Turkesterone

Last updated
Turkesterone
Turkesterone.svg
Identifiers
  • (2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C27H44O8
Molar mass 496.641 g·mol−1
3D model (JSmol)
  • C[C@]12C[C@H]([C@H]3C(=CC(=O)[C@H]4[C@@]3(C[C@@H]([C@@H](C4)O)O)C)[C@@]1(CC[C@@H]2[C@](C)([C@@H](CCC(C)(C)O)O)O)O)O
  • InChI=1S/C27H44O8/c1-23(2,33)8-7-21(32)26(5,34)20-6-9-27(35)15-11-16(28)14-10-17(29)18(30)12-24(14,3)22(15)19(31)13-25(20,27)4/h11,14,17-22,29-35H,6-10,12-13H2,1-5H3/t14-,17+,18-,19+,20-,21+,22+,24-,25+,26+,27+/m0/s1
  • Key:WSBAGDDNVWTLOM-XHZKDPLLSA-N

Turkesterone is a phytoecdysteroid found in numerous plant species, including Ajuga turkestanica , [1] various Vitex species, [2] [3] [4] Triticum aestivum , [5] and Rhaponticum acaule. [6]

See also

Related Research Articles

<span class="mw-page-title-main">Wheat</span> Genus of grass cultivated for the grain

Wheat is a grass widely cultivated for its seed, a cereal grain that is a worldwide staple food. The many species of wheat together make up the genus Triticum ; the most widely grown is common wheat. The archaeological record suggests that wheat was first cultivated in the regions of the Fertile Crescent around 9600 BC. Botanically, the wheat kernel is a caryopsis, a type of fruit.

<span class="mw-page-title-main">Mangrove</span> Shrub growing in brackish water

A mangrove is a shrub or tree that grows mainly in coastal saline or brackish water. Mangroves grow in an equatorial climate, typically along coastlines and tidal rivers. They have special adaptations to take in extra oxygen and to remove salt, which allow them to tolerate conditions that would kill most plants. The term is also used for tropical coastal vegetation consisting of such species. Mangroves are taxonomically diverse, as a result of convergent evolution in several plant families. They occur worldwide in the tropics and subtropics and even some temperate coastal areas, mainly between latitudes 30° N and 30° S, with the greatest mangrove area within 5° of the equator. Mangrove plant families first appeared during the Late Cretaceous to Paleocene epochs, and became widely distributed in part due to the movement of tectonic plates. The oldest known fossils of mangrove palm date to 75 million years ago.

<span class="mw-page-title-main">Durum</span> Species of wheat used for food

Durum wheat, also called pasta wheat or macaroni wheat, is a tetraploid species of wheat. It is the second most cultivated species of wheat after common wheat, although it represents only 5% to 8% of global wheat production. It was developed by artificial selection of the domesticated emmer wheat strains formerly grown in Central Europe and the Near East around 7000 BC, which developed a naked, free-threshing form. Like emmer, durum wheat is awned. It is the predominant wheat that grows in the Middle East.

<span class="mw-page-title-main">Aminolevulinic acid</span> Endogenous non-proteinogenic amino acid

δ-Aminolevulinic acid, an endogenous non-proteinogenic amino acid, is the first compound in the porphyrin synthesis pathway, the pathway that leads to heme in mammals, as well as chlorophyll in plants.

<span class="mw-page-title-main">Spelt</span> Species of grain

Spelt, also known as dinkel wheat or hulled wheat, is a species of wheat that has been cultivated since approximately 5000 BCE.

<span class="mw-page-title-main">20-Hydroxyecdysone</span> Chemical compound

20-Hydroxyecdysone is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. It is also a phytoecdysteroid produced by various plants, including Cyanotis vaga, Ajuga turkestanica and Rhaponticum carthamoides where its purpose is presumably to disrupt the development and reproduction of insect pests. In arthropods, 20-hydroxyecdysone acts through the ecdysone receptor. Although mammals lack this receptor, 20-hydroxyecdysone affects mammalian biological systems. 20-Hydroxyecdysone is an ingredient of some supplements that aim to enhance physical performance. In humans, it is hypothesized to bind to the estrogen receptor beta (ERβ) protein-coding gene.

<span class="mw-page-title-main">Orthosilicic acid</span> Chemical compound, Si(OH)₄

Orthosilicic acid is an inorganic compound with the formula Si(OH)4. Although rarely observed, it is the key compound of silica and silicates and the precursor to other silicic acids [H2xSiOx+2]n. Silicic acids play important roles in biomineralization and technology.

Jonathan Dallas George Jones is a senior scientist at the Sainsbury Laboratory and a professor at the University of East Anglia using molecular and genetic approaches to study disease resistance in plants.

<span class="mw-page-title-main">Common wheat</span> Species of plant

Common wheat, also known as bread wheat, is a cultivated wheat species. About 95% of wheat produced worldwide is common wheat; it is the most widely grown of all crops and the cereal with the highest monetary yield.

<span class="mw-page-title-main">Taxonomy of wheat</span> Classification of wheat

During 10,000 years of cultivation, numerous forms of wheat, many of them hybrids, have developed under a combination of artificial and natural selection. This diversity has led to much confusion in the naming of wheats. Genetic and morphological characteristics of wheat influence its classification; many common and botanical names of wheat are in current use.

<span class="mw-page-title-main">Triticeae</span> Tribe of grasses

Triticeae is a botanical tribe within the subfamily Pooideae of grasses that includes genera with many domesticated species. Major crop genera found in this tribe include wheat, barley, and rye; crops in other genera include some for human consumption, and others used for animal feed or rangeland protection. Among the world's cultivated species, this tribe has some of the most complex genetic histories. An example is bread wheat, which contains the genomes of three species with only one being a wheat Triticum species. Seed storage proteins in the Triticeae are implicated in various food allergies and intolerances.

<i>Rhaponticum</i> Genus of flowering plants in the daisy family Asteraceae

Rhaponticum is a genus of flowering plants in the tribe Cardueae within the family Asteraceae. As of November 2023, it is accepted by Plants of the World Online, but rejected by the Global Compositae Database in favour of Leuzea.

Phytoecdysteroids are plant-derived ecdysteroids. Phytoecdysteroids are a class of chemicals that plants synthesize for defense against phytophagous insects. These compounds are mimics of hormones used by arthropods in the molting process known as ecdysis. When insects eat the plants with these chemicals they may prematurely molt, lose weight, or suffer other metabolic damage and die.

<i>Vitex rotundifolia</i> Species of vine

Vitex rotundifolia, the roundleaf chastetree or beach vitex, is a species of flowering plant in the sage family Lamiaceae. It is native to seashores throughout the Pacific. Its range includes continents and islands stretching from India east to Hawaii and from Korea south to Australia. This shrub typically grows approximately 1 m in height. It has a sprawling growth habit and produces runners that root regularly at nodes. This rooting pattern allows the plant to spread rapidly. At maturity, V. rotundifolia produces blue-purple flowers that are borne in clusters and ultimately yield small brown-black fruits. Its leaves are rounded at the tips with green upper surfaces and silver lower surfaces. While the plant is a seashore obligate, it grows over a wide latitude range. It has been used for medicinal purposes throughout its native range. More recently, it was imported to the eastern United States where it has become a seashore invasive. Control efforts are presently underway to protect the fragile beach dune ecosystem.

4-Hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase (EC 3.2.1.182, DIMBOAGlc hydrolase, DIMBOA glucosidase) is an enzyme with systematic name (2R)-4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside beta-D-glucosidase. This enzyme catalyses the following chemical reaction

<i>Triticum carthlicum</i> Species of grass

Triticum carthlicum Nevski, 1934, the Persian wheat, is a wheat with a tetraploid genome.

<span class="mw-page-title-main">Flora of Nepal</span>

The flora of Nepal is one of the richest in the world due to the diverse climate, topology and geography of the country. Research undertaken in the late 1970s and early 1980s documented 5067 species of which 5041 were angiosperms and the remaining 26 species were gymnosperms. The Terai area has hardwood, bamboo, palm, and sal trees. Notable plants include the garden angelica, Luculia gratissima, Meconopsis villosa, and Persicaria affinis. However, according to ICOMOS checklist, in the protected sites, there are 2,532 species of vascular plants under 1,034 genera and 199 families. The variation in figures is attributed to inadequate floral coverage filed studies. Some of the plants contain medicinal values. It contains certain chemical which is used to heal wound by There are 400 species of vascular plants which are endemic to Nepal. Of these, two in particular are orchids Pleione coronaria and Oreorchis porphyranthes. The most popular endemic plant of Nepal is rhododendron (arboreum) which in Nepali language is called lali guras.

Ernest Robert Sears was an American geneticist, botanist, pioneer of plant genetics, and leading expert on wheat cytogenetics. Sears and Sir Ralph Riley (1924–1999) are perhaps the two most important founders of chromosome engineering in plant breeding.

<i>Ajuga turkestanica</i> Species of flowering plant

Ajuga turkestanica is a herbaceous flowering plant native to Central Asia. It was first described in 1894.

This paleobotany list records new fossil plant taxa that were to be described during the year 2022, as well as notes other significant paleobotany discoveries and events which occurred during 2022.

References

  1. Guibout L, Mamadalieva N, Balducci C, Girault JP, Lafont R (2015). "The minor ecdysteroids from Ajuga turkestanica" (PDF). Phytochemical Analysis. 26 (5): 293–300. Bibcode:2015PChAn..26..293G. doi:10.1002/pca.2563. PMID   25953625. S2CID   10373609.
  2. dos Santos TC, Delle Monache F, Leitão SG (March 2001). "Ecdysteroids from two Brazilian Vitex species". Fitoterapia. 72 (3): 215–220. doi:10.1016/s0367-326x(00)00304-x. PMID   11295296.
  3. Suksamrarn A, Kumpun S, Yingyongnarongkul BE (November 2002). "Ecdysteroids of Vitex scabra stem bark". Journal of Natural Products. 65 (11): 1690–1692. doi:10.1021/np020199o. PMID   12444704.
  4. Bunu MI, Ndinteh DT, Macdonald JR, Langat MK, Isyaka SM, Sadgrove NJ, et al. (August 2021). "Ecdysteroids from the Stem Bark of Vitex doniana Sweet (Lamiaceae; ex. Verbenaceae): A Geographically Variable African Medicinal Species". Antibiotics. 10 (8): 937. doi: 10.3390/antibiotics10080937 . PMC   8388959 . PMID   34438987.
  5. Janeczko A, Oklestkova J, Tarkowská D, Drygaś B (March 2021). "Naturally Occurring Ecdysteroids in Triticum aestivum L. and Evaluation of Fenarimol as a Potential Inhibitor of Their Biosynthesis in Plants". International Journal of Molecular Sciences. 22 (6): 2855. doi: 10.3390/ijms22062855 . PMC   7999220 . PMID   33799719.
  6. Zughdani M, Yusufoğlu HS, Ekiz G, Linden A, Çalış İ (December 2020). "Ecdysteroids from the underground parts of Rhaponticum acaule (L.) DC" (PDF). Phytochemistry. 180: 112530. Bibcode:2020PChem.180k2530Z. doi:10.1016/j.phytochem.2020.112530. PMID   33049649. S2CID   222353903.