New derivatives of 11-keto-β-boswellic acid (KBA) induce apoptosis in breast and prostate cancers cells

Asma Bani Araba, Najeeb Ur Rehman, Amna Al-Araimi, Sulaiman Al-Hashmi, Sulaiman Al-Shidhani, Rene Csuk, Hidayat Hussain, Ahmed Al-Harrasi, Fahad AL Zadjali

Research output: Contribution to journalArticle

Abstract

A series of new 11-keto-β-boswellic acid were partially-synthesized by modifying the hydroxyl and carboxylic acid functional groups of ring A. The structures of the new analogs were confirmed by detailed spectral data analysis. Compounds 4, 5 and 9 exhibited potent anti-cancer results against two human tumor cancer cell lines having IC 50 value of MCF-7 (breast) and LNCaP (prostate): 123.6, 9.6 and 88.94 μM and 9.6, 44.12 and 12.03 μM, respectively. Additionally, a maximum nuclear fragmentation was observed for 4 (78.44%) in AKBA treated cells after 24 hr followed by 5 and 9 with (74.25 and 66.9% respectively). This study suggests that the presence of hydrazone functionality (4 and 9) has effectively improved the potency of AKBA. Interestingly, compound 5 with a lost carboxylic acid group of ring A showed comparable potent activity. Highly selective AKBA requires further modification to improve its bioavailability and solubility inside the cancer cells.

Original languageEnglish
JournalNatural Product Research
DOIs
Publication statusPublished - Jan 1 2019

Fingerprint

keto acids
prostatic neoplasms
breast neoplasms
Prostatic Neoplasms
apoptosis
chemical derivatives
Cells
Apoptosis
carboxylic acids
Breast Neoplasms
Carboxylic Acids
Derivatives
Hydrazones
Neoplasms
Tumor Cell Line
Hydroxyl Radical
Solubility
spectral analysis
Functional groups
Biological Availability

Keywords

  • 11-keto-β-boswellic acid
  • 3-acetyl-11-Keto-β-boswellic acid
  • Boswellia sacra
  • breast cancer cell lines
  • normal cell lines
  • prostate cancer cell lines

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

Cite this

New derivatives of 11-keto-β-boswellic acid (KBA) induce apoptosis in breast and prostate cancers cells. / Bani Araba, Asma; Ur Rehman, Najeeb; Al-Araimi, Amna; Al-Hashmi, Sulaiman; Al-Shidhani, Sulaiman; Csuk, Rene; Hussain, Hidayat; Al-Harrasi, Ahmed; AL Zadjali, Fahad.

In: Natural Product Research, 01.01.2019.

Research output: Contribution to journalArticle

Bani Araba, Asma ; Ur Rehman, Najeeb ; Al-Araimi, Amna ; Al-Hashmi, Sulaiman ; Al-Shidhani, Sulaiman ; Csuk, Rene ; Hussain, Hidayat ; Al-Harrasi, Ahmed ; AL Zadjali, Fahad. / New derivatives of 11-keto-β-boswellic acid (KBA) induce apoptosis in breast and prostate cancers cells. In: Natural Product Research. 2019.
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abstract = "A series of new 11-keto-β-boswellic acid were partially-synthesized by modifying the hydroxyl and carboxylic acid functional groups of ring A. The structures of the new analogs were confirmed by detailed spectral data analysis. Compounds 4, 5 and 9 exhibited potent anti-cancer results against two human tumor cancer cell lines having IC 50 value of MCF-7 (breast) and LNCaP (prostate): 123.6, 9.6 and 88.94 μM and 9.6, 44.12 and 12.03 μM, respectively. Additionally, a maximum nuclear fragmentation was observed for 4 (78.44{\%}) in AKBA treated cells after 24 hr followed by 5 and 9 with (74.25 and 66.9{\%} respectively). This study suggests that the presence of hydrazone functionality (4 and 9) has effectively improved the potency of AKBA. Interestingly, compound 5 with a lost carboxylic acid group of ring A showed comparable potent activity. Highly selective AKBA requires further modification to improve its bioavailability and solubility inside the cancer cells.",
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