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Open AccessArticle

11-Keto-α-Boswellic Acid, a Novel Triterpenoid from Boswellia spp. with Chemotaxonomic Potential and Antitumor Activity against Triple-Negative Breast Cancer Cells

1
Institute of Pharmacology of Natural Products and Clinical Pharmacology, Ulm University, 89081 Ulm, Germany
2
Max Planck Institute for Chemical Ecology, 07745 Jena, Germany
3
Laboratoire PhytoChemia, Chicoutimi, QC G7J 1H4, Canada
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Lillian Barros
Molecules 2021, 26(2), 366; https://doi.org/10.3390/molecules26020366
Received: 22 November 2020 / Revised: 1 January 2021 / Accepted: 5 January 2021 / Published: 12 January 2021
Boswellic acids, and particularly 11-keto-boswellic acids, triterpenoids derived from the genus Boswellia (Burseraceae), are known for their anti-inflammatory and potential antitumor efficacy. Although boswellic acids generally occur as α-isomers (oleanane type) and β-isomers (ursane type), 11-keto-boswellic acid (KBA) was found only as the β-isomer, β-KBA. Here, the existence and natural occurrence of the respective α-isomer, 11-keto-α-boswellic acid (α-KBA), is demonstrated for the first time. Initially, α-KBA was synthesized and characterized by high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy, and a highly selective, sensitive, and accurate high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS) method was developed by Design of Experiments (DoE) using a pentafluorophenyl stationary phase. This method allowed the selective quantification of individual 11-keto-boswellic acids and provided evidence for α-KBA in Boswellia spp. oleogum resins. The contents of α-KBA as well as further boswellic acids and the composition of essential oils were used to chemotaxonomically classify 41 Boswellia oleogum resins from 9 different species. Moreover, α-KBA exhibited cytotoxicity against three treatment-resistant triple-negative breast cancer (TNBC) cell lines in vitro and also induced apoptosis in MDA-MB-231 xenografts in vivo. The respective β-isomer and the acetylated form demonstrate higher cytotoxic efficacies against TNBC cells. This provides further insights into the structure-activity relationship of boswellic acids and could support future developments of potential anti-inflammatory and antitumor drugs. View Full-Text
Keywords: Boswellia; frankincense; boswellic acid; KBA; AKBA; triterpenoids; breast cancer; TNBC Boswellia; frankincense; boswellic acid; KBA; AKBA; triterpenoids; breast cancer; TNBC
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MDPI and ACS Style

Schmiech, M.; Ulrich, J.; Lang, S.J.; Büchele, B.; Paetz, C.; St-Gelais, A.; Syrovets, T.; Simmet, T. 11-Keto-α-Boswellic Acid, a Novel Triterpenoid from Boswellia spp. with Chemotaxonomic Potential and Antitumor Activity against Triple-Negative Breast Cancer Cells. Molecules 2021, 26, 366.

AMA Style

Schmiech M, Ulrich J, Lang SJ, Büchele B, Paetz C, St-Gelais A, Syrovets T, Simmet T. 11-Keto-α-Boswellic Acid, a Novel Triterpenoid from Boswellia spp. with Chemotaxonomic Potential and Antitumor Activity against Triple-Negative Breast Cancer Cells. Molecules. 2021; 26(2):366.

Chicago/Turabian Style

Schmiech, Michael; Ulrich, Judith; Lang, Sophia J.; Büchele, Berthold; Paetz, Christian; St-Gelais, Alexis; Syrovets, Tatiana; Simmet, Thomas. 2021. "11-Keto-α-Boswellic Acid, a Novel Triterpenoid from Boswellia spp. with Chemotaxonomic Potential and Antitumor Activity against Triple-Negative Breast Cancer Cells" Molecules 26, no. 2: 366.

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