Friday, 2 October 2020

September phytochemicals! Why are shrimp and flamingos pink?

Happy #PhytochemicalFriday! Today's suggestion from @YankeeLady76. Spilanthol: a fatty amide from the 'electric daisy' Acmella oleracea. Chewing the plant's flowers releases spilanthol into the mouth, causing a tingling, static-like sensation. Signature cocktail ingredient!

Happy #PhytochemicalFriday! Today: alpha-Eleostearic acid, the primary component of tung oil - a wood finish that is believed to have been used since before the common era. The oil is harvested from Vernicia fordii (Euphorbiaceae!?) - a tree with separate male and female flowers.
Happy #PhytochemicalFriday! Today: miraculin - a glycoprotein from the miracle fruit Synsepalum dulcificum (Sapotaceae; Ericales). It binds to sweetness receptors on the tongue and makes normally sour-tasting food seem sweet, inspiring the name 'miracle berry'. Try it out!
Happy #PhytochemicalFriday! Why are flamingos and shrimp pink? Astaxanthin - a blood-red ketocarotenoid made by microalgae that makes its way up the food chain to chordates and arthropods (among others), giving them a pink hue. An important molecule to consider in aquaculture.

August Phytochemicals! From balsa wood rafts to oleandrin

On this date in 1947, Thor Heyerdahl's balsa wood raft "Kon-Tiki" crashed into a reef in Polynesia having crossed 5000 miles of Pacific Ocean in 3.5 months. The raft's strength came from lignin, but also cellulose - the most abundant organic polymer on Earth. #PhytochemicalFriday

Happy #PhytochemicalFriday! Today: helenalin, a sesquiterpene lactone from Arnica montana (Asteraceae: sunflower family!). Though a toxic (plant defense?) compound, it appears to be able to inhibit human telomerase and is thus being investigated as an antitumor agent.
#PhytochemicalFriday? Oleandrin. Cardiac glycoside of the poisonous plant Nerium oleander and cousin of digoxin, Bond's poison in Casino Royale. As @wayneriekhof correctly points out: < 1% of hits in antiviral screens are effective drugs. Let patience and hard evidence guide us.
Happy #PhytochemicalFriday - you made it! Today: amarogentin - a characteristic component of bartenders' aromatic bitters. Isolated from gentian roots, this glycoside is one of the most bitter compounds known to human kind and is used as a standard in measuring bitterness.

Wednesday, 26 August 2020

July Phytochemicals - Happy Birthday Harry Potter!

Happy #PhytochemicalFriday! Today: abietic acid - the primary component of pines' resin acid. This diterpene is a major part of rosin - a solid used to increase friction in many applications: from violinists' bows to flamenco dancers' shoe heels to drag racing starting lines.

Englerin A, a terpenoid from the bark of the (sub)tropical plant Phyllanthus engleri. This compound causes kidney cancer cells, but not healthy cells, to flood with calcium and die. Its total synthesis begins with nepetalactone, catnip's active ingredient! #PhytochemicalFriday
Happy #PhytochemicalFriday and #HappyBirthdayHarryPotter! Today: the monoterpenoids carvacrol, cymene, and thymol. These are major aroma compounds in Cretan dittany (Origanum dictamnus), the plant used to prepare Essence of Dittany, a healing potion in the Harry Potter series.

Monday, 6 July 2020

June phytochemicals: A giant genome and saffron carotenoids

Happy #PhytochemicalFriday! This week: diosgenin - a building block used by Paris polyphylla (the plant with the biggest genome sequenced to date - 70Gb!) to produce polyphyllins. Diosgenin is used in the commercial synthesis of cortisone, progesterone, and other steroid products.

Happy #PhytochemicalFriday! Worth more than their weight in gold, saffron crocus stigmata (Crocus sativus, Iridaceae) produce the carotenoid crocin – the compound that gives the "king of spices" its characteristic red color. The compound is also an antioxidant.

Monday, 1 June 2020

May phytochemicals: Cinco de Mayo and a Sherlock Holmes poison

Root bark of Uncaria tomentosa ("Cat's claw", Gentianales) is used in traditional medicine. Oxindole alkaloids like uncarine are major U. tomentosa root bark constituents. They're associated with a variety of bioactivities, but are in need of more research! #PhytochemicalFriday

Drinking tequila leftover from #CincodeMayo? I too enjoy homoisoflavones - unusual phenolic compounds that only occur in some species. Those pictured here were found in Agave tequilana, the base ingredient in tequila. #PhytochemicalFriday

Happy #PhytochemicalFriday! Today: avenacins, fluorescent antimicrobial compounds produced by oat roots (Avena sativa). These triterpenoid saponins protect the plant against soil-borne pathogens and their biosynthesis is integrated with root hair development!

This #PhytochemicalFriday, birthday of #ArthurConanDoyle (creator of Sherlock Holmes): gelsemine, a poison similar to that in The Adventure of the Devil's Foot. This highly toxic compound from Gelsemium elegans ("heartbreak grass", Gentianales) is still used by modern assassins.

Friday, 15 May 2020

April phytochemicals: Spring flowers and ibogaine

Looking forward to summer flowers like clematis? Don't forget their defensive chemistry! Many clematis species produce ranunculin, an unusual glucoside that, when the plant is attacked, is converted into the lactone protoanemonin, a toxin not to be ingested! #PhytochemicalFriday

Happy Good #PhytochemicalFriday! Today: phenol, typically thought of as a petroleum product, but is of course also a bioproduct, and a component of the essential oil of hyssop (Hyssopus officinalis), a plant mentioned repeatedly in the Bible. Thanks @HarvLovesAcct for suggesting!

Ibogaine, an alkaloid from Tabernanthe iboga (an Apocynaceae shrub). This compound can induce psychedelic effects upon ingestion and is used in some spiritual practices. Also used by some to treat opioid addiction, and is the subject of several documentaries. #PhytochemicalFriday

Friday, 3 April 2020

March phytochemicals: fenugreek and 'maple syrup urine disease'

Ever use fenugreek in a recipe but wonder what those little things actually are? Seeds of Trigonella foenum-graecum (Fabaceae) provide unique flavor to certain curries - also contain trigonelline (a zwitterion - yes!) a methylated form of niacin/vitamin B3 #PhytochemicalFriday

This #PhytochemicalFriday: sotolone, a lactone found in various plants and plant products incl. molasses and rum. It's a powerful aroma and flavor compound - tastes like maple syrup and caramel. Our bodies can also produce it, and in cases of maple syrup urine disease, to excess.

Daffodil bulbs & flowers, with their prominent coronas (the circular, yellow structures), contain lycorine - a toxic alkaloid found across the daffodil family (Amaryllidaceae) - that can inhibit protein synthesis. Do not confuse daffodil bulbs with onions! #PhytochemicalFriday

February phytochemicals: the smell of roses and "mad honey disease"

Happy #PhytochemicalFriday! This week, moronic acid, a triterpenoid compound found in some Phoradendron species (Santalaceae, one of my favorite plant families!), as well as Brucea javanica (Simaroubaceae). This compound has been found effective against the herpes simplex virus.

Happy #Valentines2020 / #PhytochemicalFriday! What chemicals make up the scent of roses? Two major contributors are beta-damascenone and beta-damascone. The plant makes these compounds by degrading a carotenoid called neoxanthin (a relative of beta-carotene). #academicvalentine

Happy #PhytochemicalFriday from a snowy visit to @MedPlantChem at @NorthernMichU. Today: grayanotoxin, a compound found in some Ericaceae species, incl. Rhododendron & Agarista. Honey made by bees that solely collect these plants' nectar can be toxic, causing 'mad honey disease'!

Happy #PhytochemicalFriday! Today, nickel. Not strictly a phytochemical, but something that can accumulate to high levels (higher than in ore!) in many species. The element can be mined from trees as described by Ian Morse in this @NYTScience article:

January Phytochemicals: hops, and compounds in filtered vs. unfiltered coffee

Happy #PhytochemicalFriday! Today: cafestol, a diterpenoid found in Coffea arabica (#Coffee; Rubiaceae) present in unfiltered preparations like French press coffee, but absent in most filtered drinks like drip coffee. Its bioactive effects are being studied using animal models.

If you enjoy the flavor of hops this #PhytochemicalFriday, you're tasting isohumulones, products of a hop chemical (humulone) as it degrades during brewing. They provide hops a characteristic bitter flavor. Their parent, humulone, seems to act as an antiviral and antimicrobial.

Happy #PhytochemicalFriday! Today: 3-carene, a piney/earthy smelling monoterpene from pine resins (Pinus species) that can also be a major component of turpentine - a solvent obtained by distilling pine resin. The compound is used in the perfume and chemical industries.

Monday, 10 February 2020

December phytochemicals: more than 100 weeks of #PhytochemicalFriday!

Indigotin: the chemical responsible for the color indigo. Originally isolated from Indigofera tinctoria (bean family) and woad (Isatis tinctoria, mustard family), it is among the first dyes used for textile dyeing and was so valuable it was called blue gold #PhytochemicalFriday

Happy #PhytochemicalFriday! Rotenone - an isoflavone highly toxic to fish and insects - is found in some plants in the bean family, including jicama (Pachyrhizus erosus). Historically, such plants were crushed and put in ponds, compelling fish to the surface for easy capture.

Happy #PhytochemicalFriday! Phellandrenes (combined with the pinenes - last year's late Dec. post) are isomeric monoterpenes and major contributors to the smell of balsam tree resin, which may perfume many houses this time of year. Thank you @HarvLovesAcct for the inspiration!

Happy #PhytochemicalFriday from #PAGXXVIII #PAG2020! Today: Aconitine: deadly poison from Aconitum spp. (aka Monkshood / Wolf's-bane) that features in modern mysteries and literature from Ancient Rome (Ovid). The alkaloid binds sodium ion channels & interferes with neuron firing.

Monday, 3 February 2020

November phytochemicals: the smell of garlic and the color of mac and cheese

Running a bit behind on the phytochemicals... but never fear: we'll catch up!
Happy #PhytochemicalFriday (and Halloween)! Today: diarylheptanoids - compounds found in various plants, including Tacca chantrieri (black bat flower: spooky!). This class of compounds includes curcumin (turmeric), and cyclic compounds (dotted orange bond) - many are antioxidants.

Happy #PhytochemicalFriday! Today: allicin, a (zwitterionic!) compound from garlic. Normal garlic cells contain alliin (an amino acid-like compound), but crushing garlic exposes alliin to an enzyme that converts it into allicin - the major contributor to the aroma of fresh garlic.

Bixin! An apocarotenoid from Bixa orellana (achiote) - a compound in the food additive annatto - an orange/red extract from achiote seeds. As ground seed, this compound is used in many South and Central American dishes and is used to color Gloucester cheese! #PhytochemicalFriday.

Galantamine, alkaloid from Galanthus spp. (snowdrops; Amaryllidaceae, perhaps antidote to Circe's poisons in Homer's Odyssey), not only has a very cool tetracyclic structure, but has been used to treat cognitive decline (Alzheimer's disease) and autism. #PhytochemicalFriday.