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

Abstract

The wood-rot basidiomycete Ganoderma colossus has been chemically investigated. Comparative analyses of the natural fruiting body, artificially cultivated fruiting bodies, and mycelial cultures resulted in the isolation, in total, of 13 new highly modified lanostanes, ganocolossusins A−H (1−8) and ganodermalactones T−X (9−13), together with 23 known compounds (14−36). There were significant overlaps of the same compounds among the three different states of the fungal materials. Ganocolossusin D (4) displayed the most potent antimalarial activity against Plasmodium falciparum K1 (multi-drug-resistant strain) with an IC 50 value of 2.4 μM, while it was noncytotoxic to Vero cells at 50 μg/mL.

Semisynthesis of 22,25-Epoxylanostane Triterpenoids: Structure Revision and Protective Effects against Oxygen-Glucose Deprivation/Reoxygenation Injury in H9c2 Cells

“…HPLC purification of these epimers yielded 5 and 6. The 1 H and 13 C NMR data of 5 were identical with the reported data of inonotsuoxide A, the structure of which was confirmed by X-ray crystallography. 14 Unexpectedly, the spectroscopic data of 6 was also the same as those of inonotsuoxide B, which was elucidated as the C-22 epimer of inonotsuoxide A according to the coupling constant of J 20,22 and NOE correlations.…”

“…14 Given that 6 may actually be the inonotsuoxide B, the previously reported structure for inonotsuoxide B, 22S,25-epoxylanosta-8-en-3β,24S-diol (7), was synthesized from 22S-inotodiol (2) according to similar procedures, along with 22S,25-epoxylanosta-8-en-3β,24R-diol (8). The absolute configurations of C- 13 C NMR data of 7 showed differences to those of inonotsuoxide B (Tables 1 and 2), especially H-20, C-20, and C-23, indicating that their structures were different, and the structure of inonotsuoxide B was revised to 22R,25epoxylanosta-8-en-3β,24R-diol (6). Epoxidation of Δ 8 (9) in 5 by m-CPBA, and subsequent acidcatalyzed dehydration, yielded 9.…”

“…The solution was stirred at room temperature (r.t.) for 10 h. Then the solution was washed with NaOH (1 M, 5 mL × 3) and brine. After removal of the organic solvent, the residue was purified on a silica gel column (petroleum-EtOAc, 8:1−4:1) to yield 3 (91 mg, yielding 80%): white amorphous powder; 1 H NMR (400 MHz, CDCl 3 , representative signals) δ H 4.03 (m, 1H), 3.26 (dd, J = 11.3, 4.8 Hz, 1H), 2.98 (dd, J = 8.5, 4.4 Hz, 1H), 1.30 (s, 3H), 1.28 (s, 3H), 1.01 (s, 3H), 1.00 (s, 3H), 0.92 (d, J = 6.7 Hz, 3H), 0.89 (s, 3H), 0.83 (s, 3H), 0.75 (s, 3H); 13 22R,25-Epoxylanosta-8-en-3β,24S-diol ( 5) and 22R,25-Eoxylanosta-8-en-3β, 24R-diol (6). Compound 3 (90 mg, 0.20 mmol) in DCM (2 mL) was treated with p-toluenesulfonic acid monohydrate (7 mg, 0.04 mmol) for 1 h. Then the solution was washed with 5% NaHCO 3 (5 mL × 3) and brine, and dried over anhydrous Na 2 SO 4 .…”

“…Ganodercochlearins A and B are lanostane triterpenoids with tetrahydrofuran side chains isolated from the fruiting bodies of Ganoderma cochlear . Interestingly, ganodercochlearin A is determined as a 22 R -lanostane triterpenoid since the 22 S configuration is prevalent in the Ganoderma lanostanoids . Inonotsuoxides A and B are another pair of diastereoisomers epimerized at C-22 identified from the fruiting bodies of Inonotus obliquus .…”

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

“…Fortunately, the protocols for commercial production (cultivation) of the medicinal mushroom lingzhi have been applicable for most of other Ganoderma species, whose natural mushroom specimens were collected in low quantities. Thus, this material preparation strategy should represent an untapped source of chemical diversity . In the present study, we have investigated Ganoderma weberianum using a strain that was collected and isolated in Thailand and preserved in the BIOTEC Culture Collection as BCC 60642.…”