Bistachybotrysins D and E, one stereoisomeric pair of cytotoxic phenylspirodrimane dimers 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 .…”

“…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 . 128,131 Another farnesane-type SQ dimer, bis-2-hydroxy-1-methoxy neogrifolin ( 545 ), has been isolated from the fungus Albatrellus yasudae .…”

“…91 The SQ dimers bistachybotrysins A–B, D–E, M ( 514–515 , 517–518 , 525 ) from S. chartarum are cytotoxic on HCT116, NCI-H460, BGC823, Daoy, and HepG2 cells with IC 50 of 1.8–8.9 μM. 175,177,178 Epoxyphomalin D ( 22 ) displays highly potent cytotoxicity by inhibiting the proliferation of 34 types of cancer cells, including liver cancer, melanoma, ovarian cancer, and renal cancer cells with IC 50 values in the range of 0.72–13.52 μM. 49 The overgrowth of angiogenesis from an existing vascular system is usually found in solid tumors, and preventing angiogenesis is an important anti-cancer approach.…”

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

“…Besides, 76 possessed neural anti-inflammatory potential by prohibiting NO production in BV2 cells induced by LPS compared to curcumin (inhibitory rate 61.1 and 67.6%, respectively, at Conc. 10 μM) [ 80 ].…”

“…Further, hydroxylation and oxidation form 3 and 1 that undergo a pinacol coupling reaction between the two aldehydic groups to produce I (vicinal diol intermediate) that is dehydrated by H-22 and OH-23′ to yield II . Subsequently, the non-stereoselective aldol reaction of II gives a stereoisomer pair, and further O-methylation affords 76 and 77 ( Scheme 5 ) [ 80 ].…”