Article

Lipoxygenase inhibitory activity of crude bark extracts and isolated compounds from Commiphora berryi

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  • Anna University, BIT Campus, Tiruchirappalli
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Abstract

Commiphora berryi is traditionally used for the treatment of cold and fever as well as for wound healing in the southern parts of India. The present study was designed to investigate in vitro soybean lipoxygenase inhibitory activity of crude extracts and compounds isolated from Commiphora berryi. The bark of Commiphora berryi was extracted with different organic solvents and subjected to chromatographic separation for isolation of bioactive compounds. Structures of isolated compounds were elucidated by spectroscopic methods. The anti-inflammatory activity of bark extracts and bioactive compounds were assessed by in vitro soybean lipoxygenase (SBL) assay. 3β-Hydroxyglutin-5-ene (1), friedelin (2), cycloeucaneol (3) nimbiol (4), sugiol (5), surianol (6), daucosterol (7) and ursolic acid (8) were isolated from crude bark extracts of the Commiphora berryi. The structure of nimbiol (4) was also confirmed by single crystal X-ray analysis. The petroleum ether, methanol, chloroform and ethyl acetate extracts of bark of Commiphora berryi showed SBL inhibitory activity with the IC(50) values of 15.3, 54.2, 71.5 and 87.8 μg/ml respectively. Among all the isolates, friedelin (2) showed significant SBL inhibitory activity with IC(50) 35.8 μM. The overall results provide evidence that the studied plant might be a potential source of anti-inflammatory agents.

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... The third groups of LOX inhibitors in this family are the bornyl cinnamoyl derivatives from Verbenisa species, such as bornyl caffeate from the South American herb Verbenisa turbacensis Kunth. Another compound, friedelin isolated from the bark of Commiphora berryi showed significant soybean lipoxygenase (SBL) inhibitory activity with IC 50 of 35.8μM (Kumari et al., 2011). Generally, an enormous number of different plant-derived compounds from various species have been found to interfere with 5-LOX activities. ...
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The authors have previously isolated and purified ursolic acid from heather flowers (Calluna vulgarts). This terpene was found to inhibit HL-60 leukaemic cell proliferation and arachidonic acid oxidative metabolism in various cell species. The effects of ursolic acid and its analogues on soybean 15-lipoxygenase activity and on the proliferation of a human gastric tumour cell line (HGT), have been assessed. These triterpenes inhibited soybean 15-lipoxygenase at its optimal activity (pH 9). The proliferation ofHGT was decreased in a dose-dependent manner. At 20 muM the rank order is: ursolic acid > uvaol > oleanolic acid > methyl ursolate. The carboxylic group at the C(28) position of ursolic acid appears to be implicated in the inhibition of both lipoxygenase activity and cell proliferation. Thus methylation of this group decreases these two inhibitory properties. Oleanolic acid, which differs by the position of one methyl group (C(20) instead of C(19)) is less inhibitory than ursolic acid. The lipophilicity of the terpene is also implicated since uvaol appears to be more inhibitory than methyl ursolate.
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A series of polymethoxylated flavonoids has been isolated from orange peel, and their inhibitory activity toward soybean 15-lipoxygenase was determined. The strongest inhibition was shown by 3,5,6,7,3‘,4‘-hexamethoxyflavone (IC50 = 49 ± 5 μM). Sinensetin, nobiletin, tangeretin, tetramethylscutellarein, and 3,5,6,7,8,3‘,4‘-heptamethoxyflavone were somewhat less active, with IC50 values of 70−86 μM, comparable to the positive control quercetin (IC50 = 68 ± 5 μM). Demethylation apparently results in less active compounds, with 5-O-demethylsinensetin having an IC50 value of 144 ± 10 μM. Some other orange peel constituents were isolated and tested as well, hesperidin (IC50 = 180 ± 10 μM) and ferulic acid (111 ± 2 μM), showing moderate activity. The polymethoxylated flavonoids were virtually inactive as scavengers of the diphenylpicrylhydrazyl radical. Hesperidin was only slightly active (24.2 ± 0.7% scavenged at a concentration of 2 mM), and ferulic acid showed good activity (IC50 = 86.4 ± 0.7 μM). From this, it appears that orange peel constituents may counteract enzymatic lipid peroxidation processes catalyzed by 15-lipoxygenase in vitro. The radical scavenging activity of orange peel extracts is only modest.
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Complete assignments of 1H and 13C NMR chemical shifts for oleanolic acid, 18α-oleanolic acid, ursolic acid and their 11-oxo derivatives based on 1H, 13C, 2D DQF-COSY, NOESY, HSQC, HMBC and HSQC-TOCSY experiments were achieved. Copyright © 2003 John Wiley & Sons, Ltd.
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N. Y. Lee and M. F. Lee [Appl. Math. Comput. 157, No. 3, 729–733 (2004; Zbl 1060.94035)] recently pointed out that the C. L. Hsu, T. S. Wu. T. C. Wu and C. Mitchell [Appl. Math. Comput. 142, No. 2–3, 305–308 (2003; Zbl 1026.94009)] authenticated key agreement scheme is vulnerable to the modification attack and further proposed an improvement of Hsu et al. However, this work shows that Lee and Lee scheme is vulnerable to the man-in-the-middle attack. A slight improvement to their scheme is proposed to overcome this weakness.
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Ten South African Commiphora (Burseraceae) species were investigated to validate their use in traditional healing rites. The leaf and stem extracts of each species were analysed for the anti-oxidant (ABTS and DPPH assays), antimicrobial (MIC and death kinetic assays), anti-inflammatory (5-LOX assay), anticancer (SRB assay) properties, as well as the cytotoxic effects (tetrazolium-based assay). The best anti-oxidant activity (ABTS assay) was observed for the stem extracts of Commiphora tenuipetiolata IC(50)=5.10 microg/ml), Commiphora neglecta (IC(50)=7.28 microg/ml) and Commiphora mollis (IC(50)=8.82 microg/ml). Extracts generally exhibited poor anti-oxidant activity in the DPPH assay, with the exception of Commiphora schimperi (stem), Commiphora neglecta (stem), Commiphora tenuipetiolata (stem and leaf), and Commiphora edulis (stem), with IC(50) values ranging between 7.31 and 10.81 microg/ml. The stem extracts exhibited moderate to good 5-LOX inhibitory activity with Commiphora pyracanthoides (stem) displaying the greatest inhibitory effect (IC(50)=27.86+/-4.45 microg/ml). For the antimicrobial (MIC) assay, a greater selectivity was exhibited by the extracts against the Gram-positive bacteria (0.01-8.00 mg/ml) and the yeasts (0.25-8.00 mg/ml) than against the Gram-negative bacteria (1.00-8.00 mg/ml). Using death kinetic studies (time-kill studies), the rate at which Commiphora marlothii (stem) kills Staphylococcus aureus over a 24h period was determined. Mostly, a concentration-dependent antibacterial activity was observed beginning after ca. 30 min. All concentrations exhibited antibacterial activity, with complete bactericidal effect achieved by the 24(th) hour. The most active Commiphora species against the HT-29 cells (SRB anticancer assay) were Commiphora glandulosa (leaf and stem) and Commiphora marlothii (leaf). The MCF-7 cells (SRB anticancer assay) exhibited the highest sensitivity to indigenous Commiphora species, with Commiphora edulis (leaf and stem), Commiphora glandulosa (leaf and stem), Commiphora marlothii (leaf), Commiphora pyracanthoides (leaf and stem), Commiphora schimperi (stem), and Commiphora viminea (stem) all possessing a percentage inhibition greater than 80% at 100 microg/ml. Commiphora glandulosa (leaf and stem) and Commiphora pyracanthoides (leaf and stem) were the two most active species against the SF-268 cells (SRB anticancer assay), with IC(50) values ranging between 68.55+/-2.01 and 71.45+/-1.24 microg/ml. The majority of the Commiphora extracts were largely non-cytotoxic against Graham human kidney epithelial cells when investigated in the MTT assay.
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Oxidative damage is involved in the pathogenesis of various hepatic injuries. In the present study the capacity of Commiphora berryi (Arn) Engl bark as an antioxidant to protect against CCl(4)-induced oxidative stress and hepatotoxicity in Albino Wistar rats was investigated. Intraperitoneal injection of CCl(4), administered twice a week, produced a marked elevation in the serum levels of aspartate transaminase, alanine transaminase, alkaline phosphatase and bilirubin. Histopathological analysis of the liver of CCl(4)-induced rats revealed marked liver cell necrosis with inflammatory collections that were conformed to increase in the levels of SOD, GPx and CAT. Daily oral administration of methanolic extract of C. berryi (Arn) Engl bark at 100 and 200mg/kg doses for 15 days produced a dose-dependent reduction in the serum levels of liver enzymes. Treatment with C. berryi normalized various biochemical parameters of oxidative stress and was compared with standard Silymarin. Therefore, the results of this study show that C. berryi (Arn) Engl bark can be proposed to protect the liver against CCl(4)-induced oxidative damage in rats, and the hepatoprotective effect might be correlated with its antioxidant and free radical scavenger effects.
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Eighteen known nonsteroidal antiinflammatory drugs (NSAID) were tested for their action against soybean lipoxygenase (E.C.1.13.11.12) using linoleic acid as substrate. It was found that the best inhibitors of lipoxygenase were naproxen, BW 755C, indomethacin and isoxicam. Drugs with intermediate potency were meclofenamic acid, phenylbutazone and benoxaprofen. Other drugs such as ibuprofen and zomepirac were only weakly active in the test.
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Soybean lipoxygenase inhibition has been proposed as an in vitro biochemical model for the antiinflammatory action of certain drugs used in the treatment of ulcerative colitis. In an extension of a recent study which showed that therapeutically active compounds, such as sulphasalazine and its colonic metabolite 5-aminosalicylic acid were soybean lipoxygenase inhibitors, it has now been shown that N-acetylaminosalicylic acid, the principal metabolite of 5-aminosalicylic acid, also inhibits soybean lipoxygenase in a dose dependent and noncompetitive manner (Ki 3.0 X 10(-8) M, IC50 250 microM). Sulphapyridine, the other major metabolite of sulphasalazine, which has been demonstrated to be inactive in the treatment of ulcerative colitis, did not inhibit the lipoxygenase activity. The findings further support the hypothesis that only the therapeutically active compounds are soybean lipoxygenase inhibitors.
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The Et2O-soluble fraction of the MeOH extract of the leaves of Aucuba japonica Thunb. showed an anti-inflammatory effect when topically applied to rats. E-Phytol, phytone, bis(2-ethylhexyl)phthalate and friedelin were isolated as active anti-inflammatory components inhibiting carrageenin-induced paw edema. The most effective, E-phytol, inhibited histamine-induced paw edema more potently than the compound 48/80-induced edema, suggesting that the mechanism of action is due to inhibition of the H1 receptor.
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1. 5-Lipoxygenase (5-LOX) products from endogenous arachidonic acid in ionophore-stimulated peritoneal polymorphonuclear leukocytes (PMNL) and from exogenous substrate (20 microM) in 105,000 g supernatants were measured. 2. The effects of natural pentacyclic triterpenes and their derivatives on 5-LOX activity were compared with the inhibitory action of acetyl-11-keto-beta-boswellic acid (AKBA), which has been previously shown to inhibit the 5-LOX by a selective, enzyme-directed, non-redox and non-competitive mechanism. 3. The 5-LOX inhibitory potency of AKBA was only slightly diminished by deacetylation of the acetoxy group or reduction of the carboxyl function to alcohol in intact cells (IC50 = 1.5 vs. 3 and 4.5 microM, respectively) and in the cell-free system (8 vs. 20 and 45 microM). 4. beta-Boswellic acid (beta-BA), lacking the 11-keto function, inhibited 5-LOX only partially and incompletely, whereas the corresponding alcohol from beta-BA, as well as amyrin, acetyl-11-keto-amyrin, 11-keto-beta-boswellic acid methyl ester had no 5-LOX inhibitory activity up to 50 microM in either system. 5. beta-BA only partially prevented the AKBA-induced 5-LOX inhibition, whereas the non-inhibitory compounds, amyrin and acetyl-11-keto-amyrin, almost totally antagonized the AKBA effect and shifted the concentration-inhibition curve for the incomplete inhibitor beta-BA to the right. In contrast, the non-inhibitory 11-keto-beta-BA methyl ester exerted no antagonizing effect. 6. The results demonstrate that the pentacyclic triterpene ring system is crucial for binding to the highly selective effector site, whereas functional groups (especially the 11-keto function in addition to a hydrophilic group on C4 of ring A) are essential for 5-LOX inhibitory activity.
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Mounting evidence suggests that lipoxygenase (LO)-catalyzed products have a profound influence on the development and progression of human cancers. Compared with normal tissues, significantly elevated levels of LO metabolites have been found in lung, prostate, breast, colon, and skin cancer cells, as well as in cells from patients with both acute and chronic leukemias. LO-mediated products elicit diverse biological activities needed for neoplastic cell growth, influencing growth factor and transcription factor activation, oncogene induction, stimulation of tumor cell adhesion, and regulation of apoptotic cell death. Agents that block LO-catalyzed activity may be effective in preventing cancer by interfering with signaling events needed for tumor growth. In fact, in a few studies, LO inhibitors have prevented carcinogen-induced lung adenomas and rat mammary gland cancers. During the past 10 years, pharmacological agents that specifically inhibit the LO-mediated signaling pathways are now commercially available to treat inflammatory diseases such as asthma, arthritis, and psoriasis. These well-characterized agents, representing two general drug effect mechanisms, are considered good candidates for clinical chemoprevention studies. One mechanism is inhibition of LO activity (5-LO and associated enzymes, or 12-LO); the second is leukotriene receptor antagonism. Although the receptor antagonists have high potential in treating asthma and other diseases where drug effects are clearly mediated by the leukotriene receptors, enzyme activity inhibitors may be better candidates for chemopreventive intervention, because inhibition of these enzymes directly reduces fatty acid metabolite production, with concomitant damping of the associated inflammatory, proliferative, and metastatic activities that contribute to carcinogenesis. However, because receptor antagonists have aerosol formulations and possible antiproliferative activity, they may also have potential, particularly in the lung, where topical application of such formulations is feasible.
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Diterpenes and phenolic acids, including the new compounds 12 beta-hydroxysandaracopimar-15-ene (4) and 2-propionoxy-beta-resorcylic acid (8) have been isolated from Trichilia heudelotti leaves. The methanol extract showed antimicrobial activity concentrated in the ethyl acetate fraction and some of its constituents.
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A series of polymethoxylated flavonoids has been isolated from orange peel, and their inhibitory activity toward soybean 15-lipoxygenase was determined. The strongest inhibition was shown by 3,5,6,7,3',4'-hexamethoxyflavone (IC(50) = 49 +/- 5 microM). Sinensetin, nobiletin, tangeretin, tetramethylscutellarein, and 3,5, 6,7,8,3',4'-heptamethoxyflavone were somewhat less active, with IC(50) values of 70-86 microM, comparable to the positive control quercetin (IC(50) = 68 +/- 5 microM). Demethylation apparently results in less active compounds, with 5-O-demethylsinensetin having an IC(50) value of 144 +/- 10 microM. Some other orange peel constituents were isolated and tested as well, hesperidin (IC(50) = 180 +/- 10 microM) and ferulic acid (111 +/- 2 microM), showing moderate activity. The polymethoxylated flavonoids were virtually inactive as scavengers of the diphenylpicrylhydrazyl radical. Hesperidin was only slightly active (24.2 +/- 0.7% scavenged at a concentration of 2 mM), and ferulic acid showed good activity (IC(50) = 86.4 +/- 0.7 microM). From this, it appears that orange peel constituents may counteract enzymatic lipid peroxidation processes catalyzed by 15-lipoxygenase in vitro. The radical scavenging activity of orange peel extracts is only modest.
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Lipoxygenase (LO) is a biological target for many diseases such as asthma, atherosclerosis, and cancer. Our labs have synthesized and investigated nordihydroguaiaretic acid (NDGA) derivatives and have established that the reductive inhibition of soybean and 15-human LO can be affected by the strength of the electron-withdrawing substituents on the phenyl rings of NDGA. In addition, we have determined that hydrophobic NDGA derivatives activate 15-HLO, suggesting a hydrophobic allosteric site.
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Three novel lipoxygenase inhibitors, tetrapetalone B (2, C(28)H(35)NO(9)), C (3, C(26)H(34)NO(8)), and D (4, C(28)H(36)NO(10)), were isolated from a culture broth of Streptomyces sp. USF-4727 that produced a lipoxygenase inhibitor tetrapetalone A (1) simultaneously. Each chemical structure was revealed by spectroscopic evidence, this suggests that these three compounds are structurally related to 1. They had a tetracyclic skeleton and a beta-D-rhodinosyl moiety. Tetrapetalone B, C, and D inhibited soybean lipoxygenase with IC(50): 320, 360, and 340 microM respectively.
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The chromatographic separation of the MeOH extract from the aerial parts of Syneilesis palmata led to the isolation of a new sesquiterpene glycoside 4, together with four known compounds. Their structures were characterized to be 4beta,5beta-epoxy-caryophill-8,(15)-ene (1), 3beta-hydroxy-gultin-5-ene (2), 4alpha,5beta-dihydroxy-caryophill-8,(15)-ene (3), (-)-oplopan-4-one-10-alpha-O-beta-D-glucose (4) and 3-hexenyl-1-O-beta-D-glucopyranose (5), based on spectroscopic and chemical methods. Compound 2 showed moderate cytotoxicity against five human tumor cell lines in vitro with its ED50 values ranging from 5.90 to approximately 10.83 microg/mL.
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Two new compounds, 24(E)-ethylidenecycloartanone (1) and 24(E)-ethylidenecycloartan-3alpha-ol (2) were isolated from the rhizomes of Polygonum bistorta, together with seven known compounds viz., cycloartane-3,24-dione (3), 24-methylenecycloartanone (4), gamma-sitosterol (5), beta-sitosterol (6), beta-sitosterone (7), friedelin (8) and 3beta-friedelinol (9). All the cycloartane type triterpenoids, compounds 7 and 8 are reported for the first time from this plant. A combination of 1D and 2D NMR spectroscopy and MS were mainly used to elucidate the structures of the new compounds 1 and 2.
Article
In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin D2 (PGD2) and leukotriene C4 (LTC4) in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with beta-sitosterol (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)-marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.
Article
We investigated the in vitro anti-inflammatory effects of Cinnamaldehyde, a cytokine production inhibitor isolated from an essential oil produced from the leaves of Cinnamomum osmophloeum Kaneh, and its mechanism of action. Although Cinnamaldehyde has been reported to have contact sensitizing properties at high concentration (mM), we found that low concentration of Cinnamaldehyde (muM) inhibited the secretion of interleukin-1beta and tumor necrosis factor alpha within lipopolysaccharide (LPS) or lipoteichoic acid (LTA) stimulated murine J774A.1 macrophages. Cinnamaldehyde also suppressed the production of these cytokines from LPS stimulated human blood monocytes derived primary macrophages and human THP-1 monocytes. Furthermore, Cinnamaldehyde also inhibited the production of prointerleukin-1beta within LPS or LTA stimulated human THP-1 monocytes. Reactive oxygen species release from LPS stimulated J774A.1 macrophages was reduced by Cinnamaldehyde. The phosphorylation of extracellular signal-regulated kinase 1/2 and c-Jun N-terminal kinase 1/2 induced by LPS was also inhibited by Cinnamaldehyde; however, Cinnamaldehyde neither antagonize the binding of LPS to the cells nor alter the cell surface expression of toll-like receptor 4 and CD14. In addition, we also noted that Cinnamaldehyde appeared to elicit no cytotoxic effect upon J774A.1 macrophages under our experimental conditions, although Cinnamaldehyde reduced J774A.1 macrophages proliferation as analysed by MTT assay. Our current results have demonstrated the anti-oxidation and anti-inflammatory properties of Cinnamaldehyde that could provide the possibility for Cinnamaldehyde's future pharmaceutical application in the realm of immuno-modulation.
Phytochemical methods
  • J B Harborne
Harborne, J.B.,1998. Phytochemical methods. In: Methods of Extraction and Isolation. Chapman & Hall, London.
Constituents and anti-inflammatory effect of Aoki
  • M Shimizu
  • T Tomoo
Shimizu, M., Tomoo, T., 1994. Constituents and anti-inflammatory effect of Aoki, Aucuba japonica Thunb. Biological Pharmaceutical Bulletin 17, 665-667.