''Euphorbia helioscopia'', the sun spurge or madwoman's milk, is a species of flowering plant in the spurge family

Euphorbiaceae Euphorbiaceae, the spurge family, is a large family of flowering plants. In English, they are also commonly called euphorbias, which is also the name of a genus in the family. Most spurges, such as '' Euphorbia paralias'', are herbs, but some, ...

. It is a herbaceous annual plant, native to most of

Europe Europe is a large peninsula conventionally considered a continent in its own right because of its great physical size and the weight of its history and traditions. Europe is also considered a subcontinent of Eurasia and it is located entirel ...

, northern

Africa Africa is the world's second-largest and second-most populous continent, after Asia in both cases. At about 30.3 million km2 (11.7 million square miles) including adjacent islands, it covers 6% of Earth's total surface area ...

, and eastward through most of

Asia Asia (, ) is one of the world's most notable geographical regions, which is either considered a continent in its own right or a subcontinent of Eurasia, which shares the continental landmass of Afro-Eurasia with Africa. Asia covers an are ...

.''Flora Europaea''
''Euphorbia helioscopia''
/ref>Blamey, M. & Grey-Wilson, C. (1989). ''Flora of Britain and Northern Europe''. Additional folk names include wart spurge, summer spurge, umbrella milkweed, and wolf's-milk. Malta Wild Plant

Description

It is an annual plant growing in

arable land Arable land (from the la, arabilis, "able to be ploughed") is any land capable of being ploughed and used to grow crops.''Oxford English Dictionary'', "arable, ''adj''. and ''n.''" Oxford University Press (Oxford), 2013. Alternatively, for th ...

and disturbed ground. It grows to 10–50 cm tall, with a single, erect, hairless stem, branching toward the top. The leaves are oval, broadest near the tip, 1.5–3 cm long, with a finely toothed margin. The

flower A flower, sometimes known as a bloom or blossom, is the reproductive structure found in flowering plants (plants of the division Angiospermae). The biological function of a flower is to facilitate reproduction, usually by providing a mechani ...

s are small, yellow-green, with two to five basal bracts similar to the leaves but yellower; flowering lasts from mid-spring to late summer.

Uses

It is highly poisonous. Active ingredients are extracted from it for use in pharmaceutical industry. It is also a plant used in Chinese traditional medicine. Its extract has been found to inhibit hepatocellular carcinoma ''in vivo'' in mice and ''in vitro'' in human cells.

Chemistry

''Euphorbia helioscopia'' contains the jatrophone-type diterpenoids euphoheliosnoid A, B, C and D and other toxic diterpenes such as euphoscopins, epieuphoscopins euphornins, cuphohelioscopins and euphohelionone. Four esters of 12-deoxy

phorbol Phorbol is a natural, plant-derived organic compound. It is a member of the tigliane family of diterpenes. Phorbol was first isolated in 1934 as the hydrolysis product of croton oil, which is derived from the seeds of the purging croton, ''Croton ...

( 12-deoxyphorbol-13-phenylacetale-20-acetate, 12-deoxyphorbol-13-dodec-dienoate-20-acetate, 12-deoxyphorbol-13- -methyl-''cis''-2-butenoate20-acetate and 12-deoxyphorbol-13- -methyl-''cis''-2-butenoate can be isolated from the fresh aerial parts. These substances are the major

skin irritant Irritation, in biology and physiology, is a state of inflammation or painful reaction to allergy or cell-lining damage. A stimulus or agent which induces the state of irritation is an irritant. Irritants are typically thought of as chemical age ...

s found in the plant. ''m''-Hydroxyphenylglycine and 3,5-dihydroxyphenylglycine are two amino acids that can be isolated from the latex of ''E. helioscopia''. Hydrolysable tannins can be found in ''E. helioscopia''. Helioscopinin A (1,6-(''S'')-hexahydroxydiphenoyl-2,4-(''S'')-dehydrohexahydroxydiphenoyl-3-''O''-galloyl-β-D-glucose), helioscopinin B (1,6-(''S'')-hexahydroxydiphenoyl-3-''O''-galloyl-β-D-glucose), helioscopin A (1,6-(''S'')-hexahydroxydiphenoyl-2,4-(''R'')-elaeocarpusinoyl-3-''O''-galloyl-β-D-glucose) and helioscopin B (1,3,6-tri-''O''-galloyl-2,4-(''R'')-elaeocarpusinoyl-β-D-glucose) can be found together with eight other tannins:

corilagin Corilagin is an ellagitannin. Corilagin was first isolated in 1951 from Dividivi extract and from ''Caesalpinia coriaria'', hence the name of the molecule. It can also be found in '' Alchornea glandulosa'' and in the leaves of ''Punica granatum'' ( ...

punicafolin Punicafolin is an ellagitannin from the leaves of ''Punica granatum'' (pomegranate) and in ''Phyllanthus emblica ''Phyllanthus emblica'', also known as emblic, emblic myrobalan, myrobalan, Indian gooseberry, Malacca tree, or amla, from the Sans ...

, geraniin, elaeocarpusin, furosin, terchebin, mallotusinin and carpinusin. Helioscopinin-A shows

anti-allergic Allergies, also known as allergic diseases, refer a number of conditions caused by the hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic derma ...

and anti-asthmatic activities in guinea pigs. It is suggested that this compound exerts its activities through antagonism on

leukotriene D4 Leukotriene D4 (LTD4) is one of the leukotrienes. Its main function in the body is to induce the contraction of smooth muscle, resulting in bronchoconstriction and vasoconstriction. It also increases vascular permeability. LTD4 is released by bas ...

-induced responses.

References

{{Authority control helioscopia Flora of Lebanon Plants described in 1753 Taxa named by Carl Linnaeus Flora of Malta