Uniquely identifiable characteristics
Distinguishing Feature :
No relation to :
Caper [a plant with similar name].
It is a biennial, taking 2 years to flower. More likely to be found in gardens, than growing wild, and even then only in the south of the UK. Cultivated as a garden plant, but it does grow natively in woods. Escapees are usually only young plants, dying later. The yield of seeds is poor. But perhaps with global warming, it is increasing its range: a report from Balvack, Aberdeenshire informs me that it has been growing for more than 15 years there.
Due to the presence of Ingenane-type and
lathyrane-type (the lathyranes are named after the scientific name for Caper Spurge, Euphorbia lathyris) diterpenes Caper Spurge is toxic if eaten, although goats are not susceptible to the poisons. However, the poisons will be transferred into the milk from goats, which is then poisonous for humans to drink.
The lathyrane-type diterpenes present include
Jokinol being potent P-gp inhibitors and used in traditional Chinese medicine. Some of these compounds are shown below.
The seeds of Euphorbia lathyris contain many diterpene esters:
The stem contains a white latex, which is composed of
16-hydroxy-ingenol, Ingenol and long chain unsaturated fatty acid esters.
In the mid 1980's it was being considered as a crop for industrial fuel, but your Author can find no evidence that it is now grown as a crop for oil. It seems that they were having problems with low yield of the seeds, although they contain c.40% essential oils, or the drying of the stems for burning in power stations. Perhaps they moved on to some more promising fuel crop. Certainly
Zea Maize and straw are now major fuel crops in the UK.
It also contains coumarins: Daphnetin, Esculetin,
isoeuphorbetin and Aesculetin.
It is called the
Mole Plant because it has a reputation to repel moles when growing in a garden. They are probably repelled by the toxic compounds in the roots (and elsewhere). The seed pods release their seeds explosively.
Aesculetin (aka Esculetin) is a Coumarin or more correctly, a
hydroxycoumarin, shown only for comparison with Euphorbetin below. Daphnetin is isomeric with Aesculetin and is found not only in Caper Spurge but also in Mezereon, Daphne mezereon, which gave its name to Daphnetin. Coumarins and bicoumarins are toxic.
Euphorbetin, sometimes called
BiAesculetin because it is a dimer of Aesculetin (where the two units of Aesculetin are upside down relative to one another) is a newly discovered bicoumarin found in Caper Spurge. An isomer of Euphorbetin, called
IsoEuphorbetin is also found in the plant where the two Aesculetin units are the sane way up, and is the less stable arrangement, therefore there will probably be less of this compound within the plant.
Dicoumarol is a natural bicoumarin, not present in Caper Spurge, but present in some other plants and fungi and was discovered in mouldy wet hay made from Ribbed Melilot (Melilotus officinalis) (elsewhere known as Sweet-Clover) where, because of its anti-coagulant properties, was the cause of a bleeding disease in cattle. Once that was recognised, it came to be used medicinally as an anti-coagulant until the mid 1950's when more effective artificial anti-coagulants such as
Warfarin were developed.
Anti-coagulants, which prevent the formation of prothrombin within blood thereby inhibiting blood-clotting, are used for the treatment of deep-vein thrombosis. The anti-coagulants do not dissolve blood-clots, merely prevent further clotting, which, like rust catalysing the formation of more rust, catalyses the formation of further clotting. Prothrombin normally makes blood which has escaped clot. Unfortunately, blood leaks all the time through tiny capillaries, and with prothrombin disabled, the anti-coagulants can lead to the pooling of blood outside of blood vessels; internal bleeding is an extremely bad condition. Anti-coagulants must be prescribed with care. The correct dose must be established to control the side effects. Too little or too much is harmful.
Warfarin (neither of which are found in Caper Spurge) are anti-coagulants used both medicinally and as rodenticides. Rodents which consume cereals or other foodstuffs deliberately laced with either warfarin or coumatetralyl die of internal bleeding. Comatetralyl also exhibits carcinogenic and teratogenic effects. In the case of rodenticides, more effective anti-coagulant poisons have been developed such as
Brodifacoum, which is also based on coumarin.
For medicinal purposes, two further anti-coagulants based upon coumarin have been developed, such as
Phenprocoumon (both of which have slightly differing characteristics to both themselves and to Warfarin).
Phenprocoumon exhibit either shorter or longer half-lives within the body, useful for some situations. Patients on Warfarin treatment should be monitored for untoward side effects and internal bleeding, which has prompted the development of yet further anti-coagulants not based on coumarin, such as
Dabigatran, and which hope to offer un-monitored treatment of deep-vein thrombosis and etc. Since none (apart from Coumatetralyl) of these anti-coagulants are produced naturally (so far as is known), they are beyond the scope of this tome.
Epoxylathyrol are lathyrane-type diterpenes which are found in Caper Spurge. They both have an active cyclopropane unit (top right), with Epoxylathyrol also possessing an active
epoxy group (bottom right). Both are toxic. Epoxylathyrane, by virtue of its extended conjugation system, can be activated by light resulting in its transformation to the cis- non-planar
enone form, and thence fragmentation to a