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Vitamin B2 (Riboflavin)
Nutrient Name: Vitamin B2, riboflavin.
Synonyms: 7,8-dimethyl-10-(11-
Trade Names Include: Aqua-Flave, Beflavin, Beflavina, Béflavine, Beflavit, Berivine, Dolo-Neurotrat, Flavaxin, Ribobis, Ribobutin, Ribipea.
Related Substance: Riboflavin-5-phosphate: Alloxazine mononucleotide, coflavinase, cytoflav, flavine mononucleotide, FMN, riboflavin phosphate.
Chemistry and Forms
- Riboflavin names: 7,8-dimethyl-10-(11-
D -ribityl)isoalloxazine, 7,8-dimethyl-10-(D -ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine, and 7,8-dimethyl-10-ribitylisoalloxazine.
- Formula: C
17 H20 N4 O6 .
- Molecular weight: 376.4 daltons.
Riboflavin is stable to heat, oxidation, and acid; it is destroyed by alkali and light, especially fluorescent light. Riboflavin is partially soluble in water.
Riboflavin is a water-soluble member of the B-vitamin family. The originally termed “yellow enzyme,” which became known as “flavin mononucleotide” or “riboflavin phosphate,” was initially synthesized in 1935. The name “riboflavine” was initially chosen because it contained the pentose side chain ribitol, and flavius is Latin for “yellow,” in recognition of the deep color of the crystals formed from the pure vitamin and the deep-yellow color it imparts to urine. The final “e” was later dropped on learning that it really was not an amine. In 1952 the Commission on Biochemical Nomenclature formally adopted the name riboflavin . At this time, riboflavin is the Approved Name for use on pharmaceutical labels in Britain.
Physiology and Function
Riboflavin plays a critical role as a component of several key metabolic substances involved in oxidation of glucose, fatty acids, and certain amino acids; reactions with several intermediaries of the Krebs cycle; activation of pyridoxine phosphate (B
As flavocoenzymes, FMN and FAD participate in oxidation-reduction reactions in metabolic pathways and in energy production through the respiratory chain. The isoalloxazine ring system of riboflavin serves as the functional moiety in both FAD and FMN by acting as a two-electron acceptor in enzymatic biochemical reductions. This property enables FMN and FAD to act as cofactors for flavoproteins, the enzymes involved in oxidation-reduction reactions of organic substrates and in intermediary metabolism. FAD and FMN serve as intermediate hydrogen carriers in the mitochondrial electron transport chain, accepting hydrogen ions and transferring electrons to the cytochrome system as part of the metabolism of carbohydrates to produce adenosine triphosphate (ATP). Riboflavin aids in beta oxidation in lipid metabolism and is involved, as a coenzyme component of the dehydrogenases, in the first step in glucose metabolism.
Xanthine oxidase, nicotinamide-adenine dinucleotide phosphate (NADP)–cytochrome c reductase, and
Riboflavin participates in other self-regulatory and protective processes, particularly by facilitating destruction of reactive oxygen species and prevention of cellular oxidative injury in a range of tissues. Glutathione reductase is a FAD-containing enzyme that generates reduced glutathione, which acts as a cofactor in the formation of glutathione peroxidases, major selenium-containing antioxidant enzymes central to the regulation of lipid peroxidation. The availability of riboflavin is also essential to maintaining the mitochondrial pool of reduced glutathione necessary to the activities of the flavoenzymes reduced nicotinamide-adenine dinucleotide phosphate (NADPH)–cytochrome P450 (CYP450) reductase and NADPH–cytochrome b reductase. Riboflavin may also play a role in maintaining the integrity of erythrocytes and nerve tissue. Flavin reductase , also known as methemoglobin reductase, is an NADPH-dependent enzyme that appears to provide protection against oxidative forms of hemeproteins, such as those involved in reperfusion injury. In this process, riboflavin acts as an antioxidant through its conversion to dihydroriboflavin, with methemoglobin reduced while riboflavin is oxidized. The dihydroriboflavin not only maintains the hemeproteins in their lower oxidation states, but also rapidly reduces higher oxidation states of hemeproteins and prevents peroxidative damage to the heme and protein groups. Moreover, because the 5,10-methylenetetrahydrofolate reductase gene product (MTHFR) is a riboflavin/FAD-dependent enzyme, riboflavin status modifies the metabolic effect of the MTHFR 677C→T polymorphism, a critical factor in regulation of plasma concentrations of total homocysteine (tHcy), coronary artery disease, and colon cancer risk. For individuals who carry the 677C→T polymorphism, improving both riboflavin and folate nutriture is protective.
Riboflavin is also required for gluconeogenesis, erythropoiesis, thyroid enzyme regulation, and the production of corticosteroids. Riboflavin is also important in deoxyribonucleic acid (DNA) and ribonucleic acid (RNA) metabolism and can be found in high concentration in the retina.
In normal physiological settings, riboflavin is readily absorbed in the upper gastrointestinal tract, principally in the duodenum, through a saturable active transport system. The presence of food can increase absorption fourfold when riboflavin is ingested with meals rather than taken separately. The gastric environment is important because acid is responsible for releasing B
Known or Potential Therapeutic Uses
Treatment of ariboflavinosis (riboflavin deficiency) is the primary application of riboflavin recognized in conventional medical practice. An emerging body of evidence supporting the efficacy of riboflavin for the prevention of migraine and ocular cataract is becoming more widely recognized but is still generally viewed as mixed. Nevertheless, clinical experience and a close review of the literature reveal a solid basis for further research through well-designed and high-powered clinical trials aimed at developing guidelines for therapeutic application. The use of riboflavin in conjunction with antiviral regimens, especially nucleoside analog reverse-transcriptase inhibitors (NNRTIs), is well established, particularly for treatment and prevention of lactic acidosis.
Riboflavin is most often administered in conjunction with other nutrients, especially B vitamins, because its physiological functions and activities as well as its depletion patterns tend to cluster, and their coadministration produces a synergistic effect.
Historical/Ethnomedicine Precedent
Vitamin B
Possible Uses
Anemia, anorexia, aphthous ulcers, ariboflavinosis (riboflavin deficiency), bulimia, burn recovery, burning feet syndrome, carpal tunnel syndrome, cataracts, depression, esophageal cancer (risk reduction and treatment), ethylmalonic encephalopathy, fatigue, glaucoma, human immunodeficiency virus (HIV) support, hyperhomocysteinemia, involuntary eye movement, ischemia-reperfusion injury, malaria, methemoglobinemia (congenital), migraine headache (prophylaxis), mitochondrial encephalomyopathy (MEM), multiple acyl-coenzyme A dehydrogenase deficiency, neonatal jaundice (with phototherapy), Parkinson's disease, posttransplant headache, preeclampsia, red blood cell aplasia, sickle cell anemia, sports performance enhancement, thyroid disorders.
Deficiency Symptoms
Cheilosis, glossitis, and angular stomatitis (cracking at lip corners) are classic deficiency symptoms, but both hyporiboflavinosis and ariboflavinosis can also manifest as lethargy, depression, generalized weakness, hyperemia, edema of the pharyngeal and oral mucous membranes, dermatitis (particularly seborrheic dermatitis affecting the scrotum or labia majora and nasolabial folds), photosensitivity, burning and itching of the eyes, corneal vascularization, and normochromic normocytic anemia, leukopenia, and thrombocytopenia, sometimes associated with pure erythrocyte cytoplasia of the bone marrow. These clinical signs of deficiency in humans may appear at intakes less than 0.5 to 0.6 mg per day. Isolated riboflavin deficiency is rare and usually occurs in conjunction with broader nutritional deficiency patterns, particularly involving other B vitamins and contexts associated with increased vulnerability. Symptoms of niacin and vitamin B
The U.S. recommended dietary (daily) allowance (RDA) for riboflavin (vitamin B
The most common cause of insufficient riboflavin status is unbalanced, nutritionally deficient diets, particularly affecting infants and children, elderly persons, low-income populations, and those in areas characterized by deprivation. Individuals in particular groups tend to be especially at risk for riboflavin deficiency, including chronic heavy alcohol use, people with chronic illnesses (especially chronic liver disease), patients with severe burns or sickle cell anemia, patients receiving total parenteral nutrition (TPN) with inadequate riboflavin, and gastric bypass bariatric surgery patients, if they neglect to take high-potency B-complex supplements. Impaired absorption and reduced assimilation of riboflavin can result from abnormal digestion caused by various conditions, including gastrointestinal (GI) infections or parasites, infectious enteritis, GI and biliary obstructions, chronic diarrhea, decreased GI passage time, celiac disease, tropical sprue, malignancy, and resection of the small intestine, as in management of patients with Crohn's enteritis. Infants receiving phototherapy for neonatal jaundice are also at risk for riboflavin deficiency. Inadequate thyroid hormone and cataract formation can also be associated with impaired riboflavin status. Inborn errors of metabolism affecting the formation of a flavoprotein, such as acyl-coenzyme A dehydrogenases, can cause deficiency in relatively rare cases. Children may be at increased risk of deficiency during phases of rapid growth. Riboflavin deficiency is relatively common in children with cardiac disease, especially congestive heart failure. Low milk consumption and lactose intolerance can also contribute to decreased riboflavin intake. Vegetarians tend to have depressed riboflavin levels, and vegans are considered at increased risk of riboflavin deficiency, although nutritional yeast is an excellent source for vegans. Individuals engaged in strenuous athletic activities tend to have increased riboflavin requirements and may be more susceptible to deficiency. Women using oral contraceptives tend to lower levels of riboflavin and other B vitamins. In many women, riboflavin levels tend to be lower during periods of exercise and calorie-restrictive dieting.
Dietary Sources
Even though all plant and animal cells contain riboflavin and it is widely distributed in foodstuffs, few foods provide abundant sources of this essential nutrient. The richest dietary sources of riboflavin are calf liver and other organ meats, torula (nutritional) yeast, brewer's yeast, and mushrooms. Milk products (especially yogurt), spinach, asparagus, broccoli and other leafy green vegetables, egg whites, fish roe, almonds and other nuts, legumes, sunflower seeds, whole grains (especially wild rice), wheat germ, and fortified grains can also contain significant amounts of vitamin B
The availability and stability of riboflavin vary with different food sources. Riboflavin from animal sources is better absorbed and thus exhibits higher bioavailability than from vegetable sources. Vegetarians, and vegans in particular, therefore are more susceptible to inadequate riboflavin intake. The milling and processing of grains usually result in substantial loss of riboflavin because the vitamin is concentrated in the germ and bran. Furthermore, being water soluble, the riboflavin in grains and vegetables is often leached away during cooking, unless those fluids are reused as soups and sauces. The riboflavin in milk is relatively abundant and generally stable, although it was often degraded by light exposure when distributed in clear-glass bottles.
Nutrient Preparations Available
Riboflavin and riboflavin 5′-monophosphate are the most common forms of riboflavin available in supplements. Riboflavin is rarely administered as a monotherapy or dispensed as an individual nutrient; it is almost always part of a multinutrient formulation, particularly as a component of a B-vitamin complex. In general, such coadministration is superior because vitamin B
Dosage Forms Available
- Oral: Capsule, soft elastic capsule, tablet, enteric-coated tablet, extended-release tablet.
- Injection: Injectable riboflavin sodium phosphate is available by prescription. Riboflavin is moderately unstable in glucose–amino acid solutions but is stabilized with addition of a lipid, typically a 3:1 mixture, in TPN admixtures.
Dosage Range
Adult
- Dietary: 5 to 30 mg per day. However, a survey conducted by the U.S. Department of Agriculture estimated that daily riboflavin intake less than the RDA occurs in about a third of Americans. In the United Kingdom the average adult daily diet for men provides 2.24 mg and 1.98 mg for women.
- Supplemental/Maintenance: The ideal level of riboflavin intake has not been established, but the 25 to 50 mg typically contained in nutritional supplements is generally considered more than adequate for most individuals.
In the United States the Food and Nutrition Board of the Institute of Medicine of the National Academy of Sciences recommends the following dietary reference intakes (DRIs) for riboflavin:
- Men (>18 years): 1.3 mg
- Women (>18 years): 1.1 mg
- Pregnant women (any age): 1.4 mg
- Lactating women (any age): 1.6 mg
Pharmacological/Therapeutic: 10 to 100 mg/day, although 400 mg/day is often administered for migraine prophylaxis.
Toxic: None established. The evidence on adverse effects has been deemed insufficient to set a tolerable upper intake level (UL) for riboflavin.
Pediatric (<18 Years)
- Dietary: 2.5 to 10 mg/day.
- Infants, birth to 6 months: 0.3 mg/day (AI, adequate intake)
- Infants, 7 to 12 months: 0.4 mg/day (AI)
- Children, 1 to 3 years: 0.5 mg/day (RDA)
- Children, 4 to 8 years: 0.6 mg/day (RDA)
- Children, 9 to 13 years: 0.9 mg/day (RDA)
- Adolescents, 14 to 18 years: 1.0 mg/day for females; 1.3 mg/day for males (RDA)
- Supplemental/Maintenance: 0.4 to 1.8 mg/day.
- Pharmacological/Therapeutic: Riboflavin is generally not administered in pharmacological doses to infants or children. Riboflavin at levels five times that in formulas for term infants is often provided in augmented preterm infant formulas (PIFs) administered enterally to very-low-birth-weight (VLBW) infants; 5 mg three times daily has been used during phototherapy for neonatal jaundice.
Toxic: Not established.
Laboratory Values
- Erythrocyte riboflavin: This test is generally not considered to provide a sensitive index. Levels below 15 µg/dL of red blood cells indicate deficiency.
- Red blood cell FAD and FMN: Because these forms constitute more than 90% of riboflavin, these levels (obtained after modest hydrolysis from FAD) have been used as indicators of the cellular concentration of riboflavin in its form as coenzyme.
- Urinary riboflavin: Urinary excretion of riboflavin reflects an excess of current intake beyond tissue requirements. A normal adult excretes 120 µg or more in 24 hours. Excretion of less than 100 µg daily indicates deficiency.
- Erythrocyte glutathione reductase (EGR) activity coefficients: Stimulation of FAD-dependent EGR in vitro, which relies on an associated oxidation of NADPH, can be readily monitored spectrophotometrically and expressed as an activity coefficient (AC) indicating the ratio of activities in the presence and absence of added FAD. Assessment of this riboflavin-dependent enzyme provides a reliable indicator of functional riboflavin status but has known limitations, particularly in individuals with glucose-6-phosphate dehydrogenase (G6PD) deficiency.
- An activity coefficient less than 1.2 is defined as “acceptable,” 1.2 to 1.4 as indicating low riboflavin status, and greater than 1.4 indicating deficiency.
- Capillary electrophoresis with laser-induced fluorescence detection: This test may provide an effective tool for accurate assessment of riboflavin status by allowing detection of all riboflavin vitamers below physiological concentrations.
Urinary riboflavin levels are often measured to assess compliance with medication regimens, particularly with patients being treated for alcohol dependence, mental disorders, and other conditions.
High intake levels of riboflavin are known to interfere with the accuracy of many laboratory tests, including urinalysis based on spectrometry, drugs of abuse assays, and fluorometric determinations of catecholamines and urobilinogen.
Overview
Riboflavin (vitamin B
Nutrient Adverse Effects
General Adverse Effects
Beyond flavinuria, the yellow discoloration of urine, with high doses and extremely rare instances of allergic reactions, riboflavin toxicity in humans is unknown. Although indications of serious adverse effects are lacking, very high doses have reportedly caused itching, numbness, and burning or prickling sensations. Only two minor, nonspecific adverse events (diarrhea and polyuria) were reported during the 4-month course of a clinical trial involving 400 mg per day for migraine prophylaxis. 2 A potential risk from the photosensitizing properties of riboflavin has been raised, but no substantial evidence is available to confirm such a concern as clinically significant.
Mutagenicity
None has been found on testing or has otherwise been proposed or suspected.
Pregnancy and Nursing
Riboflavin is excreted in breast milk but is generally considered safe during pregnancy and lactation at usual dosage levels.
Teratogenicity
None has been reported.
Infants and ChildrenNo pediatric adverse effects from vitamin B
Contraindications
No contradictions have been established for riboflavin.
Precautions and Warnings
No warnings or precautions have been established for vitamin B
Strategic Considerations
The administration of riboflavin as a monotherapy is atypical in conventional practice and nutritionally oriented therapeutics; its use in migraine prophylaxis represents its most well-known monotherapeutic application. Supplementation is usually unnecessary for individuals with a balanced diet and healthy lifestyle, although requirements can be increased with stresses such as poor nutritional intake (of riboflavin and other B vitamins), chronic illness, malabsorption disorders, alcohol consumption, hemodialysis, chemotherapy, or even vigorous athletic activity. The diagnosis of riboflavin deficiency is usually based on the symptoms and evidence of general undernutrition. Angular stomatitis is the most readily observable sign of emerging deficiency but frequently goes unrecognized at early stages. Diagnostic tests to confirm riboflavin deficiency are not readily available or particularly sensitive to functional depletion. In cases of frank riboflavin deficiency, high doses are typically administered orally until symptoms resolve. Impairment and deficiencies involving B vitamins are highly interdependent, and these nutrients are usually most effective when administered concomitantly. Riboflavin is generally considered to be nontoxic at typical supplemental and dietary dosage levels, with flavinuria (yellow-colored urine) being the primary side effect.
Although evidence from focused clinical trials is limited, adverse effects from coadministration appears to be improbable with most medications, given basic intake timing precautions. The major exception is individuals at high risk for malaria or being treated with antimalarial medications. Coadministration of riboflavin is particularly indicated with the several pharmaceuticals that impair riboflavin absorption and the many that inhibit conversion of riboflavin to its active coenzymes, FAD and FMN. The concomitant use of riboflavin and thiamine with the nucleoside analog reverse-transcriptase inhibitors used in HIV pharmacotherapy can prevent or reverse the uncommon but usually irreversible lactic acidosis caused by drug-induced mitochondrial toxicity and riboflavin deficiency. Coadministration with tricyclic antidepressants appears not only to counter drug-induced adverse effects but also to enhance therapeutic response, especially in depressed patients with low folate levels, defective methylation functions, and low thyroxine levels. Less dramatically, riboflavin's lack of toxicity suggests that it can be broadly prescribed to prevent or reverse drug-induced depletion effects, even in the absence of deficiency signs, as with oral contraceptives and CYP450-inducing antiseizure medications. Riboflavin appears to be safe even in the case of the anticholinergic agent propantheline, which can elevate riboflavin levels. Concomitant administration of other B vitamins is often indicated for full effectiveness of vitamin B
Tetracycline-class antibiotics, chlorpromazine and d phenothiazine antipsychotics, and boric acid are prominent among the drugs with notable pharmacokinetic interactions with riboflavin, typically involving binding that impairs absorption of both substances. Chlorpromazine and boric acid and its derivatives promote renal excretion of riboflavin. Preliminary evidence suggests that riboflavin could theoretically impair the therapeutic activity of doxorubicin, selegiline, and some sulfa drugs in individuals exposed to sunlight or other bright light.
The role of riboflavin in cardiovascular function is emerging as an area of significant scientific research, providing new data on interactions involving related medications. Research involving patients with migraine demonstrated a decreased mitochondrial phosphorylation potential between migraine attacks and suggests that decreased brain mitochondrial energy reserve between attacks is related to the activity of flavoenzymes, particularly FMN and FAD, in the electron transport chain and the production of cellular energy. The pivotal role of riboflavin in FAD, which is the cofactor for the MTHFR enzyme, as well as the role of MTHFR in the regulation of homocysteine, may bring riboflavin into equal prominence with folic acid, vitamins B
Oxidative forms of hemeproteins have been implicated in reperfusion injury, and elevated riboflavin levels have been reported to provide protection against such altered hemeproteins and reperfusion injury. 3-6Continued research into these activities and functions will provide new insight into the importance of riboflavin nutriture, suggest expanded therapeutic uses for riboflavin administration, and present new challenges for understanding both beneficial and harmful interactions with conventional medications.
Beneficial or Supportive Interaction, with Professional Management |
Probability: 4. Plausible or 3. Possible
Evidence Base: Preliminary to Emerging
Effect and Mechanism of Action
Thyroid hormone regulates the enzymatic conversion of riboflavin to FMN and FAD, its active coenzyme forms. 103 Specifically, triiodothyronine (T 3 ) plays a key role in the conversion of riboflavin into FMN by enhancing biosynthesis through the expression of riboflavin kinase. 104,105
Riboflavin is necessary for thyroxine synthesis, as are niacin, pyridoxine, and iodine. Inadequate riboflavin intake can also contribute to diminished thyroid function.
Research
Although a significant body of scientific research explores the physiological functions and the relationships involving riboflavin, its coenzymes, and thyroid hormones, evidence from clinical trials directly investigating coadministration and therapeutic strategies is limited.
Using a rat model, Lee and McCormick 104 reported a “correspondence of flavokinase activity with the amount of a high-affinity flavin-binding protein quantitated immunologically in hypo-, eu-, and hyperthyroid rats [which] indicated that the thyroid response is caused by an increased amount of enzyme; moreover, the concomitant decrease in a low-affinity flavin-binding protein suggests an inactive precursor form of flavokinase.” Furthermore, “FAD synthetase activity showed a similar but less pronounced trend than flavokinase.”
In 1968, Rivlin et al. 106 observed that hypothyroidism has biochemical similarities to riboflavin deficiency, including lowered FAD biosynthesis, depressed basal EGR activity, and elevated EGRAC. In 1969, Rivlin and Wolf 107 reported diminished responsiveness to thyroid hormone in riboflavin-deficient rats. Croxson and Ibbertson 108 reported low serum T 3 and hypothyroidism in patients with anorexia nervosa. They noted that “a probable decrease of peripheral T 4 to T 3 conversion leads to low serum T 3 concentrations.” In a clinical trail involving six hypothyroid human adults, Cimino et al. 105 demonstrated that the activity of EGR, an accessible FAD-containing enzyme, is decreased to levels comparable to those found in riboflavin deficiency, and thyroxine therapy resulted in normal EGR levels while the subjects were on a controlled dietary regimen. Subsequently, in a clinical trial of 17 adolescent girls diagnosed with anorexia nervosa, Capochichi et al. 109 found that “triiodothyronine concentrations were low and negatively correlated with plasma riboflavin concentrations.” They concluded that the “low triiodothyronine concentrations observed in anorexia nervosa could alter the extent of riboflavin conversion into cofactors, thus leading to high erythrocyte riboflavin concentrations, low plasma flavin adenine dinucleotide concentrations, and high rates of ethylmalonic acid and isovalerylglycine excretion.”
Notably, as discussed in reviewing interactions between riboflavin and antimalarial drugs, hypothyroidism is known to be associated with decreased susceptibility to parasitemia. 110
Some secondary sources have suggested that synthetic thyroid medication (T 4 ) tends to decrease riboflavin absorption, but evidence is lacking to support this hypothesis.
Nutritional Therapeutics, Clinical Concerns, and Adaptations
Physicians treating patients diagnosed with hypothyroidism are advised to consider concurrent nutritional support that includes riboflavin, as well as iodine, niacin, and vitamins B 6 and C, as appropriate to the patient's particular characteristics and needs. Patients receiving Synthroid or equivalent exogenous T 4 may particularly benefit from enhanced riboflavin nutriture. Further research using well-designed clinical trials is warranted to explore these potential therapeutic synergies.
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