Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A

Honda, Tadashi; Liby, Karen T.; Su, Xiaobo; Chitra, S.; Honda, Yukiko; Suh, Nanjoo; Risingsong, Renee; Williams, Charlotte R.; Royce, Darlene B.; Sporn, Michael B.; Gribble, Gordon W.

doi:10.1016/j.bmcl.2006.09.012

Cited by 42 publications

(17 citation statements)

References 18 publications

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“…Supernatants were analyzed for NO by the Griess reaction. IC 50 values are an average of three experiments. b This data was previously reported in reference 10. …”

Section: Figures and Tablessupporting

confidence: 79%

“…We have also tried to synthesize a new lupane triterpenoid anhydride, 2-cyano-3-oxolupa-1,20(29)-dien-28-oic acid anhydride (lupane anhydride 2 , Figure 2)6 to compare biological properties of 1 with those of 2 . However, these reaction conditions gave 2 in low yield (14%) from 2-cyano-3-oxolupa-1,20(29)-dien-28-oic acid ( 3 )10 and its acyl chloride 10. These results suggest that a carboxyl group at C17 of lupane skeleton is more hindered than that of oleanane skeleton.…”

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confidence: 93%

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2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

Honda

Padegimas

David

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride (CDDO anhydride) has been synthesized, which is the first example of an oleanane triterpenoid anhydride. CDDO anhydride shows potency similar to or higher than the corresponding acid (CDDO) in various in vitro and in vivo assays related to inflammation and carcinogenesis. Notably, preliminary phamacokinetics studies show that CDDO anhydride levels are higher than CDDO levels in mouse tissues and blood. Further evaluation of CDDO anhydride is in progress.

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“…Supernatants were analyzed for NO by the Griess reaction. IC 50 values are an average of three experiments. b This data was previously reported in reference 10. …”

Section: Figures and Tablessupporting

confidence: 79%

mentioning

confidence: 93%

2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

Honda

Padegimas

David

et al. 2010

Bioorganic & Medicinal Chemistry Letters

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“…125 In various in vivo models, betulinic acid was found to be effective against skin inflammation and ear edema induced by mezerein, 12-deoxyphorbol-13-tetradecanoate (DPT), DPP, bradykinin, or TPA in mice. 126 Honda et al 127 synthesized betulinic acid analogs (Fig. 6) for NO inhibitory activity in IFN-g-stimulated RAW cells.…”

Section: -118mentioning

confidence: 98%

Recent developments in anti‐inflammatory natural products

Gautam

Jachak

2009

Medicinal Research Reviews

385

230

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Many of the inflammatory diseases are becoming common in aging society throughout the world. The clinically used anti-inflammatory drugs suffer from the disadvantage of side effects and high cost of treatment (in case of biologics). Alternative to these drugs are traditional medicines and natural products, which offer a great hope in the identification of bioactive lead compounds and their development into drugs for treating inflammatory diseases. Since ancient times traditional medicines and phytopharmaceuticals are being used for the treatment of inflammatory and other disorders. The present review article describes anti-inflammatory natural products derived from plants and marine sources reported during last decade. The compounds described belong to different chemical classes such as alkaloids, steroids, terpenoids, polyphenolics, phenylpropanoids, fatty acids and lipids, and various miscellaneous compounds. The attempt is also being made to enumerate the possible leads, e.g. curcumin, resveratrol, baicalein, boswellic acid, betulinic acid, ursolic acid, and oleanolic acid, for further development with the help of structure-activity relationship (SAR) studies and their current status. In addition SAR studies carried out on the anti-inflammatory activity of flavonoid compounds and clinical studies performed on anti-inflammatory natural products are also discussed.

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“…The synthetic oleanane triterpenoid 2-cyano-3,12-dioxo olean-1,9-dien-28-olic acid (CDDO) and its derivatives are small molecules with potent antiinflammatory and anticarcinogenic properties (22)(23)(24)(25)(26)(27)(28)(29). The synthetic triterpenoids inhibit expression of inflammatory mediators, such as inducible NOS (iNOS) and inducible cyclooxygenase-2 (COX-2), through suppression of various inflammatory cytokines, such as IFN-γ, IL-1β, and TNF-α (30,31), and also by direct inhibition of the signaling intermediate STAT3 (32).…”

Section: Introductionmentioning

confidence: 99%

Synthetic triterpenoid induces 15-PGDH expression and suppresses inflammation-driven colon carcinogenesis

Choi¹,

Kim²,

Robinson³

et al. 2014

J. Clin. Invest.

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Colitis-associated colon cancer (CAC) develops as a result of inflammation-induced epithelial transformation, which occurs in response to inflammatory cytokine-dependent downregulation of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) and subsequent suppression of prostaglandin metabolism. Agents that both enhance 15-PGDH expression and suppress cyclooxygenase-2 (COX-2) production may more effectively prevent CAC. Synthetic triterpenoids are a class of small molecules that suppress COX-2 as well as inflammatory cytokine signaling. Here, we found that administration of the synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9 (11)

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Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A

Cited by 42 publications

References 18 publications

2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent

Recent developments in anti‐inflammatory natural products

Synthetic triterpenoid induces 15-PGDH expression and suppresses inflammation-driven colon carcinogenesis

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