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

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. [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

It is highly poisonous.[ citation needed ] Active ingredients are extracted from it for use in pharmaceutical industry.[ citation needed ] It is also a plant used in Chinese traditional medicine. [8] Its extract has been found to inhibit hepatocellular carcinoma in vivo in mice [9] and in vitro in human cells.[ citation needed ]

Chemistry

Euphorbia helioscopia contains the jatrophone-type diterpenoids euphoheliosnoid A, B, C [10] and D [8] and other toxic diterpenes such as euphoscopins, epieuphoscopins euphornins, cuphohelioscopins and euphohelionone. [11]

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. [12]

m-Hydroxyphenylglycine and 3,5-dihydroxyphenylglycine are two amino acids that can be isolated from the latex of E. helioscopia. [13]

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. [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.

In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is the interconversion of one epimer to the other epimer.

<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.

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

(S)-3,5-Dihydroxyphenylglycine or DHPG is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5.

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

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 the type genus of the family. Most spurges, such as Euphorbia paralias, are herbs, but some, especially in the tropics, are shrubs or trees, such as Hevea brasiliensis. Some, such as Euphorbia canariensis, are succulent and resemble cacti because of convergent evolution. This family has a cosmopolitan global distribution. The greatest diversity of species is in the tropics; however, the Euphorbiaceae also have many species in nontropical areas of all continents except Antarctica.

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<span class="mw-page-title-main">1,2,3,4,6-Pentagalloyl glucose</span> Chemical compound

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

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

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

Sanguisorbic acid is a constituent of some ellagitannins. It is constituted by a hexahydroxydiphenic acid unit linked by an O-C bond to a gallic acid. The differences with its isomers, valoneic acid and nonahydroxytriphenic acid, are that the hydroxyl that links the hexahydroxydiphenoyl (HHDP) group to the galloyl group belongs to the galloyl group in valoneic acid, while in nonahydroxytriphenic acid, the hexahydroxydiphenic acid unit is linked by a C-C bond to gallic acid.

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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.

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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. 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.
  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. 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. S2CID   29332788.
  11. 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.
  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. 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.
  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.