Bioguided chemical study of Boswellia dalzielii Hutch. (Burseraceae) for antibacterial agents and a new glucopyranoxylmethoxybenzyle

Abstract Stem barks of Boswellia dalzielii are used traditionally for the treatment of various bacterial infections. A bioassay guided fractionation of the MeOH-CH2Cl2 (1/1, v/v) stem barks extract led to the isolation of fourteen compounds 1–14, identified based on spectroscopic data. Dalzienoside (1) is reported here for the first time. The broth microdilution method was used to evaluate the antibacterial activity of the crude extract, fractions and compounds against six bacterial strains. The crude extract exhibited moderate antibacterial activity with MIC of 250 μL/ml; two fractions showed significant activities with MICs ranging from 7.8 to 125 μg/ml, while α-boswellic acid (2), β-boswellic acid (3), acetyl-11-keto-β-boswellic acid (4) from these fractions exhibited strong activities with MIC value of 3.125 µg/mL against Staphylococcus aureus, Salmonella typhi, Enterobacter cloacae, Streptococcus pneumonia and Pseudomonia aeruginosa. This study gives insight into the antibacterial constituents of the stem bark of B. dalzielii and justifies its use in ethnomedicine. Graphical Abstract

[1]  A. Zamilpa,et al.  Antimicrobial gastrodin derivatives isolated from Bacopa procumbens , 2019, Phytochemistry Letters.

[2]  Xiao Wang,et al.  Diterpenoids from the gum resin of Boswellia carterii and their biological activities , 2018, Tetrahedron.

[3]  Xiangyun Song,et al.  Extraction and purification of five terpenoids from olibanum by ultrahigh pressure technique and high-speed countercurrent chromatography. , 2017, Journal of separation science.

[4]  P. Mpiana,et al.  Antifungal evaluation and phytochemical screening of methanolic extract and fractions of Boswellia dalzielii stem bark , 2017 .

[5]  S. Wagai,et al.  Ursane and tirucallane-type triterpenes of Boswellia rivae oleo-gum resin , 2016, Journal of Asian natural products research.

[6]  Jin-Ying Tian,et al.  Hepatoprotective triterpenes from the gum resin of Boswellia carterii. , 2016, Fitoterapia.

[7]  Daniela Schuster,et al.  Tetra- and Pentacyclic Triterpene Acids from the Ancient Anti-inflammatory Remedy Frankincense as Inhibitors of Microsomal Prostaglandin E2 Synthase-1 , 2014, Journal of natural products.

[8]  Latha Diwakar,et al.  Beckmann rearrangement products of methyl 3-oxo-tirucall-8, 24-dien-21-oate from Boswellia serrata gum and their anti-tumor activity , 2014 .

[9]  O. Balemba,et al.  Ethnopharmacological Survey of Plants Used in the Traditional Treatment of Gastrointestinal Pain, Inflammation and Diarrhea in Africa: Future Perspectives for Integration into Modern Medicine , 2013, Animals : an open access journal from MDPI.

[10]  O. Werz,et al.  A novel C(28)-hydroxylated lupeolic acid suppresses the biosynthesis of eicosanoids through inhibition of cytosolic phospholipase A(2). , 2012, Biochemical pharmacology.

[11]  D. S. Arora,et al.  Antistaphylococcal and biofilm inhibitory activities of acetyl-11-keto-β-boswellic acid from Boswellia serrata , 2011, BMC Microbiology.

[12]  J. Pagés,et al.  Antibacterial activity of some natural products against bacteria expressing a multidrug-resistant phenotype. , 2011, International journal of antimicrobial agents.

[13]  Jason Eslamieh Creating “Perfect” Boswellia , 2010 .

[14]  N. Lall,et al.  Antibacterial, antifungal and antitubercular activity of (the roots of) Pelargonium reniforme (CURT) and Pelargonium sidoides (DC) (Geraniaceae) root extracts , 2006 .

[15]  G. Onawunmi,et al.  Isolation and characterization of incensole from Boswellia dalzielii stem bark , 2005 .

[16]  Atta-ur-Rahman,et al.  Bioactive constituents from Boswellia papyrifera. , 2005, Journal of natural products.

[17]  L. Binda,et al.  Evaluation of the aqueous extract of Boswellia dalzielii stem bark for antimicrobial activities and gastrointestinal effects , 2004 .

[18]  T. Syrovets,et al.  Structural analysis of pentacyclic triterpenes from the gum resin of Boswellia serrata by NMR spectroscopy , 2003 .

[19]  G. Culioli,et al.  A lupane triterpene from frankincense (Boswellia sp., Burseraceae). , 2003, Phytochemistry.

[20]  J. Eloff A Sensitive and Quick Microplate Method to Determine the Minimal Inhibitory Concentration of Plant Extracts for Bacteria , 1998, Planta medica.

[21]  S. Mahato,et al.  13C NMR spectra of pentacyclic triterpenoids--a compilation and some salient features , 1994 .

[22]  H. Hussain,et al.  Biological Activities of Boswellia Extract , 2019, Chemistry and Bioactivity of Boswellic Acids and Other Terpenoids of the Genus Boswellia.

[23]  Ahmed A. Abd-Rabou,et al.  Phytochemical Analysis and Anti-cancer Investigation of Boswellia serrata Bioactive Constituents In Vitro. , 2015, Asian Pacific journal of cancer prevention : APJCP.

[24]  Y. Gera,et al.  Ethnobotanical survey of anti-diarrheal medicinal plants among Tiv people of Nigeria , 2015 .

[25]  D. Kubmarawa Ethnomedicinal survey of the traditional medicine of Lala people of Nigeria , 2013 .

[26]  H. Sheridan,et al.  The Flavonoids , 1988, Springer US.

[27]  Sabrina Kruger,et al.  The Flavonoids Advances In Research Since 1980 , 1980 .