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: https://nyti.ms/2VDg7YC

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.