In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.
Plantago lanceolata is a species of flowering plant in the plantain family Plantaginaceae. It is known by the common names ribwort plantain, narrowleaf plantain, English plantain, ribleaf, lamb's tongue, and buckhorn. It is a common weed on cultivated or disturbed land.
Junonia coenia, known as the common buckeye or buckeye, is a butterfly in the family Nymphalidae. It is found in the United States east of the Rocky Mountains and in Mexico. Its habitat is open areas with low vegetation and some bare ground. Its original ancestry has been traced to Africa, which then experiences divergence in Asia. The species Junonia grisea, the gray buckeye, is found west of the Rocky Mountains and was formerly a subspecies of Junonia coenia.
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.
Lamium album, commonly called white nettle or white dead-nettle, is a flowering plant in the family Lamiaceae. It is native throughout Europe and Asia, growing in a variety of habitats from open grassland to woodland, generally on moist, fertile soils.
Malvidin is an O-methylated anthocyanidin, the 3',5'-methoxy derivative of delphinidin. As a primary plant pigment, its glycosides are highly abundant in nature.
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 S. phlebophylla and in the plant Rubus chingii (Rosaceae).
Iridoids are a type of monoterpenoids in the general form of cyclopentanopyran, found in a wide variety of plants and some animals. They are biosynthetically derived from 8-oxogeranial. Iridoids are typically found in plants as glycosides, most often bound to glucose.
Scrophularia californica is a flowering plant in the figwort family which is known by the common names California figwort and California bee plant.
The variable checkerspot or Chalcedon checkerspot is a butterfly in the family Nymphalidae. It is found in western North America, where its range stretches from Alaska in the north to Baja California in the south and extends east through the Rocky Mountains into Colorado, Montana, New Mexico and Wyoming. The butterfly is usually brown or black with extensive white and yellow checkering and some red coloration on the dorsal wing. Adult wingspan is 3.2–5.7 cm (1.3–2.2 in). Adult butterflies feed on nectar from flowers while larvae feed on a variety of plants including snowberry (Symphoricarpos), paintbrush (Castilleja), Buddleja, Diplacus aurantiacus and Scrophularia californica.
Cucurbitacin is a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as triterpenes, formally derived from cucurbitane, a triterpene hydrocarbon – specifically, from the unsaturated variant cucurbit-5-ene, or 19(10→9β)-abeo-10α-lanost-5-ene. They often occur as glycosides.
Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not to be confused with thujone, a neurotoxin also found in Artemisia absinthium.
Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores.
Euphydryas cynthia, or Cynthia's fritillary, is a butterfly of the family Nymphalidae. It is found in the Alps and in mountainous areas of Bulgaria in alpine meadows from 400 to 2,300 meters.
Torreyanic acid is a dimeric quinone first isolated and by Lee et al. in 1996 from an endophyte, Pestalotiopsis microspora. This endophyte is likely the cause of the decline of Florida torreya, an endangered species that is related to the taxol-producing Taxus brevifolia. The natural product was found to be cytotoxic against 25 different human cancer cell lines with an average IC50 value of 9.4 µg/mL, ranging from 3.5 (NEC) to 45 (A549) µg/mL. Torreyanic acid was found to be 5-10 times more potent in cell lines sensitive to protein kinase C (PKC) agonists, 12-o-tetradecanoyl phorbol-13-acetate (TPA), and was shown to cause cell death via apoptosis. Torreyanic acid also promoted G1 arrest of G0 synchronized cells at 1-5 µg/mL levels, depending on the cell line. It has been proposed that the eukaryotic translation initiation factor EIF-4a is a potential biochemical target for the natural compound.
Castilleja levisecta is a rare species of flowering plant in the family Orobanchaceae known by the common name golden paintbrush, or golden Indian paintbrush, listed under the Endangered Species Act in 1997. It is native to British Columbia and Washington, where it is known from eleven remaining populations. It occurred in Oregon but all natural occurrences there have been extirpated. It has been reintroduced to a few areas in Oregon, but it remains to be seen if the plants will survive. The plant is a federally listed endangered species of Canada and was listed as threatened in the United States in 1997. On June 30, 2021, the plant was proposed for delisting due to recovery.
Euphydryas editha taylori, the Whulge checkerspot or Taylor's checkerspot, is a butterfly native to an area of the northwestern United States and Vancouver Island.
(R)-prunasin is a cyanogenic glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile.
Prunin is a flavanone glycoside found in immature citrus fruits and in tomatoes. Its aglycone form is called naringenin.
Rishitin is a terpenoid compound, produced by some plants belonging to the Solanum family, including the potato and tomato. Rishitin belongs to a heterogeneous group of anti-microbial plant defense compounds termed phytoalexins and is produced upon pathogen attack. Same as the phytoalexin capsidiol, it belongs to the group of sesquiterpenes and is as such an FPP derivative. Rishitin was named after the potato cultivar Rishiri, where it was first discovered in 1968.
