Structure-activity relationships of lanostane-type triterpenoids from Ganoderma lingzhi as α-glucosidase inhibitors.
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.
Department of Agro-environmental Sciences, Faculty of Agriculture, Kyushu University, Fukuoka 812-8581, Japan; Department of Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Sepuluh Nopember, Kampus ITS-Sukolilo, Surabaya 60111, Indonesia.
Sri
S
Fatmawati
Ryuichiro
R
Kondo
Kuniyoshi
K
Shimizu
D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D048690:Fruiting Bodies, Fungal / Q000737:chemistry; D032902:Ganoderma / Q000737:chemistry*; D065089:Glycoside Hydrolase Inhibitors; D006801:Humans; D020940:Reishi; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000520:alpha-Glucosidases / Q000378:metabolism
D004365:Drugs, Chinese Herbal; D065089:Glycoside Hydrolase Inhibitors; D014315:Triterpenes; D000520:alpha-Glucosidases
Ganoderma acid; Ganoderma alcohol; Ganoderma lingzhi; Ganodermataceae; Structure–activity relationships; Triterpenoid; α-Glucosidase inhibitor