Enantiomeric chromene derivatives with anticancer effects from Mallotus apelta

Phan Van Kiem, Nguyen Xuan Nhiem, Nguyen Hoang Anh, Duong Thi Hai Yen, Nguyen The Cuong, Bui Huu Tai, Pham Hai Yen, Nguyen Hoai Nam, Chau Van Minh, Pham The Chinh, Yu Hyun Jeon, Seon Ju Park, Seung Hyun Kim, So Hee Kwon

Research output: Contribution to journalArticle

Abstract

Mallotus apelta (Lour.) Müll.Arg has been used in traditional medicine for the treatment of chronic hepatitis. Six new chromene derivatives, malloapeltas C-H (1–6) and one known compound, malloapelta B (7) were isolated and structured from the leaves of M. apelta. Two pairs of enantiomers (1a/1b and 2a/2b) were successfully separated by chiral high-pressure liquid chromatography (HPLC). The structures and absolute configurations of compounds were determined using spectroscopic methods, including 1D, 2D NMR, and MS and quantum chemical calculation methods. All compounds were evaluated for cytotoxic activity using cell counting kit-8 (CCK-8) assay against ovarian cancer cell line (TOV-21G). Compounds 1–5 and 7 exhibited significant growth and viability inhibitory effects with GI50 values ranging from 0.06 to 10.39 μM and IC50 values ranging from 1.62 to 10.42 μM on ovarian cancer cell line, TOV-21G. The most cytotoxic compounds 2, 3, and 7 were chosen for studying in apoptosis mechanism. Compounds 2, 3, and 7-induced apoptosis as evidenced by activated caspase 8, caspase 9, and PARP, increased Bak and Bax, and decreased Bcl-xL and survivin. Moreover, compounds 2, 3, and 7 significantly inhibited the NF-κB signaling pathway. Taken together, our findings propose the potential application of compounds 2, 3, and 7 for treating cancer via modulating NF-κB activity.

Original languageEnglish
Article number104268
JournalBioorganic Chemistry
Volume104
DOIs
Publication statusPublished - 2020 Nov

Bibliographical note

Funding Information:
This research was supported by the Vietnam Academy of Science and Technology ( DL0000 . 01/19-20 ) and by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology ( 2018R1A6A1A03023718 and 2019R1A2C1008619 ).

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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