Highly Modified Lanostane Triterpenes from Fruiting Bodies of the Basidiomycete Tomophagus sp.

Abstract

Thirty-one highly modified lanostanes (1–31), together with 19 known compounds (32–50), were isolated from fruiting bodies of the wood-rot basidiomycete Tomophagus sp. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. The present work demonstrates the high structural diversity of modified lanostane triterpenoids from Tomophagus. This paper also discusses structural revisions of several known derivatives. Some of the isolated compounds exhibited moderate antimalarial activity against Plasmodium falciparum K1 (IC50 5.1–19 μM).

Highly Modified Lanostane Triterpenes from the Wood-Rot Basidiomycete Ganoderma colossus: Comparative Chemical Investigations of Natural and Artificially Cultivated Fruiting Bodies and Mycelial Cultures

“…Intense NOESY correlations of H-22 with both H α -16 and H β -16 were suggestive of a 22 S configuration. The C-20–C-27 side-chain structure of the corresponding 24 E configuration and with the 22 S acetoxy configuration is very common in the Ganoderma lanostanoids, wherein similar NOESY correlation patterns are generally observed . The proposed relative configuration of 1 , including C-20 and C-22, was confirmed by chemical correlation to ganodermalactone H ( 25 ), whose stereochemistry was discussed in detail in our previous report .…”

“…Although rarely compared using the same biological material source, , the structural types of the lanostane constituents are generally different between fruiting bodies (natural or cultivated) and mycelial cultures, and there was little overlap of the same compounds when comparing the reported structures among the same species. , Fungal secondary metabolite production relies on the fermentation conditions including the choice of liquid culture media. In this study, we performed fermentation/isolation for only one large-scale batch, using our temporal optimal fermentation conditions for lanostane-triterpenoid production by Ganoderma . However, the current results should be sufficient to make the conclusions above.…”

“…As part of our research on the utilization of fungal resources in Thailand, we have been investigating polypores (bracket fungi) of the family Ganodermataceae. The studies have resulted in the isolation of antitubercular and antimalarial lanostane triterpenoids . Investigations on G. orbiforme (strains BCC 22324 and BCC 22325) and G. australe (strain BCC 22314), whose basidiome morphology is close to G. lucidum , demonstrated that structural types of lanostanes from cultivated fruiting bodies and mycelial cultures are different .…”

Ganoweberianones A and B, Antimalarial Lanostane Dimers from Cultivated Fruiting Bodies of the Basidiomycete Ganoderma weberianum

“…Our recent research has been focused on the search for novel bioactive compounds from Ganodermataceae. Previous studies have led to the isolation of antitubercular and antimalarial lanostane triterpenoids . In a continuation of the research, we have been conducting artificial fruiting body cultivation and chemical investigation of Ganoderma species.…”

Mushrooms (Basidiomycetes) as a significant source of biologically active compounds for malaria control

“…After their evaluation against P. falciparum K1, only eight compounds (9− 16) have demonstrated significant or moderate activity. Especially, colossolactone VIII (9), ganodermalactones D, O−Q (10, 11− 13), tomophagusins B and D (14 and 15) showed activity with IC 50 values <10 µM, ranging from 5.1 to 8.1 µM, while 11-oxo-colossolactone E (16) demonstrated potency with IC 50 value of 10 µM (Isaka et al, 2019).…”