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ObjectiveThe antitumor activity of sesquiterpenoid M36 isolated from Myrrha against human hepatoma HepG2 cells was investigated in this study. MethodHepG2 cells were treated with M36 at different concentrations （0， 2， 4， 6， 8， 10 μmol·L-1）. Firstly， the effects of M36 on the proliferation of human hepatoma HepG2 cells were detected by methyl thiazolyl tetrazolium （MTT）， colony formation assay， and EdU proliferation assay. Hoechst staining， flow cytometry analysis， and Western blot were used to explore the effect of M36 on the apoptosis of human hepatoma HepG2 cells. Acridine orange staining and western blotting were used to examine the effect of M36 on autophagy in HepG2 cells. Finally， Western blot was used to detect protein expression of cancer-related signaling pathways. ResultCompared with the blank group， M36 treatment significantly inhibited the proliferation of human hepatoma HepG2 cells （P<0.01）， and the half inhibitory concentration （IC50） value of M36 for 48 h was 5.03 μmol·L-1， in a dose- and time-dependent manner. M36 was also able to induce apoptosis and autophagy in human hepatoma HepG2 cells. After treatment with 8 μmol·L-1 M36 for 48 hours， the apoptosis rate of HepG2 cells was （42.03±9.65）% （P<0.01）. Compared with the blank group， HepG2 cells treated with 4 and 8 μmol·L-1 M36 for 48 h had a significant increase in cleaved poly ADP-ribose polymerase （cleaved-PARP） protein levels （P<0.01）. Acridine orange staining showed that autophagy was significantly activated in HepG2 cells treated with 4 and 8 μmol·L-1 M36 for 48 h compared with the blank group （P<0.01）， which was further verified by the up-regulation of microtubule-associated protein 1 light chain 3 Ⅱ （LC3 Ⅱ）. Western blot results showed that compared with the blank group， the levels of phosphorylated extracellular regulated protein kinase （p-ERK）， phosphorylated p38 mitogen-activated protein kinase （p-p38 MAPK）， phosphorylated c-Jun N-terminal kinase （p-JNK）， and its downstream nuclear transcription factors c-Jun and p-c-Jun protein were significantly increased in M36 group （P<0.05， P<0.01）. The mechanism may be related to the up-regulation of MAPK signaling pathway. ConclusionThe sesquiterpenoid M36 isolated from Myrrha inhibits the proliferation of human hepatoma HepG2 cells and promotes apoptosis and autophagy， which may be related to the activation of the MAPK signaling pathway.
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This paper summarized professor ZHANG Boli's experience in treating stubborn bi （痹） with the herbal pair of Ruxiang （Olibanum）- Moyao （Myrrha）. The basic pathogenesis of stubborn bi is channel and collateral stasis and obstruction. Ruxiang and Moyao are thus used in mutual reinforcement to rectify qi and diffuse bi， activate blood and relieve pain， thereby removing static and obstructed qi and blood， unblocking the obstructed channels and colla-terals， which is especially suitable for stubborn bi caused by channel and collateral obstruction. In clinical practice， the herbal pair of Ruxiang-Moyao is used together with qi-moving and blood-activating medicinals to treat chest bi by expelling stasis and diffusing stagnation， dissipating cold and unblocking vessels. To treat long-term wither and weakness in late stage of stroke， the medicinals of boosting qi and invigorating blood， unblocking channels and venting collaterals can be added to the herbal pair so as to soothe and drain vessels and collaterals， harmonize and regulate qi and blood. Simiao Yongan Decoction （四妙勇安汤） can be integrated in the treatment of vessel bi by moving qi and dissolving stasis， and for the long-term stubborn vessel bi， integrated internal and external treatment is suggested by external use of Ruxiang-Moyao to vent bi with aromatics. Moreover， it is emphasized to use the herbal pair of Ruxiang-Moyao in accordance with indications and cautions.
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Objective:To distinguish the differences between Olibanum and Myrrha by using modern analytical methods such as Differential Scanning Calorimeter (DSC) and Fourier Transform InfraRed (FT-IR). Methods:By collecting Olibanum and Myrrha in different growing areas and different processed prosecures, this paper to analizes the influence of temperature increase and its speed , as well as the particle size on the DSC experiment. The DSC method was used to perform a differential thermal map of Olibanum and Myrrha scanning and analysis; FT-IR was used to scan and analyze 20 batches of Olibanum and Myrrha. Results:TThe results of DSC analysis showed that the DSC experimental condition ranged between 30-600 ℃; the speed of temperature increase was 30 ℃/min; the particle size was 100 mesh. The DSC spectra of of Olibanum and Myrrha were significantly different. Only the processed products of frankincense had endothermic peak near 297 ℃, and there was no characteristic peak in this temperature range. Their exothermic peaks are close at 326 ℃, but their enthalpy values are quite different. The position of endothermic peak near 100 ℃ is close to the size of peak shape. FT-IR test showed that the absorption peaks of Olibanum and Myrrha at wave numbers 2 925, 1 710, 1 454, 1 371, 1 242, 1 029 cm -1 appeared, and the positions of strong peaks were also similar. The intensity of the characteristic peak of Myrrha wave number 1 029 cm -1 is greater than that of Olibanum. Conclusion:The DSC spectra of Olibanum and Myrrha are significantly different, and the difference between the two FT-IR spectra is small. Differential scanning Calorimetry is an effective, fast, and simple way to identify resinous Chinese medicinal materials, and is worthy of further popularization.
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In order to provide the basis for the development of famous classical formulas containing Myrrha， the name， origin， quality evaluation， harvest and processing of Myrrha were systematically researched by consulting the ancient herbal and medical books， combining with the modern related literature. According to textual research， the results showed that Commiphora myrrha was the main base in ancient times， which was produced in Somalia， Ethiopia and northern Kenya. In addition， raw and fried products of Myrrha were the commonly used specifications in ancient herbal medicine， which are still used today. Nowadays， Myrrha， fried Myrrha and vinegar-processed Myrrha were the commonly used specifications. Among the three specifications， Myrrha is the raw products after cleaning， fried Myrrha is a kind of processed products， which has relevant records in ancient materia medica and is still used today. Vinegar-processed Myrrha is a new processing specification in modern times. Based on the research results， it is suggested that Myrrha in Shentong Zhuyutang should be the purified raw Myrrha in accordance with the 2020 edition of Chinese Pharmacopoeia.
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Five cadinane-type sesquiterpenoids were isolated from the n-hexane extract of Commiphora myrrha by using various chromatographic techniques, including silica gel, ODS and semi-preparative HPLC. Their structures were identified by physicochemical properties and spectroscopic data. These compounds were defined as (3S,4R)-3,9-dimethoxymyrrhone (1), 9-methoxymyrrhone (2), myrrhone (3), commiterpene B (4) and comosone Ⅱ (5). Compound 1 is a new compound, of which the absolute configuration was established by single crystal X-ray crystallographic analysis. Compound 5 is firstly isolated from the Commiphora genus.
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Two terpenes, 3-keto-tirucalla-8,24-dien-21-oic acid(KTDA) and 2-methoxy-5-acetoxy-furanogermacr-1(10)-en-6-one(FSA), are isolated from Olibanum and Myrrha respectively, which are characterized by high yield and easy crystallization during the preparation. The present study explored the regulatory targets and anti-inflammatory mechanism of KTDA and FSA based on network pharmacology and cell viability assay. First, the drug-likeness of KTDA and FSA was predicted by Swiss ADME. The target prediction of active components was carried out by Swiss Target Prediction and Pharmmapper. TTD, Drug Bank, and Gene Cards were searched for inflammation-related target genes of KTDA and FSA. Protein-protein interaction(PPI) analysis was performed on the inflammatory targets of KTDA and FSA by STRING, and Cytoscape was used to conduct topological analysis of the interaction results and construct the PPI network. GO function and KEGG pathway enrichment analyses of inflammatory targets of KTDA and FSA were carried out by DAVID, and a " component-target-pathway" network was constructed. Finally, lipopolysaccharide(LPS)-induced RAW264. 7 cells were treated with KTDA and FSA at different concentrations, and nitric oxide(NO) concentration and protein and m RNA expression levels were detected. The results showed that both KTDA and FSA showed good drug-likeness. A total of 157 and 142 inflammation-related targets of KTDA and FSA were screened out. PPI network analysis showed that MAPK1, AKT1, MAPK8, PIK3 CA,PIK3 R1, EGFR, etc. might be the key proteins for the anti-inflammatory effect. PI3 K/AKT and MAPK signaling pathways were obtained by KEGG and GO-BP enrichment. Cell experiment results showed that KTDA and FSA could exert anti-inflammatory effects by inhibiting NO production, reducing the phosphorylation levels of JNK, p38, and AKT proteins, and down-regulating the m RNA expression of interleukin(IL)-1β and IL-6. Meanwhile, FSA could also inhibit ERK phosphorylation. The results indicated that KTDA and FSA had significant anti-inflammatory activity, which provided a scientific basis and important support for the further research,development, and utilization of Olibanum and Myrrha.
Subject(s)
Animals , Ants , Drugs, Chinese Herbal/pharmacology , Frankincense , Lipopolysaccharides , Molecular Docking Simulation , Network PharmacologyABSTRACT
In this paper, network pharmacology method and molecular docking technique were used to investigate the target genes of Olibanum and Myrrha compatibility and the possible mechanism of action in the treatment of rheumatoid arthritis(RA). Our team obtained the main active components of Olibanum-Myrrha based on literatures study, relevant traditional Chinese medicine systematic pharmacological databases and literature retrieval, and made target prediction of the active components through SwissTargetPrediction database. At the same time, RA-related targets were collected through DrugBank, GeneCards and Therapeutic Target Database(TDD) databases; and VENNY 2.1 was use to collect intersection targets to map common targets of drug and disease of Venn diagram online. The team used STRING database to construct PPI protein interaction network diagram, and screen out core targets according to the size of the interaction, and Cytoscape 3.6.0 software was used to construct network models of "traditional Chinese medicine-component-target" "traditional Chinese medicine-component-target-disease" and core target interaction network model. The intersection target was analyzed by using DAVID 6.8 online database for GO function analysis and KEGG pathway enrichment analysis, and Pathon was used to visualization. AutoDock Vina and Pymol were used to connect the core active components with the core targets. Sixteen active components of Olibanum-Myrrha pairs were found and collected in the laboratory, and 320 relevant potential targets, 468 RA-related targets and 62 intersection targets were obtained through the Venn diagram. It mainly acted on multiple targets, such as IL6, TNF, IL1 B and MAPK1, involving TNF signaling pathway and Toll-like receptor signaling pathway in RA treatment. Finally, in this study, possible targets and signaling pathways of Olibanum-Myrrha compatibility therapy for RA were discussed, and molecular docking between core targets and core active components was conducted, which could provide scientific basis for the study on the mechanism of Olibanum-Myrrha compatibility.
Subject(s)
Humans , Arthritis, Rheumatoid/genetics , Drugs, Chinese Herbal , Frankincense , Medicine, Chinese Traditional , Molecular Docking SimulationABSTRACT
Objective: To study the chemical constituents from Myrrha. Methods: The compounds were isolated and purified by column chromatography over silica gel, Sephadex LH-20, RP-ODS and preparative RP-HPLC. Their structures were elucidated by physicochemical properties and spectral analyses. Results: Ten sesquiterpenes were isolated and identified as 11-methoxyl- guaia-6,10-dien-4α-ol (1), (1R,4S,5R,10R)-isodauc-6-en-10,14-diol (2), 10α-hydroxy-isodauc-6-en-14-al (3), guaia-6,10-dien- 4α,11-diol (4), orientalol B (5), (1S,4R,5R,10S)-isodauc-6-en-10,14-diol (6), (1S,4S,5R,10S)- isodauc-6-en-10,14-diol (7), alismanoid C (8), guaiandiol (9) and canangaterpene VI (10). Conclusion: Compound 1 is a new compound, named as commiphorol A and compounds 2-10 are isolated from the genus for the first time.
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OBJECTIVE@#To investigate the efficacy of frankincense and myrrha in the treatment of acute interstitial cystitis/painful bladder syndrome (IC/PBS).@*METHODS@#The effects of frankincense and myrrha on the proliferation and migration of primary human urothelial cells (HUCs) were assessed in vitro. In the animal study, 48 virgin female rats were randomized into 4 groups (12 in each group): (1) control group (saline-injected control); (2) cyclophosphamide (CYP) group (intraperitoneal injected 150 mg/kg CYP); (3) CYP + pentosan polysulfate sodium group (orally received 50 mg/kg pentosan polysulfate sodium); and (4) CYP + frankincense and myrrha group [orally received frankincense (200 mg/kg) and myrrha (200 mg/kg)]. Rats orally received pentosan polysulfate sodium or frankincense and myrrha on day 1, 2, and 3. The experiments were performed on day 4. Pain and cystometry assessment behavior test were performed. Voiding interval values were assessed in rats under anesthesia. Finally, immunohistochemistry and Western blot were used to confirm the location and level, respectively, of cell junction-associated protein zonula occludens-2 (ZO-2) expression.@*RESULTS@#Low dose frankincense and myrrha increased cell proliferation and migration in HUCs compared with control (P<0.05). Rats with acute IC/PBS rats exhibited lower voiding interval values, pain tolerance, and ZO-2 expression (P<0.05). Voiding interval values and pain tolerance were higher in the frankincense and myrrha group than CYP group (P<0.05). ZO-2 expression in the bladder was increased in the CYP + pentosan polysulfate and frankincense + myrrha groups compared with the CYP-induced acute IC/PBS group (P<0.05).@*CONCLUSION@#frankincense and myrrha modulate urothelial wound healing, which ameliorates typical features of acute IC/PBS in rats.
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Objective: To study the chemical constituents of Myrrha and their antitumor activities. Methods: The constituents were isolated and purified by recrystallization, and open silica gel, Sephadex LH-20, ODS column chromatography, as well as preparative HPLC. The structures were elucidated based on the chemical and spectroscopic methods. Furthermore, the cytotoxicities of these chemical components against PC-3 cell lines were measured by MTT method. Results: Eleven compounds were obtained from the chloroform extract of myrrh, and were established as (4α,11α)-2-oxo-8,11-dihydroxycadina-1(6),7,9-trien-12-oic acid γ-lactone (1), (4α,11β)-2-oxo-8,11-dihydroxycadina-1(6),7,9-trien-12-oic acid γ-lactone (2), dihydropyrocurzerenone (3), orientalol E (4), guaianediol (5), cryptomeridiol (6), cycloartane-1α,2α,3β,25-tetrol (7), cycloartan-24-ene-1α,2α,3β-triol (8), cycloartan-24-ene-1α,3β-diol (9), 29-norlanost-8,24-dien-1α,2α,3β-triol (10), and octadecane-1,2S,3S,4R-tetrol-1-O-α-L-rhamnopyranoside (11). Conclusion: Compounds 1 and 2 are two new compounds named as (+)-myrrhalactone A and (-)-myrrhalactone A, respectively. Compounds 4 and 6 are isolated from the genus Commiphora Engl. for the first time. Compounds 8, 10, and 11 show moderate cyctotoxic activity against PC-3 cell lines.
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There are many plants used by tribunal people as an anti bacterial, among them myrrh is the one which is commonly used. Myrrh is an oleo gum resin obtained from the plant Commiphora myrrha belongs to the family Burceraceae. It can adhere to intestines because of its resinous nature and it reduces the acidity in small intestines. Generally, the resin is collected from bark and stem of the plant by the process incision. In present study ethyl acetate extract of Commiphora myrrha was used for the evaluation of Anti bacterial activity against three Gram negative organisms and two Gram positive organisms. The method used in evaluation of Anti bacterial activity was serial dilution and Agar Diffusion method. The antibacterial activity was calculated in terms of minimum inhibitory concentration (MIC) and minimum bacterial concentration (MBC). The antibacterial activity was compared with marketed antibiotic.
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Objective: To investigate the chemical constituents from the resin of Commiphora mukul. Methods: Silica gel and Sephadex LH-20 column chromatographies were used for the purification, and spectroscopic techniques were adopted for the structure elucidation. Results: Two germacrane-type sesquiterpenoids have been isolated from the resin of C. mukul, which were identified to be 1α, 8α, 12α-trihydroxy-2β-methoxy-8, 12-epoxygermacra-7(11), 9-dien-6-one (1) and 1α, 8β, 12α-trihydroxy-2β-methoxy-8, 12- epoxygermacra-7(11), 9-dien-6-one (2). Conclusion: These two sesquiterpenoids are new compounds named as mukulsin A (1) and mukulsin B (2), respectively.
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OBJECTIVE:To provide references for the further study of myrrha.METHODS:The chemical components of myrrha extractives exteracted by super-borderline CO 2 extraction method,soxhlet extraction method,supersound extraction method and water vapor distillation method were analyzed comparatively by GC-MS.RESULTS:The components of extrac?tives extracted by different ways were very different,with more chemical compositions and more varieties in the super-bor?derline CO 2 extractives-there were great amount of resin besides volatile oil;high temperature and organic solvents residual could be avoided in the extracting process by super-borderline CO 2 extraction method.CONCLUSION:Super-borderline CO 2 extraction method was initially assessed to be a suitable extraction method of myrrha.
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AIM: To optimize the extraction process of Myrrha by SFE-CO 2. METHODS: Orthogonal design was applied and GC was used to determine the contents of ?-Elemene in order to optimize the process. RESULTS: The optimized conditions were as follows: pressure 25 MPa, temperature 45 ?C and extraction time 4 h. CONCLUSION: The method of SFE-CO 2 is rapid, convenient in comparison with conventional methods.