Natural sesquiterpenoids

Fraga, Braulio M.

doi:10.1039/c0np00007h

Cited by 74 publications

(54 citation statements)

References 584 publications

(460 reference statements)

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“…Thus, obtaining these compounds in greater quantity, either by the biosynthetic path or by their synthesis, will contribute to analysis of the effi cacy of these compounds for their development as new antibiotics, along with assessment of other biological activities of pharmacological interest, including antitumoral, antimalarial, antioxidant, and antiinfl ammatory activity as previously reported for other natural sesquiterpenoid compounds (Fraga 2001(Fraga , 2002.…”

Section: Marcelo Rodrigues De Melo Luzia Doretto Paccola-meirelles Tementioning

confidence: 97%

Influence of Flammulina velutipes mycelia culture conditions on antimicrobial metabolite production

et al. 2009

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Antimicrobial metabolite production by the basidiomycete mushroom, Flammulina velutipes (Curt.: Fr.), against Bacillus subtilis, Escherichia coli, and Candida albicans was reported by Kozová and Rehácek in 1967, and against Trichoderma harzianum by Tokimoto in 1985. Sesquiterpenoids of the α-cuparene-type called enokipodins A, B, C, and D were the main compounds responsible for F. velutipes antimicrobial activity; these compounds were shown to be active against the Gram-positive bacteria B. subtilis and Staphylococcus aureus and against the fungus Cladosporium herbarum (Ishikawa et al. 2000(Ishikawa et al. , 2001(Ishikawa et al. , 2005. The antimicrobial action and the uncommon chemical structures of enokipodins A-D triggered interest in the study of their chemical synthesis. Enokipodins A and B were synthesized by Srikrishna and Rao (2004) and recently by Secci et al. (2007). Kuwahara and Saito (2004) were then successful in synthesizing the four enokipodins A-D.Although complete synthesis has been reported, the study of the viability and yield from the biosynthesis of these compounds is important to assess the advantages and disadvantages of each process for large-scale production. In this study, the infl uence of culture medium and variations in the conditions in the F. velutipes mycelia culture were assessed to investigate possible effects on the biosynthesis of the enokipodins A-D antimicrobial metabolites.The strain of F. velutipes Fv-4 used in this study was a gift from the Laboratory of Forest Resource Biology, Graduate School of Agriculture, Hokkaido University, Sapporo, Hokkaido, Japan. The F. velutipes mycelia were kept at 4°C in test tubes containing potato dextrose agar (PDA) medium. To use the fungus as inoculum, part of the stored mycelia was transferred to Petri dishes (9 cm diameter) containing PDA medium. The dishes were incubated at 25°C for 10 ± 1 days; after this time, 9-mm-diameter disks of mycelia were removed from the edge of the culture and used as inocula of the respective treatments. The culture B. subtilis LMA0011 is a gift from the Food Abstract Enokipodins A, B, C, and D are α-cuparene-type sesquiterpenoids antimicrobial metabolites produced in the stationary stage of Flammulina velutipes mycelia development in malt extract broth. This study assessed the infl uence of nutritional and environmental factors on F. velutipes mycelia culture for the production of these metabolites. The mycelia growth and antimicrobial activity were assessed by determining dry matter and the diffusion in agar method, respectively. The best F. velutipes mycelia growth was observed in dextrose potato broth, and greater antimicrobial metabolite production occurred in complete Pontecorvo's culture medium. Environmental modifi cations, such as a rise in temperature from 25° to 37°C on the 15th day of F. velutipes mycelia culture in malt extract and peptone broth, also optimized antimicrobial metabolite production. The metabolites produced in these treatments were correlated with the enokipodins A and B in thi...

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Section: Marcelo Rodrigues De Melo Luzia Doretto Paccola-meirelles Tementioning

confidence: 97%

Influence of Flammulina velutipes mycelia culture conditions on antimicrobial metabolite production

et al. 2009

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“…Several traditional natural remedies contain compounds which are modified and structurally rearranged sesquiterpene structures, called sesquiterpenoids. Fraga [30] has reviewed the structural properties of the sesquiterpenoids isolated from nature products. More than 7000 sesquiterpene structures have been characterized, but sesquiterpene lactones are the ones most frequently found in natural remedies [31].…”

Section: Sesquiterpenoids (Table 2)mentioning

confidence: 99%

Terpenoids: natural inhibitors of NF-κB signaling with anti-inflammatory and anticancer potential

Salminen

Lehtonen

Suuronen³

et al. 2008

Cell. Mol. Life Sci.

377

252

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Traditional medicine has been a fertile source for revealing novel lead molecules for modern drug discovery. In plants, terpenoids represent a chemical defense against environmental stress and provide a repair mechanism for wounds and injuries. Interestingly, effective ingredients in several plant-derived medicinal extracts are also terpenoid compounds of monoterpenoid, sesquiterpenoid, diterpenoid, triterpenoid and carotenoid groups. Inflammatory diseases and cancer are typical therapeutic indications of traditional medicines. Thus folk medicine supports the studies which have demonstrated that plant-derived terpenoid ingredients can suppress nuclear factor-kappaB (NF-kappaB) signaling, the major regulator in the pathogenesis of inflammatory diseases and cancer.We review the extensive literature on the different types of terpenoid molecules, totalling 43, which have been verified both inhibiting the NF-kappaB signaling and suppressing the process of inflammation and cancer. It seems that during evolution, plants have established a terpene-based host defense which also represents a cornucopia of effective therapeutic compounds for common human diseases.

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“…Many herbs and higher plants containing sesquiterpenoids have been exploited in traditional medicine since ancient times (Galani et al 2010;Chu et al 2011;Sauter et al 2011). The derivatives of sesquiterpenes are considered as bioactive substances with desirable fragrance and flavoring properties (Fraga 2006;Edris 2007). The hydroxylation of sesquiterpenes, an essential step in the production of flavor molecules in the flavor and fragrance industry, was often used to enhance their sensory properties (Cankar et al 2011).…”

Section: Introductionmentioning

confidence: 99%

“…Sesquiterpenes are the most diverse groups of terpenoid compounds and common constituents of essential oils in plant (Fraga 2006;Edris 2007). Many herbs and higher plants containing sesquiterpenoids have been exploited in traditional medicine since ancient times (Galani et al 2010;Chu et al 2011;Sauter et al 2011).…”

Section: Introductionmentioning

confidence: 99%

CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase

Khatri

Zapp

et al. 2012

Appl Microbiol Biotechnol

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Many terpenes and terpenoid compounds are known as bioactive substances with desirable fragrance and medicinal activities. Modification of such compounds to yield new derivatives with desired properties is particularly attractive. Cytochrome P450 monooxygenases are potential enzymes for these reactions due to their capability of performing different reactions on a variety of substrates. We report here the characterization of CYP264B1 from Sorangium cellulosum So ce56 as a novel sesquiterpene hydroxylase. CYP264B1 was able to convert various sesquiterpenes including nootkatone and norisoprenoids (α-ionone and β-ionone). Nootkatone, an important grapefruit aromatic sesquiterpenoid, was hydroxylated mainly at position C-13. The product has been shown to have the highest antiproliferative activity compared with other nootkatone derivatives. In addition, CYP264B1 was found to hydroxylate α- and β-ionone, important aroma compounds of floral scents, regioselectively at position C-3. The products, 3-hydroxy-β-ionone and 13-hydroxy-nootkatone, were confirmed by (1)H and (13)C NMR. The kinetics of the product formation was analyzed by high-performance liquid chromatography, and the K ( m ) and k (cat) values were calculated. The results of docking α-/β-ionone and nootkatone into a homology model of CYP264B1 revealed insights into the structural basis of these selective hydroxylations.

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Natural sesquiterpenoids

Abstract: This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. 421 references are cited.

Cited by 74 publications

References 584 publications

Influence of Flammulina velutipes mycelia culture conditions on antimicrobial metabolite production

Influence of Flammulina velutipes mycelia culture conditions on antimicrobial metabolite production

Terpenoids: natural inhibitors of NF-κB signaling with anti-inflammatory and anticancer potential

CYP264B1 from Sorangium cellulosum So ce56: a fascinating norisoprenoid and sesquiterpene hydroxylase

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