TY - JOUR
T1 - Anti-inflammatory activity and cytotoxicity against ovarian cancer cell lines by amide alkaloids and piperic esters isolated from Piper longum fruits
T2 - In vitro assessments and molecular docking simulation
AU - Viet Phong, Nguyen
AU - Thi Nguyet Anh, Dinh
AU - Yeong Chae, Ha
AU - Young Yang, Seo
AU - Jeong Kwon, Mi
AU - Sun Min, Byung
AU - Ah Kim, Jeong
N1 - Publisher Copyright:
© 2022 Elsevier Inc.
PY - 2022/11
Y1 - 2022/11
N2 - Three new amide alkaloids, piperlongumamides D–F (14, 19, and 32); a new piperic ester, piperlongumester A (45); and two new natural compounds, methyl (2E,4Z)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoate (46) and trans-piperolein B ester (47), along with 41 known compounds were isolated from the fruits of Piper longum L. Their structures were identified by analyzing spectroscopic data, including mass spectrometry, 1D, and 2D NMR data. The anti-inflammatory and cytotoxic activities of all isolated compounds (1–47) were evaluated. Compounds 3, 6, and 19 inhibited nitric oxide production with IC50 values of 16.1 ± 0.94, 14.5 ± 0.57, and 27.3 ± 1.11 μM, respectively, whereas compound 1 exhibited strong cytotoxic activity toward three ovarian cancer cell lines A2780, TOV-112D, and SK-OV3, with IC50 values of 6.7 ± 0.77, 5.8 ± 0.29, and 48.3 ± 0.40 μM, respectively. Molecular docking simulations were performed to identify the interaction and binding mechanisms of these active metabolites with proteins related to inflammation and cancer.
AB - Three new amide alkaloids, piperlongumamides D–F (14, 19, and 32); a new piperic ester, piperlongumester A (45); and two new natural compounds, methyl (2E,4Z)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoate (46) and trans-piperolein B ester (47), along with 41 known compounds were isolated from the fruits of Piper longum L. Their structures were identified by analyzing spectroscopic data, including mass spectrometry, 1D, and 2D NMR data. The anti-inflammatory and cytotoxic activities of all isolated compounds (1–47) were evaluated. Compounds 3, 6, and 19 inhibited nitric oxide production with IC50 values of 16.1 ± 0.94, 14.5 ± 0.57, and 27.3 ± 1.11 μM, respectively, whereas compound 1 exhibited strong cytotoxic activity toward three ovarian cancer cell lines A2780, TOV-112D, and SK-OV3, with IC50 values of 6.7 ± 0.77, 5.8 ± 0.29, and 48.3 ± 0.40 μM, respectively. Molecular docking simulations were performed to identify the interaction and binding mechanisms of these active metabolites with proteins related to inflammation and cancer.
KW - Amide alkaloid
KW - Anti-inflammatory activity
KW - Molecular docking
KW - Ovarian cancer cell lines
KW - Piper longum fruits
UR - http://www.scopus.com/inward/record.url?scp=85136710152&partnerID=8YFLogxK
U2 - 10.1016/j.bioorg.2022.106072
DO - 10.1016/j.bioorg.2022.106072
M3 - Article
C2 - 35944468
AN - SCOPUS:85136710152
SN - 0045-2068
VL - 128
JO - Bioorganic Chemistry
JF - Bioorganic Chemistry
M1 - 106072
ER -
