Remedy/Nutraceuticals

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Various foods are displayed. Credit: Unknown author.

Def. a "nutrient or food believed to have curative properties"[1] or a "food used as a drug"[1] is called a nutraceutical.

Def. "a source of nourishment, such as food, that can be metabolized by an organism to give energy and build tissue"[2] is called a nutrient.

Def. "any [solid][3] substance [that][4] can be consumed by living organisms, especially [by eating][4], [in order to sustain life][5]"[6] or "anything that nourishes or sustains"[7] is called a food.

Alcohols[edit | edit source]

International Union of Pure and Applied Chemistry (IUPAC) nomenclature in naming simple alcohols, the name of the alkane chain loses the terminal e and adds the suffix -ol, e.g., as in "ethanol" from the alkane chain name "ethane".[8] When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the -ol: propan-1-ol for CH
3
CH
2
CH
2
OH
, isopropyl alcohol (propan-2-ol) for CH
3
CH(OH)CH
3
. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then the prefix hydroxy-is used,[8] e.g., as in 1-hydroxy-2-propanone (CH
3
C(O)CH
2
OH
).[9]

Some examples of simple alcohols and how to name them
CH
3
CH
2
CH
2
–OH
Propan-2-ol displayed.svg Cyclohexanol displayed.svg 2-methylpropan-1-ol displayed.svg 2-methylbutan-2-ol displayed.svg
Propan-1-ol.svg 2-Propanol.svg Cyclohexanol acsv.svg Isobutanol.svg 2-Methyl-2-butanol FormulaV1-Seite001.svg
n-propyl alcohol,
propan-1-ol, or
1-propanol
isopropyl alcohol,
propan-2-ol, or
2-propanol
cyclohexanol isobutyl alcohol,
2-methylpropan-1-ol, or
2-methyl-1-propanol
tert-amyl alcohol,
2-methylbutan-2-ol, or
2-methyl-2-butanol
A primary alcohol A secondary alcohol A secondary alcohol A primary alcohol A tertiary alcohol

In cases where the OH functional group is bonded to an sp2 carbon on an aromatic compound (aromatic ring) the molecule is known as a phenol, and is named using the IUPAC rules for naming phenols.[10]

Type Formula IUPAC Name Common name
Monohydric
alcohols
CH
3
OH
Methanol Wood alcohol
C
2
H
5
OH
Ethanol Alcohol
C
3
H
7
OH
Propan-2-ol Isopropyl alcohol,
Rubbing alcohol
C
4
H
9
OH
Butan-1-ol Butanol,
Butyl alcohol
C
5
H
11
OH
Pentan-1-ol Pentanol,
Amyl alcohol
C
16
H
33
OH
Hexadecan-1-ol Cetyl alcohol
Polyhydric
alcohols
C
2
H
4
(OH)
2
Ethane-1,2-diol Ethylene glycol
C
3
H
6
(OH)
2
Propane-1,2-diol Propylene glycol
C
3
H
5
(OH)
3
Propane-1,2,3-triol Glycerol
C
4
H
6
(OH)
4
Butane-1,2,3,4-tetraol Erythritol,
Threitol
C
5
H
7
(OH)
5
Pentane-1,2,3,4,5-pentol Xylitol
C
6
H
8
(OH)
6
hexane-1,2,3,4,5,6-hexol Mannitol,
Sorbitol
C
7
H
9
(OH)
7
Heptane-1,2,3,4,5,6,7-heptol Volemitol
Unsaturated
aliphatic
alcohols
C
3
H
5
OH
Prop-2-ene-1-ol Allyl alcohol
C
10
H
17
OH
3,7-Dimethylocta-2,6-dien-1-ol Geraniol
C
3
H
3
OH
Prop-2-yn-1-ol Propargyl alcohol
Alicyclic
alcohols
C
6
H
6
(OH)
6
Cyclohexane-1,2,3,4,5,6-hexol Inositol
C
10
H
19
OH
5-Methyl-2-(propan-2-yl)cyclohexan-1-ol Menthol

Polycosanols[edit | edit source]

Diagram shows oleyl alcohol. Credit: .{{free media}}
Diagram shows 1-octacosanol. Credit: Benrr101.{{free media}}
Diagram shows 1-nonacosanol. Credit: .{{free media}}
Chemical structure shows 1-dotriacontanol. Credit: Edgar181.{{free media}}

Def. an "extract of plant waxes, rich in long-chain aliphatic alcohols"[11] is called a polycosanol, or policosanol.

Policosanol was originally derived from sugar cane but the chemicals can also be isolated from beeswax, cereal grains, grasses, leaves, fruits, nuts, and seeds of many foods.[12] Policosanols are very long chain alcohols with carbon backbones ranging from 24 to 34 carbons.[12]

The first policosanol supplements were produced by Dalmer Laboratories in Cuba; studies conducted and published by that group have found that policosanol is safe and effective as a lipid-lowering agent; however these studies were small, and efforts by groups outside of Cuba have failed to replicate these results.[12]

A meta-analysis in 2005 concluded that human policosanol consumption is safe and well tolerated and is effective at lowering the blood cholesterol.[13] As of 2010, they were marketed as lipid-lowering agents in the Caribbean, Central and South America, and Canada.[12] Furthermore, another meta-analysis was published in 2018 with 22 studies and 1886 subjects showed policosanol could improve dyslipidemia with raising HDL.[14] The blood pressure lowering effect of Cuban policosanol has been shown in an animal model using spontaneously hypertensive rats (SHR)[15] and a human trial.[16][17]

"Weighted estimates of percent change in LDL were -11.0% for plant sterol and stanol esters 3.4 g/day (range 2-9 g/day [893 patients]) versus -2.3% for placebo (769 patients) in 23 eligible studies, compared with -23.7% for policosanol 12 mg/day (range 5-40 mg/day [1528 patients]) versus -0.11% for placebo (1406 patients) in 29 eligible studies."[13]

A "nutraceutical combination (NC), consisting of 500 mg berberine, 200 mg red yeast rice and 10 mg policosanols, on cholesterol levels and endothelial function in patients with hypercholesterolemia [produced] a main outcome measure was decrease total cholesterol (C) levels in the NC arm. Secondary outcome measures were decreased low-density lipoprotein cholesterol (LDL-C) and triglyceride levels, and improved endothelial-dependent flow-mediated dilation (FMD) and insulin sensitivity in relation to NC. Evaluation of absolute changes from baseline showed significant reductions in NC versus placebo for C and LDL-C (C: −1.14 ± 0.88 and −0.03 ± 0.78 mmol/l, p < 0.001; LDL-C: −1.06 ± 0.75 and −00.4 ± 0.54 mmol/l, p < 0.001), and a significant improvement of FMD (3 ± 4% and 0 ± 3% respectively, p < 0.05). After the extension phase, triglyceride levels decreased significantly from 1.57 ± 0.77 to 1.26 ± 0.63 mmol/l, p < 0.05 and insulin sensitivity improved in a patient subgroup with insulin resistance at baseline (HOMA: from 3.3 ± 0.4 to 2.5 ± 1.3, p < 0.05)."[18]

"Policosanol (10 mg/day) significantly reduced total cholesterol by 17.5% and LDL cholesterol by 21.8% compared with baseline and placebo. Furthermore, high-density lipoprotein (HDL) cholesterol was raised by 11.3% (not significant), and triglycerides showed a statistically nonsignificant decrease of 6.6%. These changes in lipid profile were similar to those induced by policosanol in nondiabetic patients with type II hyperlipoproteinemia."[19]

"At 4 (p < 0.0001) and 8 (p < 0.00001) weeks, policosanol 10 mg/day significantly lowered serum LDL-C levels by 17.5 and 23.1%, respectively compared with baseline; corresponding values for atorvastatin were 28.4 and 29.8%. At study completion, policosanol significantly (p < 0.0001) reduced serum TC (16.4%), LDL-C/HDL-C ratio (25.5%) and TC/HDL-C ratio (19.3%), as well as (p < 0.001) triglyceride levels (15.4%). Atorvastatin significantly (p < 0.0001) decreased serum TC (22.6%), LDL-C/HDL-C (26.2%) and TC/HDL-C (19.8%) ratios, as well as (p < 0.001) triglyceride levels (15.5%). Atorvastatin was significantly more effective than policosanol in reducing LDL-C and TC, but similar in reducing both atherogenic ratios and triglyceride levels. Policosanol, but not atorvastatin, significantly (p < 0.05) increased serum HDL-C levels by 5.3%. Both treatments were well tolerated. At study completion, atorvastatin mildly, but significantly (p < 0.05) increased creatine phosphokinase (CPK) and creati-nine, whereas policosanol significantly reduced AST and glucose (p < 0.01) and CPK (p < 0.05) levels. All individual values, however, remained within normal limits. Three atorvastatin but no policosanol patients withdrew from the study because of adverse events: muscle cramps (1 patient), gastritis (1 patient) and uncontrolled hypertension, abdominal pain and myalgia (1 patient). Overall, no policosanol and seven atorvastatin patients (18.9%) reported a total of nine mild or moderate adverse events during the study (p < 0.01)."[20]

"Fifty-three elderly patients (60 to 77 years of age) with primary hypercholesterolemia (total serum cholesterol ⩾240 mg/dL) were enrolled in a randomized, double-masked, parallel-group, comparative study of policosanol—a new cholesterol-lowering agent obtained from sugarcane wax—and simvastatin. Before randomization, all patients were advised to follow a standard cholesterol-lowering diet for 6 weeks. Patients were randomized to receive either policosanol or simvastatin, both at doses of 10 mg/d for 8 weeks. With policosanol, total cholesterol, low-density lipoprotein cholesterol (LDL-C), and triglycerides were significantly reduced 14.7%, 17.9%, and 13.8%, respectively. Simvastatin significantly lowered total cholesterol 15.2%, LDL-C 19.8%, and triglycerides 8.7%. Neither policosanol nor simvastatin significantly changed high-density lipoprotein cholesterol (HDL-C) levels. Total cholesterol:HDL-C and LDL-C:HDL-C ratios were significantly lowered by both therapies. The effects of both drugs on lipid profile variables were statistically similar. Both drugs were well tolerated."[21]

"After 5 weeks of a standard step-1 lipid-lowering diet, 437 patients were randomized to receive, under double-blind conditions, 5 mg policosanol or placebo once a day with the evening meal for 12 weeks and 10 mg policosanol or placebo for the next 12 weeks."[22]

"Both groups were similar at randomization. Policosanol (5 and 10 mg/day) significantly reduced (P < .001) serum low-density lipoprotein cholesterol (18.2% and 25.6%, respectively) and cholesterol (13.0% and 17.4%), and it significantly raised (P < .01) high-density lipoprotein cholesterol (15.5% and 28.4%). Triglycerides remained unchanged after the first 12 weeks and lowered significantly (5.2%; P < .01) at study completion. Policosanol was safe and well tolerated, and no drug-related disturbances were observed. Two male patients who received placebo died during the study—one because of a myocardial infarction and the other because of a cardiac arrest that occurred during a surgical intervention. There were 11 serious adverse events (5.1%) in 10 patients who received placebo (4.6%), 7 of which were vascular, compared with no serious adverse events reported in patients receiving policosanol (P < .01)."[22]

Fatty alcohols (or long-chain alcohols), usually high-molecular-weight, straight-chain primary alcohols, can range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils, where the precise chain length varies with the source.[23][24]

"Policosanol is a mixture of alcohols isolated and purified from sugar cane (Saccharum officinarum L). It consists mainly of 66-percent octacosanol (C
28
H
58
O
), 12-percent triacontanol, and 7-percent hexacosanol. Other alcohols (15%), namely tetracosanol, heptacosanol, nonacosanol, dotriacontanol and tetratriacontanol, are minor components.(1)"[25]

Dodecanol, or lauryl alcohol, an organic compound (C12H26O) produced industrially from palm kernel oil or coconut oil, a fatty alcohol is tasteless and colorless with a floral odor.[26]

Oleyl alcohol,[27] or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C
18
H
36
O
or the condensed structural formula CH3(CH2)7-CH=CH-(CH2)8OH. It is a colorless oil, mainly used in cosmetics.[23]

Stearyl alcohol, or 1-octadecanol, an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH (C18H38O), application as an evaporation suppressing monolayer when applied to the surface of water.[28]

1-Tetracosanol (lignoceryl alcohol) is a fatty alcohol containing 24 carbon atoms C
24
H
50
O
, usually derived from the fatty acid lignoceric acid.

1-Hexacosanol a saturated primary fatty alcohol with a carbon chain length of 26 (C
26
H
54
O
) that is a white waxy solid at room temperature, occurs naturally in the epicuticular wax and plant cuticle of many plant species.[29]

1-Heptacosanol is a fatty alcohol with the formula C
27
H
56
O
.

1-Octacosanol (also known as n-octacosanol, octacosyl alcohol, cluytyl alcohol, montanyl alcohol) is a straight-chain aliphatic 28-carbon primary fatty alcohol (C
28
H
58
O
) that is common in the epicuticular waxes of plants, including the leaves of many species of Eucalyptus, of most forage and cereal grasses, of Acacia, Trifolium, Pisum and many other legume genera among many others, sometimes as the major wax constituent.[29] Octacosanol also occurs in wheat germ.[30]

Octacosanol is the main component in the mixture policosanol.[31] Octacosanol has been subject to preliminary study for its potential benefit for patients with Parkinson's disease.[32][33] Studies have also found that octacosanol may inhibit the production of cholesterol.[31] In mice, octacosanol reduces stress and restores stress-affected sleep back to normal.[34]

"Daily doses of 10 mg of policosanol have been shown to be equally effective in lowering total or LDL cholesterol as the same dose of simvastatin or pravastatin. Triglyceride levels are not influenced by policosanol."[35]

1-Nonacosanol is a straight-chain aliphatic 29-carbon primary fatty alcohol with the formula C
29
H
60
O
.

1-Triacontanol (n-triacontanol) is a fatty alcohol of the general formula C
30
H
62
O
, also known as melissyl alcohol or myricyl alcohol, found in plant cuticle waxes and in beeswax, a growth stimulant for many plants, most notably roses, in which it rapidly increases the number of basal breaks, a natural plant growth regulator, widely used to enhance the yield of various crops around the world, mainly in Asia.[36]

Triacontanol was first isolated in 1933 from alfalfa, identified as a saturated straight chain primary alcohol.[37] Triacontanol is found in various plant species as a minor component of the epicuticular wax, in wheat, triacontanol is about 3-4% of the leaf wax.[38] A substantial increase in yield and growth has been seen in different plants, such as cucumber, tomatoes, wheat, maize, lettuce, and rice.[39]

1-Dotriacontanol is a fatty alcohol with 32 carbon atoms for a chemical formula C
32
H
66
O
.

Geddic acid, or tetratriacontanoic acid, is a 34-carbon-long carboxylic acid and saturated fatty acid that occurs in cotton, carnauba, candelilla wax and in ghedda wax (wild beeswax), from which its common name is derived with the formula C
34
H
68
O
2
. Tetratriacontanol has the chemical formula C
34
H
70
O
.

"The total [polycosanol] PC contents of wheat straw (164 mg/kg) and sugar cane peel (270 mg/kg) were of the same order of magnitude. The total PC contents of brown beeswax were about 20 and 45 times higher than those of the [wheat germ oil] WGO-solids and sugar cane peel, respectively. Commercial dietary supplements contained less total PC than were claimed on the product labels."[40]

Alkaloids[edit | edit source]

Historically, Zanthoxylum (Prickly ash) bark was used in traditional medicine.[41]

Species identified in Nigeria contains several types of alkaloids including benzophenanthridines (nitidine, dihydronitidine, oxynitidine, fagaronine, dihydroavicine, chelerythrine, dihydrochelerythrine, methoxychelerythrine, norchelerythrine, oxychelerythrine, decarine and fagaridine), furoquinolines (dictamine, 8-methoxydictamine, skimmianine, 3-dimethylallyl-4-methoxy-2-quinolone), carbazoles (3-methoxycarbazole, glycozoline), aporphines (berberine, tembetarine,[42] magnoflorine, M-methyl-corydine), canthinones (6-canthinone), acridones (1-hydroxy-3-methoxy-10-methylacridon-9-one, 1-hydroxy-10-methylacridon-9-one, zanthozolin), and aromatic and aliphatic amides.[43] Hydroxy-alpha sanshool is a bioactive component of plants from the genus Zanthoxylum, including the Sichuan pepper.

Aporphines[edit | edit source]

Aporphines include berberine and tembetarine found in Prickly ash bark.[42]

Benzophenanthridines[edit | edit source]

Benzophenanthridines incude nitidine, dihydronitidine, oxynitidine, fagaronine, dihydroavicine, chelerythrine, dihydrochelerythrine, methoxychelerythrine, norchelerythrine, oxychelerythrine, decarine and fagaridine found in Prickly ash bark.[42]

Berberines[edit | edit source]

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids found in such plants as Berberis, such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape), Hydrastis canadensis (goldenseal), Xanthorhiza simplicissima (yellowroot), Phellodendron amurense (Amur cork tree),[44] Coptis chinensis (Chinese goldthread), Tinospora cordifolia, Argemone mexicana (prickly poppy), and Eschscholzia californica (Californian poppy).

Berberine is usually found in the roots, rhizomes, stems, and bark.[45]

The safety of using berberine for any condition is not adequately defined by evidence-based medicine, high-quality clinical research.[46]

Its potential for causing adverse effects is high, including untoward interactions with prescription drugs, reducing the intended effect of established therapies.[46] Berberine inhibits the CYP2D6 and CYP3A4 enzymes which are involved in metabolism of endogenous substances and xenobiotics, including many prescription drugs.[47][48]

It is particularly unsafe for use in children.[46] On the other hand, in May 2021, a comprehensive review article was published that highlighted the efficacy of berberine as a promising anti-oncogenic herpesvirus drug[49]

Carbazoles[edit | edit source]

Carbazoles include 3-methoxycarbazole and glycozoline found in Prickly ash bark.[42]

Furoquinolines[edit | edit source]

Furoquinolines include dictamine, 8-methoxydictamine, skimmianine, and 3-dimethylallyl-4-methoxy-2-quinolone found in Prickly ash bark.[42]

Valerian alkaloids[edit | edit source]

Actinidine,[50] chatinine,[50][51] shyanthine,[50] valerianine,[50] and valerine[50]

Alpha-lipoic acids[edit | edit source]

"Alpha-Lipoic Acid is a naturally occurring micronutrient, synthesized in small amounts by plants and animals (including humans), with antioxidant and potential chemopreventive activities. Alpha-lipoic acid acts as a free radical scavenger and assists in repairing oxidative damage and regenerates endogenous antioxidants, including vitamins C and E and glutathione. This agent also promotes glutathione synthesis. In addition, alpha-lipoic acid exerts metal chelating capacities and functions as a cofactor in various mitochondrial enzyme complexes involved in the decarboxylation of alpha-keto acids."[52]

Cynarines[edit | edit source]

Artichoke contains the bioactive agents apigenin and luteolin.[53]

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides.

Apigenin is found in many fruits and vegetables, but parsley, celery, celeriac, and chamomile tea are the most common sources.[54] Apigenin is particularly abundant in the flowers of chamomile plants, constituting 68% of total flavonoids.[55] Dried parsley can contain about 45 mg/gram and dried chamomile flower about 3-5 mg/gram apigenin.[56] The apigenin content of fresh parsley is reportedly 215.5 mg/100 grams, which is much higher than the next highest food source, green celery hearts providing 19.1 mg/100 grams.[57]

Luteolin is a flavone, a type of flavonoid, with a yellow crystalline appearance.[58] Luteolin can function as either an antioxidant or a pro-oxidant and plants rich in luteolin have been used in Chinese traditional medicine[59]

Luteolin is most often found in leaves, but it is also seen in rinds, barks, clover blossom, and ragweed pollen.[58] It has also been isolated from the aromatic flowering plant, Salvia tomentosa in the mint family, Lamiaceae.[60]

Dietary sources include celery, broccoli, artichoke, Bell pepper (green pepper), parsley, thyme, dandelion, perilla, chamomile tea, carrots, olive oil, peppermint, rosemary, navel oranges, and oregano.[61][62] It can also be found in the seeds of the palm Aiphanes aculeata.[63]

The total antioxidant capacity of artichoke flower heads is one of the highest reported for vegetables.[64] Cynarine is a chemical constituent in Cynara. The majority of the cynarine found in artichoke is located in the pulp of the leaves, though dried leaves and stems of artichoke also contain it.

Cynarine is a hydroxycinnamic acid derivative and a biologically active chemical constituent of artichoke (Cynara cardunculus).[65]

Fatty acids[edit | edit source]

Three-dimensional representations of several fatty acids are shown. Saturated fatty acids have perfectly straight chain structure. Unsaturated ones are typically bent, unless they have a trans configuration. Credit: phma.

Def. any "of a class of aliphatic carboxylic acids, of general formula CnH2n+1COOH, that occur combined with glycerol as animal or vegetable oils and fats"[66] is called a fatty acid.

"Only those with an even number of carbon atoms are normally found in natural fats"[67]

Usage notes: "The above general formula applies to the saturated fatty acids. Remove 2 hydrogen atoms for an unsaturated fatty acid, and 2 hydrogen atoms for every double bond in a polyunsaturated faty acid."[68]

The approximate concentration of fatty acids in coconut oil (midpoint of range in source):

Approximate concentration of fatty acids in coconut oil
Type of fatty acid Saturation Percentage
caprylic acid saturated C8 7
capric acid saturated C10 8
lauric acid saturated C12 48
myristic acid saturated C14 16
palmitic acid saturated C16 9.5
oleic acid monounsaturated C18:1 6.5
Other polyunsaturated 5

Flavonoids[edit | edit source]

The raw dandelion flowers contain diverse phytochemicals, including polyphenols, such as flavonoids apigenin, isoquercitrin (a quercetin-like compound), and caffeic acid, as well as terpenoids, triterpenes, and sesquiterpenes.[69] The roots contain a substantial amount of the prebiotic fiber inulin. Dandelion greens contain lutein.[70]

Flavonoids (or bioflavonoids; from the Latin word flavus, meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in diets.[57]

The tartness of cranberry juice derives from its mixed content of polyphenols, including flavonoids, proanthocyanidins, anthocyanins, phenolic acids, and ellagitannins.[71]

Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings (A and B) and a heterocyclic ring (C, the ring containing the embedded oxygen).[57][72] This carbon structure can be abbreviated C6-C3-C6. According to the IUPAC nomenclature,[73][74] they can be classified into:

  • flavonoids or bioflavonoids
  • isoflavonoids, derived from 3-phenylchromen-4-one (3-phenyl-1,4-benzopyrone) structure
  • neoflavonoids, derived from 4-phenylcoumarine (4-phenyl-1,2-benzopyrone) structure

Flavanones[edit | edit source]

Flavanones: hesperidin,[75] 6-methylapigenin,[75] and linarin[76] occur in Valerian.

Flavonols[edit | edit source]

Herbacetin is a flavonol, a type of flavonoid.

Flavonolignans[edit | edit source]

Rhodiolin, a flavonolignan, is the product of the oxidative coupling of coniferyl alcohol with the 7,8-dihydroxy grouping of herbacetin. It can be found in the rhizome of Rhodiola rosea.[77]

Proanthocyanidins[edit | edit source]

Proanthocyanidins, including the lesser bioactive and bioavailable polymers (four or more catechins) represent a group of condensed flavan-3-ols, such as procyanidins, prodelphinidins and propelargonidins, that can be found in many plants, most notably apples, maritime pine bark and that of most other pine species, cinnamon,[78] aronia fruit, cocoa beans, grape seed, grape skin (procyanidins and prodelphinidins).[79] Cocoa beans contain the highest concentrations.[80]

Proanthocyanidins also may be isolated from Quercus petraea and Quercus robur heartwood (wine barrel oaks).[81] Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in numerous procyanidin oligomers.[82]

Apples contain on average per serving about eight times the amount of proanthocyanidin found in wine, with some of the highest amounts found in the Red Delicious and Granny Smith varieties.[83]

An extract of maritime pine bark called Pycnogenol bears 65-75 percent proanthocyanidins (procyanidins).[84]

Proanthocyanidin glycosides can be isolated from cocoa liquor.[85]

The seed testas of field beans (Vicia faba) contain proanthocyanidins[86] that affect the digestibility in piglets[87] and could have an inhibitory activity on enzymes.[88] Cistus salviifolius also contains oligomeric proanthocyanidins.[89]

Dietary source[90] Proanthocyanidin

(mg/100g)

Fruits
Grape seeds 3532
Blueberries 332
Apples 70-141
Pears 32-42
Nuts
Hazelnuts 501
Other
Cinnamon bark 8108
Sorghum grains 3965
Baking chocolate 1636
Red wine 313

Grape seeds are rich in unsaturated fatty acids, which helps lowering levels of total cholesterol and LDL cholesterol in the blood.[91]

Quercetin[edit | edit source]

"Quercetin is a flavonoid that helps to control allergy symptoms of rhinitis and sinusitis. It stabilizes the membranes of mast cells, reducing the release of histamine. It is also helpful in lowering the risk of cataract by inhibiting glycoprotein formation in the lens (Cornish, et al 2002). Typical doses of quercetin are 800 mg to 1200 mg daily."[92]

Rutins[edit | edit source]

Rutin (rutoside or rutinoside)[93] and other dietary flavonols are under preliminary clinical research for their potential biological effects, such as in reducing post-thrombotic syndrome, venous insufficiency, or endothelial dysfunction, but there was no high-quality evidence for their safe and effective uses as of 2018.[93][94][95] As a flavonol among similar flavonoids, rutin has low bioavailability due to poor absorption, high metabolism, and rapid excretion that collectively make its potential for use as a therapeutic agent limited.[93]

Glycosides[edit | edit source]

Glycosides Aglycone Glycone Plants Genus species
Alcohol glycosides Alcohol Glycone Common name Genus species
Rosavin cinnamyl alcohol arabinose Rhodiola Rhodiola rosea
Salicin salicyl alcohol glucose Willow Salix
Salidrosides tyrosol glucose Rhodiola Rhodiola rosea
Anthraquinone glycosides Anthraquinone derivative Glycone Common name Genus species
Sennosides reduced anthraquinone glucose Legume Senna
Chromone glycosides Benzo-gamma-pyrone Glycone Common name Genus species
3,5,7-trihydroxylchromone-3-O-alpha-L-arabinopyranoside chromone arabinose Rhododendron Rhododendron spinuliferum
Eucryphin chromone rhamnoside Eucryphia Eucryphia cordifolia
Coumarin glycosides coumarin Glycone Common name Genus species
Aesculin coumarin glucose Horse chestnut Aesculus hippocastanum
Cyanogenic glycosides Cyanogin Glycone Common name Genus species
Amygdalin cyanohydrin glucose Apricot kernels Prunus armeniaca
Flavonoid glycosides Flavonoid Glycone Common name Genus species
Hesperidin Hesperetin Rutinose Bitter Orange Citrus aurantium
Naringin Naringenin Neohesperidose Grapefruit Citrus × paradisi
Rutin Quercetin Rutinose Common rue Ruta graveolens
Quercitrin Quercetin Rhamnose American white oak Quercus alba
Iridoid glycosides iridoid Glycone Common name Genus species
Aucubin cyclopentan-[C]-pyran glucose spotted laurel Aucuba japonica
Phenolic glycosides Phenol Glycone Common name Genus species
Arbutin Phenol glucose Common Bearberry Arctostaphylos ova-ursi
Steroidal glycosides Steroid Glycone Common name Genus species
Digitonin saraponin glucose foxglove Digitalis purpurea
Steviol glycosides Steviol Glycone Common name Genus species
Steviosides Steviol isosteviol candyleaf Stevia rebaudiana
Iridoid glycosides
Thioglycosides Thiod Glycone Common name Genus species
Sinigrin sulfur glucose Black mustard Brassica nigra
Triterpene glycosides Triterpene Glycone Common name Genus species
Saponins Triterpene glucose soapbark tree Quillaja saponaria

Lagerstroemins[edit | edit source]

Chemical compounds that have been isolated from the extract include corosolic acid, lager-stroemin, flosin B, and reginin A.[96]

Corosolic acid is a pentacyclic triterpene acid found in Lagerstroemia speciosa, similar in structure to ursolic acid, differing only in the fact that it has a 2-alpha-hydroxy attachment.[97]

In Vietnam the plant's young leaves are consumed as vegetables, and its old leaves and mature fruit are used in traditional medicine for reducing glucose in blood.[98]

Banaba plant, Lagerstroemia speciosa (giant crepe-myrtle, Queen's crepe-myrtle, banabá plant, or pride of India[99]) is a species of Lagerstroemia native to tropical southern Asia.

Lignans[edit | edit source]

The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables.[100] The name derives from the Latin word for "wood".[101] Lignans are precursors to phytoestrogens.[100][102] They may play a role as antifeedants in the defense of seeds and plants against herbivores.[103]

Lignans and lignin differ in their molecular weight, the former being small and soluble in water, the latter being high polymers that are undigestable:

  1. both are polyphenolic substances derived by oxidative coupling of monolignols
  2. most lignans feature a C18 cores, resulting from the dimerization of C9 precursors
  3. coupling of the lignols occurs at C8
  4. classes of lignans: "furofuran, furan, dibenzylbutane, dibenzylbutyrolactone, aryltetralin, arylnaphthalene, dibenzocyclooctadiene, and dibenzylbutyrolactol."[104]

Many lignans are metabolized by mammalian gut microflora, producing enterolignans.[105][106]

Flax seeds and sesame seeds contain high levels of lignans.[100][107]

The principal lignan precursor found in flaxseeds is secoisolariciresinol diglucoside.[100][107]

Other foods containing lignans include cereals (rye, wheat, oat and barley), soybeans, tofu, cruciferous vegetables, such as broccoli and cabbage, and some fruits, particularly apricots and Strawberry|strawberries.[100]

Lignans are not present in seed oil, and their contents in whole or ground seeds may vary according to geographic location, climate, and maturity of the seed crop, and the duration of seed storage.[100]

Secoisolariciresinol and matairesinol were the first plant lignans identified in foods.[100]

Lariciresinol and pinoresinol contribute about 75% to the total lignan intake, whereas secoisolariciresinol and matairesinol contribute only about 25%.[100]

Foods containing lignans:[100][108]

Source Lignan amount
Flaxseeds 85.5 mg per oz (28.35 g)
Sesame seeds 11.2 mg per oz
Brassica vegetables cup (125 ml)
Strawberries 0.2 per half cup

Magnolia[edit | edit source]

The aromatic bark contains magnolol, honokiol, 4-O-methylhonokiol, and obovatol.[109][110][111][112][113][114] Magnolol[115] and honokiol[116] activate the nuclear receptor peroxisome proliferator-activated receptor gamma.

Magnolol is an organic compound, classified as lignan, a bioactive compound found in the bark of the Houpu magnolia (Magnolia officinalis) or in Magnolia grandiflora.[117] The compound exists at the level of a few percent in the bark of species of magnolia, the extracts of which have been used in traditional Chinese and Japanese medicine. In addition to magnolol, related lignans occur in the extracts including honokiol, which is an isomer of magnolol.

It is known to act on the GABAA receptors in rat cells in vitro[118] as well as having antifungal properties.[119] Magnolol has a number of osteoblast-stimulating and osteoclast-inhibiting activities in cell culture and has been suggested as a candidate for screening for anti-osteoporosis activity.[120] It has anti-periodontal disease activity in a rat model.[121] Structural analogues have been studied and found to be strong allosteric modulators of GABAA.[122]

Magnolol is also binding in dimeric mode to PPARγ, acting as an agonist of this nuclear receptor.[123]

Prickly ash bark[edit | edit source]

Historically, Zanthoxylum (Prickly ash) bark was used in traditional medicine.[41]

Plants in the genus Zanthoxylum contain the lignan sesamin.

Terpenoids[edit | edit source]

While sometimes used interchangeably with "terpenes", terpenoids have additional functional groups, usually containing oxygen.[124] Terpenoids are the largest class of plant secondary metabolites, representing about 60% of known natural products.[125] Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.[126] Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes.[127]

See also[edit | edit source]

References[edit | edit source]

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