Published January 31, 2022
| Version v1
Journal article
Restricted
Lignans from the seeds of Herpetospermum pedunculosum and their farnesoid X receptor-activating effect
Creators
- 1. * & College of Pharmaceutical Sciences, Key Laboratory of Luminescence Analysis and Molecular Sensing (Ministry of Education), Southwest University, Chongqing
Description
Meng, FanCheng, Ma, YingXiong, Zhan, HongHong, Zong, Wei, Linghu, Lang, Wang, Zhe, Lan, XiaoZhong, Liao, ZhiHua, Chen, Min (2022): Lignans from the seeds of Herpetospermum pedunculosum and their farnesoid X receptor-activating effect. Phytochemistry (113010) 193: 1-16, DOI: 10.1016/j.phytochem.2021.113010, URL: http://dx.doi.org/10.1016/j.phytochem.2021.113010
Files
Linked records
Oops! Something went wrong while fetching results.
Additional details
Identifiers
- LSID
- urn:lsid:plazi.org:pub:F01AFE4F43026F2FBC3A384EFF994D53
References
- Cao, W.R., Ge, J.Q., Xie, X., Fan, M.L., Fan, X.D., Wang, H., Dong, Z.Y., Liao, Z.H., Lan, X. Z., Chen, M., 2017. Protective effects of petroleum ether extracts of Herpetospermum caudigerum against α -naphthylisothiocyanate-induced acute cholestasis of rats. J. Ethnopharmacol. 198, 139-147. https://doi.org/10.1016/j.jep.2017.01.003.
- Chen, L., Wang, L., Zhang, Q.W., Zhang, S.Y., Ye, W.C., 2012. Non-alkaloid chemical constituents from Coptis chinensis. Chin. Mater. Med. 37, 1241-1244. https://doi. org/10.4268/cjcmm20120915.
- Chen, Y.Y., Chang, F.R., Wu, Y.C., 1996. Isoquinoline alkaloids and lignans from Rollinia mucosa. J. Nat. Prod. 59, 904-906. https://doi.org/10.1021/np960414z.
- Cong, L.B., Yuan, H.L., Wang, Q., Li, X.Y., Gong, Q.F., Xiao, X.H., 2008. Simultaneous determination of seven bioactive lignans in Herpetospermum caudigerum by RP-HPLC method. Biomed. Chromatogr. 22, 1084-1090. https://doi.org/10.1002/bmc.1028.
- Dang, P.H., Nguyen, H.X., Nguyen, H.H.T., Vo, T.D., Le, T.H., Phan, T.H.N., Nguyen, M. T.T., Nguyen, N.T., 2017. Lignans from the roots of Taxus wallichiana and their α- glucosidase inhibitory activities. J. Nat. Prod. 80, 1876-1882. https://doi.org/ 10.1021/acs.jnatprod.7b00171.
- Dong, Z.Y., Wang, H., Ma, Y.X., Lan, X.Z., Chen, M., 2019. Chemical constituents from Herpetospermum caudigerum. Chin. Tradit. Pat. Med. 41, 341-344. https://doi.org/ 10.3969/j.issn.1001-1528.2019.02.020.
- Dong, Z.Y., Tao, X.Y., Deng, L.Q., Ge, J.Q., Quan, H., Lan, X.Z., Liao, Z.H., Chen, M., 2020. Pharmacokinetics and tissue distribution study of herpetotriol in rats by ultrahigh performance liquid chromatography with tandem mass spectrometry. Can. J. Physiol. Pharmacol. 98, 366-372. https://doi.org/10.1139/cjpp-2019-0633.
- Fang, Z.F., Zhang, T., Cao, X.Q., Shi, L., 2018. Novel sesquilignan and lignan glycoside from the twigs and leaves of Illicium majus. Fitoterapia 129, 42-46. https://doi.org/ 10.1016/j.fitote.2018.06.014.
- Feng, X., Zhong, G.J., Da-Ji, D.B., Yang, B., Chen, L.Y., Du, S.Y., 2018. Hepatoprotective effect of Herpetospermum caudigerum Wall. on carbon tetrachloride-induced hepatic fibrosis in rats. J. Cell Mol. Med. 22, 3691-3697. https://doi.org/10.1111/ jcmm.13568.
- He, S., Zeng, K.W., Jiang, Y., Tu, P.F., 2016. Nitric oxide inhibitory constituents from the barks of Cinnamomum cassia. Fitoterapia 112, 153-160. https://doi.org/10.1016/j. fitote.2016.05.005.
- Ji, X., Xu, Y., Luo, X., Yu, T., Zhou, C., Li, L., 2014. Isolation and identification of chemical constituents from seeds of Crataegus pinnatifida Bge. J. Shenyang Pharm. Univ. 31, 448-450. https://doi.org/10.14066/j.cnki.cn21-1349/r.2014.06.006, 504.
- Jiang, H.Z., Hu, S., Tan, R.X., Tan, R., Jiao, R.H., 2020. Neocucurbitacin D, a novel lactone-type norcucurbitacin as xanthine oxidase inhibitor from Herpetospermum pedunculosum. Nat. Prod. Res. 34, 1728-1734. https://doi.org/10.1080/ 14786419.2018.1528592.
- Jiang, H.Z., Tan, R., Jiao, R.H., Deng, X.Z., Tan, R.X., 2016. Herpecaudin from Herpetospermum caudigerum, a xanthine oxidase inhibitor with a novel isoprenoid scaffold. Planta Med. 82, 1122-1127. https://doi.org/10.1055/s-0042-108210.
- Jutiviboonsuk, A., Zhang, H., Tan, G.T., Ma, C., Hung, N.V., Cuong, N.M., Bunyapraphatsara, N., Soejarto, D.D., Fong, H.H.S., 2005. Bioactive constituents from roots of Bursera tonkinensis. Phytochemistry 66, 2745-2751. https://doi.org/ 10.1016/j.phytochem.2005.09.025.
- Kaouadji, M., Pieraccini, E., 1984. Herpetetradione, nouveau lignoide tetramere isole d' Herpetospermum pedunculosum wall. Tetrahedron Lett. 25, 5135-5136. https://doi. org/10.1016/S0040-4039(01)81544-6.
- Kaouadji, M., 1987. Herpetetrone, another tetrameric lignoid from Herpetospermum pedunculosum seeds. J. Nat. Prod. 50, 1089-1094. https://doi.org/10.1021/ np50054a013.
- Kawabe, Y., Ishikawa, R., Akao, Y., Yoshida, A., Inai, M., Asakawa, T., Hamashima, Y., Kan, T., 2014. Stereocontrolled total synthesis of hedyotol. A. Org. Lett. 16, 1976-1979. https://doi.org/10.1021/ol500524y.
- Li, B.B., Li, J.L., Li, N., Qi, S.Z., Lee, S.H., Zhang, L., Xing, S.S., Tuo, Z.D., Cui, L., 2017. Diacylglycerol acyltransferase 1 (DGAT1) inhibition by furofuran lignans from stems of Acanthopanax senticosus. Arch Pharm. Res. (Seoul) 40, 1271-1277. https://doi. org/10.1007/s12272-016-0842-5.
- Li, M.H., Feng, X., Da-Ji, D.B., Chen, C., Ruan, L.Y., Xing, Y.X., Chen, L.Y., Zhong, G.J., Wang, J.S., 2019. Hepatoprotection of Herpetospermum caudigerum Wall. against CCl4-induced liver fibrosis on rats. J. Ethnopharmacol. 229, 1-14. https://doi.org/ 10.1016/j.jep.2018.09.033.
- Li, Q., Li, H.J., Xu, T., Du, H., Gang, C.L.H., Fan, G., Zhang, Y., 2018. Natural medicines used in the traditional Tibetan medical system for the treatment of liver diseases. Front. Pharmacol. 9, 29/1-29/16. https://doi.org/10.3389/fphar.2018.00029.
- Liu, X., Fu, J., Yao, X.J., Yang, J., Liu, L., Xie, T.G., Jiang, P.C., Jiang, Z.H., Zhu, G.Y., 2018. Phenolic constituents isolated from the twigs of Cinnamomum cassia and their potential neuroprotective efects. J. Nat. Prod. 81, 1333-1342. https://doi.org/ 10.1021/acs.jnatprod.7b00924.
- Liu, Y.B., Cheng, X.R., Qin, J.J., Yan, S.K., Jin, H.Z., Zhang, W.D., 2011. Chemical constituents of Toona ciliata var. pubescens. Chin. J. Nat. Med. 9 https://doi.org/ 10.3724/SP.J.1009.2011.00115, 0115-0119.
- Luca, P., Elke, H.H., Mostafa, A., Fabian, M., Mawunu, M., Thea, L., Daniel, S., Stefan, S., Hermann, S., 2018. Dihydrochalcone glucosides from the subaerial parts of Thonningia sanguinea and their in vitro PTP1B inhibitory activities. J. Nat. Prod. 81, 2091-2100. https://doi.org/10.1021/acs.jnatprod.8b00450.
- Ma, Y.X., Wang, H., Wang, R., Meng, F.C., Dong, Z.Y., Wang, G.W., Lan, X.Z., Quan, H., Liao, Z.H., Chen, M., 2019. Cytotoxic lignans from the stems of Herpetospermum pedunculosum. Phytochemistry 164, 102-110. https://doi.org/10.1016/j. phytochem.2019.05.004.
- Massafra, V., Pellicciari, R., Gioiello, A., van Mil, S.W.C., 2018. Progress and challenges of selective Farnesoid X Receptor modulation. Pharmacol. Therapeut. 191, 162-177. https://doi.org/10.1016/j.pharmthera.2018.06.009.
- Meng, F.C., Zong, W., Wei, X.D., Tao, Y.Y., Wang, G.W., Liao, Z.H., Chen, M., 2021. Dolomiaea souliei ethyl acetate extract protected against α -naphthylisothiocyanate-induced acute intrahepatic cholestasis through regulation of farnesoid x receptormediated bile acid metabolism. Phytomedicine 87, 153588. https://doi.org/ 10.1016/j.phymed.2021.153588.
- Minh, C.V., Nguyen, X.N., Yen, H.T., Kiem, P.V., Tai, B.H., Hoang, L.T.A., Hien, T.T.T., Park, S.J., Kim, N., Kim, S.H., 2015. Chemical constituents of Trichosanthes kirilowii and their cytotoxic activities. Arch Pharm. Res. (Seoul) 38, 1443-1448. https://doi. org/10.1007/s12272-014-0490-6.
- Moon, S.S., Rahman, A.A., Kim, J.Y., Kee, S.H., 2008. Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii. Bioorg. Med. Chem. 16, 7264-7269. https://doi.org/10.1016/j. bmc.2008.06.032.
- Nakashima, S., Matsuda, H., Oda, Y., Nakamura, S., Xu, F., Yoshikawa, M., 2010. Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Bioorg. Med. Chem. 18, 2337-2345. https://doi.org/10.1016/j. bmc.2010.01.046.
- Qiao, L., Yang, L., Zhang, D., Zuo, J., Dai, J., 2011. Studies on chemical constitutes from callus cultures of Stellera chamaejasme. China J. Chin. Mater. Med. 36, 3457-3462. https://doi.org/10.4268/cjcmm20112415.
- Shen, B.D., Chen, H.G., Shen, C.Y., Xu, P.H., Li, J.J., Shen, G., Yuan, H.L., Han, J., 2015. Hepatoprotective effects of lignans extract from Herpetospermum caudigerum against CCl4-induced acute liver injury in mice. J. Ethnopharmacol. 164, 46-52. https://doi. org/10.1016/j.jep.2015.01.044.
- Shen, H.Y., Dai, H.F., Zhao, Y.X., Luo, Y., Chen, H.Q., Mei, W.L., 2012. Antibacterial components from Dragon' s blood of Dracaena cambodiana. Lishizhen Med. Mater. Med. Res. 23, 2954-2956. https://doi.org/10.3969/j.issn.1008-0805.2012.12.003.
- Shen, Y.C., Chen, C.Y., Lin, Y.M., Kuo, Y.H., 1997. A lignan from roots of Taxus mairei. Phytochemistry 46, 1111-1113. https://doi.org/10.1016/S0031-9422(97)00352-X.
- The Plant List, 2013. Published on the internet. http://www.theplantlist.org/. (Accessed 6 August 2021). Version 1.1.
- Wagner, M., Zollner, G., Trauner, M., 2009. New molecular insights into the mechanisms of cholestasis. J. Hepatol. (Amst.) 51, 565-580. https://doi.org/10.1016/j. jhep.2009.05.012.
- Wang, L.Q., Zhao, Y.X., Zhou, L., Zhou, J., 2009. Lignans from Gnetum montanum markgr. f. Megalocarpua. Chem. Nat. Compd. 45, 424-426. https://doi.org/10.1007/s10600- 009-9325-y.
- Wei, X.D., Fan, X.D., Feng, Z.Y., Ma, Y.X., Lan, X.Z., Chen, M., 2020a. Ethyl acetate extract of herpetospermum pedunculosum alleviates α -naphthylisothiocyanate-induced cholestasis by activating the farnesoid x receptor and suppressing oxidative stress and inflammation in rats. Phytomedicine 76, 153257. https://doi.org/10.1016/j. phymed.2020.153257.
- Wei, X.D., Ma, Y.X., Dong, Z.Y., Wang, G.W., Lan, X.Z., Liao, Z.H., Chen, M., 2020b. Dehydrodiconiferyl alcohol, a lignan from Herpetospermum pedunculosum, alleviates cholestasis by activating pathways associated with the farnesoid X receptor. Phytomedicine 80, 153378. https://doi.org/10.1016/j.phymed.2020.153378.
- Wu, Z., Lai, Y., Zhou, L., Wu, Y., Zhu, H., Hu, Z., Yang, J., Zhang, J., Wang, J., Luo, Z., Xue, Y., Zhang, Y., 2016. Enantiomeric lignans and neolignans from Phyllanthus glaucus: enantioseparation and their absolute confgurations. Sci. Rep. 6, 24809. https://doi.org/10.1038/srep24809.
- Xu, B., Liu, S., Fan, X.D., Deng, L.Q., Ma, W.H., Chen, M., 2015. Two new coumarin glycosides from Herpetospermum caudigerum. J. Asian Nat. Prod. Res. 17, 738-743. https://doi.org/10.1080/10286020.2014.996137.
- Xu, Z.H., Qin, G.W., Li, X.Y., Xu, R.S., 2001. New biflavanones and bioactive compounds from Stellera chamaejasme L. Acta Pharm. Sin. 36, 668-671. https://doi.org/ 10.16438/j.0513-4870.2001.09.008.
- Yang, F., Zhang, H.J., Zhang, Y.Y., Chen, W.S., Yuan, H.L., Lin, H.W., 2010. A hepatitis B virus inhibitory neolignan from Herpetospermum caudigerum. Chem. Pharm. Bull. 58, 402-404. https://doi.org/10.1002/chin.201033213.
- Yong, M., Kun, G., Qiu, M.H., 2007. A new lignan from the seeds of Arctium lappa. J. Asian Nat. Prod. Res. 9, 541-544. https://doi.org/10.1080/10286020600882577.
- You, M.T., Li, Y.K., Guo, M.L., 2009. Study on chemical constituents of methylene chloride extract of Rubus chingii. Acad. J. Second Mil. Med. Univ. 30, 1199-1202. https://doi.org/10.3724/SP.J.1008.2009 .01199.
- Yu, J.Q., Hang, W., Duan, W.J., Wang, J., Wang, D.J., Qin, X.M., 2014. Two new anti- HBV lignans from Herpetospermum caudigerum. Phytochem. Lett. 10, 230-234. https://doi.org/10.1016/j.phytol.2014.10.001.
- Yuan, H.L., Liu, Y., Zhao, Y.L., Xiao, X.H., 2005. Herpetin, a new bioactive lignan isolated from Herpetospermum caudigerum. J. Chin. Pharmaceut. Sci. 14, 140-143.
- Yuan, H.L., Yang, M., Li, X.Y., You, R.H., Liu, Y., Zhu, J., Xie, H., Xiao, X.H., 2006. Hepatitis B virus inhibiting constituents from Herpetospermum caudigerum. Chem. Pharm. Bull. 54, 1592-1594. https://doi.org/10.1002/chin.200717208.
- Zhang, M., Deng, Y., Zhang, H.B., Su, X.L., Chen, H.L., Yu, T., Guo, P., 2008. Two new coumarins from Herpetospermum caudigerum. Chem. Pharm. Bull. 56, 192-193. https://doi.org/10.1002/chin.200832200.
- Zhang, M., Dong, X.P., Deng, Y., Wang, H., Li, X.N., Song, Q., 2006. A new sesquinorlignan from Herpetospermum pedunculosum. Acta Pharm. Sin. 41, 659-661. https://doi.org/10.1097/00024382-200610001-00089.
- Zhang, S., Huang, Y., Li, Y., Wang, Y., He, X., 2019. Anti-neuroinflammatory and antioxidant phenylpropanoids from Chinese olive. Food Chem. 286, 421-427. https://doi.org/10.1016/j.foodchem.2019.02.031.
- Zhou, L., Yao, G.D., Song, X.Y., Wang, J., Lin, B., Wang, X.B., Huang, X.X., Song, J.J., 2018. Neuroprotective effects of 1,2-diarylpropane type phenylpropanoid enantiomers from red raspberry against H2O2-induced oxidative stress in human neuroblastoma SH-SY5Y Cells. J. Agric. Food Chem. 66, 331-338. https://doi.org/ 10.1021/acs.jafc.7b04430.