TY - JOUR
T1 - Structure-activity relationships of lanostane-type triterpenoids from Ganoderma lingzhi as α-glucosidase inhibitors
AU - Fatmawati, Sri
AU - Kondo, Ryuichiro
AU - Shimizu, Kuniyoshi
N1 - Funding Information:
We are thankful to Dr. Miyamoto for optical rotation measurement, Mr. Matsumoto for HRESIMS measurement, Faculty For The Future Award from Schlumberger Foundation for financial support to Sri Fatmawati. The publication was supported in part by the Research Grant for Young Investigators of Faculty of Agriculture, Kyushu University.
Copyright:
Copyright 2013 Elsevier B.V., All rights reserved.
PY - 2013/11/1
Y1 - 2013/11/1
N2 - A series of lanostane-type triterpenoids, identified as ganoderma alcohols and ganoderma acids, were isolated from the fruiting body of Ganoderma lingzhi. Some of these compounds were confirmed as active inhibitors of the in vitro human recombinant aldose reductase. This paper aims to explain the structural requirement for α-glucosidase inhibition. Our structure-activity studies of ganoderma alcohols showed that the OH substituent at C-3 and the double-bond moiety at C-24 and C-25 are necessary to increase α-glucosidase inhibitory activity. The structure-activity relationships of ganoderma acids revealed that the OH substituent at C-11 is an important feature and that the carboxylic group in the side chain is essential for the recognition of α-glucosidase inhibitory activity. Moreover, the double-bond moiety at C-20 and C-22 in the side chain and the OH substituent at C-3 of ganoderma acids improve α-glucosidase inhibitory activity. These results provide an approach with which to consider the structural requirements of lanostane-type triterpenoids from G. lingzhi. An understanding of these requirements is considered necessary in order to improve a new type of α-glucosidase inhibitor.
AB - A series of lanostane-type triterpenoids, identified as ganoderma alcohols and ganoderma acids, were isolated from the fruiting body of Ganoderma lingzhi. Some of these compounds were confirmed as active inhibitors of the in vitro human recombinant aldose reductase. This paper aims to explain the structural requirement for α-glucosidase inhibition. Our structure-activity studies of ganoderma alcohols showed that the OH substituent at C-3 and the double-bond moiety at C-24 and C-25 are necessary to increase α-glucosidase inhibitory activity. The structure-activity relationships of ganoderma acids revealed that the OH substituent at C-11 is an important feature and that the carboxylic group in the side chain is essential for the recognition of α-glucosidase inhibitory activity. Moreover, the double-bond moiety at C-20 and C-22 in the side chain and the OH substituent at C-3 of ganoderma acids improve α-glucosidase inhibitory activity. These results provide an approach with which to consider the structural requirements of lanostane-type triterpenoids from G. lingzhi. An understanding of these requirements is considered necessary in order to improve a new type of α-glucosidase inhibitor.
UR - http://www.scopus.com/inward/record.url?scp=84885187217&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84885187217&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2013.08.084
DO - 10.1016/j.bmcl.2013.08.084
M3 - Article
C2 - 24070782
AN - SCOPUS:84885187217
SN - 0960-894X
VL - 23
SP - 5900
EP - 5903
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 21
ER -