans and sesquiterpenoids from the stems of Schisandra bicolor var. tuberculata[J]. Natural Products and Bioprospecting, 2022, 12(3): 19-19.
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http://npb.kib.ac.cn/EN/10.1007/s13659-022-00342-3     OR     http://npb.kib.ac.cn/EN/Y2022/V12/I3/19
1.Jia YZ, Yang YP, Cheng SW.Heilaohuguosus A-S from the fruits of Kadsura coccinea and their hepatoprotective activity.Phytochemistry.2021;184:112678.
2.Shang SZ, Han YS, Shi YM.Four new lignans from the leaves and stems of Schisandra propinqua var.sinensis.Nat Prod Bioprospect.2013;3:56-60.
3.Xiao WL, Li RT, Huang SX.Triterpenoids from the Schisandraceae family.Nat Prod Rep.2008;25:871-91.
4.Shi YM, Xiao WL, Pu JX.Triterpenoids from the Schisandraceae family:an update.Nat Prod Rep.2015;32:367-410.
5.Xu HC, Hu K, Sun HD.Four 14(13→12)-abeolanostane triterpenoids with 6/6/5/6-fused ring system from the roots of Kadsura coccinea.Nat Prod Bioprospect.2019;9:165-73.
6.Wang B, Hu K, Li XN.Neuroprotective schinortriterpenoids from Schisandra neglecta collected in Medog County, Tibet, China.Bioorg Chem.2021;110:104785.
7.Chen YN, Zhou HY, Liu XH.Biochem.Cadinane-type sesquiterpenoids from Schisandra bicolor.Syst Ecol.2015;63:17-9.
8.Liu M, Hu ZX, Luo YQ.Two new compounds from Schisandra propinqua var.propinqua.Nat Prod Bioprospect.2017;7:257-62.
9.Zhang XJ, Yang GY, Wang RR.7,8-Secolignans from Schisandra wilsoniana and their anti-HIV-1 activities.Chem Biodivers.2010;7:2692-701.
10.Liu J, Pandey P, Wang X.Tetrahydrobenzocyclooctabenzofuranone lignans from Kadsura longipedunculata.J Nat Prod.2019;82:2842-51.
11.Kuo YH, Li SY, Huang RL.Schizarin B, C, D, and E, four new liganans from Kadsura matsudai and their antihepatitis activities.J Nat Prod.2001;64:1608-1608.
12.Liu Y, Yu HY, Wang YM.Neuroprotective lignans from the fruits of Schisandra bicolor var.tuberculata.J Nat Prod.2017;80:1117-24.
13.Yang YP, Jian YQ, Liu YB.Triterpenoids from Kadsura coccinea with their anti-infammatory and inhibited proliferation of rheumatoid arthritis-fbroblastoid synovial cells activities.Front Chem.2021;9:808870.
14.Ma WH, He JC, Li L.Two new triterpenoids from the stems of Schisandra bicolor.Helv Chim Acta.2009;92:2086-91.
15.Huang RM, Huang HJ, Zhang NL.Two new lignans from the stems of Schisandra bicolor.J Asian Nat Prod Res.2012;14:1116-21.
16.Chen YN, Li N, Zhu YH.Dibenzylbutane lignans from the stems of Schisandra bicolor.Nat Prod Commun.2013;8:1121-2.
17.Pu JX, Gao XM, Lei C.Three new compounds from Kadsura longipedunculata.Nat Prod Commun.2008;56:1143-6.
18.Li C, Li N, Yue J.Two new lignans from Saururus chinensis.Nat Prod Res.2017;31:1598-603.
19.Willoughby PH, Jansma MJ, Hoye TR.A guide to small-molecule structure assignment through computation of (H-1 and C-13) NMR chemical shifts.Nat Protoc.2014;9:643-60.
20.Grimblat N, Zanardi MM, Sarotti AM.Beyond DP4:an improved prob-ability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts.J Org Chem.2015;80:12526-34.
21.Kiem PV, Minh CV, Nhiem NX.Muurolane-type sesquiterpenes from marine sponge Dysidea cinerea.Magn Reson Chem.2014;52:51-6.
22.Chyu CF, Ke MR, Chang YS.New cadinane-type sesquiterpenes from the roots of Taiwania cryptomerioides hayata.Helv Chim Acta.2007;90:1514-21.
23.Sarkanen KV, Wallis AFA.PMR analysis and conformation of 2,5-bis-(3,4,5-trimethoxyphenyl)-3,4-dimethyltetrahydrofuran isomers.J Heterocycl Chem.1973;10:1025-7.
24.Kilidhar SB, Parthasarathy MR, Sharma P.Prinsepiol, a lignan from stem of Prinsepia utilis.Phytochemistry.1982;21:796-7.
25.Tsukamoto H, Hisada S, Nishibe S.Lignans from bark of Fraxinus mandshurica var.japoica and F.japonica.Chem Pharm Bull.1984;32:4482-9.
26.Wei XL, Chen Y, Chen XY.Chem.A new lignan from the roots of Ginkgo biloba.Nat Compd.2015;51:819-21.
27.Shen ZB, Theander O.(-)-Massoniresinol, a lignan from Pinus massoniana.Phytochemistry.1985;24:364-5.
28.Lee DY, Seo KH, Jeong RH.Anti-infammatory lignans from the fruits of Acanthopanax sessiliforus.Molecules.2012;18:41-9.
29.Jiang BP, Liu YM, Le L.Cajaninstilbene acid prevents corticosterone-induced apoptosis in PC12 cells by inhibiting the mitochondrial apop-totic pathway.Cell Physiol Biochem.2014;34:1015-26.
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