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IUPAC name [(1S,2S,4R,8R,9S,10Z,12R)-11-[[(2R,3S,4R,5R)-3-acetyloxy-4,5-dihydroxyoxan-2-yl]oxymethyl]-12-methoxy-1,5-dimethyl-8-propan-2-yl-15-oxatricyclo[10.2.1.04,9]pentadeca-5,10,13-trien-2-yl] (E)-3-(1-methylimidazol-4-yl)prop-2-enoate | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C35H48N2O10 | |
Molar mass | 656.773 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Infobox references | |
Eleutherobin is a marine diterpene glycoside with in vitro anticancer activity. [1]
Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), etc. A well known monoterpene is alpha-pinene, a major component of turpentine.
Digitoxin is a cardiac glycoside. It is a phytosteroid and is similar in structure and effects to digoxin. Unlike digoxin, it is eliminated via the liver, so could be used in patients with poor or erratic kidney function. However, it is now rarely used in current Western medical practice. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.
Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and antiinflammatory.
The chiral pool is a "collection of abundant enantiopure building blocks provided by nature" used in synthesis. Contributors to the chiral pool are amino acids, sugars, and terpenes. Their use improves the efficiency of total synthesis. Not only does the chiral pool contribute a premade carbon skeleton, their chirality is usually preserved in the remainder of the reaction sequence.
Taxanes are a class of diterpenes. They were originally identified from plants of the genus Taxus (yews), and feature a taxadiene core. Paclitaxel (Taxol) and docetaxel (Taxotere) are widely used as chemotherapy agents. Cabazitaxel was FDA approved to treat hormone-refractory prostate cancer.
Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids.
Fusicoccins are organic compounds produced by a fungus. It has detrimental effect on plants and causes their death.
Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant Stevia rebaudiana (Asteraceae) and the main ingredients of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species Stevia phlebophylla and in the plant Rubus chingii (Rosaceae).
Andrographolide is a labdane diterpenoid that has been isolated from the stem and leaves of Andrographis paniculata. Andrographolide is an extremely bitter substance.
Eribulin, sold under the brand name Halaven, is an anticancer medication used to treat breast cancer and liposarcoma.
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.
The salinosporamides are a group of closely related chemical compounds isolated from marine bacteria in the genus Salinispora. They possess a densely functionalized γ-lactam-β-lactone bicyclic core.
Platinum-based antineoplastic drugs are chemotherapeutic agents used to treat cancer. They are coordination complexes of platinum. These drugs are used to treat almost half of people receiving chemotherapy for cancer. In this form of chemotherapy, commonly used drugs include cisplatin, oxaliplatin, and carboplatin, but several have been proposed or are under development. Addition of platinum-based chemotherapy drugs to chemoradiation in women with early cervical cancer seems to improve survival and reduce risk of recurrence.
Salinispora arenicola is an obligate marine actinomycetes bacterium species. It produces salinosporamide, a potential anti-cancer agent. The type strain is CNH-643T.
Isotuberculosinol, also called nosyberkol or edaxadiene is a diterpene molecule produced by the bacterium Mycobacterium tuberculosis, the causative agent of TB, which aids in its pathogenesis. Isotuberculosinol functions by preventing maturation of the host-cell phagosome in which the bacterium lives. Maturation of the phagosome would enable it to kill the bacterium. Mutations in genes involved in the biosynthetic pathway of nosyberkol result in normal development of the phagosome and reduction of mycobacterial infection. These biosynthetic genes include isotuberculosinol synthase.
Erythropodium caribaeorum, commonly known as the encrusting gorgonian or encrusting polyps, is a species of soft coral in the family Anthothelidae. It inhabits coral reefs and rocky bottoms in the Caribbean, Bahamas, and Florida, growing at depths of 0.5 to 25 metres.
Bugula neritina is a cryptic species complex of sessile marine animal in the genus Bugula.
Antillogorgia elisabethae is a species of soft coral found in the Caribbean Sea in the shape of a sea plume. It resides from depths of 25 metres (82 ft) to 30 metres (98 ft), often at reef drop-offs. It looks like a plume of feathery appendages with radial symmetry. The branches of A. elisabethae are pinnate and distichous, and will orient themselves in the direction of the ocean current. It ranges in size from 0.3 metres (0.98 ft) to 2 metres (6.6 ft). It is considered commercially important as it is harvested for analgesics and cosmetic creams. The compound that is believed to cause its beneficial effects is Pseudopterosin A, a diterpene glycoside, a selective analgesic. A. elisabethae is also used in fish tanks as a part of the commercial pet industry. The species has a Least Concern conservation status.
Hypoestes forskaolii is an annual or perennial herb that grows up to 1 m tall with its stem and leaves being nearly glabrous. It has pale pink or white flowers.