Diester Chlorogenoborate Complex: A New Naturally Occurring Boron-Containing Compound

Abstract

The natural compounds of boron have many applications, including as dietary supplement. Communication is based on the discovery that diester chlorogenoborate complex can be detected and quantified from green coffee bean. The study reports that such diester molecule can also be synthesized in stable form by direct reaction of boric acid and chlorogenic acid, in a mixture of acetonitrile–water (1:1, v/v), left to evaporate over a period of 48 hours, at room temperature, resulting a spirocyclic form (diester complex). The diester complex, with its molecular structure and digestibility attributes has potential application as prebiotic in gut health, oral health and as micronutrient essential for microbiota to human and animals.

Boron-containing compounds in Dentistry: a narrative review

“…The new perspectives regarding the B essentiality for the healthy symbiosis will determine new directions for the use of B compounds, which are not digestible. An example is the recently discovered diester chlorogenoborate (DCB) complex [ 67 , 68 ] that will guide the natural B-based nutraceuticals to be used to target the human microbiome (gut, which is the most important for human health, oral cavity, vagina, skin, and scalp microbiome). In the future, we believe that indigestible B species will become essential prebiotic candidates and will ensure both the oral cavity and the colon health, as new functional foods.…”

“…In fact, indigestible B, in nutrition, will target the colon and the oral cavity, and last but not least, the vagina, the skin and the scalp. Recently, B is proposed as an essential element for AI-2 synthesis of the QS system, which affects bacterial collective behavior, population density detection, virulence, biofilm production [ 68 ]. Recent studies have shown that the addition of B species to an AI-2 precursor (which is synthesized by bacteria intracellularly) generates AI-2B in the extracellular environment of the bacteria [ 67 ].…”

“…Thereby, B can be an essential micronutrient for symbiotic interaction between microbiota and a mammalian host for healthy humans and animals. B deficiency in the microbiota can cause: (i) dysbiosis, and (ii) mucus degradation, with consequences on symbiosis [ 6 , 67 , 68 ], which produces the direct interaction of host cell membranes with bacterial biofilm, and therefore their direct infection. Consequently, the microbiota needs B to achieve: (i) biosynthesis of a furanosyl borate diester (AI-2B), a part of signaling molecules family used in quorum detection; and (ii) a protective barrier that separates the microbiota from the host (B prevents direct contact between bacteria and the host organism, thus preventing the occurrence of direct infectious effects).…”

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“…Recently, B is proposed as an essential element for AI-2 synthesis of the QS system, which affects bacterial collective behavior, population density detection, virulence, biofilm production [68]. Recent studies have shown that the addition of B species to an AI-2 precursor (which is synthesized by bacteria intracellularly) generates AI-2B in the extracellular environment of the bacteria [67].…”

“…B deficiency in the microbiota can cause: (i) dysbiosis, and (ii) mucus degradation, with consequences on symbiosis [6,67,68], which produces the direct interaction of host cell membranes with bacterial biofilm, and therefore their direct infection. Consequently, the microbiota needs B to achieve: (i) biosynthesis of a furanosyl borate diester (AI-2B), a part of signaling molecules family used in quorum detection; and (ii) a protective barrier that separates the microbiota from the host (B prevents direct contact between bacteria and the host organism, thus preventing the occurrence of direct infectious effects).…”