Abstract
The application of the Entada spiralis Ridl. (Leguminosae) stem bark containing saponin in the treatment of scalp and as body soap is well known for generations. Our previous investigation revealed that E. spiralis stem bark contains several terpenoid compounds and is responsible for the inhibitory effect against bacteria Staphylococcus epidermidis ATCC 12228 and skin disease dermatophytes, Microsporum gypseum ATCC 24102, Trichophyton mentagrophytes ATCC 9533 and Trichophyton tonsurans ATCC 28942. The aim of this work is to isolate and identify the chemical structures of terpenoid compounds from active fraction of E. spiralis stem bark. The isolation of active compounds was conducted by chromatographical separation, and the structure characterization was done based on 1D and 2D NMR analysis (1H,13C NMR, HMQC, HMBC and DEPT135) and comparison with those of the literature. We managed to isolate two terpenoid compounds known as ester saponin (1) and terpene benzoate (2). These compounds were elucidated as 16-β-D-arabinofuranosyl-15-β-D-xylopyranosyl-5,8,9,10-tetrahydroxyl-17,18,19,20-tetramethyl diterpene ester (1) and 4-(β-D-glucopyranosyl)-1-hydroxybenzene-(20-hydroxyl-18,19-dimethylcyclotetradecanol) benzoate (2). The finding is hoped to provide an alternative of new search for natural antimicrobial drug.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Mboso, E. J. T., Ngouela, S., Nguedia, J. C. A., Beng, V. P., Rohmer, M., & Tsamo, E. (2010). In vitro antimicrobial activity of extracts and compounds of some selected medicinal plants from Cameroon. Journal of Ethnopharmacology, 128, 476–481.
Liu, W. C., Kugelman, M., Wilson, R. A., & Rao, K. V. (1972). A crystalline saponin with anti-tumor activity from Entada phaseoloides. Phytochemistry, 11, 171–173.
Okada, Y., Shibata, S., Ikekawa, T., Javellana, A. M. J., & Kamo, O. (1987). Entada saponin III, a saponin isolated from the bark of Entada phaseoloides. Phytochemistry, 26, 2789–2796.
Okada, Y., Shibata, S., Javellana, A. M. J., & Kamo, O. (1988). Entada saponin (ES) II and IV, from the bark of Entada phaseoloides. Chemical and Pharmaceutical Bulletin, 36, 1264–1269.
Cioffi, G., Dal Piaz, F., De Caprariis, P., Sanego, R., Marzocco, S., Autore, G., & De Tommasi, N. (2006). Antiproliferative triterpene saponins from Entada Africana. Journal of Natural Products, 69, 1323–1329.
Tapondjou, A. L., Miyamoto, T., Mirjolet, J. F., Guilbaud, N., & Lacaille-Dubois, M. A. (2005). Pursaethosides A–E, triterpene saponins from Entada pursaetha. Journal of Natural Products, 68, 1185–1190.
Ikegami, F., Shibasaki, I., Ohmiya, S., Ruangrungsi, N., & Murakoshi, I. (1985). Entadamide A. a new sulphur-containing amide from Entada phaseoloides seeds. Chemical and Pharmaceutical Bulletin, 33, 5153–5154.
Ikegami, F., Ohmiya, S., Ruangrungsi, N., Sakai, S. I., & Murakoshi, I. (1987). A second new sulphur-containing amide from Entada phaseoloides seeds. Phytochemistry, 26, 1525–1526.
Ikegami, F., Sekine, T., Duangteraprecha, S., Matsushita, N., Matsuda, N., Ruangrungsi, N., & Murakoshi, I. (1989). A sulphur-containing amide from Entada phaseoloides. Phytochemistry, 28, 881–882.
Barua, A. K., Chakrabarty, M., Datta, P. K., & Ray, S. (1988). Phaseoloidin, a homogentisic acid glucoside from Entada phaseoloides. Phytochemistry, 27, 3259–3261.
Dai, J., Kardono, L. B. S., Tsaur, S., Padmawinata, K., Pezzuto, J. M., & Kinghorn, A. D. (1991). Phenylacetic acid derivatives and a thioamide glycosides from Entada phaseoloides. Phytochemistry, 30, 3749–3752.
Nzowa, L. K., Barboni, L., Teponno, R. B., Ricciutelli, M., Lupidi, G., Quassinti, L., Bramucci, M., & Tapondjou, L. A. (2010). Rheediinosides A and B, two antiproliferative and antioxidant triterpene saponins from Entada rheedii. Phytochemistry, 71, 254–261.
Note, O. P., Mitaine-Offer, A. C., Miyamoto, T., Paululat, T., Mirjolet, J. F., Duchamp, O., Pegnyemb, D. E., & Lacaille-Dubois, M. A. (2009). Cytotoxic acacic acid glycosides from the roots of Albizia coriaria. Journal of Natural Products, 72(10), 1725–1730.
Yodsaoue, O., Karalai, C., Ponglimanot, C., Tewtrakul, S., & Chantrapromma, S. (2010). Potential anti-inflammatory diterpenoids from the roots of Caesalpinia mimosoides Lamk. Phytochemistry, 71, 1756–1764.
Miyase, T., Melek, F. R., Ghaly, N. S., Warashina, T., El-Kady, M., & Nabil, M. (2010). Echinocystic acid 3, 16-O bisglycosides from Albizia procera. Phytochemistry, 71, 1375–1380.
Tene, M., Chaber, P., Note, O., Kenla, T. J. N., Tane, P., & Lobstein, A. (2011). Triterpenoid saponins from Cylicodiscus gabunensis. Phytochemistry, 4, 89–92.
Yokosuka, A., Kawakami, S., Haraguchi, M., & Mimaki, Y. (2010). Seven new triterpene glycosides from the pericarps of Stryphnodendron fissuratum. Phytochemistry Letters, 4(3), 259–266.
Silva, G. M., Teles, H. L., Zanardi, L. M., Marx Young, M. C., Eberlin, M. N., Hadad, R., Pfenning, L. H., Costa-Neto, C. M., Castro-Gamboa, I., Da Silva Bolzani, V., & Araujo, A. R. (2006). Cadinane sesquiterpenoids of Phomopsis cassiae, an endophytic fungus associated with Cassia spectabilis (Leguminosae). Phytochemistry, 67, 1964–1969.
Zhao, Z., Jin, J., Lin, C., Zhu, C., Liu, Y., Lin, A., Liu, Y., Zhang, L., & Luo, H. (2011). Two new chalcone glycosides from the stems of Entada phaseoloides. Fitoterapia, 82(7), 1102–1105.
Yokosuka, A., Kawakami, S., Haraguchi, M., & Mimaki, Y. (2011). Seven new triterpene glycosides from the pericarps of Stryphnodendron fissuratum. Phytochemistry Letters, 4(3), 259–266.
Mutai, C., Bii, C., Vagias, C., Abatis, D., & Roussis, V. (2009). Antimicrobial activity of Acacia mellifera extracts and lupane triterpenes. Journal of Ethnopharmacology, 123, 143–148.
Boz, J. D., Crespo, V., Rivas-Ruiz, F., & De Troya, M. (2009). Tinea incognito in children: 54 cases. Mycoses, 54, 254–258.
Acknowledgement
This work was supported by e-science fund (project no: 06-01-08-SF0074). The author wishes to express gratitude to Kulliyyah of Pharmacy IIUM, UiTM Kampus Khazanah Alam Pahang, Mr. Mohd Zahid Mohd Yusof and Mr. Alefee Ayatillah (Universiti Kebangsaan Malaysia) for carrying out NMR and MS experiments.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer Science+Business Media Singapore
About this paper
Cite this paper
Harun, A., So’ad, S.Z.M., Hassan, N.M., Ramli, N.K.C.M. (2014). Bioactive Terpenoids from the Stem Bark of Entada spiralis Ridl. (Sintok). In: Kasim, A., Wan Omar, W., Abdul Razak, N., Wahidah Musa, N., Ab. Halim, R., Mohamed, S. (eds) Proceedings of the International Conference on Science, Technology and Social Sciences (ICSTSS) 2012. Springer, Singapore. https://doi.org/10.1007/978-981-287-077-3_72
Download citation
DOI: https://doi.org/10.1007/978-981-287-077-3_72
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-287-076-6
Online ISBN: 978-981-287-077-3
eBook Packages: Humanities, Social Sciences and LawSocial Sciences (R0)