Structure Revision of (22E)-Ergosta-7,22-diene-3β,5α,6β,9α,14α-pentol from the Spores of the Medicinal Mushroom Ganoderma Lucidum

Abstract

Careful reexamination of the published 1 H and 13 C NMR spectral data of (22E)-ergosta-7,22-diene-3,5,6,9,14-pentol (1), isolated from the spores of the medicinal mushroom Ganoderma lucidum, indicates that, in reality, the compound is (22E)-ergosta-7,22-diene-3,5,6,9,14-pentol (5).

Misassigned Polyoxygenated Sterols and Reassignments of Their Structures

“…(24S)-24-ethylcholest-8-ene-3β,5α,6β,7α-tetrol (1), (24S)-24ethylcholest-8(14)-ene-3β,5α,6β,7α-tetrol (2), (22E)-24methylcholesta-8 (14),22-diene-3β,5α,6β,7α-tetrol (3), and 3β,5α,6β,8β,14α-pentahydroxy-(22E)-ergost-22-en-7-one (6).…”

“…Accordingly, the structure of 5 has been reassigned as the new structure (22E)ergosta-7,22-diene-3β,5α,6β,9α,14β-pentol (25) (Figure 14). 14 The 3β,5α,6β,9α,14β-pentahydroxy moiety is unprecedented in the natural sterols previously known.…”

“…9 However, misinterpretations of spectroscopic and/or physical data have often been known to result in structural misassignments. 10 Recently, we have reported the reassignments of structures of 5 natural polyoxygenated sterols: (24S)-24-ethylcholest-8-ene-3β,5α,6β,7α-tetrol (1), 11 (24S)-24ethylcholest-8(14)-ene-3β,5α,6β,7α-tetrol (2), 11 (22E)-24methylcholesta-8 (14),22-diene-3β,5α,6β,7α-tetrol…”

“…(3), 12 5β,6β-epoxy-(22E)-ergosta-8,22-diene-3β,7β-diol (4), 13 and (22E)-ergosta-7,22-diene-3β,5α,6β,9α,14α-pentol (5) 14 (Figure 1). Thereafter, continued literature survey on the polyoxygenated sterols from natural sources was conducted, and it was revealed that the structures of 4 sterols, 3β,5α,6β,8β,14α-pentahydroxy-(22E)-ergost-22-en-7-one (6), 15 5β,6β-epoxyergosta-8,24(28)diene-3β,7α,11α-triol (7), 16 6β-acetoxy-(22E)-10α-ergosta-7,22-diene-3β,5α-diol (8), 17 and 8α,9α-epoxy-(22E)-ergosta-6,22-diene-3β,5α,14α-triol (9), 18 would need to be reassigned ( Figure 1).…”

A New Sterol From Sporoderm-Broken Ganoderma sinense Spores and Its Anticancer Activity

“…6 As a result, more and more chemical and pharmacological research are being carried out on G. lucidum spores. [7][8][9] However, there are only a few reports on G. sinense. A study showed that the extract obtained from G. sinense spores by supercritical CO 2 fluid extraction had tumoricidal activity, thus imparting antitumor effect.…”