# Phytosterol

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Class of steroids derived from plants

[β-sitosterol](/source/%CE%92-sitosterol), a prototypical phytosterol

**Phytosterols** are [phytosteroids](/source/Phytosteroid), similar to [cholesterol](/source/Cholesterol), that serve as structural components of biological membranes of [plants](/source/Plant).[1] They encompass plant [sterols](/source/Sterol) and [stanols](/source/Stanol_ester).[1] More than 250 sterols and related compounds have been identified.[2] Free phytosterols extracted from oils are insoluble in water, relatively insoluble in oil, and soluble in alcohols.

Phytosterol-enriched foods and [dietary supplements](/source/Dietary_supplement) have been marketed for decades.[3] Despite well-documented [LDL cholesterol](/source/LDL_cholesterol)-lowering effects from long-term consumption of phytosterols, typically in the range of about 5-10%, there is no conclusive evidence from long‑term outcome trials that phytosterols themselves reduce the incidence of [cardiovascular diseases](/source/Cardiovascular_disease), improve [fasting blood sugar](/source/Fasting_blood_sugar), or [glycated hemoglobin](/source/Glycated_hemoglobin) levels, or overall [mortality rate](/source/Mortality_rate).[4][5]

Expert reviews have therefore emphasized that phytosterol‑enriched products can be considered a dietary option for LDL‑cholesterol reduction, but that their impact on ‘hard’ cardiovascular endpoints and mortality remains to be established.[6]

## Structure

Nomenclature of the structure of a tetracyclic damarane triterpene

They have a fused polycyclic structure and vary in carbon side chains and / or presence or absence of a [double bond](/source/Double_bond) (saturation).[3] They[*[clarification needed](https://en.wikipedia.org/wiki/Wikipedia:Please_clarify)*] are divided into 4,4-dimethyl phytosterols, 4-monomethyl phytosterols, and 4-desmethyl phytosterols based on the location of methyl groups at the carbon-4 position.[7] Stanols are [saturated](/source/Saturated_fat) sterols, having no double bonds in the sterol ring structure.

The molecule in the article lead is [β-sitosterol](/source/%CE%92-sitosterol). The nomenclature is shown on the right.

- By removing carbon 242, [campesterol](/source/Campesterol) is obtained.

- By removing carbons 241 and 242, [cholesterol](/source/Cholesterol) is obtained.

- Removing a hydrogen from carbons 22 and 23 yields [stigmasterol](/source/Stigmasterol) (stigmasta-5,22-dien-3β-ol).

- By hydrogenating the double bond between carbons 5 and 6, β-[sitostanol](/source/Sitostanol) (Stigmastanol) is obtained.

- By hydrogenating the double bond between carbons 5 and 6 and removing carbon 242, [campestanol](/source/Campestanol) is obtained.

- Removing carbon 242 and hydrogens from carbons 22 and 23, and inverting the stereochemistry at C-24 yields [brassicasterol](/source/Brassicasterol) (ergosta-5,22-dien-3β-ol).

- Further removal of hydrogens from carbons 7 and 8 from brassicasterol yields [ergosterol](/source/Ergosterol) (ergosta-5,7,22-trien-3β-ol). Important: Ergosterol is not a plant sterol. Ergosterol is a component of fungal cell membranes, serving the same function in fungi that cholesterol serves in animal cells.

In addition:

- Esterification of the hydroxyl group at carbon 3 with fatty/organic acids or carbohydrates results in plant [sterol esters](/source/Sterol_ester), i.e. oleates, ferulates and (acyl) glycosides.

	- Structures of some common phytosterols

		- [β-sitosterol](/source/%CE%92-sitosterol)

		- [Campesterol](/source/Campesterol)

		- [Stigmasterol](/source/Stigmasterol)

		- [Stigmastanol](/source/Stigmastanol)

		- [Campestanol](/source/Campestanol)

		- [Brassicasterol](/source/Brassicasterol)

		- [Cycloartenol](/source/Cycloartenol)

	- Structures of some common sterols, for comparison

		- [Cholesterol](/source/Cholesterol)

		- [Ergosterol](/source/Ergosterol)

## Dietary phytosterols

The richest naturally occurring sources of phytosterols are vegetable oils and products made from them. Sterols can be present in the free form and as [fatty acid esters](/source/Fatty_acid_ester) and [glycolipids](/source/Glycolipids). The bound form is usually hydrolyzed in the small intestines by [pancreatic enzymes](/source/Pancreatic_enzyme).[8] Some of the sterols are removed during the deodorization step of [refining oils](/source/Hydrotreated_vegetable_oil) and fats, without, however, changing their relative composition. Sterols are therefore a useful tool in checking authenticity.

As common sources of phytosterols, [vegetable oils](/source/Vegetable_oil) have been developed as [margarine](/source/Margarine) products highlighting phytosterol content.[3] Cereal products, vegetables, fruit and berries, which are not as rich in phytosterols, may also be significant sources of phytosterols due to their higher intakes.[9]

The intake of naturally occurring phytosterols ranges between ~200–300 mg/day depending on eating habits.[10] Specially designed vegetarian experimental diets have been produced yielding upwards of 700 mg/day.[11] The most commonly occurring phytosterols in the human diet are β-sitosterol, campesterol and stigmasterol,[3] which account for about 65%, 30% and 3% of diet contents, respectively.[12] The most common plant *stanols* in the human diet are sitostanol and campestanol, which combined make up about 5% of dietary phytosterol.[13]

Sterol composition in crude oils (as percentage of total sterol fraction)[14] Cholesterol Brassicasterol Campesterol Stigmasterol β-Sitosterol ∆5-Avenasterol ∆7-Avenasterol ∆7-Stigmasterol Coconut oil 0.6 – 2 0 – 0.9 7 – 10 12 – 18 50 – 70 5 – 16 0.6 – 2 2 – 8 Corn oil 0.2 – 0.6 0 – 0.2 18 – 24 4 – 8 55 – 67 4 – 8 1 – 3 1 – 4 Cottonseed oil 0.7 – 2.3 0.1 – 0.9 7.2 – 8.4 1.2 – 1.8 80 – 90 1.9 – 3.8 1.4 – 3.3 0.7 – 1.4 Olive oil 0 – 0.5 2.3 – 3.6 0.6 – 2 75.6 – 90 3.1 – 14 0 – 4 Palm oil 2.2 – 6.7 18.7 – 29.1 8.9 – 13.9 50.2 – 62.1 0 – 2.8 0 – 5.1 0.2 – 2.4 Palm kernel oil 1 – 3.7 0 – 0.3 8.4 – 12.7 12.3 – 16.1 62.6 – 70.4 4 – 9 0 – 1.4 0 – 2.1 Peanut oil 0.6 – 3.8 0 – 0.2 12 – 20 5 – 13 48 – 65 7 – 9 0 – 5 0 – 5 Rapeseed oil 0.4 – 2 5 – 13 18 – 39 0 – 0.7 45 – 58 0 – 6.6 0 – 0.8 0 – 5 Soybean oil 0.6 – 1.4 0 – 0.3 16 – 24 16 – 19 52 – 58 2 – 4 1 – 4.5 1.5 – 5 Sunflower oil 0.2 – 1.3 0 – 0.2 7 – 13 8 – 11 56 – 63 2 – 7 7 – 13 3 – 6

## Health claims

### EFSA

The European Foods Safety Authority (EFSA) concluded that [blood cholesterol](/source/Blood_cholesterol) can be reduced on average by 7 to 10.5% if a person consumes 1.5 to 2.4 grams of plant sterols and stanols per day, an effect usually established within 2–3 weeks. Longer-term studies extending up to 85 weeks showed that the cholesterol-lowering effect could be sustained.[15] Based on this and other efficacy data, the EFSA scientific panel provided the following health advisory: "Plant sterols have been shown to lower/reduce blood cholesterol. Blood cholesterol lowering may reduce the risk of [coronary heart disease](/source/Coronary_artery_disease)".[16]

### FDA

The [FDA](/source/Food_and_Drug_Administration) has approved the following claim for phytosterols: *For plant [sterol esters](/source/Sterol_ester)*: (i) Foods containing at least 0.65 g per serving of plant sterol esters, eaten twice a day with meals for a daily total intake of at least 1.3 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of [name of the food] supplies ___grams of vegetable oil sterol esters.[17] *For plant stanol esters*: (i) Foods containing at least 1.7 g per serving of plant stanol esters, eaten twice a day with meals for a total daily intake of at least 3.4 g, as part of a diet low in saturated fat and cholesterol, may reduce the risk of heart disease. A serving of [name of the food] supplies ___grams of plant stanol esters.[18] Reviewing clinical trials involving phytosterol supplementation, the FDA concluded that when consumed in the range of 1 to 3 grams in enriched foods, phytosterols resulted in statistically significant (5-15%) reductions in blood LDL cholesterol levels relative to placebo. The FDA also concluded that a daily dietary intake of 2 grams a day of phytosterols (expressed as non-esterified phytosterols) is required to demonstrate a relationship between phytosterol consumption and cholesterol lowering for reduced CVD risk.[19]

### Health Canada

[Health Canada](/source/Health_Canada) reviewed the evidence of 84 randomized controlled trials published between 1994 and 2007 involving phytosterol supplementation. An average 8.8% reduction in LDL-cholesterol was observed at a mean intake of 2 grams per day.[20] Health Canada concluded that sufficient scientific evidence exists to support a relationship between phytosterol consumption and blood cholesterol lowering. Based on this evidence, Health Canada approved the following statements for qualifying foods intended for [hypercholesterolemic](/source/Hypercholesterolemia) individuals: Primary statement: "[serving size from Nutrition Facts table in metric and common household measures] of [naming the product] provides X% of the daily amount* of plant sterols shown to help reduce/lower cholesterol in adults." Two additional statements that could be used in combination or alone, adjacent to the primary statement, without any intervening printed, written or graphic material: "Plant sterols help reduce [or help lower] cholesterol." This statement when used, shall be shown in letters up to twice the size and prominence as those of the primary statement. "High cholesterol is a risk factor for heart disease." This statement when used, shall be shown in letters up to the same size and prominence as those of the primary statement.

## Cholesterol lowering

The ability of phytosterols to reduce [cholesterol](/source/Cholesterol) levels was first demonstrated in humans in 1953.[21][22] From 1954 to 1982, phytosterols were subsequently marketed as a pharmaceutical under the name Cytellin as a treatment for elevated cholesterol.[23]

**Cholesterol lowering mechanisms**

Phytosterols reduce intestinal cholesterol absorption, and two main mechanisms have been proposed: (1) reduced micellar solubilization of cholesterol in the intestinal lumen (“mixed micelle hypothesis”)[24][25] and (2) modulation of cholesterol handling at the enterocyte brush border membrane (microvilli), where absorption and efflux compete (“trans-intestinal sterol efflux (TISE)” model).[26]

*Mechanism 1: Mixed micelle hypothesis (lumen)*

Ikeda and colleagues proposed that bile salt mixed micelles have a limited capacity to solubilize sterols;[24][25] when phytosterols enter the micelles, they can reduce the micellar solubility of cholesterol in vitro, suggesting decreased cholesterol availability for uptake. In this framing, the key site of action is the intestinal lumen (the contents of the gut), i.e., before cholesterol interacts with the brush border membrane. This luminal competition does not translate into an inhibitory effect in in situ intestinal loop experiments: in rat jejunal loops, β-sitosterol had no inhibitory effect on cholesterol absorption from a preformed micellar solution.

*Mechanism 2: Brush border membrane (microvilli) model*

Nakano and colleagues proposed that the brush border membrane (BBM) acts as a “dividing ridge” for opposing cholesterol fluxes—movement toward absorption (cell interior) versus movement back to the lumen (efflux, including TICE).[26][27][28] In this model, phytosterols are taken up by the BBM diffusively, and because they are poorly assimilated, they are excreted by ABCG5/G8 and/or back-diffused, repeating this shuttle between the lumen and the BBM. Through repeated interactions at the microvillar membrane, phytosterols are proposed to promote concomitant cholesterol efflux and reduce net absorption (potentially also by disturbing NPC1L1-associated trafficking of cholesterol toward the cell interior).

**Complementary to Statin Therapy: Added LDL Lowering, Uncertain Clinical Benefit**

Unlike the [statins](/source/Statin), where cholesterol lowering has been proven to reduce risk of [cardiovascular diseases](/source/Cardiovascular_diseases) (CVD) and overall mortality under well-defined circumstances, the evidence has been inconsistent for phytosterol-enriched foods or supplements to lower risk of CVD, with two reviews indicating no or marginal effect,[29][4] and another review showing evidence for use of dietary phytosterols to attain a cholesterol-lowering effect.[30]

Coadministration of statins with phytosterol-enriched foods increases the cholesterol-lowering effect of phytosterols, again without any proof of clinical benefit and with anecdotal evidence of potential [adverse effects](/source/Adverse_effects) (though statins also have adverse effects such as [myopathy](/source/Myopathy) and digestive problems).[29] Statins work by reducing cholesterol synthesis via inhibition of the rate-limiting [HMG-CoA reductase](/source/HMG-CoA_reductase) [enzyme](/source/Enzyme). Phytosterols reduce cholesterol levels by competing with cholesterol absorption in the gut via one or several possible mechanisms,[31][32][33] an effect that complements statins. Phytosterols further reduce cholesterol levels by about 9% to 17% in statin users.[34] The type or dose of statin does not appear to affect the cholesterol-lowering efficacy of phytosterols.[35]

Similarly, fixed-dose combinations of a statin with ezetimibe target complementary pathways—statins reduce hepatic cholesterol synthesis, whereas ezetimibe inhibits intestinal cholesterol absorption similarly to phytosterols —thereby producing additional LDL-C lowering compared with statin monotherapy. Ezetimibe added to statin therapy has demonstrated clinical outcome benefit in high-risk patients (e.g., IMPROVE-IT).

Because of their cholesterol reducing properties, some manufacturers are using sterols or stanols as a food additive.[3][36]

## Safety

Phytosterols have a long history of safe use,[3] dating back to Cytellin, the pharmaceutical preparation of phytosterols marketed in the US from 1954 to 1982.[23] Phytosterol esters have [generally recognized as safe](/source/Generally_recognized_as_safe) (GRAS) status in the US.[37] Phytosterol-containing [functional foods](/source/Functional_food) were subject to postlaunch monitoring after being introduced to the EU market in 2000, and no unpredicted side effects were reported.[38]

A potential safety concern regarding phytosterol consumption is in patients with [phytosterolaemia](/source/Sitosterolemia), a rare genetic disorder which results in a 50- to 100-fold increase in blood plant sterol levels and is associated with rapid development of coronary atherosclerosis. However, there is no direct evidence that phytosterols accelerate the development of atherosclerosis. On the other hand, a meta-analysis showed that premature atherosclerosis and resulting CVD observed in patients with sitosterolemia are attributable to severe hypercholesterolemia in their childhood.[39] Also, one should keep in mind that dietary phytosterols do not meaningfully raise circulating phytosgterollevels even with having phytosterol-supplemented foods.[39]

Phytosterolaemia has been linked to mutations in the ABCG5/G8 proteins which pump plant sterols out of enterocytes and hepatocytes into the lumen and bile ducts, respectively.

Plant sterol levels in the blood have been shown to be positively, negatively or not associated with CVD risk, depending on the study population investigated.[40][41][42][43][44][45][46][47] The link between plant sterols and CVD or CHD risk is complicated because phytosterol levels reflect cholesterol absorption. (See [Phytosterols as a marker for cholesterol absorption](#Phytosterols_as_a_marker_for_cholesterol_absorption)).[39]

**Sterols and stanols**

The equivalent ability and safety of plant sterols and plant [stanols](/source/Stanol) to lower cholesterol continues to be a hotly debated topic. Plant sterols and stanols, when compared head-to-head in clinical trials, have been shown to equally reduce cholesterol levels.[48][49][50] A meta-analysis of 14 randomized, controlled trials comparing plant sterols to plant stanols directly at doses of 0.6 to 2.5 g/day showed no difference between the two forms on total cholesterol, LDL cholesterol, HDL cholesterol, or triglyceride levels.[51] Trials looking at high doses (> 4 g/day) of plant sterols or stanols are very limited, and none have yet to be completed comparing the same high dose of plant sterol to plant stanol.

The debate regarding sterol vs. stanol safety is centered on their differing intestinal absorption and resulting plasma concentrations. Phytostanols have a lower estimated intestinal absorption rate (0.02 - 0.3%) than phytosterols (0.4 - 5%) and consequently blood phytostanol concentration is generally lower than phytosterol concentration.[29]

## Functions in plants

Sterols are essential for all [eukaryotes](/source/Eukaryote). In contrast to animal and [fungal](/source/Fungus) cells, which contain only one major sterol, plant cells synthesize an array of sterol mixtures in which [sitosterol](/source/Sitosterol) and [stigmasterol](/source/Stigmasterol) predominate.[52] Sitosterol regulates membrane fluidity and permeability in a similar manner to cholesterol in mammalian cell membranes.[53] Plant sterols can also modulate the activity of membrane-bound enzymes.[53] Phytosterols are also linked to plant adaptation to temperature and plant immunity against pathogens.[54]

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v t e Cholestanes, membrane lipids: sterols Adosterol Cholecalciferol/Ergocalciferols Cholesterol Dihydrotachysterol Fusidic acid Lanosterol Phytosterols

v t e Types of phytochemicals Terpenoids v t e Types of terpenes and terpenoids (# of isoprene units) Basic forms: Acyclic (linear, cis and trans forms) Monocyclic (single ring) Bicyclic (2 rings) Iridoids (cyclopentane ring) Iridoid glycosides (iridoids bound to a sugar) Steroids (4 rings) Hemiterpenoids (1) Isoprene (C5H8) Prenol Isovaleric acid Monoterpenes (C10H16)(2) Acyclic Ocimene Myrcenes Monocyclic Limonene Terpinene Phellandrene Bicyclic Pinene (α and β) Camphene Thujene Sabinene Carene Monoterpenoids (2,modified) Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Achilleol A Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol) Thymol Perillyl alcohol Carvacrol Bicyclic Camphor Borneol Bornyl acetate Eucalyptol Ascaridole Umbellulone Sesquiterpenoids (3) Artemisinin Bisabolol Cadinene Cadinol Cedrene Chanootin Farnesyl pyrophosphate Juniperol Longifolene Muurolene Nootkatin Diterpenoids (4) Acyclic Phytol Geranylgeranyl pyrophosphate Geranyl-linalool Monocyclic Retinol Retinal Bicyclic cis-Abienol Epimanool Salvinorin A Tricyclic Cembrene Forskolin Manoyl oxide Pimaral Pimarol Tetracyclic Aphidicolin Gibberellin Paclitaxel Resin acids Abietic acid Communic acid Dehydroabietic acid Isopimaric acid Lambertianic acid Levopimaric acid Mercusic acid Neoabietic acid Pimaric acid Sandaracopimaric acid Secodehydroabietic acid Palustric acid Sesterterpenoids (5) Geranylfarnesol Triterpenoids (6) Steroids Phytosterols Campesterol Citrostadienol Cycloartenol Sitostanol Sitosterol Stigmasterol Tocopherols Cholesterol Testosterone Cholecalciferol Ecdysones Other Betulin Euphol Lanosterol Madecassoside Saponins Serratenediol Squalane Acids Oleanolic acid Ursolic acid Betulinic acid Moronic acid Madecassic acid Zizyberenalic acid Sesquarterpenes/oids (7) Ferrugicadiol Tetraprenylcurcumene Tetraterpenoids (Carotenoids) (8) Carotenes Alpha-Carotene Beta-Carotene Gamma-Carotene Delta-Carotene Lycopene Neurosporene Phytofluene Phytoene Xanthophylls: Canthaxanthin Cryptoxanthin Zeaxanthin Astaxanthin Lutein Rubixanthin Polyterpenoids (many) Natural rubber Gutta percha Gutta-balatá Norisoprenoids (modified) 3-Oxo-α-ionol 7,8-Dihydroionone Synthesis Terpene synthase enzymes (many), having in common a terpene synthase N terminal domain (protein domain) Activated isoprene forms Isopentenyl pyrophosphate (IPP) Dimethylallyl pyrophosphate (DMAPP) Phenolic compounds v t e Types of phenolic compounds Natural monophenols Benzenediols Benzenetriols Apiole Carnosol Carvacrol Dillapiole Polyphenols v t e Types of polyphenols Flavonoids (C6-C3-C6) v t e Types of flavonoids Flavonoids Anthoxanthins Flavones Apigenin, Chrysin, et.c. Flavonols Quercetin, Kaempferol, et.c. Isoflavones Daidzein, Genistein, Orobol et.c. Neoflavonoids Dalbergichromene Flavans Flavan Luteoliflavan Flavan-3-ols (flavanols) Catechin, Gallocatechol, et.c. Flavan-4-ols (flavanols) Apiforol, Luteoforol, et.c. Flavan-3,4-diols Leucocyanidin, Leucodelphinidin, et.c. Flavanones Hesperidin Naringenin Eriodictyol Flavanonols Taxifolin Aromadendrin, et.c. Anthocyanidins 3-deoxyanthocyanidins Cyanidin, Delphinidin, et.c. 3-hydroxyanthocyanidin Apigeninidin, Guibourtinidin, et.c. Aurones Aureusidin Leptosidin Chalcones Chalcones Butein, Isoliquiritigenin, et.c. Dihydrochalcone Phloretin Miscellaneous List of phytochemicals in food C-methylated flavonoids O-methylated flavonoids Furanoflavonoids Pyranoflavonoids Prenylflavonoids Methylenedioxy Castavinols Category Flavonolignans Silymarin Lignans ((C6-C3)2) Matairesinol Secoisolariciresinol Pinoresinol Stilbenoids (C6-C2-C6) Resveratrol Pterostilbene Piceatannol Pinosylvin Curcuminoids Curcumin Tannins v t e Types of natural tannins Hydrolysable tannins Ellagitannins Punicalagins Castalagins Vescalagins Castalins Casuarictins Grandinins Punicalins Roburin A Tellimagrandin IIs Terflavin B Gallotannins Digalloyl glucose 1,3,6-Trigalloyl glucose Condensed tannins Proanthocyanidins Polyflavonoid tannins Catechol-type tannins Pyrocatecollic type tannins Flavolans Phlorotannins Eckol 8,8′-Bieckol 6,6'-Bieckol Dieckol Eckstolonol Diphlorethol Difucol Phlorofucofuroeckol A Tetrafucol A Trifucol Bifuhalol 7-Phloroeckol Phlorofucofuroeckol B Flavono-ellagitannins (complex tannins) Epicutissimin A Acutissimin A Other Miscellaneous Tannin sources Pseudo tannins Synthetic tannins Tannin uses Enological Drilling Ink Tanning Category Others Diarylheptanoids (C6-C7-C6) Anthraquinones Chalconoids (C6-C3-C6) Kavalactones Naphthoquinones (C6-C4) Phenylpropanoids (C6-C3) Xanthonoids (C6-C1-C6) Coumarins and isocoumarins Misc: Polyphenols Aromatic acids v t e Aromatic acids Phenolic acids Monohydroxybenzoic acids Aglycones 3-Hydroxybenzoic acid 4-Hydroxybenzoic acid Salicylic acid Glycosides p-Hydroxybenzoic acid glucoside Dihydroxybenzoic acids 2,3-Dihydroxybenzoic acid (Hypogallic acid) 2,4-Dihydroxybenzoic acid 2,6-Dihydroxybenzoic acid 3,5-Dihydroxybenzoic acid Ethyl protocatechuate Gentisic acid Homogentisic acid Orsellinic acid Protocatechuic acid Trihydroxybenzoic acids Bergenin Chebulic acid Ethyl gallate Eudesmic acid Gallic acid Tannic acid Norbergenin Phloroglucinol carboxylic acid Syringic acid Theogallin Other phenolic acids Vanillin Ellagic acid Hydroxycinnamic acids α-Cyano-4-hydroxycinnamic acid Caffeic acid Chicoric acid Cinnamic acid Chlorogenic acid Diferulic acids Coumaric acid Coumarin Ferulic acid Sinapinic acid Aromatic amino acids phenylalanine tryptophan histidine tyrosine thyroxine 5-hydroxytryptophan L-DOPA Phenylethanoids Tyrosol Hydroxytyrosol Oleocanthal Oleuropein Others Capsaicin Gingerol Alkylresorcinols Misc: Phenolic compounds Phlorotannins) Glucosinolates Precursor to isothiocyanates Sinigrin Gluconasturtiin Glucoraphanin Aglycone derivatives Isothiocyanates Sulforaphane Allyl isothiocyanate Phenethyl Isothiocyanate Nitriles Thiocyanates Organosulfides Sulfides Polysulfides Diallyl disulfide Indoles Indole-3-carbinol 3,3'-Diindolylmethane Allicin Alliin Allyl isothiocyanate Piperine Syn-propanethial-S-oxide Betalains Betacyanins Betanin Betaxanthins Indicaxanthin Vulgaxanthin Chlorophylls Chlorophyllin Organic acids Saturated cyclic acids Phytic acid Quinic acid Oxalic acid Tartaric acid Anacardic acid Malic acid Caftaric acid Coutaric acid Fertaric acid Carbohydrates Monosaccharides Hexoses Pentoses Polysaccharides Beta-glucan Chitin Lentinan Fructan Inulins Lignin Pectin Misc: List of phytochemicals and foods in which they are prominent

v t e Phytosterols C28 Brassicasterol Campesterol Ergosterol (Vitamin D2) Ergostenol Ergostatrienol Ergostadienol C29 δ-7-avenasterol δ-5-avenasterol β-Sitosterol δ-7-stigmasterol Momordenol Spinasterol Stigmastanol Stigmastenol Stigmastadienol Stigmastadienone Stigmasterol Stigmastenone C30 Citrostadienol

v t e Cholesterol and steroid metabolic intermediates Mevalonate pathway to HMG-CoA Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA Ketone bodies Acetone Acetoacetic acid β-Hydroxybutyric acid to DMAPP Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate Geranyl- Geranyl pyrophosphate Geranylgeranyl pyrophosphate Carotenoid Prephytoene diphosphate Phytoene Non-mevalonate pathway DOXP MEP CDP-ME CDP-MEP MEcPP HMB-PP IPP DMAPP To Cholesterol Farnesyl pyrophosphate Squalene 2,3-Oxidosqualene Lanosterol Lanosterol 14-demethyllanosterol 4alpha-Methylzymosterol Zymosterone Zymosterol Zymosterol Zymostenol Lathosterol 7-Dehydrocholesterol Cholesterol Zymosterol Cholesta-7,24-dien-3-ol 7-Dehydrodesmosterol Desmosterol Cholesterol From Cholesterol to Steroid hormones 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol See here instead. Nonhuman To Sitosterol Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead. To Ergocalciferol Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

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Adapted from the Wikipedia article [Phytosterol](https://en.wikipedia.org/wiki/Phytosterol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Phytosterol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.