A new bitter diterpenoid from Sarcodon scabrosus

Abstract

The new cyathane-type diterpenoid sarcodonin I was isolated from the fruiting bodies of the basidiomycete Sarcodon scabrosus. Its structure was determined on the basis of spectroscopic means, including 2D-NMR (HMBC, HMQC, ROESY, 1H, 1H-COSY).

Anti-inflammatory and cytotoxic cyathane diterpenoids from the medicinal fungus Cyathus africanus

“…Out of approximately 15,000 known mushroom species, 2000 are safe for human consumption, and about 650 of them have medicinal properties [1]. In particular, the species belonging to the genus Cyathus (Nidulariaceae family) are recognized as prolific producers of bioactive cyathane diterpenoids with a unique [5][6][7] tricyclic ring skeleton. Cyathane diterpenoids represent a group of natural products with great diversity in both structure and bioactivity [2][3][4].…”

“…Cyathane diterpenoids represent a group of natural products with great diversity in both structure and bioactivity [2][3][4]. Since the first discovery of cyathin A 3 and allocyathin B 3 from the liquid culture of Cyathus helenae in 1972 [5], a number of cyathane diterpenoids have been isolated from the fruiting bodies of mushroom Sarcodon scabrous [6][7][8][9][10][11][12][13][14], Sarcodon glaucopus [15,16], and Sarcodon cyrneus [17,18], the culture of fungi C. helenae [5,[19][20][21], Cyathus africanus [22], Cyathus earlei [23], Cyathus striatius [24], Strobilurus tenacellus [25] and Hericium erinaceum [26][27][28][29][30][31][32][33]. Some cyathane diterpenoids exhibited interesting and significant biological activities: scabronines B, C, and E from the mushroom Sarcodon scabrosus and erinacines A-I from the mycelia of H. erinaceum showed potent stimulating activity for nerve growth factor-synthesis [12,[26][27][28]30]; cyneines A and B from S. cyrneus and scabronines G and A from S. scabrosus showed significant neurite outgrowth (neuritegenesis)-promoting activity [18,34].…”

Diterpenoids of macromycetes

“…All these compounds exhibited inhibitory activity against TPA-induced inflammation on mouse ears at topical application [36]. Scabronines G, H, and I (85 -87) were also isolated from the same mushroom [37][38] Glaucopine A, B and C (88 -90), new cyathane diterpenes isolated from the fruiting bodies of Sarcodon glaucopus, exhibited topical anti-inflammatory activity [39 -40] (Scheme 15). Cyrneines A (91) and B (92), two new cyathane diterpenoids were isolated from the fruiting bodies of Sarcodon cyrneus.…”

7-6-5 Tricarbocyclic Diterpenes

“…5.6 by the exciton chirality method [54]. Since the 1970s, a large number of compounds with a cyathane skeleton have been isolated, so this nomenclature became obsolete; and, as the number of diterpenes increased they were incorporated into new groups with different names, such as cyafrins, sarcodonins, scabronines, erinacines, Sarcodonins, Neosarcodonins [66][67][68][69][70][71][72]75], and Scabronines [73,74,[76][77][78][79][80][81][82] Sarcodonins, neosarcodonins, and scabronines are compounds with cyathane skeletons, isolated from the fungus Sarcodon scabrosus (Fig. The natural products with 20 carbons and 30 hydrogens are classified as cyathins A series; the ones with 28 hydrogens are series B, and ones with 26 hydrogens are classified as series C. The subscript after the letter refers to the number of oxygens in the molecules.…”