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

Research output: Contribution to journalArticle

9 Citations (Scopus)

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

Fingerprint

Annona
Fruit
HL-60 Cells
Apoptosis
Methanol
Acetogenins
Kaurane Diterpenes
Annonaceae
Cell Line
Chinese Traditional Medicine
Phytochemicals
Traditional Medicine
Alkaloids
Pharmaceutical Preparations
Antineoplastic Agents
Inhibitory Concentration 50
Phosphorylation
HIV
Pharmacology
Peptides

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., ... 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
Hien, Nguyen Thi Thu ; Nhiem, Nguyen Xuan ; Yen, Duong Thi Hai ; Hang, Dan Thi Thuy ; Tai, Bui Huu ; Quang, Tran Hong ; Anh, Hoang Le Tuan ; Van Kiem, Phan ; Van Minh, Chau ; Kim, Eun Ji ; Kim, Seung Hyun ; Kang, Hee Kyoung ; Kim, Young Ho. / Chemical constituents of the Annona glabra fruit and their cytotoxic activity. In: Pharmaceutical Biology. 2015 ; Vol. 53, No. 11. pp. 1602-1607.
@article{60316cef7a7444dfa7fc0f2a95ad8e72,
title = "Chemical constituents of the Annona glabra fruit and their cytotoxic activity",
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.",
author = "Hien, {Nguyen Thi Thu} and Nhiem, {Nguyen Xuan} and Yen, {Duong Thi Hai} and Hang, {Dan Thi Thuy} and Tai, {Bui Huu} and Quang, {Tran Hong} and Anh, {Hoang Le Tuan} and {Van Kiem}, Phan and {Van Minh}, Chau and Kim, {Eun Ji} and Kim, {Seung Hyun} and Kang, {Hee Kyoung} and Kim, {Young Ho}",
year = "2015",
month = "1",
day = "1",
doi = "10.3109/13880209.2014.993042",
language = "English",
volume = "53",
pages = "1602--1607",
journal = "Pharmaceutical Biology",
issn = "1388-0209",
publisher = "Informa Healthcare",
number = "11",

}

Hien, NTT, Nhiem, NX, Yen, DTH, Hang, DTT, Tai, BH, Quang, TH, Anh, HLT, Van Kiem, P, Van Minh, C, Kim, EJ, Kim, SH, Kang, HK & Kim, YH 2015, 'Chemical constituents of the Annona glabra fruit and their cytotoxic activity', Pharmaceutical Biology, vol. 53, no. 11, pp. 1602-1607. https://doi.org/10.3109/13880209.2014.993042

Chemical constituents of the Annona glabra fruit and their cytotoxic activity. / Hien, Nguyen Thi Thu; Nhiem, Nguyen Xuan; Yen, Duong Thi Hai; Hang, Dan Thi Thuy; Tai, Bui Huu; Quang, Tran Hong; Anh, Hoang Le Tuan; Van Kiem, Phan; Van Minh, Chau; Kim, Eun Ji; Kim, Seung Hyun; Kang, Hee Kyoung; Kim, Young Ho.

In: Pharmaceutical Biology, Vol. 53, No. 11, 01.01.2015, p. 1602-1607.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Chemical constituents of the Annona glabra fruit and their cytotoxic activity

AU - Hien, Nguyen Thi Thu

AU - Nhiem, Nguyen Xuan

AU - Yen, Duong Thi Hai

AU - Hang, Dan Thi Thuy

AU - Tai, Bui Huu

AU - Quang, Tran Hong

AU - Anh, Hoang Le Tuan

AU - Van Kiem, Phan

AU - Van Minh, Chau

AU - Kim, Eun Ji

AU - Kim, Seung Hyun

AU - Kang, Hee Kyoung

AU - Kim, Young Ho

PY - 2015/1/1

Y1 - 2015/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84945914726&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84945914726&partnerID=8YFLogxK

U2 - 10.3109/13880209.2014.993042

DO - 10.3109/13880209.2014.993042

M3 - Article

C2 - 25856711

AN - SCOPUS:84945914726

VL - 53

SP - 1602

EP - 1607

JO - Pharmaceutical Biology

JF - Pharmaceutical Biology

SN - 1388-0209

IS - 11

ER -

Hien NTT, Nhiem NX, Yen DTH, Hang DTT, Tai BH, Quang TH et al. Chemical constituents of the Annona glabra fruit and their cytotoxic activity. Pharmaceutical Biology. 2015 Jan 1;53(11):1602-1607. https://doi.org/10.3109/13880209.2014.993042