Sains Malaysiana 46(1)(2017): 83–89

http://dx.doi.org/10.17576/jsm-2017-4601-11

Phytochemical Study of Hedychium malayanum (Zingiberaceae)

(Kajian Fitokimia Hedychium malayanum (Zingiberaceae) )

MOHAMMED YAHYA ABDO, WAN YAACOB WAN AHMAD*, LAILY BIN DIN

 & NAZLINA IBRAHIM

Pusat Pengajian Sains Kimia dan Teknologi Makanan, Fakulti Sains & Teknologi

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor Darul Ehsan, Malaysia

Received: 26 March 2015/Accepted: 28 April 2016

ABSTRACT

A phytochemical study was conducted on the stems and leaves of Hedychium malayanum (Zingiberaceae). Three steroids namely stigmasterol (1), sitostenone (2) and stigmast-4-ene-3,6-dione (3) as well as one triterpene, lupenone (4) and one oxygenated sesquiterpene, caryophyllene oxide (5) were successfully isolated from the respective stems and leaves, utilizing several chromatographic techniques. Their structures were elucidated by spectroscopic means (IR, MS, NMR), and by comparison with the literature data.

Keywords: Hedychium malayanum; NMR; steroids; terpenoids; Zingiberaceae

ABSTRAK

Kajian fitokimia dijalankan terhadap batang dan daun Hedychium malayanum (Zingiberaceae). Tiga steroid stigmasterol (1), sitostenon (2) dan stigmast-4-ena-3,6-dion (3) berserta triterpena, lupenon (4) dan seskuiterpena beroksigen, kariofilena oksida (5) berjaya dipisahkan masing-masing daripada batang dan daun, menggunakan beberapa teknik kromatografi. Struktur mereka dikenal pasti dengan cara spektroskopi (IM, SJ, RMN) dan secara perbandingan dengan data kepustakaan.

Kata kunci: Hedychium malayanum; RMN; steroid; terpenoid; Zingiberaceae

REFERENCES

Aziz, A.N., Ibrahim, H., Syamsir, D.R., Mohtar, M., Vejayan, J. & Awang, K. 2013. Antimicrobial compounds from Alpinia conchigera. Journal of Ethnopharmacology 145: 798-802.

Carvalho, M.J., Carvalho, L.M., Ferreira, A.M. & Silva, A.M. 2003. A new xanthone from Hedychium gardnerianum. Natural Product Research 17(6): 445-449.

Chen, J.J., Ting, C.W., Wu, Y.C., Hwang, T.L., Cheng, M.J., Sung, P.J., Wang, T.C. & Chen, J.F. 2013. New labdane-type diterpenoids and anti-inflammatory constituents from Hedychium coronarium. International Journal of Molecular Sciences 14(7): 13063-13077.

De Medeiros, J.M.R., Medeiros, H. & Mascarenhas, C. 2008. Flavonoid anticoagulant agents extracted from Hedychium gardnerianum. Port. Pat. Appl. PT 103685 A 20080909.

De-Eknamkul, W. & Potduang, B. 2003. Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry 62(3): 389-398.

Hussain, M.M., Rahman, M.S., Jabbar, A. & Rashid, M.A. 2008. Phytochemical and biological investigations of Albizzia lebbeck Benth. Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 7(5): 273-278.

Kiem, P.V., Thuy, N.T.K., Anh, H.L.T., Nhiem, N.X., Minh, C.V., Yen, P.H., Ban, N.K., Hang, D.T., Tai, B.H., Tuyen, N.V., Mathema, V.B., Koh, Y.S. & Kim, Y.H. 2011. Chemical constituents of the rhizomes of Hedychium coronarium and their inhibitory effect on the pro inflammatory cytokines production LPS-stimulated in bone marrow-derived dendritic cells. Bioorganic & Medicinal Chemistry Letters 21(24): 7460-7465.

Kumrit, I., Suksamrarn, A., Meepawpan, P., Songsri, S. & Nuntawong, N. 2010. Labdane-type diterpenes from Hedychium gardnerianum with potent cytotoxicity against human small cell lung cancer cells. Phytotherapy Research 24(7): 1009-1013.

Le, H.T., Phan, M.G. & Phan, T.S. 2007. Biologically active phenolic constituents from Alpinia gagnepainii K. Schum. Tap Chi Hoa Hoc 45(1): 126-130.

Li, Y.P., Zhao, S.M., Xu, J.J., Zeng, G.Z., Li, Y., Tan, N.H. & Yang, Y. 2016. New labdane diterpenes from Hedychium yunnanense with cytotoxicity and inhibitory effects on nitric oxide production. Natural Product Research 30(23): 2669-2674.

Lin, Y.S., Lin, J.H., Chang, C.C. & Lee, S.S. 2015. Tetrahydropyran-and tetrahydrofuran-containing diarylheptanoids from Hedychium coronarium rhizomes. Journal of Natural Products 78(2): 181-187.

Liu, L.J., Guo, W.C., Peng, Q.L., Yan, S.J., Su, J.Y. & Zeng, L.M. 2004. Studies of the chemical constituents of Hedychium forrestii Diels. Zhongshan Daxue Xuebao, Ziran Kexueban 43(5): 58-60.

Lognay, G., Marlier, M., Haubruge, E., Trevejo, E. & Severin, M. 1989. Study of the lipids from Renealmia alpinia (Rott) Maas. Grasas y Aceites 40(6): 351-355.

Luo, M., Lei, L. & Lin, H. 2009. Studies on chemical constituents from rhizomes of Hedychium chrysoleucum. Zhongguo Zhong yao za zhi= Zhongguo zhongyao zazhi= China Journal of Chinese Materia. Medica. 34(2): 180-182.

Mahdavi, B. 2014. Chemical constituents of the aerial parts of Etlingera brevilabrum (Zingiberaceae). Pharma Chemica 6(2): 360-365.

Mohamad, H., Lajis, N.H., Abas, F., Ali, A.M., Sukari, M.A., Kikuzaki, H. & Nakatani, N. 2005. Antioxidative constituents of Etlingera elatior. Journal of Natural Products 68(2): 285-288.

Mohamed, S.M., El-Gengaihi, S.E. & Motawe, H.M. 2003. Terpenoid from Curcuma longa. Egyptian Journal of Pharmaceutical Sciences 43(1-2): 139-151.

Orihara, Y., Saiki, K. & Furuya, T. 1994. Biotransformation of caryophyllene oxide by cultured cells of Eucalyptus perriniana. Phytochemistry 35(3): 635-639.

Pardo, F., Perich, F., Torres, R. & Delle Monache, F. 2000. Stigmast-4-ene-3,6-dione an unusual phytotoxic sterone from the roots of Echium vulgare L. Biochemical Systematics and Ecology 28: 911-913.

Peng, W., Zhang, Y., Yang, K. & Xiao, Y. 2007. Chemical constituents of Zingiber officinale (Zingiberaceae). Yunnan Zhiwu Yanjiu 29(1): 125-128.

Phan, M.G. & Phan, T.S. 2004. Phytochemical investigation of Alpinia globosa (Lour.) Horaninov, Zingiberaceae. Tap Chi Hoa Hoc 42(3): 376-378.

Phan, M.G., Dang, T.T.A., Le, H.T. & Phan, T.S. 2012. Diarylheptanoids and flavanones from Alpinia napoensis. Tap Chi Hoa Hoc 50(5): 537-541.

Phan, M.G., Le, H.T., Phan, T.S. & Otsuka, H. 2007. Chemical constituents of the fruits of Alpinia conchigera Griff. (Zingiberaceae). Tap Chi Hoa Hoc 45(4): 509-512.

Phan, M.G., Dang, B.T. & Phan, T.S. 2005. Flavonoid compounds from the rhizomes of Alpinia conchigera Griff., Zingiberaceae. Tap Chi Hoa Hoc 43(1): 105-108.

Prachayasittikul, S., Saraban, P., Cherdtrakulkiat, R., Ruchirawat, S. & Prachayasittikul, V. 2010. New bioactive triterpenoids and antimicrobial activity of Diospyros rubralec. Experimental and Clinical Sciences Journal 9: 1-10.

Qiao, C., Xu, L., Shen, Y. & Hao, X. 1999. Chemical constituents from Globba racemosa Smith. Huaxue Yanjiu Yu Yingyong 11(5): 575-576.

Reddy, P.P., Rao, R.R., Shashidhar, J., Sastry, B.S., Rao, J.M. & Babu, K.S. 2009. Phytochemical investigation of labdane diterpenes from the rhizomes of Hedychium spicatum and their cytotoxic activity. Bioorganic & Medicinal Chemistry Letters 19(21): 6078-6081.

Saleh, M.M., Shabana, M.K.S., Guindi, E.R. & Kamal, R.M. 1981. Phytochemical and molluscicidal study on Hedychium gardnerianum, Wall. as a method for control of schistosoma. Int. Conf. Chem. Biotechnol. Act. Nat. Prod. [Proc.], 1st 3(1): 293-297.

Seca, A., Silva, A., Silvestre, A., Cavaleiro, J.A.S., Domingues, F. & Pascoal Neto, C. 2000. Chemical composition of the light petroleum extract of Hibiscus cannabinus bark and core. Phytochemical Analysis 11: 345-350.

Shamim, A., Mohd, A. & Husain, A.S. 2011. New aliphatic constituents from the rhizomes of Curcuma oligantha Trimen var. oligantha. International Journal of Research in Ayurveda & Pharmacy 2(3): 797-800.

Sravani, T., Paarakh, P.M. & Shruthi, S.D. 2014. In silico and in vitro anthelmintic activity of stigmasterol β- D- glucoside isolated from rhizomes of Hedychium spicatum Buch. Ham. World Journal of Pharmacy and Pharmaceutical Sciences 3(9): 664-672.

Sravani, T., Paarakh, P.M. & Vedamurthy, A.B. 2012. Isolation of phytoconstituents from the rhizomes of Hedychium spicatum Buch. Ham. Journal of Pharmacy Research 5(1): 526-527.

Suresh, G., Poornima, B., Babu, K.S., Yadav, P.A., Rao, M.S., Siva, B., Parsad, K.R., Nayak, V.L. & Ramakrishna, S. 2013. Cytotoxic sesquiterpenes from Hedychium spictum: Isolation, structure elucidation and structure-activity relationship studies. Fitoterapia 86: 100-107.

Xiao, P., Sun, C., Zahid, M., Ishrud, O. & Pan, Y. 2001. New diterpene from Hedychium villosum. Fitoterapia 72(7): 837-838.

Yahya, M.A.A., Yaacob, W.A. & Nazlina, I. 2011. Isolation of chemical constituents from rhizomes of Etlingera sphaerocephala var. grandiflora. Malaysian Journal of Analytical Sciences 15(1): 22-26.

Zhao, H., Zeng, G., Zhao, S., Xu, J., Kong, L., Li, Y., Tan, N. & Yang, S. 2015. Cytotoxic labdane-type diterpenes from Hedychium longipetalum inhibiting production of nitric oxide. Bioorganic & Medicinal Chemistry Letters 25(20): 4572-4575.

Zhao, Q., Hao, X.J., Chen, Y.Z. & Zou, C. 1995. Sesquiterpenoids from Hedychium yunnanense. Yunnan Zhiwu Yanjiu 17(2): 201- 203.

*Corresponding author; email: wanyaa@ukm.edu.my