Spiro Meroterpenoids from Ganoderma applanatum

Abstract

Spiroapplanatumines A-Q (1-12, 14-16, 18, and 20), new spiro meroterpenoids respectively bearing a 6/5/7 or 6/5/5 ring system, along with three known compounds, spirolingzhines A, B, and D, were isolated from the fruiting bodies of the fungus Ganoderma applanatum. Their structures including absolute configurations were assigned by using spectroscopic methods, ECD and C NMR calculations, and single-crystal X-ray diffraction analysis. Biological evaluation of all the compounds disclosed that compounds 7 and 8 inhibited JAK3 kinase with IC values of 7.0 ± 3.2 and 34.8 ± 21.1 μM, respectively.

Triterpenes and Meroterpenes with Neuroprotective Effects from Ganoderma leucocontextum

“…A lanostane tripterpenoid skeleton was deduced for 1 based on the above NMR data ( Table 1). The 1 H, 1 H-COSY correlations of CH 2 (1)/ CH 2 (2), H-C(5)/CH 2 (6)/H-C (7), H-C(15)/CH 2 (16)/H-C (17) and CH 2 (22)/CH 2 (23) together with the key HMBCs from Me (18) to C(12), C(13), C (14), and C(17), from Me (19) to C(1), C(5), C(9), and C(10), from Me(26) to C(3), C(4), C(5), and C(25), from Me(25) to C(3), C(4), C(5), from H-C(5) to C(3), C(7), C(25), and C(26), from H-C (7) to C(5), C(6), C(8), and C(9), from CH 2 (12) to C(9), C(11), C(13), C(14), C(17), and C(18), from CH 2 (21) to C(17), C (20), and C (22), as well as from CH 2 (22) to C(23) and C(24) confirmed the planar structure of 1 ( Figure 2). The relative configuration of 1 was determined by ROESY experiments.…”

“…Thus, the absolute configuration of 3 was determined as (5R,7S,10S,13R,14R,15S,17R). Thirteen known compounds were identified as ganomycin J (4), [16] spiroapplanatumine M (5), [17] spiroapplanatumine D (6), [18] spirolingzhine A (7), [18] ganosinensine (8), [19] spirolingzhine B (9), [18] 7b,20,23f-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic acid (10), [20] ganoderenic acid C (11), [21] ganoderic acid C 2 (12), [13] ganoderic acid L (13), [22] ganoderic acid I (14), [23] methyl ganoderate L (15), [22] ganoderic GS-2 (16), [15] respectively, by comparison of their NMR data with those in the literature.…”

Direct Oxidative Disulfenylation/Cyclization of 2′‐Hydroxyacetophenones with Thiophenols for the Synthesis of 2,2‐Dithio‐Benzofuran‐3(2H)‐Ones

“…Benzofuranones are an important class of heterocycles existing in a number of natural products and bioactive molecules . Among them, 2,2‐disubstituted benzofuran‐3(2 H )‐ones are frequently found in a variety of pharmaceutically‐active compounds, such as mutisicoumaranone A (antifungal activity), griseofulvin (antifungal agent),– spiroapplanatumines (kinase inhibitors), geodin (antibacterial activity and glucose uptake stimulatory activity),– linobiflavonoid (antitumor), Sch 202596 (non‐peptidic antagonist of the galanin receptor subtype GalR1), armeniaspirols A−C (antibiotic activity), as well as many others . Consequently, the development of efficient methods for the synthesis of 2,2‐disubstituted benzofuran‐3(2 H )‐ones are of remarkable value.…”

(±)-Applanatumines B–D: novel dimeric meroterpenoids from Ganoderma applanatum as inhibitors of JAK3

“…2 Despite the medicinal importance of Ganoderma, chemical investigation on this genus has mainly focused on triterpenoids and polysaccharides, 3,4 which could only in part unveil the scientic connotation of Ganoderma-based traditional medicine; the chemical and biological proles of Ganoderma fungi need further exploration. Oxidative stress and inammation are implicated in multiple diseases; with this context, we have characterized a series of structurally novel meroterpenoids from Ganoderma with antioxidant or anti-inammatory properties; a subsequent investigation revealed that they are either Nrf2 activators or TGF-b/Smad3 inhibitors, [5][6][7] showing that meroterpenoids in Gnoderma are promising structure templates. Indeed, lingzhiols have attracted great attention since they were reported in 2013.…”