Gancochlearols E − I, meroterpenoids from Ganoderma cochlear against COX-2 and triple negative breast cancer cells and the absolute configuration assignment of ganomycin K

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

“…An in-depth investigation has been carried out on Ganoderma species by Y. X. Cheng's group and they reported cochlearoids A, B, and E ( 280–282 ), cochlearoids H–J ( 283–285 ), (±)-cochlearoids N–Q ( 286–289 ), cochlearols C, D, R, Q ( 290–293 ), gancochlearols D, E, and I ( 294–296 ), and ganomycin K and F ( 297–298 ) from Ganoderma cochlear ; lucidumones B–H ( 299–305 ), dayaolingzhiols C–E ( 306–308 ), ganodermaone B ( 309 ), and chizhine F ( 310 ) from Ganoderma lucidum ; and (±)-zizhines A–F ( 311–316 ) from Ganoderma sinensis . 124–135 Compounds 280–282 and 286–289 possess a unique methanobenzo[ c ]oxocino[2,3,4- ij ]-isochromene scaffold. 125,126,128 The stereogenic centers of 292 were assigned as 1′ S , 2′ S , and 3′ S using a combination of MAD, Δ δ max , and R 2 analysis of its 1 H NMR chemical shifts in CHCl 3 , DMSO, and MeOH, and the NMR calculation method was proven to be an effective tool for determining the absolute configuration of compounds that lack efficient ROESY data.…”

“…130,131,136 The first stereochemical establishment of compound 297 was assigned as 1 R ,10 S using the Rh 2 (OCOCF 3 ) 4 -induced ECD method according to the bulkiness rule. 127 There are also many other studies focusing on the constituents of Ganoderma sp., such as ganomycin C ( 317 ), cochlearins B–E and I ( 318–322 ) from G. cochlear , ganofuran B ( 323 ) from G. lucidum , ganoduriporols C–L ( 324–333 ) from Ganoderma ahmadii , and ganoresinains A, B, and E ( 334–336 ) from G. resinaceum , among which the unique oxepane was formed in the structures of compounds 331–333 . 137–142 Serial fractionation and purification of the marine fungi Stachybotrys chartarum and Stachybotrys longispora has led to the identification of isoindolinone chartarutines A–H ( 337–344 ), stachybotrysams A–D ( 345–348 ), stachybotrin G ( 349 ), and FGFC2 4–7 ( 350–354 ), and orsellinic acid-based stachybonoids A–C ( 355–357 ).…”

“…161,162 The chemical investigation of G. cochlear and G. resinaceum has yielded gancochlearols G and H ( 455–456 ), cochlearol P ( 457 ), and ganoresinain C ( 458 ). 127,130,142 The anti-bacterial and cytotoxic extract of the culture media of Streptomyces niveus SCSIO 3406 afforded four naphthoquinones, marfuraquinocins A–D ( 459–462 ). 163 …”

“…135 Gancochlearol I ( 296 ) suppresses the epithelial–mesenchymal transition of triple-negative breast cancer cells (MDA-MB-231) by downregulating the key factors of TWIST1 and SNAI1 at 20 μM, providing valuable drug candidates for the treatment of cancer metastasis. 127 Nuclear factor κB (NF-κB) plays a key role in the proliferation, migration, and apoptosis of cancer cells, and is an important target for anti-cancer drug discovery. Dysidaminones C, E, H, and J ( 155 , 157 , 160 , and 162 ), and 18-aminoavarone ( 167 ) inhibit NF-κB in HEK293 cells with IC 50 values in the range of 0.05–0.27 μM, and they are also cytotoxic toward NCI-H929, HepG2, B16F10, and SK-OV-3 cancer cells with IC 50 values in the range of 0.45–9.65 μM.…”

Structural Optimization and Improving Antitumor Potential of Moreollic Acid from Gamboge

“…In recent years, we have focused on chemical and pharmacological investigations of natural products, and further uncovered a number of interesting molecules with satisfied antitumor activities [5][6][7][8]. Gamboge, the resin secreted by the Garcinia hanburyi tree, has been used as a natural health product in China for thousands of years [9].…”