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

annual plant An annual plant is a plant that completes its life cycle, from germination to the production of seeds, within one growing season, and then dies. The length of growing seasons and period in which they take place vary according to geographical ...

, 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 Continent#Subcontinents, subcontinent of Eurasia ...

, 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 area ...

.''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

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 the ...

and disturbed ground. It grows to 10–50 cm tall, with a single, erect, hairless stem, branching toward the top. The

leaves A leaf (plural, : leaves) is any of the principal appendages of a vascular plant plant stem, stem, usually borne laterally aboveground and specialized for photosynthesis. Leaves are collectively called foliage, as in "autumn foliage", wh ...

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

bract In botany, a bract is a modified or specialized leaf, especially one associated with a reproductive structure such as a flower, inflorescence axis or cone scale. Bracts are usually different from foliage leaves. They may be smaller, larger, or of ...

s 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 Hepatocellular carcinoma (HCC) is the most common type of primary liver cancer in adults and is currently the most common cause of death in people with cirrhosis. HCC is the third leading cause of cancer-related deaths worldwide. It occurs in t ...

''in vivo'' in

mice A mouse ( : mice) is a small rodent. Characteristically, mice are known to have a pointed snout, small rounded ears, a body-length scaly tail, and a high breeding rate. The best known mouse species is the common house mouse (''Mus musculus' ...

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, '' Croto ...

(

12-deoxyphorbol-13-phenylacetale-20-acetate 1 (one, unit, unity) is a number representing a single or the only entity. 1 is also a numerical digit and represents a single unit of counting or measurement. For example, a line segment of ''unit length'' is a line segment of length 1 ...

12-deoxyphorbol-13-dodec-dienoate-20-acetate 1 (one, unit, unity) is a number representing a single or the only entity. 1 is also a numerical digit and represents a single unit of counting or measurement. For example, a line segment of ''unit length'' is a line segment of length 1 ...

, 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 irritants found in the plant. ''m''-Hydroxyphenylglycine and

3,5-dihydroxyphenylglycine (''S'')-3,5-Dihydroxyphenylglycine or DHPG is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5. DHPG was the first agonist shown to be selective for group I mGluRs. Agonist activity is found in only the ( ...

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,

punicafolin Punicafolin is an ellagitannin from the leaves of ''Punica granatum'' (pomegranate) and in ''Phyllanthus emblica''. Punicafolin is an isomer of tellimagrandin II and nupharin A, but the hexahydroxydiphenoyl Hexahydroxydiphenic acid is an organ ...

geraniin Geraniin is a dehydroellagitannin found in geraniums. It is found for instance in ''Geranium thunbergii'', which is one of the most popular folk medicines and also an official antidiarrheic drug in Japan. It can also be found in the rind of ''Neph ...

, 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 Asthma is a long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wheezing, cou ...

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