Antioxidant Activities and Electrochemical Behaviors of Xanthones from Cratoxylum cochinchinense and Cratoxylum formasum


Benjamat Chailap Thanesuan Nuanyai


     Seven xanthones; dulcisxanthone B (1), ß-mangostin (2), 1,3,7-trihydroxy-2,4-di-(3-methylbut-2-eyl)-xanthone (3), cudratricusxanthone E (4), cochinchinone A (5), 2-geranyl-1,3,7-trihydroxy-4-(3,3-dimethylallyl)-xanthone (6), and cochinchinone B (7) were isolated from twigs of Cratoxylum cochinchinense and Cratoxylum formasum. The structures of all isolated compounds were elucidated by spectroscopic methods (1H, 13C, 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC) and compared with previous literatures. All compounds were evaluated in vitro for antioxidant activity using DPPH assay. Their electrochemical behaviors were investigated by cyclic voltammetry. The results derived from two techniques were consistent. Compounds 1, 2, 4 and 7 exhibited strong antioxidant activities. Considering the structure-activity relationship, the hydroxy group at C-6 played an important role to antioxidant power.

Keywords: Xanthone, Cratoxylum cochinchinense, Cratoxylum formasum, Antioxidant, Electrochemical


Anantachoke, N., Tuchinda, P., Kuhakarn, C., Pohmakotr, M., & Reutrakul, V. (2012). Prenylated caged xanthones: Chemistry and biology. Pharmaceutical Biology, 50, 78-91. doi:10.3109/13880209.20
Antolovich, M., Prenzle, P. D., Patsalide, E., McDonald, S., & McDonald, K. (2002). Methods for testing antioxidant activity. Analyst, 127, 183-198. doi:10.1039/B009171p
Arteaga, J. F., Ruiz-Montoya, M., Palma, A., Alonso-Garrido, G., Pintado, S., & Rodriguez-Mellado, J. M. (2012) Comparison of the simple cyclic voltammetry (CV) and DPPH assays for the determination of antioxidant capacity of active principles. Molecules, 17, 5126-5138. doi:10.3390/molecules17055
Bennett, G. J., Harrison, L. J., Sia, G. L., & Sim, K.Y. (1993). Triterpenoids, tocotrienols and xanthones from the bark of Cratoxylum Cochinchinense. Phytochemistry, 32, 1245-1251. doi:10.1016/S0031-9422(98)00467-1
Boonnak, N., Chantrapromma, S., Tewtrakul, S., & Sudsai, T. (2014). Inhibition of nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophages by isolated xanthones from the roots of Cratoxylum formosum ssp. pruniflorum. Archives of Pharmacal Research, 37, 1329-1335. doi:10.1 007/s12272-014-0338-0
Braca, A., Tommasi, N. D., Bari, L. D., Pizza, C., Politi, M., & Morelli, L. (2001). Antioxidant principles from Bauhinia tarapotensis. Journal of Natural Product, 64, 892-895. doi: 10.1021/np0100845
Chailap, B., & Tuntulani, T. (2012). Optical and electrochemical properties of heteroditopic ion receptors derived from crown ether-based calix[4]arene with amido-anthraquinone pendants. Organic and Biomolecular Chemistry, 10, 3617-3625. doi:10.1039/ C2OB00048B
Chevion, S., Roberts, M.A., & Chevion, M. (2000). The use of cyclic voltammetry for the evaluation of antioxidant capacity. Free Radical Biology & Medicine, 28, 860-870.
Deachathai, S., Mahabusarakam, W., Phongpaichit, S., & Taylor, W. C. (2005). Phenolic compounds from the fruit of Garcinia dulcis. Phytochemistry, 66, 2368–2375. doi:10.1016/j.phytochem.2005.06.
Duan, Y. H., Dai, Y., Wang, G. H., Zhang, X., Chen, H. F., Chen, J. B., … Zhang, X. K. (2010). Bioactive xanthones from the stems of Cratoxylum formosum ssp. pruniflorum. Journal of Natural Products, 73, 1283-1287. doi:10.1021/np1001797
Fotie, J., & Bohle, D. S. (2006). Pharmacological and biological activities of xanthones. Anti-Infective Agents in Medicinal Chemistry, 5, 15-31. doi:10.2174/187152106774755563
Huang, D., Ou, B., & Prior, R. L. (2005). The Chemistry behind antioxidant capacity assays. Journal of Agricultural and food chemistry, 53, 1841-1856. doi:10.1021/jf030723c
Iinuma, M., Tosa, H., Tanaka, T., & Riswan, S. (1996). Three new xanthones from the bark of Garcinia dioica. Chemical and Pharmaceutical Bulletin, 44, 232-234. doi:10.1248/cpb.44.232
Judzentiene, A., Garjonyte, R., & Budiene, J. (2016). Variability, toxicity, and antioxidant activity of Eupatorium cannabinum (hemp agrimony) essential oils. Pharmaceutical Biology, 54, 945–953. doi: 10.3109/13880209.2015.1078384
Laphookhieo, S., Maneerat, W., & Koysomboon, S. (2009). Antimalarial and cytotoxic phenolic compounds from Cratoxylum maingayi and Cratoxylum cochinchinense. Molecules, 14, 1389-1395. doi:10.33
Lee, B. W., Lee, J. H., Lee, S. T., Lee, H. S., Lee, W. S., Jeong, T. S., & Park, K. H. (2005). Antioxidant and cytotoxic activities of xanthones from Cudrania tricuspidata. Bioorganic and Medicinal Chemistry Letters, 15, 5548-5552. doi:10.1016/j.bmcl.2005.08.099
Likhitwitayawuid, K., Phadungcharoen, T., & Krungkrai J. (1998). Antimalarial Xanthones from Garcinia cowa Planta Medica, 64, 70-72. doi:10.1055/s-2006-957370
Mahabusarakam, W., Nuangnaowarat, W., & Taylor, W.C. (2005). Xanthone derivatives from Cratoxylum cochinchinense roots. Phytochemistry, 67, 470-474. doi:10.1016/j.phytochem.2005.10.008
Moon, J. K., & Shibamoto, T. (2009). Antioxidant assays for plant and food components. Journal of Agricultural and Food Chemistry, 57, 1655-1666. doi:10.1021/jf803537k
Nuanyai, T., Benjamat, C., Songchan, P., & Anumart, B. (2015). Cytotoxicity of xanthone from twigs of Cratoxylum cochinchinense (Lour.) Blume. Journal of Science Ladhrabang, 24, 1–12.
Raksat, A., Laphookhieo, S., Cheenpracha, S., Ritthiwigrom, T., & Maneerat, W. (2014). Antibacterial compounds from the roots of Cratoxylum formosum spp. pruniflorum. Natural Product Communications, 9, 1487-1489.
Rattanaburi, S., Daus, M., Watanapokasin, R., & Mahabusarakam, W. (2014). A new bisanthraquinone and cytotoxic xanthones from Cratoxylum cochinchinense. Natural Product Research, 28, 606-610. doi: 10.1080/14786419.2014. 886212
Sochor, J., Dobes, J., Krystofova, O., Ruttkay-Nedecky, B., Babula, P., Pohanka, M, … Kizek, R. (2013). Electrochemistry as a tool for studying antioxidant properties. International Journal of Electrochemical Science, 8, 8464–8489.
Tchamo, D.N., Silvere, N., & Etienne, T. (2006). Xanthones as therapeutic agents: chemistry and pharmacology. Advances in Phytomedicine, 2, 273-298. doi:10.1016/S1572-557X(05)02016-7
Udomchotphruet, S., Phuwapraisirisan, P., Sichaem, J., & Tip-Pyang, S. (2012). Xanthones from the stems of Cratoxylum cochinchinense. Phytochemistry, 73, 148-151. doi:10.1016/j.phytochem.2010.04.
Zou, Y. S., Hou, A. J., Zhu, G. F., Chen, Y. F., Sun, H. D., & Zhao, Q. S. (2004). Cytotoxic isoprenylated xanthones from Cudrania tricuspidata. Bioorganic and Medicinal Chemistry, 12, 1947-1953. doi:10.

Research Articles


How to Cite
CHAILAP, Benjamat; NUANYAI, Thanesuan. Antioxidant Activities and Electrochemical Behaviors of Xanthones from Cratoxylum cochinchinense and Cratoxylum formasum. Naresuan University Journal: Science and Technology (NUJST), [S.l.], v. 27, n. 3, p. 35-42, july 2019. ISSN 2539-553X. Available at: <>. Date accessed: 30 jan. 2023. doi: