Chemical Constituents of Fruits and Leaves of Cratoxylum cochinchinense and Their Cytotoxic Activities
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Published
Jul 17, 2017
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Abstract
Seven compounds; Vismiaquinone A (1), 7-geranyloxy-1,3-dihydroxyxanthone (2), Cochinchinone G (3), Fuscaxanthone E (4), g-tocotrienol (5), δ-tocotrienol (6), and a-tocopherol (7) were isolated from fruits and leaves of Cratoxylum cochinchinense. The structures of all isolated compounds were elucidated by basic NMR spectroscopy (1H, 13C, COSY, HSQC and HMBC) and compared with previous literatures. Interestingly, g-tocotrienol (5) and a-tocopherol (7) were the first time being isolated from C. cochinchinense. The chemical constituents of C. cochinchinense such as g-tocotrienol (5), δ-tocotrienol (6), and a-tocopherol (7) are vitamin E derivatives that have been used for cosmetic ingredients. Thus, this plant extract should be promising probability for applying to cosmetic ingredients. Furthermore, all isolated compounds were also tested for in vitro cytotoxic activity against five human cancer cell lines; breast (BT474), lung (ChaGo-K-1), liver (HepG2), gastric (KATO-III), and colon (SW-620) cancer cell lines by MTT assay method. The cytotoxic activity of compound 3 against SW-620 (colon cancer cell line, IC50 4.64 mg/mL) was found to be stronger than other compounds.
Keywords: Cratoxylum cochinchinense, cytotoxicity, xanthone, tocotrienol, vitamin E derivatives, structure elucidation
References
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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(10), 1329-1335.
Boonnak, N., Karalai, C., Chantrapromma, S., Ponglimanont, C., Kanjana-Opas, A., Chantrapromma, K., & Kato, S. (2010). Chromene and Prenylated Xanthones from the Roots of Cratoxylum formosum ssp. pruniflorum. Chemical and Pharmaceutical Bulletin, 58(3), 386-389.
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Nagem, T. J., & de Jesus Faria, T. (1990). Quinonoid and other constituents of Vismia martiana. Phytochemistry, 29(10), 3362-3364.
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Nguyen, L. H. D., & Harrison, L. J. (1999). Triterpenoid and xanthone constituents of Cratoxylum cochinchinense. Phytochemistry, 50(3), 471-476.
Nuanyai, T., Chailap, B., Puthong, S., & Buakeaw, A. (2015). Cytotoxicity of xanthone from twigs of Cratoxylum cochinchinense (Lour.) Blume. J. Sci. Ladkrabang. 24(2), 1-13.
Ohnmacht, S., West, R., Simionescu, R., & Atkinson, J. (2008). Assignment of the 1H and 13C NMR of tocotrienols. Magnetic Resonance in Chemistry, 46(3), 287-294.
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(10), 1487-1489.
Rattanaburi, S., Daus, M., Watanapokasin, R., & Mahabusarakam, W. (2014). A new bisanthraquinone and cytotoxic xanthones from Cratoxylum cochinchinense. Natural product research, 28(9), 606-610.
Reutrakul, V., Chanakul, W., Pohmakotr, M., Jaipetch, T., Yoosook, C., Kasisit, J., ... & Tuchinda, P. (2006). Anti-HIV-1 constituents from leaves and twigs of Cratoxylum arborescens. Planta medica, 72(15), 1433-1435.
Sen, C. K., Khanna, S., & Roy, S. (2006). Tocotrienols: Vitamin E beyond tocopherols. Life sciences, 78(18), 2088-2098.
Serbinova, E., Kagan, V., Han, D., & Packer, L. (1991). Free radical recycling and intramembrane mobility in the antioxidant properties of alpha-tocopherol and alpha-tocotrienol. Free Radical Biology and Medicine, 10(5), 263-275.
Sim, W. C., Ee, G. C. L., Lim, C. J., & Sukari, M. A. (2011). Cratoxylum glaucum and Cratoxylum arborescens (Guttiferae)-two potential source of antioxidant agents. Asian Journal of Chemistry, 23(2), 569-572.
Twentyman, P. R., & Luscombe, M. (1987). A study of some variables in a tetrazolium dye (MTT) based assay for cell growth and chemosensitivity. British journal of cancer, 56(3), 279-285.
Udomchotphruet, S., Phuwapraisirisan, P., Sichaem, J., & Tip-pyang, S. (2012). Xanthones from the stems of Cratoxylum cochinchinense. Phytochemistry, 73, 148-151.
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(5), 1245-1251.
Boonnak, N., Chantrapromma, S., Fun, H. K., Yuenyongsawad, S., Patrick, B. O., Maneerat, W., ... & Andersen, R. J. (2014). Three Types of Cytotoxic Natural Caged-Scaffolds: Pure Enantiomers or Partial Racemates. Journal of natural products, 77(7), 1562-1571.
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(10), 1329-1335.
Boonnak, N., Karalai, C., Chantrapromma, S., Ponglimanont, C., Kanjana-Opas, A., Chantrapromma, K., & Kato, S. (2010). Chromene and Prenylated Xanthones from the Roots of Cratoxylum formosum ssp. pruniflorum. Chemical and Pharmaceutical Bulletin, 58(3), 386-389.
Carmichael, J., DeGraff, W. G., Gazdar, A. F., Minna, J. D., & Mitchell, J. B. (1987). Evaluation of a tetrazolium-based semiautomated colorimetric assay: Assessment of chemosensitivity testing. Cancer research, 47(4), 936-942.
Duan, Y., Dai, Y., Chen, L., Liu, M., Li, Y., & Yao, X. (2012). Xanthones from the stems of Cratoxylum cochinchinense. Magnetic Resonance in Chemistry, 50(9), 642-645.
Duan, Y. H., Dai, Y., Wang, G. H., Chen, L. Y., Chen, H. F., Zeng, D. Q., ... & Yao, X. S. (2015). Bioactive prenylated xanthones from the stems of Cratoxylum cochinchinense. Journal of Asian natural products research, 17(5), 519-531.
Ito, C., Itoigawa, M., Takakura, T., Ruangrungsi, N., Enjo, F., Tokuda, H., ... & Furukawa, H. (2003). Chemical Constituents of Garcinia fusca: Structure Elucidation of Eight New Xanthones and Their Cancer Chemopreventive Activity 1. Journal of natural products, 66(2), 200-205.
Jin, S. L., Wang, N. L., Zhang, X., Dai, Y., & Yao, X. S. (2009). Two new xanthones from the stems of Cratoxylum cochinchinense. Journal of Asian natural products research, 11(4), 322-325.
Laphookhieo, S., Maneerat, W., & Koysomboon, S. (2009). Antimalarial and cytotoxic phenolic compounds from Cratoxylum maingayi and Cratoxylum cochinchinense. Molecules, 14(4), 1389-1395.
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.
Mahabusarakam, W., Rattanaburi, S., Phongpaichit, S., & Kanjana-Opas, A. (2008). Antibacterial and cytotoxic xanthones from Cratoxylum cochinchinense. Phytochemistry Letters, 1(4), 211-214.
Nagem, T. J., & de Jesus Faria, T. (1990). Quinonoid and other constituents of Vismia martiana. Phytochemistry, 29(10), 3362-3364.
Nguyen, H. D., Trinh, B. T., Nguyen, N. K., Dang, S. V., Pham, H. D., & Nguyen, L. H. D. (2011). Xanthones from the twigs of Cratoxylum cochinchinense. Phytochemistry Letters, 4(1), 48-51.
Nguyen, L. H. D., & Harrison, L. J. (1999). Triterpenoid and xanthone constituents of Cratoxylum cochinchinense. Phytochemistry, 50(3), 471-476.
Nuanyai, T., Chailap, B., Puthong, S., & Buakeaw, A. (2015). Cytotoxicity of xanthone from twigs of Cratoxylum cochinchinense (Lour.) Blume. J. Sci. Ladkrabang. 24(2), 1-13.
Ohnmacht, S., West, R., Simionescu, R., & Atkinson, J. (2008). Assignment of the 1H and 13C NMR of tocotrienols. Magnetic Resonance in Chemistry, 46(3), 287-294.
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(10), 1487-1489.
Rattanaburi, S., Daus, M., Watanapokasin, R., & Mahabusarakam, W. (2014). A new bisanthraquinone and cytotoxic xanthones from Cratoxylum cochinchinense. Natural product research, 28(9), 606-610.
Reutrakul, V., Chanakul, W., Pohmakotr, M., Jaipetch, T., Yoosook, C., Kasisit, J., ... & Tuchinda, P. (2006). Anti-HIV-1 constituents from leaves and twigs of Cratoxylum arborescens. Planta medica, 72(15), 1433-1435.
Sen, C. K., Khanna, S., & Roy, S. (2006). Tocotrienols: Vitamin E beyond tocopherols. Life sciences, 78(18), 2088-2098.
Serbinova, E., Kagan, V., Han, D., & Packer, L. (1991). Free radical recycling and intramembrane mobility in the antioxidant properties of alpha-tocopherol and alpha-tocotrienol. Free Radical Biology and Medicine, 10(5), 263-275.
Sim, W. C., Ee, G. C. L., Lim, C. J., & Sukari, M. A. (2011). Cratoxylum glaucum and Cratoxylum arborescens (Guttiferae)-two potential source of antioxidant agents. Asian Journal of Chemistry, 23(2), 569-572.
Twentyman, P. R., & Luscombe, M. (1987). A study of some variables in a tetrazolium dye (MTT) based assay for cell growth and chemosensitivity. British journal of cancer, 56(3), 279-285.
Udomchotphruet, S., Phuwapraisirisan, P., Sichaem, J., & Tip-pyang, S. (2012). Xanthones from the stems of Cratoxylum cochinchinense. Phytochemistry, 73, 148-151.
Keywords
Cratoxylum cochinchinense; cytotoxicity; xanthone; tocotrienol; vitamin E derivatives; structure elucidation
Section
Research Articles
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How to Cite
CHAILAP, Benjamat et al.
Chemical Constituents of Fruits and Leaves of Cratoxylum cochinchinense and Their Cytotoxic Activities.
Naresuan University Journal: Science and Technology (NUJST), [S.l.], v. 25, n. 3, p. 22-30, july 2017.
ISSN 2539-553X.
Available at: <https://www.journal.nu.ac.th/NUJST/article/view/1892>. Date accessed: 19 apr. 2024.