Euphorbia helioscopia

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Euphorbia helioscopia
Euphorbia helioscopia2.jpg
Flowers and immature fruit
Scientific classification OOjs UI icon edit-ltr.svg
Kingdom: Plantae
Clade: Tracheophytes
Clade: Angiosperms
Clade: Eudicots
Clade: Rosids
Order: Malpighiales
Family: Euphorbiaceae
Genus: Euphorbia
Species:
E. helioscopia
Binomial name
Euphorbia helioscopia
L.

Euphorbia helioscopia, the sun spurge or madwoman's milk, [1] 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. [2] [3] [4]

Contents

Additional folk names include wart spurge, summer spurge, umbrella milkweed, and wolf's-milk. [5] [6]

Description

Euphorbia helioscopia 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. [4] [5]

Similar species include Euphorbia rhabdotosperma , having the appearance of E. helioscopia with smaller parts and differing seed surface [7] (Iran, North Caucasus, Transcaucasus, Turkey, Turkmenistan).

Uses

Active ingredients are extracted from it for use in pharmaceutical industry.[ citation needed ] The plant is used in Chinese traditional medicine. [8]

Its extract has been found to inhibit hepatocellular carcinoma in vivo in mice. [9]

Chemistry

Euphorbia helioscopia contains toxic diterpenes [10] and diterpenoids [11] and phorbol esters. These substances are the major skin irritants found in the plant. [12] The plant is considered poisonous when eaten raw. Nausea, allergic reactions, skin irritation, vomiting may occur after eating. [13]

A number of tannins can be found in E. helioscopia. [14] 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. [15]

Related Research Articles

<i>Euphorbia</i> Genus of flowering plants in the spurge family Euphorbiaceae

Euphorbia is a very large and diverse genus of flowering plants, commonly called spurge, in the family Euphorbiaceae. "Euphorbia" is sometimes used in ordinary English to collectively refer to all members of Euphorbiaceae, not just to members of the genus.

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

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<i>Hydrangea macrophylla</i> Species of flowering plant in the family Hydrangeaceae

Hydrangea macrophylla is a species of flowering plant in the family Hydrangeaceae, native to Japan. It is a deciduous shrub growing to 2 m (7 ft) tall by 2.5 m (8 ft) broad with large heads of pink or blue flowers in summer and autumn. Common names include bigleaf hydrangea, French hydrangea, lacecap hydrangea, mophead hydrangea, and hortensia. It is widely cultivated in many parts of the world in many climates. It is not to be confused with H. aspera 'Macrophylla'.

<span class="mw-page-title-main">Resiniferatoxin</span> Chemical compound

Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge, a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.

<span class="mw-page-title-main">Phorbol</span> Chemical compound

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 tiglium. The structure of phorbol was determined in 1967. Various esters of phorbol have important biological properties, the most notable of which is the capacity to act as tumor promoters through activation of protein kinase C. They mimic diacylglycerols, glycerol derivatives in which two hydroxyl groups have reacted with fatty acids to form esters. The most common and potent phorbol ester is 12-O-tetradecanoylphorbol-13-acetate (TPA), also called phorbol-12-myristate-13-acetate (PMA), which is used as a biomedical research tool in contexts such as models of carcinogenesis.

<i>Euphorbia peplus</i> Species of plant

Euphorbia peplus, is a species of Euphorbia, native to most of Europe, northern Africa and western Asia, where it typically grows in cultivated arable land, gardens and other disturbed land.

<i>Bifurcaria</i> Genus of seaweeds

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<span class="mw-page-title-main">Euphorbiaceae</span> Family of Eudicot flowering plants

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Galanolactone is a diterpenoid lactone first isolated from ginger. It is present in acetone extracts of ginger, and appears to be an antagonist at 5-HT3 receptors.

<span class="mw-page-title-main">Taxodone</span> Chemical compound

Taxodone is a naturally occurring diterpenoid found in Taxodium distichum, Rosmarinus officinalis (rosemary), several salvia species and other plants, along with its oxidized rearrangement product, taxodione. Taxodone and taxodione exhibit anticancer, antibacterial, antioxidant, antifungal, insecticide, and antifeedant activities.

<span class="mw-page-title-main">Quinone methide</span> Chemical compound

A quinone methide is a type of conjugated organic compound that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene unit. It is analogous to a quinone, but having one of the double bonded oxygens replaced with a carbon. The carbonyl and methylidene are usually oriented either ortho or para to each other. There are some examples of transient synthetic meta quinone methides.

<span class="mw-page-title-main">Ingenol mebutate</span> Chemical compound

Ingenol mebutate, sold under the brand name Picato, is a substance that is found in the sap of the plant Euphorbia peplus, commonly known as petty spurge, and is an inducer of cell death. This compound was isolated first from this plant in 2000. A gel formulation of the drug has been approved by the U.S. Food and Drug Administration (FDA) and by the European Medicines Agency (EMA) for the topical treatment of actinic keratosis. Two different strengths of the gel have been approved for use on either the face and scalp (0.015%) or the trunk and extremities (0.05%), respectively. In 2020 the drug was withdrawn from the market in the EU.

<span class="mw-page-title-main">Punigluconin</span> Chemical compound

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<i>Mallotus japonicus</i> Species of flowering plant

Mallotus japonicus, also known as East Asian mallotus, the food wrapper plant or "Akamegashiwa" in Japanese, is a plant species in the genus Mallotus native to China. It is also found in Japan and Korea. This species was first described in 1865, its name was verified by AAS Systematic Botanists on October 2, 2015.

<span class="mw-page-title-main">Mallotusinic acid</span> Chemical compound

Mallotusinic acid is a hydrolysable tannin found in the bark of Mallotus japonicus. It is more generally present in Geraniales.

<span class="mw-page-title-main">Mallojaponin</span> Chemical compound

Mallojaponin is a hydrolysable tannin found in the bark of Mallotus japonicus. This compound contains the moiety elaeocarpusinic acid, an oxidized hexahydroxydiphenic acid group which reacted with a dehydroascorbic acid molecule. It also contains a valoneic acid and a gallic acid moieties linked to a glucose molecule.

Plaunotol (18-hydroxygeranylgeraniol) is a chemical compound with the molecular formula C20H34O2. It is a diterpene that was first isolated from Croton sublyratus.

References

  1. "Euphorbia helioscopia (Madwoman's Milk) - Practical Plants". practicalplants.org. Retrieved 2024-03-28.
  2. "Euphorbia helioscopia". Germplasm Resources Information Network . Agricultural Research Service, United States Department of Agriculture . Retrieved 14 January 2018.
  3. Flora Europaea: Euphorbia helioscopia
  4. 1 2 Blamey, M. & Grey-Wilson, C. (1989). Flora of Britain and Northern Europe. ISBN   0-340-40170-2
  5. 1 2 Malta Wild Plants Euphorbia helioscopia Archived 2007-08-07 at the Wayback Machine
  6. "Euphorbia helioscopia". Global Biodiversity Information Facility . Retrieved 4 December 2022.
  7. Davis. Flora of Turkey and the East Aegean Islands, vol. 7.
  8. 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.
  9. 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.
  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. Bibcode:1989PChem..28.3421Y. doi:10.1016/0031-9422(89)80360-7.
  11. Zhang, Wen; Guo, Yue-Wei (2005). "Three New Jatrophone-Type Diterpenoids from Euphorbia helioscopia". Planta Medica. 71 (3): 283–6. doi:10.1055/s-2005-837832. PMID   15770554. S2CID   29332788.
  12. 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.
  13. Abid Aqsa, Mushtaq Ahmad, Muhammad Zafar, Sadia Zafar, Mohamed Fawzy Ramadan, Ashwaq T. Althobaiti, Shazia Sultana, Omer Kilic, Trobjon Makhkamov, Akramjon Yuldashev, Oybek Mamarakhimov, Khislat Khaydarov, Afat O. Mammadova, Komiljon Komilov, and Salman Majeed (December 2023). "Foliar epidermal and trichome micromorphological diversity among poisonous plants and their taxonomic significance". Folia Horticulturae . 35 (2): 243–274. doi: 10.2478/fhort-2023-0019 . ISSN   2083-5965.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  14. 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 .
  15. 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.