Euphorbia helioscopia
Flowers and immature fruit
Scientific classification Edit this classification
Kingdom: Plantae
Clade: Tracheophytes
Clade: Angiosperms
Clade: Eudicots
Clade: Rosids
Order: Malpighiales
Family: Euphorbiaceae
Genus: Euphorbia
Species:
E. helioscopia
Binomial name
Euphorbia helioscopia

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, native to most of Europe, northern Africa, and eastward through most of Asia.[1][2][3]

Additional folk names include wart spurge, summer spurge, umbrella milkweed, and wolf's-milk. [4][5]

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]

Similar species include Euphorbia rhabdotosperma, having the appearance of E. helioscopia with smaller parts and differing seed surface [6] (Iran, North Caucasus, Transcaucasus, Turkey, Turkmenistan).

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.[7] Its extract has been found to inhibit hepatocellular carcinoma in vivo in mice[8] and in vitro in human cells.

Chemistry

Euphorbia helioscopia contains the jatrophone-type diterpenoids euphoheliosnoid A, B, C[9] and D[7] and other toxic diterpenes such as euphoscopins, epieuphoscopins euphornins, cuphohelioscopins and euphohelionone.[10]

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.[11]

m-Hydroxyphenylglycine and 3,5-dihydroxyphenylglycine are two amino acids that can be isolated from the latex of E. helioscopia.[12]

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.[13] 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.[14]

References

  1. ↑ "Euphorbia helioscopia". Germplasm Resources Information Network. Agricultural Research Service, United States Department of Agriculture. Retrieved 14 January 2018.
  2. ↑ Flora Europaea: Euphorbia helioscopia
  3. 1 2 Blamey, M. & Grey-Wilson, C. (1989). Flora of Britain and Northern Europe. ISBN 0-340-40170-2
  4. 1 2 Malta Wild Plants Euphorbia helioscopia Archived 2007-08-07 at the Wayback Machine
  5. ↑ "Euphorbia helioscopia". Global Biodiversity Information Facility. Retrieved 4 December 2022.
  6. ↑ Davis. Flora of Turkey and the East Aegean Islands, vol. 7.
  7. 1 2 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ 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.
  13. ↑ 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.
  14. ↑ 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.
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