Published January 31, 2022 | Version v1

Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica

Description

Li, Jiayuan, Ni, Gang, Liu, Yanfei, Wang, Renzhong, Yu, Dequan (2022): Long-chain fatty acid acylated derivatives of isoflavone glycosides from the rhizomes of Iris domestica. Phytochemistry (112977) 193: 1-7, DOI: 10.1016/j.phytochem.2021.112977, URL: http://dx.doi.org/10.1016/j.phytochem.2021.112977

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:DF4AFFD495264A55FFBAFFF3FFD10A3C

References

  • Bhullar, K.S., Ziaullah, Z., Rupasinghe, V.H.P., 2014. In vitro regulation of enzymes of the renin-angiotensin-aldosterone system by isoquercitrin, phloridzin and their long chain fatty acid derivatives. Funct. Foods Health D 4, 208-221. https://doi.org/ 10.31989/ffhd.v4i5.11.
  • Bock, K., Pedersen, C., 1983. Carbon-13 nuclear magnetic resonance spectroscopy of monosaccharides. Adv. Carbohydr. Chem. Biochem. 41, 27-66. https://doi.org/ 10.1016/S0065-2318(08)60055-4.
  • Bugoni, S., Merlini, V., Porta, A., Gailard, S., Zanoni, G., Nolan, S.P., Vidari, G., 2015. Competitive gold-promoted Meyer-Schuster and oxy-Cope rearrangements of 3- acyloxy-1,5-enynes: selective catalysis for the synthesis of (+ )-(S)-γ- Ionone and (-)-(2S,6R)-cis-γ- irone. Chem. Eur J. 21, 14068-14074. https://doi.org/10.1002/ chem.201502382.
  • Chen, X.Y., Wang, H.Q., Zhang, T., Liu, C., Kang, J., Chen, R.Y., Yu, D.Q., 2013. Aromatic glucosides from the seeds of Prunus davidiana. J. Nat. Prod. 76, 1528-1534. https:// doi.org/10.1021/np4000922.
  • Farag, S.F., Kimura, Y., Ito, H., Takayasu, J., Tokuda, H., Hatano, T., 2009. New isoflavone glycosides from Iris spuria L. (Calizona) cultivated in Egypt. J. Nat. Med. 63, 91-95. https://doi.org/10.1007/s11418-008-0291-7.
  • Gunstone, F.D., Polard, M.R., Scrimgeour, C.M., Vedanayagam, H.S., 1977. Fatty acids. 13
  • Han, S.W., Wang, C., Cui, B.S., Sun, H., Zhang, J.J., Li, S., 2019. Hepatoprotective activity of glucosyloxybenzyl succinate derivatives from the pseudobulbs of pleione bulbocodioides. Phytochemistry 157, 71-81. https://doi.org/10.1016/j. phytochem.2018.10.003.
  • Li, J.Y., Ni, G., Liu, Y.F., Li, L., Mai, Z.P., Wang, R.Z., Yu, D.Q., 2019a. New iridal-type triterpenoid derivatives with cytotoxic activities from Belamcanda chinensis. Bioorg. Chem. 83, 20-28. https://doi.org/10.1016/j.bioorg.2018.08.039.
  • Li, J.Y., Ni, G., Liu, Y.F., Mao, Z.P., Wang, R.Z., Yu, D.Q., 2019b. Iridal-type triterpenoids with a cyclopentane unit from the rhizomes of Belamcanda chinensis. J. Nat. Prod. 82, 1759-1767. https://doi.org/10.1021/acs.jnatprod.8b00993.
  • Lim, H.S., Kim, Y.J., Kim, B.Y., Park, G., Jeong, S.J., 2018. The anti-neuroinflammatory activity of tectorigenin pretreatment via downregulated NF- κ B and ERK/JNK pathways in BV-2 microglial and microglia inactivation in mice with lipopolysaccharide. Front. Pharmacol. 9, 462-475. https://doi.org/10.3389/ fphar.2018.00462.
  • Liu, Q., Wang, Y.F., Chen, R.J., Zhang, M.Y., Wang, Y.F., Yang, C.R., Zhang, Y.J., 2009. Anti-coxsackie virus B3 norsesquiterpenoids from the roots of phyllanthus emblica. J. Nat. Prod. 72, 969-972. https://doi.org/10.1021/np800792d.
  • Liu, Y.Y., Yang, Y.N., Feng, Z.M., Jiang, J.S., Zhang, P.C., 2019. Eight new triterpenoid saponins with antioxidant activity from the roots of Glycyrrhiza uralensis Fisch. Fitoterapia 133, 186-192. https://doi.org/10.1016/j.fitote.2019.01.014.
  • Monthakantirat, O., Wanchai, De-Eknamkul, Umehara, K., Yoshinaga, Y., Miyase, T., Warashina, T., Noguchi, H., 2005. Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines. J. Nat. Prod. 68, 361-364. https://doi.org/10.1021/np040175c.
  • Noh, D., Choi, J.G., Huh, E., Oh, M.S., 2018. Tectorigenin, a flavonoid-based compound of Leopard Lily Rhizome, attenuates UV-B-induced apoptosis and collagen degradation by inhibiting oxidative stress in human keratinocytes. Nutrients 10. https://doi.org/10.3390/nu10121998, 1998-2008.
  • Oh, K.B., Kang, He, Matsuoka, H., 2001. Detection of antifungal activity in Belamcanda chinensis by a single-cell bioassay method and isolation of its active compound, tectorigenin. Biosci. Biotechnol. Biochem. 65, 939-942. https://doi.org/10.1271/ bbb.65.939.
  • Sekhon-Loodu, S., Ziaullah, Z., Rupasinghe, H.P.V., 2015. Novel quercetin-3-O-glucoside eicosapentaenoic acid ester ameliorates inflammation and hyperlipidemia. Inflammopharmacology 23, 173-185. https://doi.org/10.1007/s10787-015-0237-0.
  • Song, J.G., Tang, W., Wang, X.J., Su, J.C., Huang, X.J., Shi, L., Ye, W.C., Wang, Y., 2021. Phloroglucinol-derived lipids from the leaves of Syzygium cumini and their neuroprotective activities. Fitoterapia 153, 104968. https://doi.org/10.1016/j. fitote.2021.104968.
  • Sudan, S., Rupasinghe, H.V., 2015. Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells. Exp. Biol. Med. 240, 1452-1464. https://doi.org/10.1177/1535370215570828.
  • Thelen, P., Scharf, J.G., Burfeind, P., Hemmerlein, B., Wuttke, W., Spengler, B., Christoffel, V., Ringert, R.H., Seidlov´a-Wuttke, D., 2005. Tectorigenin and other phytochemicals extracted from leopard lily Belamcanda chinensis affect new and established targets for therapies in prostate cancer. Carcinogenesis 26, 1360-1367. https://doi.org/10.1093/carcin/bgi092.
  • Usui, A., Matsuo, Y., Tanaka, T., Ohshima, K., Fukuda, S., Mine, T., Yakashiro, I., Ishimaru, K., 2017. Ferulic acid esters of glucosylglucose from Allium macrostemon Bunge. J. Asian Nat. Prod. Res. 19, 215-221. https://doi.org/10.1080/ 10286020.2016.1213722.
  • Warnakulasuriya, S.N., Ziaullah, Rupasinghe, H.P.V., 2016a. Long chain fatty acid esters of Quercetin-3-O-glucoside attenuate H2O2-induced acute cytotoxicity in human lung fibroblasts and primary hepatocytes. Molecules 21, 452. https://doi.org/ 10.3390/molecules21040452.
  • Warnakulasuriya, S.N., Ziaullah, Rupasinghe, H.P.V., 2016b. Novel long chain fatty acid derivatives of quercetin-3-O-glucoside reduce cytotoxicity induced by cigarette smoke toxicants in human fetal lung fibroblasts. Eur. J. Pharmacol. 781, 128-138. https://doi.org/10.1016/j.ejphar.2016.04.011.
  • Wozniak, D., Matkowski, A., 2015. Belamcandae chinensis rhizoma a review of phytochemistry and bioactivity. Fitoterapia 107, 1-14. https://doi.org/10.1016/j. fitote.2015.08.015.
  • Xin, R.H., Zheng, J.F., Cheng, L., Peng, W.J., Luo, Y.J., 2015. Belamcanda chinensis (L.) DC: ethnopharmacology, phytochemistryand pharmacology of an important traditional Chinese medicine. Afr. J. Tradit., Complementary Altern. Med. 12, 39-70. https://doi.org/10.4314/ajtcam.v12i6.6.
  • Xin, X., Zhang, M., Li, X.F., Zhao, G.L., 2019. Biocatalytic synthesis of lipophilic Baicalin derivatives as antimicrobial agents. J. Agric. Food Chem. 67, 11684-11693. https:// doi.org/10.1021/acs.jafc.9b04667.
  • Zhang, L., Wei, K.H., Xu, J.P., Yang, D.W., Zhang, C.H., Wang, Z.P., Li, M.H., 2016. Belamcanda chinensis (L.) DC-An ethnopharmacological, phytochemical and pharmacological review. J. Ethnopharmacol. 186, 1-13. https://doi.org/10.1016/j. jep.2016.03.046.
  • Ziaullah, Rupasinghe, H.P.V., 2013. An efficient microwave-assisted enzyme-catalyzed regioselective synthesis of long chain acylated derivatives of flavonoid glycosides. Tetrahedron Lett. 54, 1933-1937. https://doi.org/10.1016/j.tetlet.2013.01.103.
  • Ziaullah, Bhullar, K.S., Warnakulasuriya, S.N., Rupasinghe, H.P.V., 2013. Biocatalytic synthesis, structural elucidation, antioxidant capacity and tyrosinase inhibition activity of long chain fatty acid acylated derivatives of phloridzin and isoquercitrin. Bioorg. Med. Chem. 21, 684-692. https://doi.org/10.1016/j.bmc.2012.11.034.
  • Ziaullah, Rupasinghe, H.P.V., 2016. Sonochemical enzyme-catalyzed regioselective acylation of flavonoid glycosides. Bioorg. Chem. 65, 17-25. https://doi.org/ 10.1016/j.bioorg.2016.01.005.