February Phytochemicals - Chemistry of the herb Rosemary

Happy #PhytochemicalFriday! Today: tanshinones - diterpenoid compounds from medicinal herb Salvia miltiorrhiza (Red shage, or "danshen") that have rather unique chemical structures. A recent study reports genes involved in the synthesis of these compounds https://go.nature.com/3tzoGST

Happy #PhytochemicalFriday! Today: kauniolide, a sesquiterpene with action against prostate cancer, mycobacteria, and parasites. This compound is found in a variety of asters (including chicory, Cichorium intybus) and its biosynthesis includes remarkable P450 action.

Happy #PhytochemicalFriday! Today: carnosolic acid and carnosol - phenolic diterpenes from rosemary and sage (Lamiaceae). Apart from their interesting structures, these compounds are antioxidants used in food products ("extracts of rosemary") and may have anti-cancer activity.

January Phytochemicals - The chemistry of oatmeal baths

Happy #PhytochemicalFriday and #HappyNewYear2021! Today: hederagenin, a triterpenoid from English ivy (Hedera helix) that is used as a biopesticide (HeadsUp Plant Protectant) to help prevent fungal growth, bacterial growth, and viral plant diseases, including white mold.

#PhytochemicalFriday! Today: deguelin - a flavonoid found in some members the bean family (Fabaceae, e.g. Lonchocarpus. Though found in nature, it's highly toxic to fish & not considered environmentally safe if used on a large scale. It's also under study as a chemotherapeutic!

Happy #PhytochemicalFriday! Today: kaempferol - a bitter-tasting compound that is found in a wide variety of fruits and vegetables, particularly capers - the flower buds of Capparis spinosa (Brassicales). Kaempferol is an antioxidant and features in many traditional medicines.

Happy #PhytochemicalFriday! Today: avenanthramides - phenolic alkaloids from oats (Avena sativa). These anti-itch compounds are abundant in colloidal oatmeal - the reason oatmeal baths can help provide relief from, for example, chicken pox!

December phytochemicals - the flavor of cinnamon

We made it to #PhytochemicalFriday! Today: phyllodulcin - a coumarin found in several Hydrangea species (incl. macrophylla, shown here). It is hundreds of times sweeter than sugar. Several synthetic organic routes to this compound are known... but biosynthesis is unknown!

Happy #PhytochemicalFriday! Continuing the theme of molecules >100 times sweeter than sugar (thanks @TunnicliffeRoss!), let's look at mogroside V - a triterpenoid glycoside from Siraitia grosvenorii (Cucurbitaceae). A sweetener Asia for 100s (if not 1000s) of years - amazing!

Happy #PhytochemicalFriday! Raise a glass of #Christmas cheer to cinnamaldehyde. Isolated from bark of Cinnamomum verum (the cinnamon tree), this small, simple molecule underlies the cinnamon flavor and is a favorite in gum, beverages, and cereals - it can even repel mosquitos!

November Phytochemicals - Another month, another sweetener

Happy #PhytochemicalFriday! Today: trilobatin, a compound from apple leaves (Malus domestica) with potential as a plant-based low-calorie sweetener. A new report in @PlantPhys (https://bit.ly/3n0aqOZ) describes the reconstruction of trilobatin biosynthesis in tobacco. So cool!

Happy #PhytochemicalFriday! Today: momilactone B - a diterpenoid produced in Oryza sativa (rice) roots. This compound is allelopathic - it's able to inhibit the growth of plants competing with its maker. Its biosynthetic pathway was recently discovered (https://go.nature.com/3lutXqp)!

October phytochemicals - Inconceivable!

Happy #PhytochemicalFriday! Today: lycorine, a toxic alkaloid (a nitrogen-containing compound) found in daffodils and some lilies (such as Clivia miniata, Amaryllidaceae). It seems to interfere with protein synthesis if ingested - i.e. don't confuse daffodil bulbs with onions!

Today, iocaine - an odorless, tasteless, plant-based powder from Australia that dissolves instantly in liquid and is among the more deadly poisons known to man. At least one can build up an immunity to it! Happy 33rd birthday to The Princess Bride, and happy #PhytochemicalFriday!

#PhytochemicalFriday! Eugenol, a phenylpropene with a pleasant, spicy scent: the main aroma compound in cloves (Syzygium aromaticum buds). Experience it by lighting a festive autumn candle or have your dentist mix it with zinc oxide to make a tooth filling. Thanks @nicole_groth_!

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.