Spiroganodermaines A−G from Ganoderma species and their activities against insulin resistance and renal fibrosis

Insights into Ganoderma fungi meroterpenoids opening a new era of racemic natural products in mushrooms

“…68 Of which, spiroapplanatumines K-M were also generated from G. leucocontextum, and spiroapplanatumines K and L possessed a reported suppressive activity on aldose reductase from bovine lens tissue. 69,70 Study of G. australe gave rise to the elucidation of optically pure spiroganodermaines A-E (166-168, 177, and 181), 71 which are relatively rare in contrast to the racemic nature of the majority of GMs. (±)-Spiroganodermaines D-J (178-184 and 190-195) and (+)-spiroapplanatumine K (172) were characterized in the chemical investigation of G. lucidum.…”

“…3 (−)-Spiroganodermaine G (184) exerted an inhibitory effect against fibronectin and α-SMA in TGF-β1-induced NRK-52e cells, and (+)-spiroganodermaine G (183) increased glucose uptake and p-IRS1 in IR C2C12 cells. 71 A study of the meroterpenoids from G. lingzhi reported the elucidation of (±)-spirolingzhines A-C (185-188, 196, and 197) and optically pure spirolingzhine D (174), they promoted NSC proliferation and were also yielded by G. applanatum and G. leucocontextum except for spirolingzhine C. Meanwhile, the enantiomers of (±)-spirolingzhine A (185 and 186) reduced aldose reductase. 69 Further, spirolingzhines B and D were identified from G. capense and G. lucidum, respectively.…”

“…Chiral analysis on GMs has not been materialized until the reporting of the foremost racemate lingzhiol, and many have been found racemic in later research, including, fornicins A-C (23 and 24, 274 and 275, 253 and 254), 37,41,52 ganomycin I (284 and 285), 37,56 ganoresinain B (280 and 281), 52 ganoduriporols A and B (582-585), 49 lucidimine C (665 and 666), 116 and sinensine E (671 and 672). 116 Meanwhile, some GMs are known to be optically pure in one Ganoderma species but racemic or scalemic in another, such as lingzhiol (135 and 136) (racemic in G. lucidum and optically pure in G. australe), 3,52 spiroganodermaine D (177 and 178) (scalemic in G. lucidum and optically pure in G. australe), 71 applanatum and optically pure in G. sinense), 38,62 ganotheaecolumols A and B (406-409) (racemic in G. australe and optically pure in G. theaecolum), 45,52 ganomycin E (255 and 256) (racemic in G. lucidum and G. capense, and optically pure in G. australe), 52,75,79 lingzhines E and F (58-61) (racemic in G. lingzhi, and optically pure in G. lucidum and G. australe), [50][51][52] and dayaolingzhiol H (257 and 258) (racemic in G. petchii and optically pure in G. lucidum). 57,82 Furthermore, a pair of enantiomers distributed optically pure in different Ganoderma species exemplified by (±)spiroapplanatumine K (172 and 173) that (+)-spiroapplanatumine K (172) was obtained from G. lucidum while (−)spiroapplanatumine K (173) was isolated from G. applanatum.…”

“…Study of G . australe gave rise to the elucidation of optically pure spiroganodermaines A–E ( 166 – 168 , 177 , and 181 ), 71 which are relatively rare in contrast to the racemic nature of the majority of GMs. (±)‐Spiroganodermaines D–J ( 178 – 184 and 190 – 195 ) and (+)‐spiroapplanatumine K ( 172 ) were characterized in the chemical investigation of G .…”

Structural diversity, hypothetical biosynthesis, chemical synthesis, and biological activity ofGanodermameroterpenoids

“…The spiroganodermaines B ( 69 ) and C ( 70 ) 50 from G. australe are a kind of GMs with a characteristic spiro skeleton formed between a benzodihydrofuran ketone and a five-membered carbon ring. The benzodihydrofuran ketone (intermediate I ) could be generated by a Michael addition from the 1-OH to the α,β-unsaturated carboxyl function (C-2′/C-3′/10′) of ganodercin C ( 9 ).…”