Euphorbia helioscopia

Life-forms

Classification System: APG IV

Superregnum: Eukaryota
Regnum: Plantae
Cladus: Angiosperms
Cladus: Eudicots
Cladus: Core eudicots
Cladus: Rosids
Cladus: Eurosids I
Ordo: Malpighiales

Familia: Euphorbiaceae
Subfamilia: Euphorbioideae
Tribus: Euphorbieae
Subtribus: Euphorbiinae
Genus: Euphorbia
Subgenus: E. subg. Esula
Sectio: E. sect. Helioscopia
Species: Euphorbia helioscopia
Subspecies: E. h. subsp. helioscopia – E. h. subsp. hiemalis
Name

Euphorbia helioscopia L., Sp. Pl. 1: 459 (1753).
Synonyms

Homotypic
Tithymalus helioscopius (L.) Hill, Hort. Kew.: 172.3 (1768).
Galarhoeus helioscopius (L.) Haw., Syn. Pl. Succ.: 152 (1812).
Euphorbion helioscopium (L. St.-Lag., Ann. Soc. Bot. Lyon 7: 126 (1880).

Distribution
Native distribution areas:

Continental: Europe
Regional: Northern Europe
Finland, Great Britain, Ireland, Norway, Sweden.
Regional: Middle Europe
Austria, Belgium, Czechoslovakia, Germany, Hungary, Netherlands, Poland, Switzerland.
Regional: Southwestern Europe
Baleares, Corse, France, Portugal, Sardegna, Spain.
Regional: Southeastern Europe
Albania, Bulgaria, Greece, Italy, Kriti, Romania, Sicilia, Yugoslavia.
Regional: Eastern Europe
Belarus, Baltic States, Krym, Central European Russia, East European Russia, South European Russia, Northwest European Russia, Ukraine.
Continental: Africa
Regional: Northern Africa
Algeria, Egypt, Libya, Morocco, Tunisia.
Regional: Macaronesia
Azores, Canary Islands, Madeira.
Regional: Middle Atlantic Ocean
St. Helena (introduced).
Continental: Asia-Temperate
Regional: Siberia
Altay, West Siberia.
Regional: Middle Asia
Kazakhstan, Kirgizstan, Turkmenistan, Tadzhikistan, Uzbekistan.
Regional: Caucasus
Transcaucasus.
Regional: Western Asia
Afghanistan, Cyprus, East Aegean Islands, Iran, Iraq, Lebanon-Syria, Palestine, Sinai, Turkey.
Regional: Arabian Peninsula
Gulf States, Saudi Arabia.
Regional: China
China South-Central, Hainan, Inner Mongolia, Manchuria, China North-Central, Qinghai, China Southeast, Xinjiang.
Regional: Eastern Asia
Japan, Korea, Nansei-shoto, Taiwan.
Continental: Asia-Tropical
Regional: Indian Subcontinent
Bangladesh, India, Pakistan, West Himalaya.
Regional: Indo-China
Vietnam.
Continental: Australasia
Regional: New Zealand
New Zealand North, New Zealand South (all introduced).
Continental: Pacific
Regional: Southwestern Pacific
New Caledonia (introduced).
Continental: Northern America (all introduced)
Regional: Western Canada
Alberta, British Columbia, Saskatchewan.
Regional: Eastern Canada
New Brunswick, Newfoundland, Nova Scotia, Ontario, Prince Edward Isle, Québec.
Regional: Northwestern U.S.A.
Idaho, Montana, Oregon, Washington, Wyoming.
Regional: North-Central U.S.A.
Illinois, Wisconsin.
Regional: Northeastern U.S.A.
Connecticut, Maine, Massachusetts, Michigan, New Hampshire, New Jersey, New York, Ohio, Pennsylvania, Vermont.
Regional: Southwestern U.S.A.
California.
Regional: South-Central U.S.A.
Texas.
Regional: Southeastern U.S.A.
Alabama, Delaware, District of Columbia, Georgia, Louisiana, Maryland, North Carolina, South Carolina, Tennessee, Virginia.
Continental: Southern America
Regional: Southern South America
Argentina Northeast (introduced).
Continental: Antarctic
Regional: Subantarctic Islands
Falkland Islands (introduced).

References: Brummitt, R.K. 2001. TDWG – World Geographical Scheme for Recording Plant Distributions, 2nd Edition
References
Primary references

Linnaeus, C. 1753. Species Plantarum. Tomus I: 459. Reference page.

Links

Govaerts, R. et al. 2020. Euphorbia helioscopia in World Checklist of Selected Plant Families. The Board of Trustees of the Royal Botanic Gardens, Kew. Published online. Accessed: 2020 Jun 30. Reference page.
International Plant Names Index. 2020. Euphorbia helioscopia. Published online. Accessed: Jun 30 2020.
Govaerts, R. et al. 2020. Euphorbia helioscopia in Kew Science Plants of the World online. The Board of Trustees of the Royal Botanic Gardens, Kew. Published online. Accessed: 2020 Jun 30. Reference page.
Tropicos.org 2020. Euphorbia helioscopia. Missouri Botanical Garden. Published online. Accessed: 30 Jun 2020.
USDA, ARS, Germplasm Resources Information Network. Euphorbia helioscopia in the Germplasm Resources Information Network (GRIN), U.S. Department of Agriculture Agricultural Research Service. Accessed: 08-Apr-12.

Vernacular names
Afrikaans: Sambreel-melkkruid
العربية: جيجان
azərbaycanca: Günəbaxan südləyən
català: Lleterola, Lleterola d'hort
kaszëbsczi: Psotnik
čeština: pryšec kolovratec
Cymraeg: Llaethlys yr ysgyfarnog
dansk: Skærm-Vortemælk
Deutsch: Sonnwend-Wolfsmilch
dolnoserbski: Słyńcne wjelkowe mloko
Ελληνικά: Ευφορβία η ηλιοσκόπια, Ευβορβία η ηλιοσκόπια
English: sun Spurge, madwoman's milk, umbrella milkweed
español: lecherula, lechetrezna girasol, pichoga, tornagallos, carajera, euforbia madrugadora, hierba curandera, lecheinterna, leche interna, lechera, lecherina, lecherinas, lecheterna, lechetrezna, lechetrezna común, lechetrezna solar, lechintenna, lechiterna, lechitrezna que sigue al sol, lechocino, lechuguino, mirasol, rechiruela, ésula, titimalo helioscopio, untapijas
eesti: Harilik piimalill, Tithymalus helioscopius
فارسی: شیرسگ
suomi: Viisisädetyräkki
français: Euphorbe réveille-matin, Euphorbe helioscope, Herbe aux verrues, Euphorbe reveille-matin, Petite éclaire, Euphorbe réveil-matin
Gàidhlig: Lus nam Foinneachan
galego: Leitarega
hornjoserbsce: Słónčna mlóčeń
italiano: Erba calenzola, Euforbia elioscopia, Erba calenzuola
日本語: トウダイグサ
한국어: 등대풀, 택칠
lietuvių: Dirvinė karpažolė
Nederlands: Kroontjeskruid
polski: Wilczomlecz obrotny
پنجابی: چھتری دودک
português: Maleiteira, Tititalo-dos-vales
română: Laptele Cucului
русский: Молочай-солнцегляд, Молочай солнцегляд
slovenčina: mliečnik kolovratcový
slovenščina: sončni mleček
svenska: Revormstörel
Türkçe: Sarı sütleğen, Seher otu
中文（简体）: 泽漆
中文（繁體）: 澤漆
中文（臺灣）: 澤漆
中文: 泽漆

Euphorbia helioscopia, the sun spurge, is a species of flowering plant in the spurge family Euphorbiaceae. It is a herbaceous annual plant, native to most of Europe, northern Africa, and eastward through most of Asia.[1][2][3]

Folk names include wart spurge, umbrella milkweed and madwoman's milk.[4]

Description

It is an annual plant growing in arable land 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 flowers are small, yellow-green, with two to five basal bracts similar to the leaves but yellower; flowering lasts from mid-spring to late summer.[3][4]
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.[5] Its extract has been found to inhibit hepatocellular carcinoma in vivo in mice[6] and in vitro in human cells.
Chemistry

Euphorbia helioscopia contains the jatrophone-type diterpenoids euphoheliosnoid A, B, C[7] and D[5] and other toxic diterpenes such as euphoscopins, epieuphoscopins euphornins, cuphohelioscopins and euphohelionone.[8]

Four esters of 12-deoxyphorbol (12-deoxyphorbol-13-phenylacetale-20-acetate, 12-deoxyphorbol-13-dodec-dienoate-20-acetate, 12-deoxyphorbol-13-[2-methyl-cis-2-butenoate]-20-acetate and 12-deoxyphorbol-13-[2-methyl-cis-2-butenoate]) can be isolated from the fresh aerial parts. These substances are the major skin irritants found in the plant.[9]

m-Hydroxyphenylglycine and 3,5-dihydroxyphenylglycine are two amino acids that can be isolated from the latex of E. helioscopia.[10]

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, geraniin, elaeocarpusin, furosin, terchebin, mallotusinin and carpinusin.[11] Helioscopinin-A shows anti-allergic and anti-asthmatic activities in guinea pigs. It is suggested that this compound exerts its activities through antagonism on leukotriene D4-induced responses.[12]
References

"Euphorbia helioscopia". Germplasm Resources Information Network (GRIN). Agricultural Research Service (ARS), United States Department of Agriculture (USDA). Retrieved 14 January 2018.
Flora Europaea: Euphorbia helioscopia
Blamey, M. & Grey-Wilson, C. (1989). Flora of Britain and Northern Europe. ISBN 0-340-40170-2
Malta Wild Plants Euphorbia helioscopia Archived 2007-08-07 at the Wayback Machine
Zhang, Wen; Guo, Yue-Wei (2006). "Chemical Studies on the Constituents of the Chinese Medicinal Herb Euphorbia helioscopia L". Chemical & Pharmaceutical Bulletin. 54 (7): 1037–9. doi:10.1248/cpb.54.1037. PMID 16819227.
Cheng J, Han W, Wang Z, Shao Y, Wang Y, Zhang Y, Li Z, Xu X, Zhang Y (2015). "Hepatocellular Carcinoma Growth Is Inhibited by Euphorbia helioscopia L. Extract in Nude Mice Xenografts". Biomed Res Int. 2015: 1–9. doi:10.1155/2015/601015. PMC 4450285. PMID 26090427.
Zhang, Wen; Guo, Yue-Wei (2005). "Three New Jatrophone-Type Diterpenoids fromEuphorbia helioscopia". Planta Medica. 71 (3): 283–6. doi:10.1055/s-2005-837832. PMID 15770554.
Yamamura, Shosuke; Shizuri, Yoshikazu; Kosemura, Seiji; Ohtsuka, Jiro; Tayama, Takao; Ohba, Shigeru; Ito, Masatoki; Saito, Yoshihiko; Terada, Yukimasa (1989). "Diterpenes from Euphorbia helioscopia". Phytochemistry. 28 (12): 3421. doi:10.1016/0031-9422(89)80360-7.
Schmidt, Richard J.; Evans, Fred J. (1980). "Skin irritants of the sun spurge (Euphorbia helioscopia L)". Contact Dermatitis. 6 (3): 204–10. doi:10.1111/j.1600-0536.1980.tb05599.x. PMID 7389328. S2CID 22253978.
Müller, P; Schütte, HR (1968). "M-Hydroxyphenylglycine and 3,5-dihydroxyphenylglycine, 2 new amino acids from the latex of Euphorbia helioscopia L". Zeitschrift für Naturforschung B (in German). 23 (5): 659–63. doi:10.1515/znb-1968-0516. PMID 4385921. S2CID 94822221.
Lee, Seung-Ho; Tanaka, Takashi; Nonaka, Gen-Ichiro; Nishioka, Itsuo (1990). "Tannins and related compounds. XCV. Isolation and characterization of helioscopinins and helioscopins, four new hydrolyzable tannins from Euphorbia helioscopia L. (1)". Chemical & Pharmaceutical Bulletin. 38 (6): 1518. doi:10.1248/cpb.38.1518.
Park Kwan Ha; Koh Dongsoo; Lee Seungho; Jung Illmin; Kyung Hyun Kim; Lee Chul-Hoon; Kim Kye-Hoon; Lim Yoongho (2001). "Anti-allergic and anti-asthmatic activity of helioscopinin-A, a polyphenol compound, isolated from Euphorbia helioscopia". Journal of Microbiology and Biotechnology. 11 (1): 138–142. INIST:995613.