Optimized conversion of antiproliferative lignans pinoresinol and epipinoresinol: Their simultaneous isolation and identification by centrifugal partition chromatography and high performance liquid chromatography

A Comprehensive Study on Lathyrus tuberosus L.: Insights into Phytochemical Composition, Antimicrobial Activity, Antioxidant Capacity, Cytotoxic, and Cell Migration Effects

“…Compounds 13 , 21 , and 25 at m / z 551 were characterized as methoxylariciresinol- O -hexoside isomers [ 48 ], while compounds 2 and 9 with [M−H] − at m / z 713 consisting of an additional hexose moiety ( m / z 713 → 551) were identified as methoxylariciresinol-di- O -hexoside isomers [ 49 ]. Compound 77 exhibited the molecular ion at m / z 519 with a neutral loss of 162 Da that yielded an aglycone ion at m / z 357, while the other fragment ions showed similarity to epipinoresinol or pinoresinol [ 50 , 51 ]. In the case of compounds 38 and 55 , the aglycone fragment ions [M−H−162] − and [M−H−132] − at m / z 373 contain an extra hydroxyl group, and their [M−H] − ions can be detected at m / z 535 and 505, respectively.…”

“…Compounds 51, 54, and 65 were characterized as dicaffeoylquinic acid isomers, which could be distinguished based on the relative intensities of their fragment ions [39]. For 3,4-Odicaffeoylquinic acid (51), the fragment ion at m/z 173 is the base peak, while the intensity of the secondary fragment ions at m/z 191 and 179 is relatively high. The domination of the fragment ion at m/z 191 indicated 3,5-O-dicaffeoylquinic acid as compound 54, while the base peak at m/z 173 with relatively low intensity secondary peaks referred to 4,5-O-dicaffeoylquinic acid (65) [39].…”

“…In the case of compounds 38 and 55, the aglycone fragment ions [M−H−162] − and [M−H−132] − at m/z 373 contain an extra hydroxyl group, and their [M−H] − ions can be detected at m/z 535 and 505, respectively. Thus, they were characterized as hydroxypinoresinol-O-hexoside (38) and hydroxypinoresinol-O-pentoside (55) [50,51].…”

GC-MS/MS Quantification of EGFR Inhibitors, β-Sitosterol, Betulinic Acid, (+) Eriodictyol, (+) Epipinoresinol, and Secoisolariciresinol, in Crude Extract and Ethyl Acetate Fraction of Thonningia sanguinea

“…Secoisolariciresinol diglucoside showed cytotoxic effects against different malignant tumors, including breast, lung, and colon cancers, due to its antiproliferative and antioxidant activities [23]. Epipinoresinol upregulated the tumor suppressor gene P53 that inhibits the proliferation of the HCT116 colon cancer cell line [17]. Additionally, β-sitosterol showed a chemo-prophylactic agent in colon carcinogenesis, while betulinic acid was incorporated into chemotherapeutic agents due to its ability to inhibit invasion of lung cancer cells [24,25].…”

“…Eriodictyol exhibited significant anticancer activity toward the A549 human lung cancer cell line [16]. Additionally, epipinoresinol showed significant antiproliferative effects when tested against two types of colon cancer cell lines (HCT116 and SW480) [17]. Finally, secoisolariciresinol was shown to act as a re-sensitizer of P-glycoprotein-dependent doxorubicin-resistance NCI/ADR-RES cancer cells [18].…”