Malaysian
Journal of Analytical Sciences Vol 18 No 3 (2014): 676 - 682
BENZOFURAN GLYCOSIDES FROM STYRAX BENZOIN
(Glikosida
bezofuran daripada Styrax benzoin)
Hasliza Yusof, Laily B. Din, Wan A. Yaacob*
School of
Chemical Sciences and Food Technology, Faculty of Science and Technology,
Universiti
Kebangsaan Malaysia, 43600 UKM Bangi, Selangor D.E., Malaysia
*Corresponding author: wanyaa@ukm.edu.my
Abstract
Separation
of methanol extracts of the fruits and stem bark of Styrax benzoin using various chromatography (vacuum liquid
chromatography, column chromatography and preparative thin layer
chromatography) gave four benzofuran glycosides namely egonol gentiobioside (1), egonol gentiotrioside (2), egonol glucoside (3) and masutakeside (4). The compounds were identified by
spectroscopic analysis (NMR, mass and infra-red spectral data) and by
comparison of the data with that of the literature. Isolation of compounds from
this plant has never been reported before.
Keywords: styrax benzoin, styracaceae, egonol
gentiobioside, egonol gentiotrioside, egonol glucoside, masutakeside
Abstrak
Pemisahan
kromatografi ke atas ekstrak metanol buah dan kulit batang Styrax benzoin menggunakan pelbagai teknik kromatografi
(kromatografi cecair vakum, kromatografi turus dan kromatografi lapisan thin
preparatif) memberikan empat benzofuran glikosida yang bernama egonol
gentiobiosida (1), egonol
gentiotriosida (2), egonol glukosida
(3) dan masutakesida (4). Sebatian ini telah dikenal pasti
dengan analisis spektroskopi (data spektrum RMN, jisim dan infra merah) dan
membandingkan data ini dengan data kepustakaan. Pemisahan sebatian daripada
tumbuhan ini belum pernah dilaporkan sebelum ini
Kata
kunci:
styrax benzoin, styracaceae, egonol
gentiobiosida, egonol gentiotriosida, egonol glukosida, masutakesida
References
1.
Ng,
F. S. P. (1992). Manual of forest fruits,
seeds and seedlings. Vol. II. Forest Research Institute Malaysia
2.
Li,
Q. L., Li, B. G., Qi, H. Y., Gao, X. P. & Zhang, G. L. (2005). Four new
benzofurans from seeds of Styrax
perkinsiae. Planta Medica, 71:
847-851
3.
Pauletti,
P. M., Araujo, A. R., Young, M. C. M., Giesbrecht, A. M. & Bolzani, V. d.
S. (2000). nor-Lignans from the leaves of Styrax
ferrugineus (Styracaceae) with antibacterial and antifungal activity. Phytochemistry, 55: 597-601
4.
Anil,
H. (1980). Four benzofuran glycosides from Styrax
officinalis, Phytochemistry 19:
2784-2786
5.
Nakano,
T., Hasegawa, M., Fukumaru, T & Tobinaga, S. (1967). The structure of
jeposapogenol. Tetrahedron Letters,
4: 365-371
6.
Segal,
R., Govrin, H. & Zaitechek, D. V. (1964). A new type of saponin from Styrax officinalis L. Tetrahedron Letters, 10: 527-530
7.
Yayla,
Y., Caliskan, O. A., Anil, H., Bates, R. B., Stessman, C. C. & Kane, V. V.
(2002). Saponins from Styrax officinalis.
Fitoterapia, 73: 320-326
8.
Lou,
Y., He, Z. & Li, H. (2007). 2-aryl benzofurans and their derivatives from
seeds of Styrax macranthus. Fitoterapia, 78: 211-214
9.
Min,
B. S., Oh, S. R., Ahn, K. S., Kim, J. H., Lee, J., Kim, D. Y., Kim, E. H. &
Lee, H. K. (2004a). Anti-complement activity of norlignans and terpenes from
the stem bark of Styrax japonica. Planta Medica, 70: 1210-1215
10.
Min,
B. S., Na, M. K., Oh, S. R., Ahn, K. S., Jeong, G. S., Lee, S. K., Joung, H.
& Lee, H. K. (2004b). New furofuran and butyrolactone lignans with
antioxidant activity from the stem bark of Styrax
japonica. Journal of Natural Product, 67: 1980-1984
11.
Feng,
C. Q., Zhen, C. X., You, L. G., Chun, W. & Lin, Z. G. (2012). Two new
2-phenylbenzofurans from the bark of Styrax
perkinsiae. Chinese Journal of
Natural Medicines, 10: 92-97
12.
Ulubelen,
A., Saiki, Y., Lotter, H., Chari, V. M. & Wagner, H. (1978). Chemical
components of Styrax officinalis L. -
IV the structure of a new lignan styraxin. Planta
Medica, 34: 403-407
13.
Akgul,
Y. Y. & Anil, H. (2003a). Benzofurans and another constituents from seeds
of Styrax officinalis. Phytochemistry, 63: 939-943
14.
Akgul,
Y. Y. & Anil, H. (2003b). Benzofuran from seeds of Styrax officinalis. Fitoterapia,
74: 743-745
15.
Takanashi,
M. & Takizawa, Y. (1988). New benzofurans related to egonol from immature
seeds of Styrax obassia. Phytochemistry, 27: 1224-1226
16.
Takanashi,
M. & Takizawa, Y. (2002). New egonol glycoside having D-xylose from
immature seeds of Styrax obassia
Sieb. et Zucc. Journal of Oleo Science,
51: 423-426
17.
Burkill,
I. H. (1966). A dictionary of the
economic products of the Malay Peninsula. Vol II (I-Z). Kuala Lumpur:
Ministry of Agriculture & Co-operatives
18.
Ridley,
H. N. (1967). The flora of the Malay
Peninsula. Vol II. London: L. Reeve & Co.