Antioxidant Activities of Triterpenoids and Steroid from the Roots of  Millettia utilis Dunn

Thanatip Ruksilp; Napatsorn Wongpriaw; Thitinan Thammasom; Niramon Srichana; Wira Isaro

doi:10.14456/nujst.2022.25

Authors

Thanatip Ruksilp Department of Chemistry, Faculty of Science and Technology, Loei Rajabhat University, Muang Loei, Loei, 42000, Thailand
Napatsorn Wongpriaw Department of Chemistry, Faculty of Science and Technology, Loei Rajabhat University, Muang Loei, Loei, 42000, Thailand
Thitinan Thammasom Department of Chemistry, Faculty of Science and Technology, Loei Rajabhat University, Muang Loei, Loei, 42000, Thailand
Niramon Srichana Department of Chemistry, Faculty of Science and Technology, Loei Rajabhat University, Muang Loei, Loei, 42000, Thailand
Wira Isaro General Education, Loei Rajabhat University, Muang Loei, Loei, 42000, Thailand

DOI:

https://doi.org/10.14456/nujst.2022.25

Keywords:

Millettia utilis Dunn., steroids, triterpenoids, DPPH, ABTS

Abstract

Two triterpenoids, oleanolic acid acetate (1), corosolic acid (2) and one steroid, stigmasterol (3) were isolated from dichloromethane crude extract in the roots of Millettia utilis Dunn. The structures of all isolated compounds were elucidated by spectroscopic methods and compared with previous literatures. The antioxidant activities using DPPH and ABTS assays of three isolated compounds were tested. Oleanolic acid acetate (1), corosolic acid (2) were revealed moderate and stigmasterol (3) was weak activity against DPPH and ABTS assays.

References

Buyinza, D., Chalo, D. M., Derese, S., Ndakala, A., & Yenesew, A. (2020). Flavonoids and isoflavonoids of Millettia dura and Millettia ferruginea : Phytochemical review and chemotaxonomic values. Biochemical Systematics and Ecology, 91, 104053.

Deyou, T., Gumula, I., Pang, F., Gruhonjic, A., Mumo, M., Holleran, J., … Yenesew, A. (2015). Rotenoids, flavonoids, and chalcones from the root bark of Millettia usaramensis. Journal of Natural Products, 78, 2932-2939.

Deyou, T., Marco, M., Heydenreich, M., Pan, F., Gruhonjic, A., Fitzpatrick, P. A., … Erdélyi, M. (2017). Isoflavones and rotenoids from the leaves of Millettia oblata ssp. teitensis. Journal of Natural Products, 80, 2060-2066.

Endo, M., Shigetomi, K., Mitsuhashi, S., Igarashi, M., & Ubukata, M. (2019). Isolation, structure determination and structure activity relationship of anti toxoplasma triterpenoids from Quercus crispula Blume outer bark. Journal of Wood Science, 65, 1-11.

Forgo, P., & Kover. K. E. (2004). Gradient enhanced selective experiments in the 1H NMR chemicalshift assignment of the skeleton and side-chain resonances of stigmasterol, a phytosterol derivative. Steroids, 69, 43-50.

Jo, H., Oh, J. H., Park, D. W., Lee, C., & Min, C. K. (2020). Oleanolic acid 3-acetate, a minor element of ginsenosides, induces apoptotic cell death in ovarian carcinoma and endometrial carcinoma cells via the involvement of a reactive oxygen specieseindependent mitochondrial pathway. Journal of Ginseng Research, 44, 96-104.

Ma, X., Zhao, M., Tang, M. H., Xue, L. L., Zhang, R. J., Liu, L., … Chen, L. J. (2020). Flavonoids with inhibitory effects on NLRP3 inflammasome activation from Millettia velutina. Journal of Natural Products, 83, 2950-2959.

Pailee, P., Mahidol, C., Ruchirawat, S., & Prachyawarakorn, V. (2019). Diverse flavonoids from the roots of Millettia brandisiana. Phytochemistry, 162, 157-164.

Pérez, L. B., Pan, L., Acuña, U. M., Li, J., Chai, H. B., Gallucci, J. C., … Kinghorn, A. D. (2014). Caeruleanone A, a rotenoid with a new arrangement of the D‑ring from the fruits of Millettia caerulea. Organic Letters, 16, 1462-1465.

Qusti, Y. S., Abo-khatwa, N. A. and Bin-Lahwa, A. M. (2010). Screening of antioxidant activity and phenolic content of selected food items cited in the holly ouran. European Journal of Biological Science. 2(1). 40-51.

Raksat, A., Maneerat, W., Andersen, R. J., Pyne, S. G., & S Laphookhieo, S. (2018). Antibacterial prenylated isoflavonoids from the stems of Millettia extensa. Journal of Natural Products, 81, 1835-1840.

Ruksilp, T. (2020a). A triterpenoid and steroids from the twigs of Millettia utilis Dunn. and their antioxidant activities. Naresuan University Journal : Science and Technology, 28(1), 49-54.

Ruksilp, T. (2020b). Fatty acids and an ester from the leaves of Millettia utilis Dunn. Naresuan University Journal : Science and Technology, 28(3), 63-68.

Sridhar, K., & Charles, A. L. (2019). In vitro antioxidant activity of Kyoho grape extracts in DPPH ֗ and ABTS ֗ assays: Estimation methods for EC50 using advanced statistical programs. Food Chemistry, 275, 41-49.

Woo, K. W., Sang, J. Y., Choi, S. U., Kim, K. H., & Lee, K. R. (2014). Triterpenes from Perilla frutescens var. acuta and their cytotoxic activity. Natural Product Sciences, 20(2), 71-75.

Xu, S., Wang, G., Peng, W., Xu, Y., Zhang, Y., Ge, Y., … Gong, Z. (2019). Corosolic acid isolated from Eriobotrya japonica leaves reduces glucose level in human hepatocellular carcinoma cells, zebrafish and rats. Scientific Reports, 9, 4388.

Xue, L. L., Wub, W. S., Maa, X., Peia, H. Y., Tanga, M. H., Kuanga, S., … & Chena, L. J. (2020). Modulation of LPS-induced inflammation in RAW264.7 murine cells by novel isoflavonoids from Millettia pulchra. Bioorganic Chemistry, 97, 103693.

Yan, W., Yang, J., Tang, H., Xue, L., Chen, K., Wang, L., … Chen, L. (2019). Flavonoids from the stems of Millettia pachyloba Drake mediate cytotoxic activity through apoptosis and autophagy in cancer cells. Journal of Advanced Research, 20, 117-127.