11α‐Ethoxy‐β‐boswellic Acid and Nizwanone, a New Boswellic Acid Derivative and a New Triterpene, Respectively, from Boswellia sacra

Abstract

A new boswellic acid derivative, 11α-ethoxy-β-boswellic acid (EBA; 1) and a new ursane-type triterpene, named nizwanone (2), were isolated from Omani frankincense Boswellia sacra Flueck. together with two known compounds papyriogenin B and rigidenol. The structures of 1 and 2 were elucidated by detailed spectroscopic analysis using (1) H- and (13) C-NMR, (1) H,(1) H-COSY, HMQC, HMBC, and HR-EI-MS techniques. The relative configurations of 1 and 2 were assigned by comparative analysis of the NMR spectral data with those of known analogs together with NOESY experiments. Structures of known compounds were identified by comparison with the reported data.

RETRACTED CHAPTER: Apharsemon, Myrrh and Olibanum: Ancient Medical Plants

“…12 ), which were isolated from Boswellia spp. for the fi rst time (Al-Harrasi et al 2013 ). (Fattorusso et al 1983 ;Klein and Obermann 1978 ;Basar et al 2001 ;Hamm et al 2005 ;Hanuš et al 2007 ) Table 1 The main terpenes identifi ed in Boswellia sacra E -β-ocimene (32.3 %) Sabinene (5.2 %) β-pinene 1.8 %) Myrcene (6.9 %) α-pinene (5.3 %) Limonene (33.5 %) γ-terpinene (1.0 %) E -caryophyllene (0.9 %) Al-Harrasi and Al-Saidi ( 2008 ) Boswellia sacra Boswellia carterii α-thujene (0.6 %) α-thujene (7.9 %) α-pinene (68.2 %) α-pinene (37.3 %) Camphene (2.1 %) Camphene (0.8 %) Sabinene (2.9 %) Sabinene (4.9 %) β-pinene (2.0 %) β-pinene (1.8 %) Myrcene (0.7 %) Myrcene (7.3 %) Limonene + β-phellandrene …”

Neuroprotective Norsesquiterpenoids and Triterpenoids from Populus euphratica Resins

“…The nine known compounds were identified as populeuphroid L ( 5 ) [7], epimansumbinol ( 6 ) [12], ergosta-4,6,8(15),22-tetraen-3-one ( 7 ) [15], mansumbin-13(17)-en-3,16-dione ( 8 ) [16], 3 α -acetoxy-mansumbin-13(17)-en-16-one ( 9 ) [17], 3-epi-δ-amyrin ( 10 ) [18], α-boswellic acid ( 11 ) [19], 11α-ethoxy-β-boswellic acid ( 12 ) [20], acetyl-11-keto-β-boswellic acid ( 13 ) [21] by a comparison of their spectroscopic data with those reported in the literature. Although compound 12 is a known one, it might be an artefact produced during extraction procedure.…”

Taxonomical Investigation, Chemical Composition, Traditional Use in Medicine, and Pharmacological Activities of Boswellia sacra Flueck

“…In contrast, boscartin M, isoincensole oxide, incensole oxide, and incensole oxide acetate had a mild hepatoprotective effect at 10 μM [25]. In the other report by Wang et al, the investigation of B. sacra led to the isolation of ten new cembrane-type diterpenes, including boscartins AL-AU (25)(26)(27)(28)(29)(30)(31)(32)(33)(34) and five known analogs (35)(36)(37)(38)(39). Moreover, biological evaluations revealed that compounds 27, 29, 36, and 37 displayed hepatoprotective activities against paracetamol-induced HepG2 cell damage at 10 μM.…”

“…Compounds 70 and 71 were evaluated for their antiproliferative activity against MDA-MB-231 breast cancer cells, and it was observed that these pyrolysate products were able to inhibit cancer cell growth [31]. A new ursane-type triterpene, namely, nizwanone (72) was reported from Omani frankincense B. sacra Flueck along with two known compounds papyriogenin B (73) and rigidenol (74) by Al-Harrasi et al [32]. 11-ketoursolic acid (75), 3α-hydroxy-8, 24-dien-tirucallic acid (76), 3-O-acetyl-oleanolic acid (77), and 3-O-acetyl-ursulic acid (78) were reported as triterpenoid compounds from a methanolic extract [33].…”