Kadsindutalignans A-C: three new dibenzocyclooctadiene lignans from Kasura induta A.C.Sm. and their nitric oxide production inhibitory activities

• Published in: Natural product research 2024-04, Vol.38 (7), p.1127-1134
• Main Authors: Thi Thu Hien, Truong, Thang, Hoang Dac, Anh Tuan, Hoang, Thanh Chung, Nguyen, Tuan, Do Thanh, Ba Hung, Nguyen, Thi Kim Thuy, Nguyen, Hien, Nguyen Thi Thu, Hoang, Nguyen Huy, Hang, Dan Thi Thuy, Tai, Bui Huu, Nhiem, Nguyen Xuan, Kiem, Phan Van
• Format: Article
• Language: English
• Subjects: Acetic acid; Arginine; Circular dichroism; Cyclooctanes; Dichroism; kadsindutalignan A; kadsindutalignan B; kadsindutalignan C; Kadsura induta; Lignans; Lignans - chemistry; Lignans - pharmacology; Molecular Structure; Monomethyl-L-arginine; Nitric Oxide; nitric oxide inhibitor; NMR; Nuclear magnetic resonance; Plant Extracts - chemistry; Plant Extracts - pharmacology; Schisandraceae
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2022.2134361

Phytochemical study on the methanol extract of the stems and leaves of Kadsura induta led to the isolation of six dibenzocyclooctadiene lignans, including three new compounds named kadsindutalignans A-C (1-3), and three known ones, heteroclitalignan B (4), kadsuphilin C (5) and kadsulignan E (6). Their structures were elucidated based on extensive spectroscopic analyses, including HRESIMS, 1D- ( 1 H NMR and 13 C NMR), 2D-NMR (HSQC, HMBC, 1 H- 1 H COSY and NOESY), and experimental circular dichroism (CD) spectra. All the isolates inhibited NO production in LPS-activated RAW264.7 cells with IC 50 values in the range from 5.67 ± 0.54 µM to 38.19 ± 2.03 µM, compared to that of the positive control of N G -monomethyl-L-arginine acetate (L-NMMA) with an IC 50 value of 8.90 ± 0.48 µM. Interestingly, the new compound 2 showed potential inhibition of NO production with an IC 50 value of 5.67 ± 0.54 µM, which was higher than that of the positive control.