Published February 29, 2020 | Version v1

The asarone-derived phenylpropanoids from the rhizome of Acorus calamus var. angustatus Besser

Description

Bai, Yajun, Sun, Ying, Xie, Jing, Li, Bin, Bai, Yujun, Zhang, Dongxu, Liang, Jing, Xiao, Chaoni, Zhong, Aiguo, Cao, Yanjun, Zheng, Xiaohui (2020): The asarone-derived phenylpropanoids from the rhizome of Acorus calamus var. angustatus Besser. Phytochemistry (112212) 170: 1-9, DOI: 10.1016/j.phytochem.2019.112212, URL: http://dx.doi.org/10.1016/j.phytochem.2019.112212

Files

Restricted

The record is publicly accessible, but files are restricted. Log in to check if you have access.

Linked records

Additional details

Identifiers

LSID
urn:lsid:plazi.org:pub:8C26FFB4FFD4414EA411FFCAD917FFCD

Related works

References

  • Bode, J.W., Doyle, M.P., Protopopova, M.N., Zhou, Q.-L., 1996. Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones. J. Org. Chem. 61, 9146-9155.
  • Cao, S., Radwan, M.M., Norris, A., Miller, J.S., Ratovoson, F., Mamisoa, A., Andriantsiferana, R., Rasamison, V.E., Rakotonandrasana, S., Kingston, D.G.I., 2006. Cytotoxic and other compounds from didymochlaena truncatula from the Madagascar rain forest. J. Nat. Prod. 69, 284-286.
  • Cartus, A.T., Schrenk, D., 2016. Metabolism of the carcinogen alpha-asarone in liver microsomes. Food Chem. Toxicol. 87, 103-112.
  • Cartus, A.T., Stegmuller, S., Simson, N., Wahl, A., Neef, S., Kelm, H., Schrenk, D., 2015. Hepatic metabolism of carcinogenic β- asarone. Chem. Res. Toxicol. 28, 1760-1773.
  • Chang, C.-L., Wang, G.-J., Zhang, L.-J., Tsai, W.-J., Chen, R.-Y., Wu, Y.-C., Kuo, Y.-H., 2010. Cardiovascular protective flavonolignans and flavonoids from Calamus quiquesetinervius. Phytochemistry (Elsevier) 71, 271-279.
  • Cho, J., Kong, J.-Y., Jeong, D.-Y., Lee, K.D., Lee, D.-U., Kang, B.-S., 2001. NMDA receptormediated neuroprotection by essential oils from the rhizomes of Acorus gramineus. Life Sci. 68, 1567-1573.
  • Cowan, S., Stewart, M., Abbiw, D.K., Latif, Z., Sarker, S.D., Nash, R.J., 2001. Lignans from strophanthus gratus. Fitoterapia 72, 80-82.
  • Della Greca, M., Monaco, P., Previtera, L., Aliotta, G., Pinto, G., Pollio, A., 1989. Studies on aquatic plants. Part 12. Allelochemical activity of phenylpropanes from Acorus gramineus. Phytochemistry 28, 2319-2321.
  • Dewick, P.M., 2009. Medicinal Natural Products A Biosynthetic Approach, third ed. John Wiley and Sons Ltd., Chichester.
  • Gao, E., Zhou, Z.-Q., Zou, J., Yu, Y., Feng, X.-L., Chen, G.-D., He, R.-R., Yao, X.-S., Gao, H., 2017. Bioactive asarone-derived phenylpropanoids from the rhizome of Acorus tatarinowii Schott. J. Nat. Prod. 80, 2923-2929.
  • Geng, H.M., Chen, J.L.-Y., Furkert, D.P., Jiang, S., Brimble, M.A., 2012. A convergent synthesis of the 2-formylpyrrole spiroketal natural product acortatarin A. Synlett 23, 855-858.
  • Ghelani, H., Chapala, M., Jadav, P., 2016. Diuretic and antiurolithiatic activities of an ethanolic extract of Acorus calamus L. rhizome in experimental animal models. J. Tradit. Complement. Med. 6, 431-436.
  • Gilani, A.U.H., Shah, A.J., Ahmad, M., Shaheen, F., 2006. Antispasmodic effect of Acorus calamus Linn. is mediated through calcium channel blockade. Phytother Res. 20, 1080-1084.
  • Hao, Z.-Y., Liang, D., Luo, H., Liu, Y.-F., Ni, G., Zhang, Q.-J., Li, L., Si, Y.-K., Sun, H., Chen, R.-Y., Yu, D.-Q., 2012. Bioactive sesquiterpenoids from the rhizomes of Acorus calamus. J. Nat. Prod. 75, 1083-1089.
  • He, X., Bai, Y., Zeng, M., Zhao, Z., Zhang, Q., Xu, N., Qin, F., Wei, X., Zhao, M., Wu, N., Li, Z., Zhang, Y., Fan, T.-P., Zheng, X., 2018. Anticonvulsant activities of α- asaronol ((E)- 3'-hydroxyasarone), an active constituent derived from α- asarone. Pharmacol. Rep. 70, 69-74.
  • Hu, J., Feng, X., 2000. Phenylpropanes from Acorus tatarinowii. Planta Med. 66, 662-664.
  • Jin, M., Zhang, B., Sun, Y., Zhang, S., Li, X., Sik, A., Bai, Y., Zheng, X., Liu, K., 2019. Involvement of peroxisome proliferator-activated receptor gamma in anticonvulsant activity of alpha-asaronol against pentylenetetrazole-induced seizures in zebrafish. Neuropharmacology 107760-107760.
  • Kikuzaki, H., Tesaki, S., Yonemori, S., Nakatani, N., 2001. Phenylbutanoid dimers from the leaves of Alpinia flabellata. Phytochemistry 56, 109-114.
  • Kim, K.H., Kim, H.K., Choi, S.U., Moon, E., Kim, S.Y., Lee, K.R., 2011. Bioactive lignans from the rhizomes of Acorus gramineus. J. Nat. Prod. 74, 2187-2192.
  • Kim, K.H., Moon, E., Kang, K.S., Kim, S.Y., Choi, S.U., Lee, K.R., 2015. Alkaloids from Acorus gramineus rhizomes and their biological activity. J. Braz. Chem. Soc. 26, 3-8.
  • Kim, K.H., Moon, E., Kim, H.K., Oh, J.Y., Kim, S.Y., Choi, S.U., Lee, K.R., 2012. Phenolic constituents from the rhizomes of Acorus gramineus and their biological evaluation on antitumor and anti-inflammatory activities. Bioorg. Med. Chem. Lett. 22, 6155-6159.
  • Koul, S.K., Taneja, S.C., Agarwal, V.K., Dhar, K.L., 1988. Minor amides of Piper species. Phytochemistry 27, 3523-3527.
  • Lee, J.Y., Lee, J.Y., Yun, B.-S., Hwang, B.K., 2004. Antifungal activity of β- asarone from rhizomes of Acorus gramineus. J. Agric. Food Chem. 52, 776-780.
  • Li, J., Li, Z.X., Zhao, J.P., Wang, W., Zhao, X.F., Xu, B., Li, L., Zhang, L., Ren, J., Khan, I.A., Li, S.X., 2017. A novel tropoloisoquinoline alkaloid, neotatarine, from Acorus calamus L. Chem. Biodivers. 14.
  • Liu, H., Wu, Z.-L., Huang, X.-J., Peng, Y., Huang, X., Shi, L., Wang, Y., Ye, W.-C., 2018. Evaluation of diarylheptanoid-terpene adduct enantiomers from alpinia officinarum for neuroprotective activities. J. Nat. Prod. 81, 162-170.
  • Lu, Y., Xue, Y., Liu, J., Yao, G., Li, D., Sun, B., Zhang, J., Liu, Y., Qi, C., Xiang, M., Luo, Z., Du, G., Zhang, Y., 2015. ( ± )-Acortatarinowins A-F, norlignan, neolignan, and lignan enantiomers from Acorus tatarinowii. J. Nat. Prod. 78, 2205-2214.
  • Luo, X.-H., Zhang, Y.-Y., Chen, X.-Y., Sun, M.-L., Li, S., Wang, H.-B., 2016. Lignans from the roots of Acorus tatarinowii Schott ameliorate β amyloid-induced toxicity in transgenic Caenorhabditis elegans. Fitoterapia 108, 5-8.
  • Mehrotra, S., Mishra, K.P., Maurya, R., Srimal, R.C., Yadav, V.S., Pandey, R., Singh, V.K., 2003. Anticellular and immunosuppressive properties of ethanolic extract of Acorus calamus rhizome. Int. Immunopharmacol. 3, 53-61.
  • Muthuraman, A., Singh, N., Jaggi, A.S., 2011. Protective effect of Acorus calamus L. in rat model of vincristine induced painful neuropathy: an evidence of anti-inflammatory and anti-oxidative activity. Food Chem. Toxicol. 49, 2557-2563.
  • Ni, G., Shen, Z.-F., Lu, Y., Wang, Y.-H., Tang, Y.-B., Chen, R.-Y., Hao, Z.-Y., Yu, D.-Q., 2011. Glucokinase-Activating sesquinlignans from the rhizomes of Acorus tatarinowii Schott. J. Org. Chem. 76, 2056-2061.
  • Ni, G., Shi, G.-R., Zhang, D., Fu, N.-J., Yang, H.-Z., Chen, X.-G., Yu, D.-Q., 2016. Cytotoxic lignans and sesquiterpenoids from the rhizomes of Acorus tatarinowii. Planta Med. 82, 632-638.
  • Parab, R.S., Mengi, S.A., 2002. Hypolipidemic activity of Acorus calamus L. in rats. Fitoterapia 73, 451-455.
  • Park, C., Kim, S.-I., Ahn, Y.-J., 2003. Insecticidal activity of asarones identified in Acorus gramineus rhizome against three coleopteran stored-product insects. J. Stored Prod. Res. 39, 333-342.
  • Rajput, S.B., Tonge, M.B., Karuppayil, S.M., 2014. An overview on traditional uses and pharmacological profile of Acorus calamus Linn. (Sweet flag) and other Acorus species. Phytomedicine 21, 268-276.
  • Saxena, D.B., 1986. Phenyl indane from Acorus calamus. Phytochemistry 25, 553-555.
  • Schreiber, S.L., 1998. Chemical genetics resulting from a passion for synthetic organic chemistry. Bioorg. Med. Chem. 6, 1127-1152.
  • Shoba, F.G., Thomas, M., 2001. Study of antidiarrhoeal activity of four medicinal plants in castor-oil induced diarrhoea. J. Ethnopharmacol. 76, 73-76.
  • Singh, S., 2012. Determination of phenol & flavonoid contents in Acorus calamus. Asian J. Biochem. Pharmaceut. Res. 2, 388-392.
  • Sinha, A.K., Acharya, R., Joshi, B.P., 2002. A mild and convenient procedure for the conversion of toxic beta-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and gamma-asarone. J. Nat. Prod. 65, 764-765.
  • Stegmueller, S., Schrenk, D., Cartus, A.T., 2018. Formation and fate of DNA adducts of alpha- and beta-asarone in rat hepatocytes. Food Chem. Toxicol. 116, 138-146.
  • Sun, Y., Bai, Y., Zeng, M., Chen, X., Xie, J., Li, B., He, X., Bai, Y., Jia, P., Meng, X., Liang, J., Wang, S., Fan, T.-P., Wu, B., Zheng, X., 2019. Pharmacokinetics and tissue distribution evaluation of α- asaronol and its main metabolite in rats by HPLC method. J. Pharm. Biomed. Anal. 172, 349-356.
  • Tong, X.-G., Qiu, B., Luo, G.-F., Zhang, X.-F., Cheng, Y.-X., 2010a. Alkaloids and sesquiterpenoids from Acorus tatarinowii. J. Asian Nat. Prod. Res. 12, 438-442.
  • Tong, X.-G., Wu, G.-S., Huang, C.-G., Lu, Q., Wang, Y.-H., Long, C.-L., Luo, H.-R., Zhu, H.- J., Cheng, Y.-X., 2010b. Compounds from Acorus tatarinowii: determination of absolute configuration by quantum computations and cAMP regulation activity. J. Nat. Prod. 73, 1160-1163.
  • Tong, X.-G., Zhou, L.-L., Wang, Y.-H., Xia, C., Wang, Y., Liang, M., Hou, F.-F., Cheng, Y.- X., 2010c. Acortatarins A and B, two novel antioxidative spiroalkaloids with a naturally unusual morpholine motif from Acorus tatarinowii. Org. Lett. 12, 1844-1847.
  • Wang, M.F., Lao, A.N., Wang, H.C., 1997a. Two new amides from the roots of Acorus tatarinowii Schott. Chin. Chem. Lett. 8, 35-36.
  • Wang, M.F., Lao, A.N., Wang, H.C., 1997b. Two new isopimarane diterpenes from the roots of Acorus tatarinowii Schott. Chin. Chem. Lett. 8, 37-38.
  • Xiao, Q., Jackson, J.J., Basak, A., Bowler, J.M., Miller, B.G., Zakarian, A., 2013. Enantioselective synthesis of tatanans A-C and reinvestigation of their glucokinase-activating properties. Nat. Chem. 5, 410-416.
  • Zanoli, P., Avallone, R., Baraldi, M., 1998. Sedative and hypothermic effects induced by β- asarone, a main component of Acorus calamus. Phytother. Res. 12, S114-S116. Zhang, W.-Y., Feng, X.-L., Lu, D., Gao, H., Yu, Y., Yao, X.-S., 2018. New lignans attenuating cognitive deterioration of Aβ transgenic flies discovered in Acorus tatarinowii. Bioorg. Med. Chem. Lett. 28, 814-819.
  • Zheng, X., Bai, Y., Qin, F., Wang, S., Zhang, Y., Liu, P., He, X., 2015. α- Asaryl Alcohol, and its Preparing Method and Application. Northwest University, Peop. Rep. Xi'an Puyang Technology Development Co., Ltd., China 10pp.