Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• the presence of more than 100 ava cluster-related biosynthetic gene clusters (BGCs) in actinomycetes; however, their functions remained unclear. In this study, we focused on an ava cluster-related BGC in Kutzneria albida (cma cluster), and revealed that it is responsible for p-coumaric acid

• -dependent deamination pathway for the production of avenalumic acid or p-coumaric acid. Keywords: actinomycetes; avenalumic acid; biosynthesis; p-coumaric acid; polyketides; Introduction The genomes of microorganisms possess diverse biosynthetic gene clusters (BGCs) to produce natural products [1]. In

• on an ava cluster-related BGC in Kutzneria albida JCM 3240. We showed that this BGC is involved in p-coumaric acid biosynthesis by heterologous expression in Streptomyces albus J1074 and several in vitro biochemical experiments using recombinant proteins. CmaA6 was shown to catalyze the diazotization

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

• Naganna Narra,
• Shiva Shanker Kaki,
• Rachapudi Badari Narayana Prasad,
• Sunil Misra,
• Koude Dhevendar,
• Venkateshwarlu Kontham and
• Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

• calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these

• derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines. Keywords: anticancer; anti-oxidants; caffeic acid; coumaric acid; ferulic acid; phenolic lipids; sinapic acid; undecenoic acid; Introduction Phenolic compounds

• showed interesting activity. Experimental Materials 10-Undecenoic acid, 1,1’-azobis(cyclohexanecarbonitrile) (ABCN), hydroxybenzotriazole (HOBt) and 1-ethyl-3-(3’-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl), cysteamine hydrochloride, cinnamic acid, sinapic acid, ferulic acid, p-coumaric acid

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• , 3,4-dihydroxy-L-phenylalanine (L-DOPA), 4-coumaric acid or caffeic acid. Grisanes. Many fungal spirobenzofuranones contain the grisane (191) moiety as the central structural motif (Scheme 26a). The spiro linkage between the B and C rings is installed by oxidative phenol coupling starting from type II

Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity

• Miriana Kfoury,
• David Landy,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241

• hydoxycinnamic acids (p-coumaric acid (5), caffeic acid (6) and ferulic acid (7)) (Figure 1) was investigated with α-CD, β-CD, hydroxypropyl-β-cyclodextrin (HP-β-CD), randomly methylated β-cyclodextrin (RAMEB) and a low methylated β-cyclodextrin (CRYSMEB). These PPs were selected mainly according to their

• . Isoeugenol (3), eugenol (4), caffeic acid (6) and ferulic acid (7) reacted rapidly with DPPH• while trans-anethole (1), estragole (2) and p-coumaric acid (5) had a slow kinetic behavior. These observations were consistent with the literature data [42]. Results obtained in the absence and presence of CDs, are

• presented in Figure 5. Isoeugenol (3), eugenol (4), p-coumaric acid (5), caffeic acid (6) and ferulic acid (7) presented higher antioxidant activity than trans-anethole (1) and estragole (2). It is well known that the antioxidant activity of phenolic compounds such as PPs depends mainly on the degree of

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

• Ramona Riclea,
• Julia Gleitzmann,
• Hilke Bruns,
• Corina Junker,
• Barbara Schulz and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2012, 8, 941–950, doi:10.3762/bjoc.8.106

• ), which may have an important function in mutualistic symbioses of P. gallaeciensis and marine algae by protecting the algal host from pathogenic bacteria in emerging blooms. In ageing blooms p-coumaric acid (5) is released from lysing algal cells as a lignin breakdown product. This compound causes a