Sulforaphane (sometimes sulphoraphane in

British English British English (BrE, en-GB, or BE) is, according to Oxford Dictionaries, "English as used in Great Britain, as distinct from that used elsewhere". More narrowly, it can refer specifically to the English language in England, or, more broadl ...

) is a compound within the

isothiocyanate In organic chemistry, isothiocyanate is the functional group , formed by substituting the oxygen in the isocyanate group with a sulfur. Many natural isothiocyanates from plants are produced by enzymatic conversion of metabolites called glu ...

group of

organosulfur compounds Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulf ...

. It is produced when the

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products ...

myrosinase Myrosinase (, ''thioglucoside glucohydrolase'', ''sinigrinase'', and ''sinigrase'') is a family of enzymes involved in plant defense against herbivores, specifically the mustard oil bomb. The three-dimensional structure has been elucidated and is ...

transforms

glucoraphanin Glucoraphanin is a glucosinolate found in broccoli, mustard and other cruciferous vegetables. Glucoraphanin is converted to sulforaphane by the enzyme myrosinase. In plants, sulforaphane deters insect predators and acts as a selective antibio ...

, a

glucosinolate Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damage ...

, into sulforaphane upon damage to the plant (such as from chewing or chopping during food preparation), which allows the two compounds to mix and react. Sulforaphane is present in

cruciferous vegetables Cruciferous vegetables are vegetables of the family Brassicaceae (also called Cruciferae) with many genera, species, and cultivars being raised for food production such as cauliflower, cabbage, kale, garden cress, bok choy, broccoli, Brussels sp ...

, such as

broccoli Broccoli (''Brassica oleracea'' var. ''italica'') is an edible green plant in the cabbage family (family Brassicaceae, genus ''Brassica'') whose large flowering head, stalk and small associated leaves are eaten as a vegetable. Broccoli is cla ...

Brussels sprout The Brussels sprout is a member of the Gemmifera cultivar group of cabbages (''Brassica oleracea''), grown for its edible buds. The leaf vegetables are typically 1.5–4.0 cm (0.6–1.6 in) in diameter and resemble miniature cabbages ...

s, and

cabbage Cabbage, comprising several cultivars of ''Brassica oleracea'', is a leafy green, red (purple), or white (pale green) biennial plant grown as an annual vegetable crop for its dense-leaved heads. It is descended from the wild cabbage ( ''B.&n ...

Occurrence and isolation

Sulforaphane occurs in

broccoli sprouts Broccoli sprouts are three- to four-day-old broccoli plants that look like alfalfa sprouts, but taste like radishes. History While health-conscious people in the 1970s embraced raw sprouts as a dietary staple, it was not until the 1990s that ...

, which, among cruciferous vegetables, have the highest concentration of

, the precursor to sulforaphane. It is also found in

cauliflower Cauliflower is one of several vegetables in the species ''Brassica oleracea'' in the genus '' Brassica'', which is in the Brassicaceae (or mustard) family. It is an annual plant that reproduces by seed. Typically, only the head is eaten – t ...

bok choy Bok choy (American English, Canadian English, and Australian English), pak choi (British English) or pok choi (''Brassica rapa'' subsp. ''chinensis'') is a type of Chinese cabbage, used as food. ''Chinensis'' varieties do not form heads and have g ...

kale Kale (), or leaf cabbage, belongs to a group of cabbage (''Brassica oleracea'') cultivars grown for their edible leaves, although some are used as ornamentals. Kale plants have green or purple leaves, and the central leaves do not form a hea ...

collards Collard is a group of certain loose-leafed cultivars of ''Brassica oleracea'', the same species as many common vegetables including cabbage (Capitata group) and broccoli (Italica group). Collard is a member of the Viridis group of ''Brassica ol ...

mustard greens ''Brassica juncea'', commonly brown mustard, Chinese mustard, Indian mustard, leaf mustard, Oriental mustard and vegetable mustard, is a species of mustard plant. Cultivar ''Brassica juncea'' cultivars can be divided into four major subgroups ...

, and

watercress Watercress or yellowcress (''Nasturtium officinale'') is a species of aquatic flowering plant in the cabbage family Brassicaceae. Watercress is a rapidly growing perennial plant native to Europe and Asia. It is one of the oldest known leaf ve ...

Research

Although there has been some

basic research Basic research, also called pure research or fundamental research, is a type of scientific research with the aim of improving scientific theories for better understanding and prediction of natural or other phenomena. In contrast, applied resear ...

on how sulforaphane might have effects ''

in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and ...

'', there is no clinical evidence that consuming cruciferous vegetables and sulforaphane affects the risk of cancer or any other disease, as of 2017.

References

{{Cruciferous Biochemistry Experimental cancer drugs Isothiocyanates Sulfoxides 1,4-Butanediyl compounds

Occurrence and isolation

Research

See also

References