PERTANIKA JOURNAL OF TROPICAL AGRICULTURAL SCIENCE

 

e-ISSN 2231-8542
ISSN 1511-3701

Home / Regular Issue / JTAS Vol. 46 (1) Feb. 2023 / JTAS-2532-2022

 

Comprehensive Review of Cratoxylum Genus: Ethnomedical Uses, Phytochemistry, and Pharmacological Properties

Chui Yin Bok, Eric Kat Jun Low, Digsha Augundhooa, Hani’ Ariffin, Yen Bin Mok, Kai Qing Lim, Shen Le Chew, Shamala Salvamani, Khye Er Loh, Chui Fung Loke, Baskaran Gunasekaran and Sheri-Ann Tan

Pertanika Journal of Tropical Agricultural Science, Volume 46, Issue 1, February 2023

DOI: https://doi.org/10.47836/pjtas.46.1.12

Keywords: Cratoxylum genus, conventional therapeutics, ethnomedical uses, pharmacological properties, phytochemical compounds

Published on: 22 Febuary 2023

In the past, the Cratoxylum genus has often been utilized as traditional medicines, culinary ingredients, health supplements, as well as manufacturing materials. This flowering plant belongs to the family Hypericaceae and is classified into six species: Cratoxylum arborescens, Cratoxylum cochinchinense, Cratoxylum formosum, Cratoxylum glaucum, Cratoxylum maingayi, and Cratoxylum sumatranum. The Cratoxylum genus is native to Asia as a traditional medicinal plant. It is currently being translated into conventional therapeutics as a preventive agent for diabetes mellitus and cardiovascular diseases. The phytochemical analysis and pharmacological investigations on the Cratoxylum species have unveiled the wide spectrum of phytoconstituents, including xanthones, triterpenoids, flavonoids, and phenolic compounds. These compounds are attributed to their significant pharmacological effects, such as antibacterial, antifungal, antioxidant, antimalarial, anti-gastric ulcer, anti-HIV-1 reverse transcriptase, antidiabetic, and anticancer activities. These research findings have strengthened the foundation of the Cratoxylum genus as a traditional medicinal plant to be further developed and applied as selective therapeutic drugs for various ailments. This paper discusses the Cratoxylum genus regarding its traditional uses, phytochemical compounds, and pharmacological properties.

  • Ahn, E.-Y., Jin, H., & Park, Y. (2019). Assessing the antioxidant, cytotoxic, apoptotic and wound healing properties of silver nanoparticles green-synthesized by plant extracts. Materials Science and Engineering: C, 101, 204-216. https://doi.org/10.1016/j.msec.2019.03.095

  • Bi, W., He, C., Ma, Y., Shen, J., Zhang, L. H., Peng, Y., & Xiao, P. (2016). Investigation of free amino acid, total phenolics, antioxidant activity and purine alkaloids to assess the health properties of non-Camellia tea. Acta Pharmaceutica Sinica B, 6(2), 170-181. https://doi.org/10.1016/j.apsb.2015.11.003

  • Boo, B. C., Omar-Hor, K., & Ou-Yang, C. L. (2003). 1001 Garden plants in Singapore (2nd ed.). National Parks Board.

  • Boonnak, N., Karalai, C., Chantrapromma, S., Ponglimanont, C., Fun, H.-K., Kanjana-Opas, A., Chantrapromma, K., & Kato, S. (2009). Anti-Pseudomonas aeruginosa xanthones from the resin and green fruits of Cratoxylum cochinchinense. Tetrahedron, 65(15), 3003-3013. https://doi.org/10.1016/j.tet.2009.01.083

  • Boonsri, S., Karalai, C., Ponglimanont, C., Kanjana-opas, A., & Chantrapromma, K. (2006). Antibacterial and cytotoxic xanthones from the roots of Cratoxylum formosum. Phytochemistry, 67(7), 723-727. https://doi.org/10.1016/j.phytochem.2006.01.007

  • Buranrat, B., Mairuae, N., & Konsue, A. (2017). Cratoxy formosum leaf extract inhibits proliferation and migration of human breast cancer MCF-7 cells. Biomedicine and Pharmacotherapy, 90, 77-84. https://doi.org/10.1016/j.biopha.2017.03.032

  • Cassels, B. K., & Asencio, M. (2010). Anti-HIV activity of natural triterpenoids and hemisynthetic derivatives 2004–2009. Phytochemistry Reviews, 10(4), 545-564. https://doi.org/10.1007/s11101-010-9172-2

  • Chailap, B., & Nuanyai, T. (2019). Antioxidant activities and electrochemical behaviors of xanthones from Cratoxylum cochinchinense and Cratoxylum formasum. Naresuan University Journal: Science and Technology, 27(3), 35-42. https://doi.org/10.14456/nujst.2019.24

  • Chailap, B., Nuanyai, T., Puthong, S., & Buakeaw, A. (2017). Chemical constituents of fruits and leaves of Cratoxylum cochinchinense and their cytotoxic activities. Naresuan University Journal: Science and Technology, 25(3), 22-30.

  • Chinsembu, K. C. (2019). Chemical diversity and activity profiles of HIV-1 reverse transcriptase inhibitors from plants. Revista Brasileira De Farmacognosia, 29(4), 504-528. https://doi.org/10.1016/j.bjp.2018.10.006

  • Choi, S.-J., Tai, B. H., Cuong, N. M., Kim, Y.-H., & Jang, H.-D. (2012). Antioxidative and anti-inflammatory effect of quercetin and its glycosides isolated from mampat (Cratoxylum formosum). Food Science and Biotechnology, 21(2), 587-595. https://doi.org/10.1007/s10068-012-0075-4

  • Dapar, M. L. G. (2020). Cratoxylum sumatranum (Jack) Blume Hypericaceae. In F. M. Franco (Ed.), Ethnobotany of mountain regions of Southeast Asia (pp. 1-5). Springer. https://doi.org/10.1007/978-3-030-14116-5_114-1

  • Dapar, M. L. G., Alejandro, G. J. D., Meve, U., & Liede-Schumann, S. (2020). Quantitative ethnopharmacological documentation and molecular confirmation of medicinal plants used by the Manobo tribe of Agusan del Sur, Philippines. Journal of Ethnobiology and Ethnomedicine, 16, 14. https://doi.org/10.1186/s13002-020-00363-7

  • El Habbash, A. I., Mohd Hashim, N., Ibrahim, M. Y., Yahayu, M., Omer, F. A. E., Abd Rahman, M., Nordin, N., & Lian, G. E. C. (2017). In vitro assessment of anti-proliferative effect induced by α-mangostin from Cratoxylum arborescens on HeLa cells. PeerJ, 5, e3460. https://doi.org/10.7717/peerj.3460

  • Enggiwanto, S., Riyani, N., Pratama, Y., Roanisca, O., & Mahardika, R. G. (2019). Antibacterial effectiveness of formulations nanoemulsion Cratoxylum glaucum Korth. extract. In IOP Conference Series: Earth and Environmental Science (Vol. 353, No. 1, p. 012038). IOP Publishing. https://doi.org/10.1088/1755-1315/353/1/012038

  • Giridharan, S., & Srinivasan, M. (2018). Mechanisms of NF-κB p65 and strategies for therapeutic manipulation. Journal of Inflammation Research, 11, 407-419. https://doi.org/10.2147/JIR.S140188

  • Huang, Y., Xiao, D., Burton-Freeman, B. M., & Edirisinghe, I. (2016). Chemical changes of bioactive phytochemicals during thermal processing. In Reference module in food science. Elsevier. https://doi.org/10.1016/b978-0-08-100596-5.03055-9

  • Ibrahim, M. Y., Hashim, N. M., Mohan, S., Abdulla, M. A., Abdelwahab, S. I., Arbab, I. A., Yahayu, M., Ali, L. Z., & Ishag, O. E. (2015). α-Mangostin from Cratoxylum arborescens: An in vitro and in vivo toxicological evaluation. Arabian Journal of Chemistry, 8(1), 129-137. https://doi.org/10.1016/j.arabjc.2013.11.017

  • Juanda, D., Fidrianny, I., Ruslan, K., & Insanu, M. (2019). Overview of phytochemical compounds and pharmacology activities of Cratoxylum genus. Rasayan Journal of Chemistry, 12(4), 2065-2073. https://doi.org/10.31788/rjc.2019.1245303

  • Juanda, D., Fidrianny, I., Wirasutisna, K. R., & Insanu, M. (2021). Evaluation of xanthine oxidase inhibitory and antioxidant activities of three organs of idat (Cratoxylum glaucum Korth.) and correlation with phytochemical content. Pharmacognosy Journal, 13(4), 971-976. https://doi.org/10.5530/pj.2021.13.125

  • Kukongviriyapan, U., Luangaram, S., Leekhaosoong, K., Kukongviriyapan, V., & Preeprame, S. (2007). Antioxidant and vascular protective activities of Cratoxylum formosum, Syzygium gratum and Limnophila aromatica. Biological and Pharmaceutical Bulletin, 30(4), 661-666. https://doi.org/10.1248/bpb.30.661

  • Laphookhieo, S., Maneerat, W., & Koysomboon, S. (2009). Antimalarial and cytotoxic phenolic compounds from Cratoxylum maingayi and Cratoxylum cochinchinense. Molecules, 14(4), 1389-1395. https://doi.org/10.3390/molecules14041389

  • Laphookhieo, S., Syers, J. K., Kiattansakul, R., & Chantrapromma, K. (2006). Cytotoxic and antimalarial prenylated xanthones from Cratoxylum cochinchinense. Chemical and Pharmaceutical Bulletin, 54(5), 745-747. https://doi.org/10.1248/cpb.54.745

  • Li, Z. P., Lee, H.-H., Uddin, Z., Song, Y. H., & Park, K. H. (2018). Caged xanthones displaying protein tyrosine phosphatase 1B (PTP1B) inhibition from Cratoxylum cochinchinense. Bioorganic Chemistry, 78, 39-45. https://doi.org/10.1016/j.bioorg.2018.02.026

  • Li, Z. P., Song, Y. H., Uddin, Z., Wang, Y., & Park, K. H. (2018). Inhibition of protein tyrosine phosphatase 1B (PTP1B) and α-glucosidase by xanthones from Cratoxylum cochinchinense, and their kinetic characterization. Bioorganic and Medicinal Chemistry, 26(3), 737-746. https://doi.org/10.1016/j.bmc.2017.12.043

  • Mahabusarakam, W., Nuangnaowarat, W., & Taylor, W. C. (2006). Xanthone derivatives from Cratoxylum cochinchinense roots. Phytochemistry, 67(5), 470-474. https://doi.org/10.1016/j.phytochem.2005.10.008

  • Mahabusarakam, W., Rattanaburi, S., Phongpaichit, S., & Kanjana-Opas, A. (2008). Antibacterial and cytotoxic xanthones from Cratoxylum cochinchinense. Phytochemistry Letters, 1(4), 211-214. https://doi.org/10.1016/j.phytol.2008.09.012

  • Maisuthisakul, P., Pongsawatmanit, R., & Gordon, M. H. (2007). Characterization of the phytochemicals and antioxidant properties of extracts from Teaw (Cratoxylum formosum Dyer). Food Chemistry, 100(4), 1620-1629. https://doi.org/10.1016/j.foodchem.2005.12.044

  • Natrsanga, P., Jongaramruong, J., Rassamee, K., Siripong, P., & Tip-pyang, S. (2020). Two new xanthones from the roots of Cratoxylum cochinchinense and their cytotoxicity. Journal of Natural Medicines, 74(2), 467-473. https://doi.org/10.1007/s11418-019-01376-7

  • Neo, L., Chong, K. Y., Tan, S. Y., Lim, R. C. J., Loh, J. W., Ng, W. Q., Seah, W. W., Yee, A. T. K., & Tan, H. T. W. (2016). Towards a field guide to the trees of the Nee Soon Swamp Forest (II): Cratoxylum (Hypericaceae). Nature In Singapore, 9, 29-39.

  • Ngamsurach, P., & Praipipat, P. (2021). Modified alginate beads with ethanol extraction of Cratoxylum formosum and Polygonum odoratum for antibacterial activities. ACS Omega, 6(47), 32215-32230. https://doi.org/10.1021/acsomega.1c05056

  • Nonpunya, A., Sethabouppha, B., Rufini, S., & Weerapreeyakul, N. (2018). Cratoxylum formosum ssp. pruniflorum activates the TRAIL death receptor complex and inhibits topoisomerase I. South African Journal of Botany, 114, 150-162. https://doi.org/10.1016/j.sajb.2017.11.003

  • Omer, F. A. A., Mohd Hashim, N., Ibrahim, M. Y., Dehghan, F., Yahayu, M., Karimian, H., Salim, L. Z. A., & Mohan, S. (2017). Beta-mangostin from Cratoxylum arborescens activates the intrinsic apoptosis pathway through reactive oxygen species with downregulation of the HSP70 gene in the HL60 cells associated with a G0/G1 cell-cycle arrest. Tumor Biology, 39(11). https://doi.org/10.1177/1010428317731451

  • Pattanaprateeb, P., Ruangrungsi, N., & Cordell, G. A. (2005). Cytotoxic constituents from Cratoxylum arborescens. Planta Medica, 71(2), 181-183. https://doi.org/10.1055/s-2005-837788

  • Promraksa, B., Ponlatham, C., Chaiyarit, P., Ratree, T., Tueanjit, K., Narintorn, R., Roongpet, T., & Patcharee, B. (2015). Cytotoxicity of Cratoxylum formosum subsp. pruniflorum Gogel extracts in oral cancer cell lines. Asian Pacific Journal of Cancer Prevention, 16(16), 7155-7159. https://doi.org/10.7314/apjcp.2015.16.16.7155

  • Putthawan, P., Poeaim, S., & Areekul, V. (2018). Cytotoxic activity and apoptotic induction of some edible Thai local plant extracts against colon and liver cancer cell lines. Tropical Journal of Pharmaceutical Research, 16(12), 2927-2933. https://doi.org/10.4314/tjpr.v16i12.17

  • Raksat, A., Sripisut, T., & Maneerat, W. (2015). Bioactive xanthones from Cratoxylum cochinchinense. Natural Product Communications, 10(11), 1969-1972. https://doi.org/10.1177/1934578x1501001141

  • Ren, Y., Matthew, S., Lantvit, D. D., Ninh, T. N., Chai, H., Fuchs, J. R., Soejarto, D. D., de Blanco, E. J. C., Swanson, S. M., & Kinghorn, A. D. (2011). Cytotoxic and NF-κB inhibitory constituents of the stems of Cratoxylum cochinchinense and their semisynthetic analogues. Journal of Natural Products, 74(5), 1117-1125. https://doi.org/10.1021/np200051j

  • Reutrakul, V., Chanakul, W., Pohmakotr, M., Jaipetch, T., Yoosook, C., Kasisit, J., Napaswat, C., Santisuk, T., Prabpai, S., Kongsaeree, P., & Tuchinda, P. (2006). Anti-HIV-1 constituents from leaves and twigs of Cratoxylum arborescens. Planta Medica, 72(15), 1433-1435. https://doi.org/10.1055/s-2006-951725

  • Senggunprai, L., Thammaniwit, W., Kukongviriyapan, V., Prawan, A., Kaewseejan, N., & Siriamornpun, S. (2016). Cratoxylum formosum extracts inhibit growth and metastasis of cholangiocarcinoma cells by modulating the NF-κB and STAT3 pathways. Nutrition and Cancer, 68(2), 328-341. https://doi.org/10.1080/01635581.2016.1142580

  • Seo, E.-K., Kim, N.-C., Wani, M. C., Wall, M. E., Navarro, H. A., Burgess, J. P., Kawanishi, K., Kardono, L. B. S., Riswan, S., Rose, W. C., Fairchild, C. R., Farnsworth, N. R., & Kinghorn, A. D. (2002). Cytotoxic prenylated xanthones and the unusual compounds anthraquinobenzophenones from Cratoxylum sumatranum. Journal of Natural Products, 65(3), 299-305. https://doi.org/10.1021/np010395f

  • Sharifi-Rad, M., Fokou, P. V. T., Sharopov, F., Martorell, M., Ademiluyi, A. O., Rajkovic, J., Salehi, B., Martins, N., Iriti, M., Sharifi-Rad, J. (2018). Antiulcer agents: From plant extracts to phytochemicals in healing promotion. Molecules, 23(7), 1751. https://doi.org/10.3390/molecules23071751

  • Sidahmed, H. M. A., Abdelwahab, S. I., Mohan, S., Abdulla, M. A., Taha, M. M. E., & Hashim, N. M., Hadi, A. H. A., Vadivelu, J., Fai, M. L., Rahmani, M., & Yahayu, M. (2013). α-Mangostin from Cratoxylum arborescens (Vahl) Blume demonstrates anti-ulcerogenic property: A mechanistic study. Evidence-Based Complementary and Alternative Medicine, 2013, 450840. https://doi.org/10.1155/2013/450840

  • Sidahmed, H. M. A., Mohd Hashim, N., Syam, M., Abdelwahab, S. I., Taha, M. M. E., Dehghan, F., Yahayu, M., Ee, G. C. L., Loke, M. F., & Vadivelu, J. (2016). Evidence of the gastroprotective and anti-Helicobacter pylori activities of β-mangostin isolated from Cratoxylum arborescens (Vahl) Blume. Drug Design, Development and Therapy, 10, 297-313. https://doi.org/10.2147/dddt.s80625

  • Sim, W. C., Ee, G. C. L., Lim, C. J., & Sukari, M. A. (2010). Cratoxylum glaucum and Cratoxylum arborescens (Guttiferae) - Two potential source of antioxidant agents. Asian Journal of Chemistry, 23(2), 569-572.

  • Soepadmo, E., & Wong, K. M. (1995). Tree flora of Sabah and Sarawak. Forest Research Institute Malaysia (FRIM).

  • Sripanidkulchai, K., Teepsawang, S., & Sripanidkulchai, B. (2010). Protective effect of Cratoxylum formosum extract against acid/alcohol-induced gastric mucosal damage in rats. Journal of Medicinal Food, 13(5), 1097-1103. https://doi.org/10.1089/jmf.2009.1237

  • Srisombat, N., Bapia, S., Ratanabunyong, S., Choowongkomon, K., Vajrodaya, S., & Duangsrisai, S. (2019). Isolation of betulinic acid and antioxidant and anti-HIV-1 reverse transcriptase activity of Cratoxylum formosum subsp. pruniflorum (Kurz) Gogelein extract. Agriculture and Natural Resources, 53(6), 674-680. https://doi.org/10.34044/j.anres.2019.53.6.16

  • Suddhasthira, T., Thaweboon, S., Dendoung, N., Thaweboon, B., & Dechkunakorn, S. (2006). Antimicrobial activity of Cratoxylum formosum on Streptococcus mutans. Southeast Asian Journal of Tropical Medicine and Public Health, 37(6), 1156-1159.

  • Syam, S., Bustamam, A., Abdullah, R., Sukari, M. A., Mohd Hashim, N., Yahayu, M., Hassandarvish, P., Mohan, S., & Abdelwahab, S. (2014). Cytotoxicity and oral acute toxicity studies of β-mangostin isolated from Cratoxylum arborescens. Pharmacognosy Journal, 6(1), 47-56. https://doi.org/10.5530/pj.2014.1.8

  • Takamatsu, S., Galal, A. M., Ross, S. A., Ferreira, D., ElSohly, M. A., Ibrahim, A.-R., & El-Feraly, F. S. (2003). Antioxidant effect of flavonoids on DCF production in HL-60 cells. Phytotherapy Research, 17(8), 963-966. https://doi.org/10.1002/ptr.1289

  • Tan, S.-A., Yam, H. C., Cheong, S. L., Chow, Y. C., Bok, C. Y., Ho, J. M., Lee, P. Y., & Gunasekaran, B. (2021). Inhibition of Porphyromonas gingivalis peptidyl arginine deiminase, a virulence factor, by antioxidant-rich Cratoxylum cochinchinense: In vitro and in silico evaluation. Saudi Journal of Biological Sciences, 29(4), 2573-2581. https://doi.org/10.1016/j.sjbs.2021.12.037

  • Tang, S. Y., Whiteman, M., Jenner, A., Peng, Z. F., & Halliwell, B. (2004). Mechanism of cell death induced by an antioxidant extract of Cratoxylum cochinchinense (YCT) in Jurkat T cells: The role of reactive oxygen species and calcium. Free Radical Biology and Medicine, 36(12), 1588-1611. https://doi.org/10.1016/j.freeradbiomed.2004.03.018

  • Tang, S. Y., Whiteman, M., Peng, Z. F., Jenner, A., Yong, E. L., & Halliwell, B. (2004). Characterization of antioxidant and antiglycation properties and isolation of active ingredients from traditional Chinese medicines. Free Radical Biology and Medicine, 36(12), 1575-1587. https://doi.org/10.1016/j.freeradbiomed.2004.03.017

  • Tantapakul, C., Maneerat, W., Sripisut, T., Ritthiwigrom, T., Andersen, R. J., Cheng, P., Cheenpracha, S., Raksat, A., & Laphookhieo, S. (2016). New benzophenones and xanthones from Cratoxylum sumatranum ssp. neriifolium and their antibacterial and antioxidant activities. Journal of Agricultural and Food Chemistry, 64(46), 8755-8762. https://doi.org/10.1021/acs.jafc.6b03643

  • Thakur, M., Singh, K., & Khedkar, R. (2020). Phytochemicals. In Functional and preservative properties of phytochemicals (pp. 341-361). Academic Press. https://doi.org/10.1016/b978-0-12-818593-3.00011-7

  • Thaweboon, S., Thaweboon, B., Dechkunakorn, S., Nisalak, P., & Kaypetch, R. (2014). Anticandidal activity of Cratoxylum formosum gum and its cytotoxicity. Advanced Materials Research, 974, 394-397. https://doi.org/10.4028/www.scientific.net/amr.974.394

  • Thu, Z. M., Aung, H. T., Sein, M. M., Maggiolini, M., Lappano, R., & Vidari, G. (2017). Highly cytotoxic xanthones from Cratoxylum cochinchinense collected in Myanmar. Natural Product Communications, 12(11), 1759-1762. https://doi.org/10.1177/1934578x1701201127

  • Udomchotphruet, S., Phuwapraisirisan, P., Sichaem, J., & Tip-pyang, S. (2012). Xanthones from the stems of Cratoxylum cochinchinense. Phytochemistry, 73, 148-151. https://doi.org/10.1016/j.phytochem.2010.04.028

  • Vu, T. T., Kim, H., Tran, V. K., Dang, Q. L., Nguyen, H. T., Kim, H., Kim, I. S., Choi, G. J., & Kim, J.-C. (2015). In vitro antibacterial activity of selected medicinal plants traditionally used in Vietnam against human pathogenic bacteria. BMC Complementary and Alternative Medicine, 16, 32. https://doi.org/10.1186/s12906-016-1007-2

  • Waiyaput, W., Payungporn, S., Issara-Amphorn, J., & Panjaworayan, N. T.T. (2012). Inhibitory effects of crude extracts from some edible Thai plants against replication of hepatitis B virus and human liver cancer cells. BMC Complementary and Alternative Medicine, 12, 246. https://doi.org/10.1186/1472-6882-12-246

  • Xiong, J., Liu, X.-H., Bui, V.-B., Hong, Z.-L., Wang, L.-J., Zhao, Y., Fan, H., Yang, G.-X., & Hu, J.-F. (2014). Phenolic constituents from the leaves of Cratoxylum formosum ssp. pruniflorum. Fitoterapia, 94, 114-119. https://doi.org/10.1016/j.fitote.2014.02.002

  • Yahayu, A. M., Rahmani, M., Mohd Hashim, N., Ee G. C. L., Sukari, M. A., & Md Akim, A. (2013). Cytotoxic and antimicrobial xanthones from Cratoxylum arborescens (Guttiferae). Malaysian Journal of Science, 32(1), 53-60. https://doi.org/10.22452/mjs.vol32no1.9