Chemical, molecular and structural studies of Boswellia species: β-Boswellic Aldehyde and 3-epi-11β-Dihydroxy BA as precursors in biosynthesis of boswellic acids

Al‐Harrasi, Ahmed; Rehman, Najeeb Ur; Khan, Abdul Latif; Al-Broumi, Mohammed; Al-Amri, Issa; Hussain, Javid; Hussain, Hidayat; Csuk, René

doi:10.1371/journal.pone.0198666

Cited by 52 publications

(49 citation statements)

References 70 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…One should therefore pay attention using bacosine as a reference substance or extracted substance from B. monnieri as it might be betulinic acid. This assumption can also be reinforced, since in comparison with the literature [24], a α-hydroxy group at C-3 and lupeol-type configurations for the other substituents at the pentacyclic ring (▶ Fig. 1) are rather unusual.…”

Section: Resultsmentioning

confidence: 74%

Where Is Bacosine in Commercially Available Bacopa monnieri?

et al. 2020

View full text Add to dashboard Cite

Bacopa monnieri is an Ayurvedic plant with rising interest in the pharmacological effects of its extract and constituents, including flavonoids, saponins, and triterpenes such as cucurbitacins, betulinic acid, and bacosine. The latter two compounds are isomeric 3-hydroxy lupenoic acids, which vary only in the arrangement of the carboxylic acid group and the methyl group at C-27 and C-28 and the orientation of the hydroxy group at C-3. In this study, we have reinvestigated the contents of betulinic acid and bacosine, respectively, in extracts from various commercially available B. monnieri powders and food supplements. To our surprise, HPLC-ion trap time-of-flight analyses identified only betulinic acid, but not bacosine, in all extracts under study, which was verified by GC-MS, HPLC-ELSD, 1D NMR (1H,13C), and 2D NMR (1H,1H COSY, 1H,13C HMBC, 1H,13C HSQC, 1H,1H NOESY) experiments. Moreover, it turned out that commercially available reference samples of bacosine were structurally identical with betulinic acid.

show abstract

Section: Resultsmentioning

confidence: 74%

Where Is Bacosine in Commercially Available Bacopa monnieri?

et al. 2020

View full text Add to dashboard Cite

show abstract

“…However, in 2005, 70 years after the discovery of the first boswellic acids, we could demonstrate that in addition to β-AKBA, the α-isomer acetyl-11-keto-α-boswellic acid (α-AKBA) naturally occurs in Boswellia oleogum resins [ 17 , 18 ]. As a result, it was hypothesized that also the deacetylated form, 11-keto-α-boswellic acid (α-KBA), might exist, because biosynthesis of α-AKBA takes place by acetylation of the precursor α-KBA [ 6 ]. In this study, we demonstrate for the first time the existence and the natural occurrence of α-KBA by using a novel, highly selective high-performance liquid chromatography coupled with tandem mass spectrometry HPLC-MS/MS method with a pentafluorophenyl (PFP) stationary phase.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

View full text Add to dashboard Cite

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.

show abstract

“…This species of Arabian Peninsula has been regarded as the source of one of the highest quality and the best aromatic gum-resins. 1 It's obtained by making an incision in the tree bark. The secreted resin upon drying is hardened and is called "tears".…”

Section: Introductionmentioning

confidence: 99%

In vitro Cytotoxic, Antioxidant and Antimicrobial Activities of Alcoholic and Chloroform Extracts of Dhofari Frankincense

Soliman

Majeed

Himyari

et al. 2020

Dhaka Univ. J. Pharm. Sci

View full text Add to dashboard Cite

Omani (Dhofari) frankincense is world famous for its high quality and fragrance. The oleo-gum resin obtained from the tree of Omani species i.e., Boswellia sacra (local name: luban) is widely used by the natives. The aim of the study was to determine the presence of phytochemicals in chloroform and ethanol extracts of B. sacra resin and to evaluate the in vitro cytotoxic, antimicrobial- and antioxidant-activities. The ethanol and chloroform extracts of Hojari luban were obtained in good yield. The extracts were subjected to phytochemical screenings, quantification of total phenolics (TP) and evaluation of in vitro biological activities viz. antioxidant, antibacterial and cytotoxic potential. The bioactivities of four boswellic acids, the major constituents of the oleo-gum resin, were also predicted with the help of PASS and CLC-pred software. Both the extracts showed similar level of TP (14.67 mg/g and 14.79 mg/g in terms of gallic acid equivalent) but polar fraction was noted to be more active against E. coli. A moderate antioxidant activity was shown by the resin extracts however their cytotoxic activity was observed to be quite remarkable at 1000 μg/l which could be attributed to their high boswellic acid content. Results of in silico PASS studies showed boswellic acids to possess an array of useful biological activities including chemopreventive activity. Further, CLC-pred software revealed that only keto boswellic acid is expected to exert antineoplastic activity against pancreatic carcinoma cell lines, however all the four major boswellic acids are likely to be active against non-tumor embryonic lung fibroblast (MRC5). The study confirmed that frankincense is rich in bioactive metabolites which are of significant economic and therapeutic importance. Dhaka Univ. J. Pharm. Sci. 19(2): 105-110, 2020 (December)

show abstract

Chemical, molecular and structural studies of Boswellia species: β-Boswellic Aldehyde and 3-epi-11β-Dihydroxy BA as precursors in biosynthesis of boswellic acids

Cited by 52 publications

References 70 publications

Where Is Bacosine in Commercially Available Bacopa monnieri?

Where Is Bacosine in Commercially Available Bacopa monnieri?

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

In vitro Cytotoxic, Antioxidant and Antimicrobial Activities of Alcoholic and Chloroform Extracts of Dhofari Frankincense

Contact Info

Product

Resources

About