Biological Activities and Crystal Structure Determination of trans, trans-Cyclohexane- 1,2,4,5-tetrol Monohydrate from Pseuduvaria phuyensis (R.M.K. Saunders)

http://www.doi.org/10.26538/tjnpr/v7i7.7

Authors

  • Ruttayaporn Sukyod Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Phansuang Udomputtimekakul Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Wilart Pompimon Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Samroeng Narakaew Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Suwadee Jiajaroen Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TUMcMa), Faculty of Science and Technology, Thammasat University, 12121, Pathum Thani, Thailand
  • Kittipong Chainok Thammasat University Research Unit in Multifunctional Crystalline Materials and Applications (TUMcMa), Faculty of Science and Technology, Thammasat University, 12121, Pathum Thani, Thailand
  • Chayaporn Laohakul Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Siriphut Khonghuayrob Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Aphiruk Chaisena Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Saranya Wattananon Department of Food Science and Technology, Faculty of Agricultural Technology, Lampang Rajabhat University, 52100, Lampang, Thailand
  • Narong nuntasaen Department of Chemistry, Faculty of Science and Center of Innovation in Chemistry, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
  • Kanoknetr Suksen Department of Physiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, 10600, Thailand
  • Arthit Chairoungdua Department of Physiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, 10600, Thailand
  • Jitra Limthongkul Department of Microbiology, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
  • Chanita Naparswad Department of Microbiology, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
  • Nichapa Charoenphakinrattana Department of Microbiology, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand
  • Suttiporn Pikulthong Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand

Keywords:

Cytotoxicity Activity, Anti-HIV-1 Virus, Antibacterial, Polyoxygenated Cyclohexane, Annonaceae, Psuduvaria phuyensis

Abstract

Pseuduvaria phuyensis (Annonaceae), was collected from Kanchanaburi Province, western Thailand. The study aimed to evaluate the antibacterial, anti-HIV-1RT, anti-syncytium (MC99+1A2), and cytotoxic potentials of the crude hexane, ethyl-acetate, and methanol extracts of P. phuyensis leaf-twigs and stems, all in comparison with standard drugs. Also, the isolation and characterization of a compound from one of the active extracts as well as its antibacterial and cytotoxicity activities were carried out. The MIC and MBC values of selected bacterial strains ranged from 3.125 – 200 and 6.25 – 200 mg/mL, respectively for all the extracts, while the isolated compound was not active. The anti-HIV-1 RT and the anti-syncytium assay of the hexane and ethyl acetate extracts revealed they were very active, with % inhibitions of 90.50 and 89.36, respectively. The best inhibitory concentration at 50% (IC50) value was 44.33 µM as exhibited by the hexane extract of the stems of the reverse transcriptase assay, while, the best effective concentration at 50% (EC50) value was 10.4 µM (TI>4.83) as displayed by the ethyl acetate extract of the stems. The cytotoxicity study showed that the hexane extract of the stems displayed high cytotoxicity with ED50 value at 13.07 µg/mL against the FaDu cancer cell line, whil that of the isolated compound was not active. The structure of the isolated compound was characterized and elucidated as trans, trans-cyclohexane-1, 2, 4, 5-tetrol monohydrate using spectroscopic technique and X-ray crystallography analysis. 

Author Biography

Arthit Chairoungdua, Department of Physiology, Faculty of Science, Mahidol University, Rama 6 Road, Bangkok, 10600, Thailand

- Excellent Center for Drug Discovery (ECDD), Mahidol University, Bangkok, 10400, Thailand

- Toxicology Graduate Program, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand

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Published

2023-07-31

How to Cite

Sukyod, R., Udomputtimekakul, P., Pompimon, W., Narakaew, S., Jiajaroen, S., Chainok, K., … Pikulthong, S. (2023). Biological Activities and Crystal Structure Determination of trans, trans-Cyclohexane- 1,2,4,5-tetrol Monohydrate from Pseuduvaria phuyensis (R.M.K. Saunders): http://www.doi.org/10.26538/tjnpr/v7i7.7. Tropical Journal of Natural Product Research (TJNPR), 7(7), 3314–3319. Retrieved from https://tjnpr.org/index.php/home/article/view/2217

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