283
Views
18
CrossRef citations to date
0
Altmetric
Review Articles

Dioscorea bulbifera L.-induced hepatotoxicity and involvement of metabolic activation of furanoterpenoids

, &
Pages 568-584 | Received 03 May 2020, Accepted 20 Jul 2020, Published online: 06 Aug 2020

References

  • Byrns MC, Predecki DP, Peterson LA. 2002. Characterization of nucleoside adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem Res Toxicol. 15(3):373–379.
  • Byrns MC, Vu CC, Peterson LA. 2004. The formation of substituted 1,N6-etheno-2′-deoxyadenosine and 1,N2-etheno-2′-deoxyguanosine adducts by cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem Res Toxicol. 17(12):1607–1613.
  • Chen XW, Serag ES, Sneed KB, Zhou SF. 2011. Herbal bioactivation, molecular targets and the toxicity relevance. Chem Biol Interact. 192(3):161–176.
  • Cheng F. 1995. 8 case reports of toxic hepatitis induced by Dioscorea bulbifera. Jangsu J Tradit Chin Med. 16(7):9.
  • Chinese Pharmacopoeia Commission. 2015. Pharmacopoeia of the People’s Republic of China. Beijing (China): Chemical Industry Press.
  • Demetzos C, Dimas K, Hatziantoniou S, Anastasaki T, Angelopoulou D. 2001. Cytotoxic and anti-inflammatory activity of labdane and cis-clerodane type diterpenes. Planta Med. 67(7):614–618.
  • Feng JH. 1989. 2 case reports of toxic hepatitis induced by Dioscorea bulbifera. Shandong J Tradit Chin Med. 8(2):30.
  • Gao Y. 2006. Liver damage associated with combination of Sanjin tablets and Longbishu capsules. Adv Drug Reactions J. 8(4):305.
  • Gao HY, Hou BL, Kuroyanagi M, Wu LJ. 2007. Constituents from anti-tumor-promoting active part of Dioscorea bulbifera L. in JB6 mouse epidermal cells. Asian J Tradit Med. 2(3):104–109.
  • Gingipalli L, Dedon PC. 2001. Reaction of cis- and trans-2-Butene-1,4-dial with 2′-deoxycytidine to form stable oxadiazabicyclooctaimine adducts. J Am Chem Soc. 123(11):2664–2665.
  • Grynberg NF, Echevarria A, Lima JE, Pamplona SS, Pinto AC, Maciel MA. 1999. Anti-tumour activity of two 19-nor-clerodane diterpenes, trans-dehydrocrotonin and trans-crotonin, from Croton cajucara. Planta Med. 65(8):687–689.
  • Guan XR, Zhu L, Xiao ZG, Zhang YL, Chen HB, Yi T. 2017. Bioactivity, toxicity and detoxification assessment of Dioscorea bulbifera L.: a comprehensive review. Phytochem Rev. 16(3):573–601.
  • Guengerich FP. 2003. Cytochrome P450 oxidations in the generation of reactive electrophiles: epoxidation and related reactions. Arch Biochem Biophys. 409(1):59–71.
  • Guengerich FP. 2008. Cytochrome P450 and chemical toxicology. Chem Res Toxicol. 21(1):70–83.
  • Hu Z, Zhou S, Zhang N, Li W, Lin D, Peng Y, Zheng J. 2018. Development of polyclonal antibodies for detection of diosbulbin B-derived cis-enedial protein adducts. Chem Res Toxicol. 31(4):231–237.
  • Huang ZF, Hua BC, Chen XF, Shi DH, Cheng XL, Wang YH, Liao HJ. 2013. Analysis of liver injury in 78 cases caused by Rhizoma Dioscoreae bulbiferae and related preparation. Chin J Exp Med Formul. 19(23):295–297.
  • Ji H, Song N, Ren J, Li W, Zhang L, Xu B, Li H, Shen G, Li H. 2020. Systems toxicology approaches reveal the mechanisms of hepatotoxicity induced by diosbulbin B in male mice. Chem Res Toxicol. 33(6):1389–1402.
  • Jiang DS. 1976. 4 case reports of toxic hepatitis induced by Dioscorea bulbifera (Abstract). New Med. 7(01):30.
  • Jiang S. 1978. Dictionary of Chinese Crude Drugs. Shanghai (China): Shanghai Scientific Technological Publisher.
  • Jiang H, Cai B, Zhao W. 2011. A case of severe liver damage induced by Longbishu capsules. People Mil Surg. 54(10):893.
  • Jiang JZ, Yang BH, Ji LL, Yang L, Mao YC, Hu ZH, Wang ZT, Wang CH. 2017. Metabolic-induced cytotoxicity of diosbulbin B in CYP3A4-expressing cells. Toxicol in Vitro. 38:59–66.
  • Jiang M, Xiong NN, Liu SL, Fu WM, Ye B, Chen J. 2004. Adverse drug reaction of compound prescription of Huangyaozi (Dioscorea Bulbifera L.) in clinical trial and its management. Chin J Evid-Based Med. 04(4):255–257.
  • Jiang ZF. 1981. 17 case reports of drug-induced liver disease induced by Dioscorea bulbifera. J Tradit Chin Med. 2:37–38.
  • Jin AP. 1996. A case of abnormal liver function associated with Dioscorea bulbifera use. China J Chin Mater Med. 2(6):57.
  • Kawasaki T, Komori T, Setoguchi S. 1968. Furanoid Norditerpenes from Dioscoreaceae Plants. I. Diosbulbins A, B and C from Dioscorea bulbifera L. forma spontanea MAKINO et NEMOTO. Chem Pharm Bull. 16(12):2430–2435.
  • Komori T. 1997. Glycosides from Dioscorea bulbifera. Toxicon. 35(10):1531–1535.
  • Kong XL, Li H, Zhu JX, Wang Y. 2004. A case of suspected drug-induced liver disease induced by Chinese patent medicine Baishi Pills. Jiangsu Pharm Clin Res. 12(S1):79.
  • Li JX, Yu HS, Song YT, Jia QH. 2013. Advances in modern research on Dioscorea bulbifera. Guide China Med. 11(26):52–55.
  • Li Q. 2006. Icterohepatitis associated with Zhaoyulongyikong pills. Adv Drug Reactions J. 8(3):216.
  • Li SS, Deng JZ, Zhao SX. 1999. Steroids from tuber of Dioscorea bulbifera L. J Plant Res Environ. 8(2):61–62.
  • Li W, Lin D, Gao H, Xu Y, Meng D, Smith CV, Ying P, Zheng J. 2016. Metabolic activation of furan moiety makes Diosbulbin B hepatotoxic. Arch Toxicol. 90(4):863–872.
  • Li WC, Yang J, Li HW, Wang BY. 2009. A case of drug-induced liver disease caused by Dioscorea bulbifera. Chin J Clin Rational Drug Use. 2(15):79.
  • Liao ZQ. 1980. 11 case reports of toxic hepatitis induced by Dioscorea bulbifera. Zhejiang Med J. 3:30–31.
  • Liao ZQ, Chen AY. 1994. 16 case reports of toxic hepatitis induced by Dioscorea bulbifera. Chin J Integr Tradit West Med on Liver. 4(1):55.
  • Lin D, Guo X, Gao H, Cheng L, Cheng M, Song S, Peng Y, Zheng J. 2015. In vitro and in vivo studies of the metabolic activation of 8-epidiosbulbin E acetate. Chem Res Toxicol. 28(9):1737–1746.
  • Lin D, Li C, Peng Y, Gao H, Zheng J. 2014. Cytochrome P450-mediated metabolic activation of diosbulbin B. Drug Metab Dispos. 42(10):1727–1736.
  • Lin D, Li W, Peng Y, Jiang C, Xu Y, Gao H, Zheng J. 2016. Role of metabolic activation in 8-epidiosbulbin E acetate-induced liver injury: mechanism of action of the hepatotoxic furanoid. Chem Res Toxicol. 29(3):359–366.
  • Lin D, Li W, Tian X, Peng Y, Zheng J. 2019. In vitro DNA adduction resulting from metabolic activation of diosbulbin B and 8-epidiosbulbin E acetate. Chem Res Toxicol. 32(1):38–48.
  • Lin D, Wang K, Guo X, Gao H, Peng Y, Zheng J. 2016. Lysine- and cysteine-based protein adductions derived from toxic metabolites of 8-epidiosbulbin E acetate. Toxicol Lett. 264:20–28.
  • Lin HW, Zhang G, Zhao HB, Zhang C, Lin GL. 2002. Advances in studies on Dioscorea bulbifera. Chin Tradit Herb Drugs. 33(2):175–177.
  • Liu H, Chou GX, Guo YL, Ji LL, Wang JM, Wang ZT. 2010. Norclerodane diterpenoids from rhizomes of Dioscorea bulbifera. Phytochemistry. 71(10):1174–1180.
  • Liu H, Chou GX, Wang JM, Ji LL, Wang ZT. 2011. Steroidal saponins from the rhizomes of Dioscorea bulbifera and their cytotoxic activity. Planta Med. 77(8):845–848.
  • Liu H, Chou GX, Wu T, Guo YL, Wang SC, Wang CH, Wang ZT. 2009. Steroidal sapogenins and glycosides from the rhizomes of Dioscorea bulbifera. J Nat Prod. 72(11):1964–1968.
  • Liu SL, Xiong NN, Zou JD, Jiang M, Ning KQ, Wang H. 2005. Clinical report on hepatic function lesion caused by Rongbishu capsule for treating benign prostatic hyperplasia. Chin J Evid-Based Med. 05(3):229–231.
  • Liu TT. 1982. 1 case report of hepatic damage induced by Dioscorea bulbifera. J Tradit Chin Med. 23(04):32.
  • Liu X, Liu YO, Liang Y. 2013. A case of drug-induced liver injury caused by simvastatin and Longbishu capsules. Pharmacy Administration Commision of Chinese Hospital Association. Proceedings of the 2013 China Clinical Pharmacy Academic Annual Meeting and the 9th Clinical Pharmacists Forum; Jun 14–15; Nanchang (China): Pharmacy Administration Commision of Chinese Hospital Association.
  • Liu XD, Wen W. 1999. A case of severe liver damage associated with Dioscorea bulbifera use. Chin J Integr Tradit West Med on Liver. 9(2):20.
  • Lu XH, Wu QH. 2014. Literature analysis of 33 cases of liver injury induced by the compound preparation of Dioscorea bulbifera L. Sichuan J Tradit Chin Med. 32(9):162–164.
  • Ma M, Jiang Z, Ruan J, Tan X, Liu J, Wang C, Zha XM, Zhang L. 2012. The furano norclerodane diterpenoid disobulbin-D induces apoptosis in normal human liver L-02 cells. Exp Toxicol Pathol. 64(6):611–618.
  • Ma Y, Niu C, Wang J, Ji L, Wang Z. 2014. Diosbulbin B-induced liver injury in mice and its mechanism. Hum Exp Toxicol. 33(7):729–736.
  • Murray RDH, Jorge ZD, Khan NH, Shahjahan M, Quaisuddin M. 1984. Diosbulbin D and 8-epidiosbulbin E acetate, norclerodane diterpenoids from Dioscorea bulbifera tubers. Phytochemistry. 23(3):623–625.
  • Niu C, Wang J, Ji L, Wang Z. 2014. Protection of Angelica sinensis (Oliv) diels against hepatotoxicity induced by Dioscorea bulbifera L. and its mechanism. Biosci Trends. 8(5):253–259.
  • Okigbo RN, Anuagasi CL, Amadi JE, Ukpabi UJ. 2009. Potential inhibitory effects of some African tuberous plant extracts on Escherichia coli, Staphylococcus aureus and Candida albicans. Int J Integr Biol. 6(2):91–98.
  • Ravindranath V, Burka LT, Boyd MR. 1984. Reactive metabolites from the bioactivation of toxic methylfurans. Science. 224(4651):884–886.
  • Shen XR, Dong JY. 2015. Determination of diosbulbin B in Dioscorea bulbifera L. from different regions. Herald Med. 34(7):394–397.
  • Shi HY, Wang ZX. 2005. 2 cases of liver damage induced by Dioscorea bulbifera. Zhejiang Integr Tradit Chin West Med. 15(3):63–64.
  • Shriram V, Jahagirdar S, Latha C, Kumar V, Puranik V, Rojatkar S, Dhakephalkar PK, Shitole MG. 2008. A potential plasmid-curing agent, 8-epidiosbulbin E acetate, from Dioscorea bulbifera L. against multidrug-resistant bacteria. Int J Antimicrob Agents. 32(5):405–410.
  • Song FL, Gan RY, Zhang Y, Xiao Q, Kuang L, Li HB. 2010. Total phenolic contents and antioxidant capacities of selected Chinese medicinal plants. Int J Mol Sci. 11(6):2362–2372.
  • Su L, Zhu JH, Cheng LB. 2003. Experimental pathological study of subacute intoxication by Dioscorea bulbifera L. J Forensic Med. 19(2):81–83.
  • Subasini U, Thenmozhi S, Sathyamurthy D, Vetriselvan S, Rajamanickam GV, Dubey GP. 2013. Pharmacognostic and phytochemical investigations of Dioscorea bulbifera L. Int J Pharm Life Sci. 4(5):2693–2700.
  • Tan XQ, Ruan JL, Chen HS, Wang JY. 2003. Studies on liver-toxicity in Rhigoma of Dioscorea bulbifera. China J Chin Mater Med. 28(7):661–663.
  • Tang Y, Xue YB, Zhou L, Zhang JW, Yao GM, Luo ZW, Du G, Zhang YH. 2014. New norclerodane diterpenoids from the tubers of Dioscorea bulbifera. Chem Pharm Bull. 62(7):719–724.
  • Wang G, Liu JS, Lin BB, Wang GK, Liu JK. 2009. Two new furanoid norditerpenes from Dioscorea bulbifera. Chem Pharm Bull. 57(6):625–627.
  • Wang J, Liang Q, Ji L, Liu H, Wang C, Wang Z. 2011. Gender-related difference in liver injury induced by Dioscorea bulbifera L. rhizome in mice. Hum Exp Toxicol. 30(9):1333–1341.
  • Wang JM, Ji LL, Liu H, Wang ZT. 2010. Study of the hepatotoxicity induced by Dioscorea bulbifera L. rhizome in mice. Biosci Trends. 4(2):79–85.
  • Wang JZ, Liu SM, Zhao Y, Tang Q. 2009. The effects of different treatments of Dioscorea bulbifera alcohol extract on hepatotoxicity. Inf Tradit Chin Med. 26(2):21–22.
  • Wang K, Li W, Chen J, Peng Y, Zheng J. 2015. Detection of cysteine- and lysine-based protein adductions by reactive metabolites of 2,5-dimethylfuran. Anal Chim Acta. 896:93–101.
  • Wang K, Lin D, Guo X, Huang W, Zheng J, Peng Y. 2017. Chemical identity of interaction of protein with reactive metabolite of diosbulbin B in vitro and in vivo. Toxins. 9(8):249.
  • Wang K, Zheng L, Peng Y, Song J, Zheng J. 2014. Selective and sensitive platform for function-based screening of potentially harmful furans. Anal Chem. 6(21):10755–10762.
  • Wang LL, Zhao DS, Shi W, Li ZQ, Wu ZT, Li P, Li HJ. 2017. Describing the holistic toxicokinetics of hepatotoxic Chinese herbal medicines by a novel integrated strategy: Dioscorea bulbifera rhizome as a case study. J Chromatogr B Analyt Technol Biomed Life Sci. 1064:40–48.
  • Wu XX, Zhong H, Zang KT. 2000. A case of liver damage induced by Dioscorea bulbifera. Lishizhen Med Mater Med Res. 11(2):186.
  • Wu ZM, Liao F, Jia GQ. 2012. A case of acute liver failure induced by Bashi Pills. Chin J Dermatol. 45(12):858.
  • Xu Y, Chen CC, Yang L, Wang JM, Ji LL, Wang ZT, Hu ZB. 2011. Evaluation on hepatotoxicity caused by Dioscorea bulbifera based on analysis of bile acids. Acta Pharm Sin. 46(1):39–44.
  • Xu YZ, Bai CX, Zhou Q, Shen XW, Zheng SZ, Fu ZS, Chen H. 1988. Study on the ethanol extract of Dioscorea bulbifera in inhibiting inactivated-virus. Chin Pharm J. 23(09):535–537.
  • Xu ZL, Ding ZZ. 1999. Study of Dioscorea bulbifera L. Chinese Herb Med. 24(8):496–498.
  • Yang B, Liu W, Chen K, Wang Z, Wang C. 2014. Metabolism of diosbulbin B in vitro and in vivo in rats: formation of reactive metabolites and human enzymes involved. Drug Metab Dispos. 42(10):1737–1750.
  • Yang F, Liang Y, Xu L, Ji L, Yao N, Liu R, Shi L, Liang T. 2016. Exploration in the cascade working mechanisms of liver injury induced by total saponins extracted from Rhizoma Dioscorea bulbifera. Biomed Pharmacother. 83:1048–1056.
  • Ye J, Xue M, Liu Y, Zhu S, Li Y, Liu X, Cai D, Rui J, Zhang L. 2019. Diosbulbin B-induced mitochondria-dependent apoptosis in L-02 hepatocytes is regulated by ROS-mediated autophagy. Front Pharmacol. 10:676.
  • Yonemitsu M, Fukuda N, Kimura T, Komori T. 1993. Diosbulbin-B from the leaves and stems of Dioscorea bulbifera: 1H-1H and 13C-1H COSY NMR studies. Planta Med. 59(6):577.
  • Zhang HM, Yuan JY. 2009. The progress of diosbulbin B research on pharmacology and toxicology. Herald Med. 28:490–492.
  • Zhang JZ. 2007. Zengshengping tablets-induced hepatic damage. Adv Drug Reactions J. 9(3):215.
  • Zhang LP, Zhou HP. 2009. A case of death caused by Dioscorea bulbifera. Herald Med. 28(8):1097.
  • Zhang QL, Jia Y, Yixia L. 2010. Liver damage due to Baishi Pills. Adv Drug Reactions J. 12(4):297–298.
  • Zhang Y, Miao H, Guan H, Wang C, Wang Z, Ji L. 2019. Long-term diosbulbin B treatment induced liver fibrosis in mice. Chem Biol Interact. 298:15–23.
  • Zhang Z, Lin D, Li W, Gao H, Peng Y, Zheng J. 2017. Sensitive bromine-based screening of potential toxic furanoids in Dioscorea bulbifera L. J Chromatogr B Analyt Technol Biomed Life Sci. 1057:1–14.
  • Zhang Z, Tang W. 2018. Drug metabolism in drug discovery and development. Acta Pharm Sin B. 8(5):721–732.
  • Zhao DS, Jiang LL, Wang LL, Wu ZT, Li ZQ, Shi W, Li P, Jiang Y, Li HJ. 2018. Integrated metabolomics and proteomics approach to identify metabolic abnormalities in rats with Dioscorea bulbifera rhizome-induced hepatotoxicity. Chem Res Toxicol. 31(9):843–851.
  • Zhao DS, Wu ZT, Li ZQ, Wang LL, Jiang LL, Shi W, Li P, Jiang Y, Li HJ. 2018. Liver-specific metabolomics characterizes the hepatotoxicity of Dioscorea bulbifera rhizome in rats by integration of GC-MS and 1H-NMR. J Ethnopharmacol. 226:111–119.
  • Zhao WY. 2004. 2 cases of drug-induced liver disease induced by Baishi Pills. J Qiqihar Med Coll. 25(7):766.
  • Zhao XJ, Yan XS, Sun DD. 2012. Pharmacological research and clinical progress of Rhizoma Dioscorea bulbiferae. Drug Eval Res. 35(2):147–149.
  • Zhou HM, Wang JC. 1989. 3 case reports of toxic hepatitis caused by Dioscorea bulbifera in the treatment of Hashimoto’s thyroiditis. Shandong J Tradit Chin Med. 8(2):29.
  • Zhou KM, Shi LL, Yin YY. 2006. A case of acute jaundice type drug-induced hepatitis induced by Baishi Pills. J Clin Dermatol. 35(11):737–738.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.