Euphorbia helioscopia | |
---|---|
Flowers and immature fruit | |
Scientific 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, [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]
Additional folk names include wart spurge, summer spurge, umbrella milkweed, and wolf's-milk. [5] [6]
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).
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 ]
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]
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.
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.
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.
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.
(S)-3,5-Dihydroxyphenylglycine or DHPG is a potent agonist of group I metabotropic glutamate receptors (mGluRs) mGluR1 and mGluR5.
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.
A hydrolysable tannin or pyrogallol-type tannin is a type of tannin that, on heating with hydrochloric or sulfuric acids, yields gallic or ellagic acids.
The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.
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.
1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.
The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of the pomegranate fruit.
Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.
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.
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.
β-amyrin synthase is an enzyme with systematic name (3S)-2,3-epoxy-2,3-dihydrosqualene mutase . This enzyme catalyses the following chemical reaction
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.
Balanophora japonica is a plant species in the genus Balanophora found in Japan.
Elaeocarpus sylvestris, the woodland elaeocarpus, is a tree species in the genus Elaeocarpus.