1258
Vol. 56, No. 9
Table 4. Antioxidant Activity and Cytotoxicity to HL-60 Cells
17) Zhang J., Zhi-Hong Y., Bo-Yang C., Geoffrey A., Qiu S., Tetrahedron
Lett., 46, 2337—2340 (2005).
Antioxidant activity
Cytotoxicity
IC50 (mg/ml)
18) De Mejia G., Castano-Tostado E., Loarca-Pina G., Mutat. Res., 441,
1—9 (1999).
Compound
IC50 (mg/ml)
19) Wagner H., Luck R., Naturwissenschaften, 42, 607 (1955).
20) Park J., Rho H., Kim D., Chang., J. Agric. Food Chem., 54, 2951—
2956 (2006).
1
2
12
25
17
26
3
4
5
7
0.21
18
NC
NC
NC
NC
NC
NT
0.25
21) Rao Y., Geethangili M., Fang S., Tzeng Y., Food Chem. Toxicol., 45,
1770—1776 (2007).
22) Tu Y., Lian T. W., Yen J., Chen Z., Wu M., J. Agric. Food Chem., 55,
9969—9976 (2007).
23) Parveen Z., Deng Y., Saeed M., Dai R., Ahamad W., Yu Y., Yakugaku
Zasshi, 127, 1275—1279 (2007).
24) Hosseinzadeh H., Motamedshariaty V., Hadizadeh F., Pharmacology-
online, 2, 367—370 (2007).
25) Srisilam K., Ciddi V., Biotechnol. Adv., 21, 3—39 (2003).
26) Venisetty R., Ciddi V., Curr. Pharm. Biotech., 4, 153—167 (2003).
27) Rosazza P. N., Duffel M. W., “Alkaloids: Chemistry and Pharmacol-
ogy,” Vol. 27, Chap. 4, ed. by Brossi A., Academic Press, New York,
1986, pp. 391—392.
28) Davis P. J., “Antibiotics and Microbial Transformations,” ed. by Lamba
S. S., Walker C. A., CRC, Boca Raton, Florida, 1987, pp. 47—70.
29) Abourashed E. A., Khan I. A., Chem. Pharm. Bull., 48, 1996—1998
(2000).
30) Abbas F. A., Almassarrany S., Khan S., Al-Howarreeny T., Moussa G.,
Abourashed E., Nat. Prod. Res., 21, 383—391 (2007).
31) Hara S., Okabe H., Mihashi K., Chem. Pharm. Bull., 35, 501—506
(1987).
32) Reddy M., Gupta S., Jacob M., Khan S., Ferreira D., Planta Med., 73,
461—467 (2007).
0.15
0.46
1.7
0.6
NT
8
Vitamin C
Doxorubicin
NC: no cytotoxicity, NT: not tested.
was much less active than 3, 5 and 7.
In conclusion, there were four types of reactions through
microbial biotransformation in this report, i.e., oxidation,
glycosylation, hydroxylation as well as sulfate conjugation.
This study proved that microbial transformation was a useful
way to increase the diversity of the natural products as well
as the conversion of abundant prototypes to rare products.
Acknowledgment We are grateful to Dr. Bharthi Avula and Mr. Frank
Wiggers for assistance with the HR-ESI-MS and H-NMR data collection,
respectively. Ibrahim A. K. is greatly indebted to the Egyptian government
for the JSP scholarship.
33) Ziyan L., Jinghua Y., Yunsong W., Rong H., Liang H., Zhongcaoyao,
37, 826—829 (2006).
34) Jin Y., Wei X. N., Shi Y. P., Helv. Chim. Acta, 90, 776—782 (2007).
35) Mabry T. J., Markham K. R., Thomas M. B., “The Systematic Identifi-
cation of Flavonoids,” ed. by Mabry T. J., Springer-Verlag, New York,
1970, pp. 41—61.
36) Dianpeng L., Ikeda T., Matsuoka N., Nohara T., Zhang H., Sakamoto
T., Nonaka G., Chem. Pharm. Bull., 54, 1425—1428 (2006).
37) Yoshikawa M., Wang T., Morikawa T., Xie H., Matsuda H., Chem.
Pharm. Bull., 55, 1308—1315 (2007).
38) Zhan J., Gunatilaka A., Leslie A., J. Nat. Prod., 69, 1525—1527
(2006).
39) Herath M., Mikelle J. R., Hale A., Ferreira D., Khan I. A., Chem.
Pharm. Bull., 54, 320—324 (2006).
40) Markham K. R., Geiger H., “The Flavonoids: Advances in Research
Since 1986,” Chap. 10, ed. by Harbone J. B., Chapman and Hall, Lon-
don, 1993, pp. 441—493.
41) Gallant M., Link J. T., Danishefsky S., J. Org. Chem., 58, 343—349
(1993).
42) Vigne B., Archelas A., Fourneron J. D., Furstoss R., Tetrahedron, 42,
2451—2456 (1986).
43) Vigne B., Archelas A., Furstoss R., Tetrahedron, 47, 1447—1458
(1991).
References
1) Huq M. M., Jabbar A., Rashid M. A., Hasan C. M., Fitoterapia, 70,
5—9 (1999).
2) Burrows G. E., Tyrl R. J., “Toxic Plants of North America,” Iowa State
University Press, Ames, 2001, pp. 78—82.
3) Le M. J., Pourrat H., Ann. Pharm. Fr., 10, 349—351 (1952).
4) Paris R. R., Duret S., Bull. Soc. Botan. Fr., 119, 531—542 (1972).
5) Chiang L., Ng L. T., Cheng P. W., Chiang W., Chun C., Clin. Exp.
Pharmacol. Physiol., 32, 811—816 (2005).
6) Ma C., Cai S., Cui J., Wang R., Tu P., Hattori M., Daneshtalab M., Eur.
J. Med. Chem., 40, 582—589 (2005).
7) Zhang P., Li X., Li N., Xu J., Li Z. L., Wang Y., Wang J., Arch. Phar-
macal. Res., 28, 889—891 (2005).
8) Xiong X., Chen W., Xiao X., Cui J. X., Zhongcaoyao, 36, 1207—1209
(2005).
9) Taketa A., Gnoatto S., Gosmann G., Pires V. S., Schenkel F., Guil-
laume D., J. Nat. Prod., 67, 1697—1700 (2004).
10) Wachter G., Valcic S., Flagg M., Franzblau S., Montenegro G., Suarez
E., Timmermann B. N., Phytomedicine, 6, 341—345 (1999).
11) Jung S., Ha Y., Shim E., Choi S., Jin J., Yun-Choi H., Lee J., Biochem.
J., 403, 243—250 (2007).
44) Akihisa T., Yasukawa K., “Studies in Natural Products Chemistry,” ed.
by Rahman A.,Vol. 25, Part F, Elsevier, Amsterdam, 2001, p. 57.
45) Ryu S., Choi S., Lee. C., Ahn J., Arch. Pharm. Res., 17, 375—377
(1994).
44) Min B., Kim Y., Lee S., Jung H., Lee J., Na M., Lee C., Lee J., Bae K.,
Arch. Pharm. Res., 23, 155—158 (2000).
12) Hung C., Yen G., J. Agric. Food Chem., 50, 2993—2997 (2002).
13) Deepak M., Handa S., Phytother. Res., 14, 463—465 (2000).
14) Beindorff C., Cain F. W., Pierce J., Schmid U., Schweitzer E., Van
Straalen J., Eur. Pat. Appl., 2001, 9 (2001).
15) Singh A., Sharma O. P., Dawra R. K., Kanwar S. S., Mahato S. B.,
Biodegradation, 10, 373—381 (1999).
46) Huang R., Wang W., Kuo Y., Lin Y., Chin. Pharm. J., 53, 179—184
(2001).
16) Mallavadhani U. V., Panda A., Rao Y. R., Phytochemistry, 49, 901—
951 (1998).