Coventry, RI, United States
Coventry, RI, United States

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A wide variety of compounds present in spices that are extensively used as food seasoning agents possess potent antioxidant, antiinflammatory, antimutagenic, and cancer preventive activities. Turmeric (Curcuma longa) and ginger (Zingiber officinale) are rhizomes and they originate from the same family, Zingiberaceae. These two major natural products are known to have a variety of medicinal and biological properties. This review is a closer look at the structural parameters of the active compounds present in these two natural products that lead to common biological properties. The volatile oils and the nonvolatile oleoresins are the chief source for these active ingredients. The rhizomes of turmeric and ginger contain pungent vanillyl ketones and have been reported to possess strong antiinflammatory activity. The chemical composition of the components is similar yet different and shares a number of biological properties. The constituents of turmeric oil (TO) and ginger oil (GO) have sesquiterpene hydrocarbons and oxygenated sesquiterpenes. GO displays considerable diversity, yet it comprises of mostly sesquiterpenes such as zingiberene, ar-curcumene, β-bisabolene, and β-sesquiphellandrene. Many of these are in common with TO even though the major constituents in TO consist of turmerones. The common structural aspects will be discussed and this will also shed light in to the common biological properties. The oleoresins of turmeric and ginger containing the nonvolatile fractions consist of polyphenols. Wide arrays of phenolic substances in these natural products have been reported to possess substantial anticarcinogenic and antimutagenic activities along with antioxidative and antiinflammatory properties which appear to contribute to their chemopreventive or chemoprotective activity. Curcuminoids in turmeric contain curcumin, demethoxy curcumin, and bis-demethoxy curcumin. The active compounds in ginger are gingerols, shogaols, and zingerones. It was shown that 6-, 8-, and 10-gingerols and [6]-shogaol showed efficacy in antiinflammatory, antibacterial, antipyretic, antilipidemic, antitumorigenic, and antiangiogenic effects. They have structural similarities with curcuminoids which result in common biological properties and mechanism of action. The structural similarities and differences of these compounds will be discussed in relation to the biological and medicinal properties. Cyclo-oxygenase-2 is regulated by the eukaryotic transcription factor nuclear factor κB and it has been recognized as a molecular target of many antiinflammatory agents. This review will examine the molecular mechanisms underlying biological effects of the active compounds in these natural products in terms of their effects on intracellular signaling cascades. The structural correlation and biochemical properties of these compounds will help the design and development of drug targets and lead compounds for new drug discovery. © 2016 Elsevier B.V.


Jacob J.N.,Organomed Corporation | Badyal D.K.,Christian Medical College | Bala S.,Christian Medical College | Toloue M.,Bioo Scientific Corporation
Natural Product Communications | Year: 2013

Curcumin, obtained from turmeric, has several biological properties to make it a desirable template for drug development. A lipophilic derivative of curcumin, diacetyl curcumin (DAC) and a hydrophilic derivative, diglutaryl curcumin (DGC) were synthesized and their in vivo analgesic and anti-inflammatory activities were compared with those of curcumin and aspirin. The in vitro anti-cancer activities of curcumin and the two derivatives against three cell cancer lines were compared with those against a non-cancerous cell line. The inhibitory effects were comparable to each other and nearing that of curcumin while they showed low inhibitory effect towards the non-cancerous cell line. The mouse tail flick assay showed that curcumin, DAC and DGC increased latency time. DGC was most effective as an analgesic, even more so than aspirin. The maximum percentage effect (MPE) was highest with DGC at 3 hours. The carrageenan induced paw edema model indicated anti-inflammatory activity of all three curcumin formulations. The percentage inhibition of paw edema was maximum for DAC, followed by aspirin and curcumin.


Jacob J.N.,Organomed Corporation | Toloue M.,Bioo Scientific Corporation
Natural Product Communications | Year: 2013

The oil from turmeric (Curcuma longa ) contains several sesquiterpenes with medicinal properties. The oil fractions were purified by repeated high vacuum distillations to constant boiling points and by column chromatography. The major components in the oil fractions were identified as α,β and ar-turmerones. The purified turmeric oil (TO) fractions had growth inhibitory activity against breast (SKBR-3), pancreatic (PANC-1), and prostate (PC-3) cancers, and reduced activity against a non-cancerous cell line, WI-38. A combination of the distillation fraction of turmeric oil and paclitaxel showed substantial increase in growth inhibitory activity against the three cancer cell lines compared with paclitaxel alone, while having reduced activity against the non-cancerous cell line. Percent inhibition may be related to the structural parameters of the turmerones. These results suggest that components in turmeric oil fractions have anticancer activity against breast, pancreatic and prostate cancer and a strong positive effect on the activity of paclitaxel.


Yan W.,Brown University | Bowen W.D.,Brown University | Hopson R.,Brown University | Mathew A.E.,Molecular Architect | Jacob J.N.,Organomed Corporation
Natural Product Communications | Year: 2013

The current study is directed at identifying compounds that have biological activity in the less studied oil fraction of Curcuma longa (turmeric) to treat pancreatic cancer, which has no good treatment options. Fractional distillation and chromatographic separation of turmeric oil (TO) gave column fractions (CF) having biological activity against the PANC-1 pancreatic cancer cell line, with an EC50 in the range of 23 to 33 μg/mL. These fractions were analyzed by NMR and GCMS and found to contain the sesquiterpenes, ar-curcumene, 7-epi-zingiberene, β-sesquiphellandrene, curlone, α-turmerone, β-turmerone and ar-turmerone. The ability of TO components to induce cell death was independent of caspase activity. Potency was higher at lower cell density and was reduced by increasing serum concentration, the latter indicating serum binding of active components.


Jacob J.N.,Organomed Corporation | Badyal D.K.,Christian Medical College
Natural Product Communications | Year: 2014

Turmeric and fish oil have been gaining interest as food supplements because of their beneficial properties. Turmeric oil contains sesquiterpenes and fish oil has eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), possessing anti-inflammatory activity. The present study is to evaluate and compare the anti-inflammatory and analgesic properties of these two natural food products with aspirin as a standard. The percent inhibition as a measure of paw edema for turmeric oil and fish oil at 100 mg/kg was 76% and 31%, respectively, while the percent inhibition by the combination of the two at 100 mg/kg was 62%, which was the same as that of aspirin at the same dose. The inhibitory activity of fish oil at 50 mg/kg was 86% and with an increase in dose the activity decreased. The analgesic activity measured by the tail flick method showed optimum activities for turmeric oil and fish oil at 60 and 90 minutes, respectively, whereas the combination of the two decreased the analgesic activity. Thus the two common food ingredients, oils from turmeric and fish, have desirable biochemical properties to develop further their use as food and medicine.


Jacob J.N.,Organomed Corporation | Tazawa M.J.,Organomed Corporation
Bioorganic and Medicinal Chemistry Letters | Year: 2012

Glucose-aspirin (GA) was synthesized by conjugating aspirin (ASA) to glucose. The water solubility and biological activity of GA was studied in comparison to aspirin. The human serum protease activity on the ester showed a slower hydrolysis rate, compared to ASA. Glucose-aspirin was sevenfold more water soluble than aspirin and it was about 8- to 9-fold more active in inhibiting cell growth than aspirin in their anti-cancer cell culture activity on breast (SKBR3), pancreatic (PANC-1), and prostate (PC3) cell lines, whereas the activity was similar on a benign non-cancerous cell line (WI 38). In conclusion, GA is a highly water soluble derivative of aspirin. Although the serum hydrolysis for GA was slower, there was significant anti-cancer activity at the doses studied under the experimental conditions. © 2012 Elsevier Ltd. All rights reserved.


Patent
Organomed Corporation | Date: 2012-06-29

The invention provides novel compounds and formulations of turmeric oil, fish oil, aspirin and anti-cancer drugs (paclitaxel) having anti-inflammatory, analgesic and/or anti-cancer activity.


PubMed | Organomed Corporation
Type: Journal Article | Journal: Bioorganic & medicinal chemistry letters | Year: 2012

Glucose-aspirin (GA) was synthesized by conjugating aspirin (ASA) to glucose. The water solubility and biological activity of GA was studied in comparison to aspirin. The human serum protease activity on the ester showed a slower hydrolysis rate, compared to ASA. Glucose-aspirin was sevenfold more water soluble than aspirin and it was about 8- to 9-fold more active in inhibiting cell growth than aspirin in their anti-cancer cell culture activity on breast (SKBR3), pancreatic (PANC-1), and prostate (PC3) cell lines, whereas the activity was similar on a benign non-cancerous cell line (WI 38). In conclusion, GA is a highly water soluble derivative of aspirin. Although the serum hydrolysis for GA was slower, there was significant anti-cancer activity at the doses studied under the experimental conditions.


PubMed | Organomed Corporation
Type: Journal Article | Journal: Basic & clinical pharmacology & toxicology | Year: 2013

Glucose-aspirin (GA) was synthesized by conjugating aspirin (ASA) to the 3-carbon of glucose to produce a stable water-soluble aspirin derivative. The in vivo activities were compared with those of aspirin. The mouse tail flick assay showed that at 120 min., both aspirin and GA showed the maximum possible effect, and the higher dose (200 mg/kg) generally had less of an effect than the lower dose (100 mg/kg). Per cent inhibition of paw oedema was 63% and 69% for ASA and GA at 100 mg/kg, respectively. In the tail immersion test, the increase in reaction time was significantly greater with GA as compared to aspirin (100 mg/kg) at 60 min. In conclusion, there was significant anti-inflammatory and analgesic activity for GA at the doses studied under the experimental conditions.

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