Bistachybotrysins A–C, three phenylspirodrimane dimers with cytotoxicity from Stachybotrys chartarum

Natural sesquiterpene quinone/quinols: chemistry, biological activity, and synthesis

“…Bistachybotrysins A–J and L–V ( 514–534 ) from S. chartarum CGMCC 3.5365, stachybochartins A–D ( 535–538 ) from endophytic S. chartarum PT2-12, stachartarin A ( 539 ), and stachartone A ( 540 ) from tin mine tailings derived S. chartarum , chartarlactam L ( 541 ), and their corresponding precursor, chartarlactam A, from sponge-derived S. chartarum have all been identified as SQ dimers. 63,67,175–180 Among these compounds, 514–516 possess an unusual 2,10-dioxabicyclo[4,3,1]decan-7-ol linkage core, 517–523 and 537–540 are characterized by a central cyclopentanone linkage, and the monomers of 524 and 525 are connected with each other via a unique [5,6]-spiroketal core, indicating the diversity of the dimerization patterns formed between the phenylspirodrimane-type SQ monomers. 175–178 The farnesane-type SQ dimers cochlearoids F and G ( 542–543 ) and gancochlearol C ( 544 ) are found in the Chinese folk medicine G. cochlear .…”

Stachybotrys chartarum—A Hidden Treasure: Secondary Metabolites, Bioactivities, and Biotechnological Relevance

“…Further investigation is worth pursuing for 73 and 74 as new promising antitumor lead compounds [ 79 ]. They were postulated to be originated from farnesyl-diphosphate and orsellinic acid that give phenylspirodrimane monomer ( Scheme 4 ).…”

“…Subsequently, the dehydration of the mer-NF5003E ( 3 ) CH 2 OH and hemiacetal OH groups yields 73 through 6/7 oxygen heterocyclic linkage. Further, 74 is resulted from bistachybotrysin A by selective acetylation, whereas 75 is generated from 5 and 2 through pinacol-coupling reaction, intermolecular acetalization, and dehydration [ 79 ].…”

Chemical Diversity and Biosynthesis of Drimane‐Type Sesquiterpenes in the Fungal Kingdom

“…Notably, some phenylspirodrimanes exhibited antibacterial activities against the methicillin-resistant Staphylococcus aureus. [57] Lastly, stachybocins (129 and 130), which are presumably formed by the reaction between phenylspirodrimane and lysine with subsequent decarboxylation, [58] and bistachybotrysins (131-133), which harbour an unusual [6,6,7,7]-tetracyclic skeleton and exhibited a potent cytotoxicity, [59] have also been isolated from the genus Stachybotrys.…”