UPLC-QTOFMS^E-Guided Dereplication of the Endangered Chinese Species Garcinia paucinervis to Identify Additional Benzophenone Derivatives

Abstract

A number of Garcinia species accumulate benzophenone derivatives that may be useful for the treatment of breast cancer. The dereplication of new benzophenone derivatives from Garcinia species is challenging due to the occurrence of multiple isomers and the known compounds found in their extracts. In the current study, a strategy is described using the UPLC-QTOFMS(E) technique to identify tentatively the known and uncharacterized benzophenones of interest based upon the characteristic fragmentation ions. Several UPLC-QTOFMS peaks (a-ee) appeared to contain benzophenone derivatives, and 12 of these peaks contained compounds with MS ionization profiles not consistent with previously identified compounds from the seeds of Garcinia paucinervis, an endangered Chinese species. The targeted isolation of unidentified compounds of interest afforded five new benzophenones, paucinones E-I (1-5), which were determined by MS and NMR analysis and ECD spectroscopy. These compounds were evaluated for cytotoxicity against three breast cancer cell lines inclusive of MDA-MB-231, SKBR3, and MCF-7. These results indicate that the UPLC-QTOFMS(E)-guided isolation procedure is an efficient strategy for isolating new benzophenones from Garcinia species.

Dereplication of Bioactive Spirostane Saponins from Agave macroacantha

“…Conventional isolation techniques often require large amounts of the starting material as well as time-consuming and costly purification procedures. 8 In order to overcome such difficulties, several dereplication approaches have been applied to the chemical profiling of natural products. Such procedures are intended to accelerate the identification of the biologically active substances in the extracts and involve clearly defined step-by-step operations or workflows based on their different separation, analytical, and elucidation steps.…”

Cycloartane Triterpenoids with Anti-melanin Deposition Activity

“…The residue obtained under N 2 blow was subjected to SiO 2 column chromatography (CHCl 3 ) to obtain the (S)-MTPA ester of 3 (4). The same procedure was used to obtain of the (R)-MTPA ester of 3 (5).…”

“…In addition to their edible fruits, the plants of Garcinia are also valuable as sources of medicines, color pigments, resins and lumber [2,3]. Phytochemically, this genus is mostly known for its unique prenylated xanthones and benzophenones [2,[4][5][6][7][8][9], though triterpenoids [10,11] and flavonoids [12][13][14] were also reported.…”

Anti-Hyperuricemic Effect of 2-Hydroxy-4-methoxy-benzophenone-5-sulfonic Acid in Hyperuricemic Mice through XOD

“…In addition to the above, benzophenone-type compounds [ 13 , 14 ] from natural products and synthesized ones have demonstrated important and valuable biological activities, with anti-inflammatory, antimicrobial, cytotoxic activities [ 15 , 16 ] and anti-angiogenesis effects [ 17 ] as examples. Nemorosone has anti-proliferative activity by targeting Akt/PKB against LAN-1 parental cell line [ 18 ] and cytotoxic activity against HeLa, eHep-2, PC-3 and U251 cancer cells [ 19 , 20 ].…”