Antidiabetic and Antioxidative Activities of Butyrolactone I from Aspergillus terreus MC751
The bioassay-guided isolation and purification of an
ethyl acetate extract of Aspergillus terreus MC751 led to the
characterization of butyrolactone I as an antidiabetic and antioxidant.
The antidiabetic activity of butyrolactone I was evaluated by α-
glucosidase and α-amylase inhibition assays. Butyrolactone I
demonstrated significant concentration-dependent, mixed-type
inhibitory activity against yeast α-glucosidase with an IC50 of 54μM.
However, the compound exhibited less activity against rat intestinal
α-glucosidase and α-amylase. This is the first report on α-glucosidase
inhibitory activity of butyrolactone I. The antioxidative activity of
butyrolactone I was evaluated based on scavenging effects on 1,1-
diphenyl-2-picrylhydrazyl (DPPH) (IC50 =51 μM) and hydrogen
peroxide (IC50= 141 μM) radicals as well as a reducing power assay.
The results suggest that butyrolactone I is a promising antidiabetic as
well as antioxidant and should be considered for clinical trials.
[1] Ramkumar, K.H., Thayumanavan, B., Palvannan, T., Rajaguru, P.,
"Inhibitory effect of Gymnema montanum leaves on ╬▒-glucosidase
activity and ╬▒-aylase activity and their relationship with polyphenolic
content," Med. Chem. Res., 19, 948-96, 2009.
[2] Yao Y, Sang W, Zhou M, Ren G, "Antioxidant and alpha-glucosidase
inhibitory activity of colored grains in China," J. Agric. Food Chem., 58:
770-774, 2010.
[3] Mayur, B., Sandesh, S., Shruti, S., Yum, S.S, "Antioxidant and ╬▒-
glucosidase inhibitory properties of Carpesium abrotanoides L," J.
Medic. Plant Res., 4(15), 1547-1553, 2010.
[4] Lee, S.H., Li, Y., Karadeniz, F., Kim, M.M., and Kim, S.K., "╬▒-
Glucosidase and ╬▒-amylase inhibitory activities of phloglucinal derivates
from edible marine brown alga, Ecklonia cava," J Sci. Food Agric., 89,
1552-1558, 2009.
[5] Tadera, K., Minami, Y., takamatsu, K., and Matsuoka, T., "Inhibitor of
╬▒-glucosidase and ╬▒-amylase by flavonoids," J. Nutr. Sci. Vitaminol.
52, 149-153, 2006.
[6] Shibano, M., Kakutani, K., Taniguchi, M., Yasuda, M., Baba, K.,
"Antioxidant constituents in the dayflower (Commelina communis L.)
and their ╬▒-glucosidase inhibitory activity," J. Nat. Med., 62, 349-353,
2008.
[7] Zhu, Y.P., Yin, L.J., Cheng, Y.Q., Yamaki, K., Mori, Y., Su, Y.C., and
Li, L.T., "Effect of source of carbon and nitrogen on production of ╬▒-
glucosidase inhibitory by a newly isolated strain of Bacillus subtilis B2,"
Food Chemistry 109, 737-742, 2008.
[8] Meng, P. and Zhou, X., "╬▒-Glucosidase inhibitory effect of a bioactive
guided fraction GIB-638 from Streptomyces fradiae PWH638," Med.
Chem. Res., DOI 10.1007/s00044-012-9984-2, 2012.
[9] Ingavat, N., Dobereiner, J., Wiyakrutta, S., Mahidol, C., Ruchirawat, S.,
and Kittakoop, P., "Aspergillusol A, an ╬▒-glucosidase inhibitor from the
marine-derived fungus Aspergillus aculeatus," J. Nat. Prod. 72, 2409-
2052, 2009.
[10] Dewi R.T., Iskandar, Y., Hanafi, M., Kardono, L.B.S., Angelina, M.,
Dewijanti, D.I., Banjarnahor, S.D.S., "Inhibitory Effect of Koji
Aspergillus terreus on ╬▒-Glucosidase Activity and Postprandial
Hyperglycemia," PJBS, 10 (18), 3131-3135, 2007.
[11] Dewi, R.T., Tachibana, S., Itoh, Kazutaka., and Ilyas, M., "Isolation of
antioxidant compounds from Aspergillus terreus LS01," JMBT, 4(1):
010-014, 2012.
[12] Rao, K.V., Sadhukhan, A.K., Veerender, M., Mohan, E.V.S.,
Dhanvantri, S.D., Sitaramkumar, S., Babu, M.J., Vyas, K., Reddy, O.G.,
"Butyrolactones from Aspergillus terreus," Chem. Pharm. Bull. (Tokyo)
48(4), 559-562, 2000.
[13] Cazar, M.E., Hirschmann, G.S., and Astudillo, L., "Antimicrobial
butyrolactone I derivatives from the Ecuadorian soil fungus Aspergillus
terreus Thorn. var terreus," Word J. Microbiol.& Biotech. 21, 1067-
1075, 2005.
[14] Parvatkar, R.R., D-Souza, C., Tripathi, S., and Naik, C.G.,
"Aspernolides A and B, butanolides from a marine-dderived fungus
Aspergillus terreus," Phytochemistry 70, 128-132, 2009.
[15] Niu, X., Dahse, HM., Menzel, KD., Lozach, O., Walther, G., Meijer, L.,
Grabley, S., and Sattler, I., "Butyrolactone I derivatives from Aspergillus
terreus carrying an unusual solfate moiety," J. Nat. Prod. 71, 689-692,
2008.
[16] Kim, K.Y., Nam, H., and Kim, S.M., "Potent ╬▒-glucosidase inhibitors
purified from the red alga Grateleupia elliptica," Phytochemistry 69,
2820-2825, 2008.
[17] Sancheti, S., Sancheti, S., Bafna, Mayur, B., Lee, SH., and Seo, SY.,
"Persimon leaf (Diospyrus kaki), a potent ╬▒-glucosidase inhibitor and
antioxidant: alleviation of postprandial hyperglycemia in normal and
diabetic rats," Med. Plant Resc. 5(9), 1652-1658, 2011.
[18] Gowri, P. M., Tiwari A.K., Ali, Z., and Rao, M., "Inhibition of ╬▒-
glucosidase and amylase by bartogenic acid isolated from Barringtonia
racemosa Roxb. seeds," Phytother. Res. 21: 796-799, 2007.
[19] Yen, G.C., and Chen, H.Y., "Antioxidant activity of various tea extracts
in relation to heir antimutagenicity," J Agric Food Chem 43: 27-32,
1995.
[20] Sugiyama, Y., Yoshida, K., and Hirota, "A., Soybean lipoxigenase
inhibitory and DPPH radical-scavenging activities of aspernolide A and
Butyrolactone I and II," Biosci. Biotechnol. Biochem. 74 (4), 881-883,
2010.
[21] Kim G.N., Shin J.G., and Jang H.D., "Antioxidant and antidiabetic
activity of Dangyuja (Citrus grandis Osbeck) extract treated with
Aspergillus saitoi," Food Chemistry 117, 35-41, 2009.
[22] Kim, Y.M.,Wang, M.H., Rhee, H.I., "A novel a-glucosidase inhibitor
from pine bark," Carbohydrate Research, 339, 715-717, 2004.
[23] Li, Y.Q., Zhou, F.C., Gao, F., Bian, J.S., and Shan, F., "Comparative
evaluation of quercetin, isoquercetin, and rutin as inhibitors of ╬▒-
glucosidase," J. Agric. Food Chem., 57, 11463-11468, 2009.
[24] Sancheti, S., Sancheti, S., Bafna, M., and Seo, S.Y., "2,4,6-
Trihdroxybenzaldehyde as a potent antidiabetic agent alleviates
postprandial hyperglycemia in normal and diabetic rats," Med. Chem.
Res., 20, 1181-1187, 2011.
[25] Thupari, J.N., Landree, L.E., Ronnett, G.V., and kuhajda, F.P., "C75
increase peripheral energy utilization and fatty acid oxidation in dietinduced
obesity," PNAS 99(4), 9498-9502, 2002.
[26] Evans, J.L., Golfine, I.D., Maddux, B.A., and Grodsky, G.M.,
"Oxidative stress and stress-activated signaling pathways: a unifying
hypothesis of type 2 diabetes," Endocrin 23(5), 599-622, 2002.
[27] Chandra, S and Dave, R, "In vitro models for antioxidant activity
evaluation and some medicinal plants possessing antioxidant properties:
an overview," Afr. J. Microbiol. Res. 3(13), 981-996, 2009.
[28] Bondet V, Williams WB, and Berset C, "Kinetics and Mechanisms of
Antioxidant Activity using the DPPHÔÇó Free Radical Method," Lebensm.-
Wiss. u.-Technol 30: 609-615, 1997.
[29] Jung, J.Y., Lee, I.K., Seok, S.J., Kim, Y.H., and Yun, B.S., "Antioxidant
polyphenols from the mycelia culture of the medicinal fungi Inootus
xeranticus and Phellinus linteus," J. Appl. Microbiol., 104, 1824-1832,
2008.
[1] Ramkumar, K.H., Thayumanavan, B., Palvannan, T., Rajaguru, P.,
"Inhibitory effect of Gymnema montanum leaves on ╬▒-glucosidase
activity and ╬▒-aylase activity and their relationship with polyphenolic
content," Med. Chem. Res., 19, 948-96, 2009.
[2] Yao Y, Sang W, Zhou M, Ren G, "Antioxidant and alpha-glucosidase
inhibitory activity of colored grains in China," J. Agric. Food Chem., 58:
770-774, 2010.
[3] Mayur, B., Sandesh, S., Shruti, S., Yum, S.S, "Antioxidant and ╬▒-
glucosidase inhibitory properties of Carpesium abrotanoides L," J.
Medic. Plant Res., 4(15), 1547-1553, 2010.
[4] Lee, S.H., Li, Y., Karadeniz, F., Kim, M.M., and Kim, S.K., "╬▒-
Glucosidase and ╬▒-amylase inhibitory activities of phloglucinal derivates
from edible marine brown alga, Ecklonia cava," J Sci. Food Agric., 89,
1552-1558, 2009.
[5] Tadera, K., Minami, Y., takamatsu, K., and Matsuoka, T., "Inhibitor of
╬▒-glucosidase and ╬▒-amylase by flavonoids," J. Nutr. Sci. Vitaminol.
52, 149-153, 2006.
[6] Shibano, M., Kakutani, K., Taniguchi, M., Yasuda, M., Baba, K.,
"Antioxidant constituents in the dayflower (Commelina communis L.)
and their ╬▒-glucosidase inhibitory activity," J. Nat. Med., 62, 349-353,
2008.
[7] Zhu, Y.P., Yin, L.J., Cheng, Y.Q., Yamaki, K., Mori, Y., Su, Y.C., and
Li, L.T., "Effect of source of carbon and nitrogen on production of ╬▒-
glucosidase inhibitory by a newly isolated strain of Bacillus subtilis B2,"
Food Chemistry 109, 737-742, 2008.
[8] Meng, P. and Zhou, X., "╬▒-Glucosidase inhibitory effect of a bioactive
guided fraction GIB-638 from Streptomyces fradiae PWH638," Med.
Chem. Res., DOI 10.1007/s00044-012-9984-2, 2012.
[9] Ingavat, N., Dobereiner, J., Wiyakrutta, S., Mahidol, C., Ruchirawat, S.,
and Kittakoop, P., "Aspergillusol A, an ╬▒-glucosidase inhibitor from the
marine-derived fungus Aspergillus aculeatus," J. Nat. Prod. 72, 2409-
2052, 2009.
[10] Dewi R.T., Iskandar, Y., Hanafi, M., Kardono, L.B.S., Angelina, M.,
Dewijanti, D.I., Banjarnahor, S.D.S., "Inhibitory Effect of Koji
Aspergillus terreus on ╬▒-Glucosidase Activity and Postprandial
Hyperglycemia," PJBS, 10 (18), 3131-3135, 2007.
[11] Dewi, R.T., Tachibana, S., Itoh, Kazutaka., and Ilyas, M., "Isolation of
antioxidant compounds from Aspergillus terreus LS01," JMBT, 4(1):
010-014, 2012.
[12] Rao, K.V., Sadhukhan, A.K., Veerender, M., Mohan, E.V.S.,
Dhanvantri, S.D., Sitaramkumar, S., Babu, M.J., Vyas, K., Reddy, O.G.,
"Butyrolactones from Aspergillus terreus," Chem. Pharm. Bull. (Tokyo)
48(4), 559-562, 2000.
[13] Cazar, M.E., Hirschmann, G.S., and Astudillo, L., "Antimicrobial
butyrolactone I derivatives from the Ecuadorian soil fungus Aspergillus
terreus Thorn. var terreus," Word J. Microbiol.& Biotech. 21, 1067-
1075, 2005.
[14] Parvatkar, R.R., D-Souza, C., Tripathi, S., and Naik, C.G.,
"Aspernolides A and B, butanolides from a marine-dderived fungus
Aspergillus terreus," Phytochemistry 70, 128-132, 2009.
[15] Niu, X., Dahse, HM., Menzel, KD., Lozach, O., Walther, G., Meijer, L.,
Grabley, S., and Sattler, I., "Butyrolactone I derivatives from Aspergillus
terreus carrying an unusual solfate moiety," J. Nat. Prod. 71, 689-692,
2008.
[16] Kim, K.Y., Nam, H., and Kim, S.M., "Potent ╬▒-glucosidase inhibitors
purified from the red alga Grateleupia elliptica," Phytochemistry 69,
2820-2825, 2008.
[17] Sancheti, S., Sancheti, S., Bafna, Mayur, B., Lee, SH., and Seo, SY.,
"Persimon leaf (Diospyrus kaki), a potent ╬▒-glucosidase inhibitor and
antioxidant: alleviation of postprandial hyperglycemia in normal and
diabetic rats," Med. Plant Resc. 5(9), 1652-1658, 2011.
[18] Gowri, P. M., Tiwari A.K., Ali, Z., and Rao, M., "Inhibition of ╬▒-
glucosidase and amylase by bartogenic acid isolated from Barringtonia
racemosa Roxb. seeds," Phytother. Res. 21: 796-799, 2007.
[19] Yen, G.C., and Chen, H.Y., "Antioxidant activity of various tea extracts
in relation to heir antimutagenicity," J Agric Food Chem 43: 27-32,
1995.
[20] Sugiyama, Y., Yoshida, K., and Hirota, "A., Soybean lipoxigenase
inhibitory and DPPH radical-scavenging activities of aspernolide A and
Butyrolactone I and II," Biosci. Biotechnol. Biochem. 74 (4), 881-883,
2010.
[21] Kim G.N., Shin J.G., and Jang H.D., "Antioxidant and antidiabetic
activity of Dangyuja (Citrus grandis Osbeck) extract treated with
Aspergillus saitoi," Food Chemistry 117, 35-41, 2009.
[22] Kim, Y.M.,Wang, M.H., Rhee, H.I., "A novel a-glucosidase inhibitor
from pine bark," Carbohydrate Research, 339, 715-717, 2004.
[23] Li, Y.Q., Zhou, F.C., Gao, F., Bian, J.S., and Shan, F., "Comparative
evaluation of quercetin, isoquercetin, and rutin as inhibitors of ╬▒-
glucosidase," J. Agric. Food Chem., 57, 11463-11468, 2009.
[24] Sancheti, S., Sancheti, S., Bafna, M., and Seo, S.Y., "2,4,6-
Trihdroxybenzaldehyde as a potent antidiabetic agent alleviates
postprandial hyperglycemia in normal and diabetic rats," Med. Chem.
Res., 20, 1181-1187, 2011.
[25] Thupari, J.N., Landree, L.E., Ronnett, G.V., and kuhajda, F.P., "C75
increase peripheral energy utilization and fatty acid oxidation in dietinduced
obesity," PNAS 99(4), 9498-9502, 2002.
[26] Evans, J.L., Golfine, I.D., Maddux, B.A., and Grodsky, G.M.,
"Oxidative stress and stress-activated signaling pathways: a unifying
hypothesis of type 2 diabetes," Endocrin 23(5), 599-622, 2002.
[27] Chandra, S and Dave, R, "In vitro models for antioxidant activity
evaluation and some medicinal plants possessing antioxidant properties:
an overview," Afr. J. Microbiol. Res. 3(13), 981-996, 2009.
[28] Bondet V, Williams WB, and Berset C, "Kinetics and Mechanisms of
Antioxidant Activity using the DPPHÔÇó Free Radical Method," Lebensm.-
Wiss. u.-Technol 30: 609-615, 1997.
[29] Jung, J.Y., Lee, I.K., Seok, S.J., Kim, Y.H., and Yun, B.S., "Antioxidant
polyphenols from the mycelia culture of the medicinal fungi Inootus
xeranticus and Phellinus linteus," J. Appl. Microbiol., 104, 1824-1832,
2008.
@article{"International Journal of Biological, Life and Agricultural Sciences:54282", author = "Rizna Triana Dewi and Sanro Tachibana and Ahmad Darmawan", title = "Antidiabetic and Antioxidative Activities of Butyrolactone I from Aspergillus terreus MC751", abstract = "The bioassay-guided isolation and purification of an
ethyl acetate extract of Aspergillus terreus MC751 led to the
characterization of butyrolactone I as an antidiabetic and antioxidant.
The antidiabetic activity of butyrolactone I was evaluated by α-
glucosidase and α-amylase inhibition assays. Butyrolactone I
demonstrated significant concentration-dependent, mixed-type
inhibitory activity against yeast α-glucosidase with an IC50 of 54μM.
However, the compound exhibited less activity against rat intestinal
α-glucosidase and α-amylase. This is the first report on α-glucosidase
inhibitory activity of butyrolactone I. The antioxidative activity of
butyrolactone I was evaluated based on scavenging effects on 1,1-
diphenyl-2-picrylhydrazyl (DPPH) (IC50 =51 μM) and hydrogen
peroxide (IC50= 141 μM) radicals as well as a reducing power assay.
The results suggest that butyrolactone I is a promising antidiabetic as
well as antioxidant and should be considered for clinical trials.", keywords = "Aspergillus terreus MC751, antidiabetic, antioxidant,
Butyrolactone I.", volume = "6", number = "10", pages = "883-6", }
