Chiral separation and bioactivities of six pairs of enantiomeric dilignans from Magnolia officinalis var. biloba

• Published in: Phytochemistry (Oxford) Vol. 219; p. 113964
• Main Authors: Zang, Ying-Da, Zang, Cai-xia, Tian, Jin-Ying, Xu, Kai-Ling, Li, Chuan, Li, Chuang-Jun, Yang, Yang, Ye, Fei, Zhang, Dan, Zhang, Dong-Ming, Ma, Jie
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.03.2024; Elsevier
• Subjects: Anti-oxidative effect; Biochemistry & Molecular Biology; Enantiomeric dilignans; Hepatoprotective activity; Life Sciences & Biomedicine; Magnolia officinalis var. biloba; Magnoliaceae; Plant Sciences; PTP1B inhibition activity; Science & Technology; α-glucosidase inhibition activity; Hepatoprotective activity; Magnolia officinalis var. biloba; PTP1B inhibition activity; α-glucosidase inhibition activity; Enantiomeric dilignans; Magnoliaceae; Anti-oxidative effect; GLYCOSIDES; alpha-glucosidase inhibition activity; LIGNANS; NEOLIGNANS
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2024.113964

Six pairs of enantiomeric dilignans, (+)/(−)-magdiligols A–F, have been isolated from an ethanolic extract of the barks of Magnolia officinalis var. biloba. Their chemical structures were elucidated by extensive spectroscopic analyses, NMR calculation with DP4+ analysis, and the electronic circular dichroism spectra calculation. (+)/(−)-1–3 possessed a dihydrobenzopyran ring, while a propyl chain of 1 was linked via ether bond. (+)/(−)-Magdiligols D and E ((+)/(−)-4 and 5) were dilignans possessing a furan ring. (+)-Magdiligol B ((+)/(−)-2), (+)/(−)-magdiligol C ((+)/(−)-3), and racemes 2, 3, and 5 showed potential hepatoprotective effects against APAP-induced HepG2 cell damage, increased the cell viability from 65.4% to 72.7, 78.7.76.6, 73.9, 77.9 and 73.2%, via decreasing the level of the live enzymes ALH and LDH consistently. (+)/(−)-Magdiligols B–D ((+)/(−)-2–4) and (+)/(−)-magdiligol F ((+)/(−)-6) exhibited significant antioxidative activity. (+)/(−)-Magdiligols B–C ((+)/(−)-2 and 3), (−)-magdiligol D ((−)-4), and (+)-magdiligol E ((+)-5) displayed significant PTP1B inhibitory activity with IC50 values 1.41–3.42 μM. (+)/(−)-Magdiligol B ((+)/(−)-2), and its raceme (2) demonstrated α-glucosidase inhibitory activity with the IC50 values 1.47, 2.88 and 1.85 μM, respectively. Six pairs of enantiomeric dilignans, (+)/(−)-magdiligols A–F, were chiral-separated from the barks of Magnolia officinalis var. biloba. Some isolates showed excellent hepatoprotective activity, anti-oxidative effect and hypoglycemic activity in vitro. [Display omitted] •Six pairs of enantiomeric dilignans from the barks of M. officinalis var. biloba.•(+)-Magdiligol B and (+)/(−)-magdiligol C showed potential hepatoprotective effects via decreasing the level of the live enzymes ALH and LDH consistently in vitro.•Some isolated diligans displayed significant antioxidative, PTP1B and α-glucosidase inhibitory activity.•(+)/(−)-Magdiligols B–C, (−)-magdiligol D, and (+)-magdiligol E displayed significant PTP1B and α-glucosidase inhibitory activity.