Chemical constituents of the Annona glabra fruit and their cytotoxic activity

Nguyen Thi Thu Hien, Nguyen Xuan Nhiem, Duong Thi Hai Yen, Dan Thi Thuy Hang, Bui Huu Tai, Tran Hong Quang, Hoang Le Tuan Anh, Phan Van Kiem, Chau Van Minh, Eun Ji Kim, Seung Hyun Kim, Hee Kyoung Kang, Young Ho Kim

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Abstract

Context: Traditional Chinese medicines have attracted increasing interest as potential sources of novel drugs with a wide range of biological and pharmacological activities. Annona glabra Linn (Annonaceae) is used in traditional medicine as an anticancer drug. Phytochemical investigation of this plant led to the isolation of acetogenins, ent-kauranes, peptides, and alkaloids. In addition, compounds exhibited anticancer, anti-HIV-reserve, and antimalaria. Objective: Isolation, structure determination, and cytotoxic activity evaluation of compounds from the methanol extract from A. glabra fruits. Materials and methods: Using chromatographic methods to isolate compounds from the A. glabra methanol extract. The cytotoxic activity of compounds was evaluated by a 3-[4,5- dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay. In addition, compounds which showed significant cytotoxic activity were chosen for further study apoptosis characteristics. Results: One new, (2E,4E,1'R,3'S,5'R,6'S)-dihydrophaseic acid 1,3'-di-O-β-D-glucopyranoside, and eight known compounds, (2E,4E,1'R,3'S,5'R,6'S)-dihydrophaseic acid 3'-O-β-D-glucopyranoside (2), icariside D2 (3), icariside D2 6'-O-β-D-xylopyranoside (4), 3,4-dimethoxyphenyl O-β-Dglucopyranoside (5), 3,4-dihydroxybenzoic acid (6), blumenol A (7), cucumegastigmane I (8), and icariside B1 (9), were isolated from the fruits of A. glabra. Icariside D2 (3) was found to show significant cytotoxic activity on the HL-60 cell line with the IC50 value of 9.0 ± 1.0 μM and did not show cytotoxic activity on the Hel-299 normal cell line. The further test indicated that compound 3 induced apoptosis via alteration of expression of apoptosis-related proteins and decreased phosphorylation of AKT in HL-60 cells. Discussion and conclusion: The results suggested that the constituents from A. glabra may contain effective compounds which can be used as anticancer agents.

Original languageEnglish
Pages (from-to)1602-1607
Number of pages6
JournalPharmaceutical Biology
Volume53
Issue number11
DOIs
Publication statusPublished - 2015 Jan 1

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All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine

Cite this

Hien, N. T. T., Nhiem, N. X., Yen, D. T. H., Hang, D. T. T., Tai, B. H., Quang, T. H., Anh, H. L. T., Van Kiem, P., Van Minh, C., Kim, E. J., Kim, S. H., Kang, H. K., & Kim, Y. H. (2015). Chemical constituents of the Annona glabra fruit and their cytotoxic activity. Pharmaceutical Biology, 53(11), 1602-1607. https://doi.org/10.3109/13880209.2014.993042