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Eight new cembrane-type diterpenoids, boscartins AH–AK (1–8), along with two known ones (9-10), were isolated from the gum resin of Boswellia carterii. Compounds 1–3 were characteristic of high oxidation assignable to three epoxy groups, while compounds 4–8 were characteristic of two epoxy groups. Spectroscopic examination was used to elucidate the...
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ABSTRACT
Introduction
Frankincense (Boswellia sp.) gum resins have been employed as an incense in cultural and religious ceremonies for many years. Frankincense resin has over the years been employed to treat depression, inflammation, and cancer in traditional medicines.
Areas covered
This inclusive review focuses on the significance of frankincens...
Citations
... AKBA also chemosensitized cancer cells toward cisplatin and gemcitabine treatment (79,82). Compounds other than AKBA have been investigated, but their anti-proliferative properties have been studied at higher concentrations, making them less effective (79,(84)(85). Boswellia extracts and isolated components, especially AKBA, are also able to inhibit tumor growth in vivo (79). This activity is principally reported in glioblastoma, but experimental data indicate promising effects for cancers. ...
... The larvicidal activity of monoterpenes against certain mosquito species (Gad et al., 2022), including toxic effects on A. aegypti (Giang An et al., 2020) and antioviposition effects on A. aegypti (Waliwitiya et al., 2009), has also been reported. It has been observed that monoterpenes and terpenoids are efficient acetylcholinesterase enzyme inhibitors in different insects and larvae (Waliwitiya et al., 2009), whereas diterpenes like Cembrene have antifeed activity against herbivores (Sun et al., 2019). ...
Aedes mosquitoes are the major cause of several vector-borne diseases in tropical and subtropical regions. Synthetic pesticides against these mosquitoes have certain limitations; hence, natural, eco-friendly, and safe larvicides obtained from plant resources are used to overcome these. In the present study, the larvicidal efficiency of Commiphora wightii against the fourth instar stage of the dengue fever mosquito Aedes aegypti (Linnaeus, 1762) was studied. The gum resin of C. wightii was collected using the borehole tapping method, and hexane extracts in different concentrations were prepared. The fourth-instar larvae were exposed to the extracts, and percent mortality, as well as LC20, LC50, and LC90, was calculated. Volatile compounds of the hexane gum extract were analyzed by Headspace GC/MS, and the sequence of the acetylcholine, Gamma-aminobutyric acid (GABA) receptor, and octopamine receptor subunit of A. aegypti was obtained. It was found that the hexane gum extract was toxic and lethal for larvae at different concentrations. Minimum mortality was observed at 164 µg mL⁻¹ (10%/h), while maximum mortality was at 276 µg mL⁻¹ (50%/h). The lethal concentrations LC20, LC50, and LC90 were 197.38 µg mL⁻¹, 294.13 µg mL⁻¹, and 540.15 µg mL⁻¹, respectively. The GC/MS analysis confirmed the presence of diterpenes, monoterpenes, monoterpene alcohol, and sesquiterpenes in the gum samples, which are lethal for larvae due to their inhibitory activity on the acetylcholinesterase enzyme, GABA receptor, and octopamine receptor subunit. The use of commonly occurring plant gum for the control of mosquitoes was explored, and it was found that the gum of C. wightii had larvicidal activities and could be potentially insecticidal.
... 20 In another case, the main components of frankincense oil by steam distillation contains mono-, sesqui-, di-, and tri-terpenoids, with anti-inflammatory, cytotoxic, hepatoprotective, antibacterial, and antifungal activities. 21,22 However, the main components of FVO in this study are cembranetype diterpenoids. It mainly includes incensole, incensole oxide, acetate incensole, acetate incensole oxide, cembrene, cembrene A To understand its action mechanism, the top 20 hub genes were screened out by network pharmacology (Table S1) and its related receptor MC1R in keratinocytes. ...
Background:
Frankincense volatile oil (FVO) has long been considered a side product in pharmaceutical industry since frankincense of large molecular weight is the prime target. However, the volatile oil recycled in the extract process might contain a series of functional actives, serving as promising ingredients in the cosmetic field.
Methods:
Gas chromatography-mass spectrometer was utilized to determine the species and amount of active ingredients in FVO. Subsequently, zebrafish models were used to evaluate pigmentation inhibition, ROS elimination and neutrophil activation. In vitro DPPH test was also conducted to consolidate the anti-oxidation efficacy. Based on the test results, network pharmacology was incorporated, where GO and KEGG enrichment analyses were performed to discover the interrelations between active ingredients.
Results:
About 40 actives molecules were identified, including incensole, acetate incensole, and acetate incensole oxide. The FVO demonstrated great depigmentation activity by suppressing melanin synthesis, as well as providing free radical scavenging and anti-inflammation effect. In network pharmacology analysis, 192 intersected targets were identified. By enrichment analysis and network construction, a series of whitening signal pathways, and hub genes, containing STAT3，MAPK3，MAPK1 were identified.
Conclusion:
The current study quantified the components of FVO, evaluated its efficacy in skin depigmentation, and give pioneering insights on the possible mechanism. The results confirmed that the FVO could serve as whitening agent in topical uses.
... On the other hand, the same compound was the least active in terms of its hepatoprotective effects with cell viability rates of 44.0%. Moreover, compounds 28 and 29 displayed potent hepatoprotective effects with cell viability rates of 75.5% and 68.8% respectively [35]. Notably, these compounds have better hepatoprotective effects than the standard bicyclol (67.7%). ...
... Although compound 30, which is less active than compounds 28 and 29, also has one furan ring and two epoxide rings. However, this former compound (30) has the second epoxide ring at a different position compared to compounds 28 and 29 [35]. ...
ABSTRACT
Introduction
Frankincense (Boswellia sp.) gum resins have been employed as an incense in cultural and religious ceremonies for many years. Frankincense resin has over the years been employed to treat depression, inflammation, and cancer in traditional medicines.
Areas covered
This inclusive review focuses on the significance of frankincense diterpenoids, and in particular, incensole derivatives for establishment future treatments of depression, neurological disorders, and cancer. The authors survey the available literature and furnish an overview of future perspectives of these intriguing molecules.
Expert opinion
Numerous diterpenoids including cembrane, prenylaromadendrane, and the verticillane-type have been isolated from various Boswellia resins. Cembrane-type diterpenoids occupy a crucial position in pharmaceutical chemistry and related industries because of their intriguing biological and encouraging pharmacological potentials. Several cembranes have been reported to possess anti-Alzheimer, anti-inflammatory, hepatoprotective, and antimalarial effects along with a good possibility to treat anxiety and depression. Although some slight drawbacks of these compounds have been noted, including the selectivity of these diterpenoids, there is a great need to address these in future research endeavors. Moreover, it is vitally important for medicinal chemists to prepare libraries of incensole-heterocyclic analogs as well as hybrid compounds between incensole or its acetate and anti-depressant or anti-inflammatory drugs.
... The investigated gum resin of B. carterii Birdw. in this study was the same as used in our previous reports (Yu et al., 2018a, b;Sun et al., 2020). ...
... The pretreatment of the gum resin of B. carterii (6 Kg) was the same as that described in our previous reports (Yu et al., 2018a, b;Sun et al., 2020). Briefly, the gum resin was extracted firstly by 95 % EtOH to obtain the crude extracts, which were extracted subsequently with petroleum ether (PE), CH 2 Cl 2 , ethyl acetate (EtOAc), and n-BuOH to obtain parts of different polarities. ...
... Bioactivity assays of anti-inflammatory and hepatoprotective were carried out by experiment procedures reported previously in our research (Yu et al., 2018a, b;Sun et al., 2020). Briefly, as for the anti-inflammatory assay, LPS-induced RAW 264.7 cell model was treated with compounds 1-3, which were dissolved in DMSO and diluted to five concentrations of 1.25, 2.5, 5.0, 10.0, 20.0 μM with a Dulbecco's modified Eagle's medium (DMEM, HyClone, USA) supplemented with 10 % FBS (Gibco, USA), 100 μg/mL penicillin and 100 μg/mL streptomycin (Beyotime, China) and then the cell supernatants was taken and reacted with Griess reagents I and II (Beyotime, China) to measure the NO production. ...
Three undescribed cembrane type diterpenoids, boscartins AX-AZ (1-3) were discovered from the gum resin of Boswellia carterii. Their structures were elucidated by analyzing the spectroscopic data. Notably, all these three compounds preserved an isopropyl type cembranoid skeleton, featured the same groups of one epoxy ring at C1-C12 and one hydroxy group at C-11, as well as an epoxy ring migrating from C6-C7 to C3-C4. These cembranoids were evaluated for the hepatoprotective and anti-inflammatory activities using two cell models of APAP-induced HepG2 and LPS-induced RAW 264.7. Results showed that compound 1 displayed remarkable hepatoprotective activity at 10 μM (inhibition rate of 47.81 %) and significant anti-inflammatory activity (IC50 of 2.39 μM), with the other two compounds (2 and 3) giving less potently biological activities.
... However, the wrong structures of incensole (6) and incensole acetate (7) have resulted from the wrong configuration of 5-β-OH (Fig. 6) (J. Wang et al., 2019). ...
... It is interesting to mention that several cembranoids (such as boscartins AL-AO (67-70, 67A-70A) were also reported with the same names but with different structures (Table 2, Fig. 2) (Sun et al., 2019;Wang et al., 2020). ...
... Incensole (6) and incensole acetate (7) have been considered as the biogenetic precursors of various boscartin-type cembranoids (Schemes 4 and 5) (Sun et al., 2019;J. Wang et al., 2019). ...
Frankincense of Boswellia species has long been used in traditional medicines, mainly for its interesting anti-inflammatory and anti-depressant properties of its di- and triterpenes. Boswellic acids (triterpenes) and cembranoids (diterpenes) are the major constituents of frankincense from all reported species which are responsible for the overall biological activity of frankincense. Boswellic acids have been thoroughly investigated for decades but cembranoids have attracted considerable attention only recently, and a good number of publications have highlighted the important role of these 14-membered rings in contributing to the superior anti-inflammatory activity of the sacred resin. Partial and total syntheses of some cembranoids from frankincense have been reported. Their therapeutic potential is not limited to the well proven anti-inflammatory activity but also to their recently reported anti-depressant properties.
There is a considerable number of publications in the field of cembranoids of Boswellia species where we feel a review in this topic will be of interest to the readership of Phytochemistry. In this article we have discussed the chemistry (isolation and chemical structures as well as synthetic studies), biogenesis and bioactivity of the reported cembranoids of Boswellia species. The structural discrepancies due to wrongly assigned structures of some cembranoids have been highlighted and corrected. We have covered the related literature up to the end of 2020.
... (Al-Harrasi et al., 2019;Jiangsu New Medical College, 1977;Liu, 1999;Pharmacopia, 2015;Xiao et al., 2002). Previous phytochemical and pharmacological investigations of olibanum have revealed abundant quantities of triterpenoids, diterpenoids and prenylaromadendranoids as the dominant chemical constituents which display multiple intriguing bioactivities such as hepatoprotective, anti-inflammatory, antiulcerative colitis and antitumor activity (Ren et al., 2015;Wang et al., 2013Wang et al., , 2019aWang et al., , 2019bZhou and Cui, 2002;Yu et al., 2018;Corsano and Nicoletti, 1967;Sun et al., 2020). ...
Ten undescribed cembrane-type diterpenes boscartins AL-AU, as well as five known analogues were isolated from Boswellia sacra Flueck. The relative configurations of these boscartins were established by extensive spectroscopic analysis of NMR spectra, IR and MS. The absolute configurations of boscartin AL, boscartin AN and isoincensole oxide were unequivocally assigned by single crystal X-ray diffraction. Meanwhile, the absolute configurations of boscartin AM, boscartin AP and boscartin AQ were determined by an empirical in situ formed Rh-complex ECD method. Biological evaluations showed that four compounds exhibited obvious hepatoprotective activities against paracetamol-induced HepG2 cell damage at 10 μM. Regarding neuroprotective activity, some isolates displayed moderate to evident protective effects against glutamate-induced toxicity in primary cultured fetal rat cortical neurons or oxygen-glucose deprivation toxicity in SK-N-SH Cells at 10 μM.
... Baghel et al. (2012) found that kaempferol can control cancer, and quercetin showed antioxidant and anticarcinogenic activities. Sun et al. (2020) isolated a new eight active compounds from the gum resin of Boswellia carterii as mainly as cembrane-type diterpenoids and they found that these compounds have many activities like anti-inflammatory with (IC 50 of 14.8 µM), cytotoxic with (IC 50 > 100 µM), and hepatoprotective with (IC 50 > 30 µM). Alyahya & Asad (2020) found that Boswellia sacra extract does not possess any toxic effect on the testis, revealed its antioxidant potential that may protect testes against the effect of toxicants. ...
The discovery of novel antitumor agents derived from natural plants is a principal objective of anticancer drug research. Frankincense, a widely recognized natural antitumor medicine, has undergone a systematic review encompassing its species, chemical constituents, and diverse pharmacological activities and mechanisms. The different species of frankincense include Boswellia serrata, Somali frankincense, Boswellia frereana, and Boswellia arabica. Various frankincense extracts and compounds exhibit antitumor, anti-inflammatory, and hepatoprotective properties and antioxidation, memory enhancement, and immunological regulation capabilities. They also have comprehensive effects on regulating flora. Frankincense and its principal chemical constituents have demonstrated promising chemoprophylactic and therapeutic abilities against tumors. This review provides a systematic summary of the mechanism of action underlying the antitumor effects of frankincense and its major constituents, thus laying the foundations for developing effective tumor-combating targets.
This review explores medicinal plant resin natural products from six genera, encompassing 1115 structures and their biological activities, offering insights into the chemical and biological profiling of plant resins produced under various stress.
