Uniquely identifiable characteristics
Distinguishing Feature :
Not to be semantically confused with :
Angelica or Garden Angelica, which are also umbellifers beginning with the letter 'A'.
In the home counties, but very few other hectads,
Perfoliate Alexanders (Smyrnium perfoliatum) is found (as well as
Alexanders itself). At only 60cm (1m maximum)
Perfoliate Alexanders grows to half the height of
Alexanders and has yellowish-green leaves rather than the dark glossy green of
Alexanders. It was introduced and naturalised in grassy places and flower borders. However, another huge difference is that the leaves strongly clasp the stem, encircling it, which is not the case with some of the photos above taken on the St. Helens Canal, although they certainly have yellowish-green leaves.
When crushed, both leaves and stem smell (and taste) of
Myrrh, hence the scientific name 'smyrnium'. It has a taste similar to that of
Celery, another umbellifer.
There are not many yellow-flowered umbellifers, only about seven, the others being Wild Parsnip, Fennel,
Pepper-saxifrage, Rock Samphire, Garden Parsley and
Hog's Fennel which is quite rare. Alexanders can not be mistaken for any of these because it has glossy large dark-green leaves which are in threes like the Ace of Clubs. Its solid stem is also stouter stem than most others. The flower umbels lack bracts.
Alexanders is native to the Mediterranean, but now well established in the UK, almost always not far from the sea. It used to be cultivated, but is now almost forgotten as a foodstuff. In taste it is intermediate in flavour between
Celery. The latter has now replaced it culinarily. It is common around mediaeval monasteries around which it was once cultivated. The
parsnip-flavoured root is boiled before eating and is mildly diuretic. The roots can be candied.
In the first year it is low and bushy with many leaves, in the second year it sprouts tall flowering stems. It was once grown in kitchen gardens of Monasteries and Castles as Wild Celery.
The genus Smyrnia are noted for their PolyAcetylides (aka Polyynes) and
FuroCoumarins. The highest concentration of Coumarins are said to be found in the seeds and in the roots of Alexanders, but your Author has been unable to ascertain which polyynes or which furocoumarins are present.
USE BY BUTTERFLIES
|LAYS EGGS ON
The brown fruit contains an essential oil,
Cuminal) which has an odour reminiscent of the spice
cumin (which also contains cuminal), its main aroma compound. Cuminal is another name for
Cumaldehyde or 4-isopropylbenzaldehyde, which is contained in the essential oils of
Cumin and some other plants.
Cuminaldehyde is related to
Cumene (isoPropylBenzene) which is not a component of Cumin (nor of Alexanders).
Phellandral is a
Monoterpenoid of the
p-Menthane) family, as are the first 4 shown (CuminAldehyde, Phellandral, α-Terpinolene and β-Elemenone). It has a fairly high concentration of 1.4% in the composition of the oil in the seeds of Garden Angelica (Angelica archangelica) and in several herbs and spices.
para-Menthanes often have high concentrations in species of
Eucalyptus especially Eucalyptol, (aka
meta-Menthanes are much rarer].
α-Terpinene) has an aroma but is mainly used to provide a pleasant smell to certain industrial fluids. All four possible Terpinene isomers (α-, β-, γ- and δ-Terpenene) smell similarly of Terpentine. Terpinenes are to be found in Hemp (Cannabis species), Tea Tree (Melaleuca alternifolia) and
Cumin (Cuminum cyminum).
β-Elemenone is found in herbs and spices and also in Bog Myrtle (Myrica gale) but apparently is not for use in fragrances. It acts as an effective larvicide against several insects, as does
Curzerene [above] and
Although drawn on it's side, 2-Caren-10-al is another terpenoid, this one with a
cycloPropane ring fused to the main ring and is also found in
Cumin (Cuminum cyminum) and has acaricidal effects on certain cattle ticks, killing them. It has a Cyclo-Propane ring fused to a 6-membered carbon ring.
CONSTITUENTS of ESSENTIAL OIL
All these are found in the essential oil obtained from Alexanders and contribute to its aroma when crushed.
Germacrone is a ketone derivative of Germacrene D. Germacrone is also found in Thyme and the spice Turmeric and has a cyclo-decane skeleton. It exhibits anti-tumour activity, inhibiting the proliferation of breast cancer cells, but its practical use is limited by multi-drug resistance. It also inhibits early stages of influenza - but only against H1N1 and H3N2 types of Influenza A virus and also against Influenza B but in a dose-dependent manner.
Curzerene is just one of the many aromatic compounds which are also found in the non-native Myrrh (Commiphora myrrha) and is one of the three principal sesquiterpenoids which contributes to its distinct aroma profile (the two others being
β-Bourbonene and other isomers of
Bourbonene - neither of which are present in Alexanders). Several other species of the shrub Myrrh occur, one (Commiphora gileadensis) producing the Biblical Balm of Gilead oil. Curzerene is used by the perfume industry.
δCadinol are just stereoisomers of each other, the only difference being which way the two hydrogen atoms shown are attached. The top one is attached slightly differently in the two cases, with everything else being the same. They are both found not only in Alexanders, but also in several other plants mostly foreign. α-Cadinol is said to act as a fungicide and as a hepatoprotective to combat liver damage, although whether it is licensed for such is unknown.
δ-Cadinol occurs in many coniferous trees as well as Yarrow (Achillea millefolium) and acts as a pheromone in the butterfly Lycaeides argyrognomon.
Just for interest one of the aromatic sesquiterpenes within Myrrh,
β-Bourbonene (which is not a constituent of Alexanders) has an unusual chemical structure with a cyclo-butane ring joined each side to a cyclo-pentane ring.
β-Guaiene has a skeleton structure consisting of fused 7 and 5 membered rings as does Azulene. There are two other isomers of it,
δ-Guiaene which have their two double-bonds in differing places, but neither of these isomers are claimed to be present in Alexanders, Hops and many other plants. It was first isolated from Guiaiac Wood Oil which was extracted from the foreign plant Bulnesia sarmienta. All the Guaienes are used as fragrances and flavours to impart earthy, woody and spicy tastes and aromas to foodstuffs. It is found in many plants including Hop where it imparts an earthy woody aroma and taste to beer.
isoAromadendrene Oxide (aka
AlloAromadendrene Oxide) is another molecule with an Azulene skeleton with a spiro epoxide group opposite a fused CycloPropane.
1,5-EpoxySalvia-4,(14)-ene is also found in Echinaceae purpurea and in Salvia limbata, neither of which are found in the UK, but other than this your Author has not found anything about this compound worthy of mention, other than its existence in Alexanders. With it's epoxy link across a 7-membered carbon ring, it fuses a 6-membered ring to a 5-membered ring.
FuranoEremophil-1-one is a
Naphthofuran (containing a Naphthalene moiety) found in green vegetables. It belongs to the class of chemicals called FuroEremophilanes and are derived in plants from
Eudesmanes. Both Butterbur and Giant Butterbur also contain this substance.
IsoFuranoDiene is similar to the above FuranoEremophil-1-one but has a broken ring and lacks the ketone =O moiety and gains another two double-bonds. This compound is able to induce apoptosis (cell-death) in cancerous cells of the colon, which may give it pharmaceutical uses. IsoFuranoDiene is heat-sensitive and changes into another substance when the temperature exceeds a certain unspecified value when it undergoes a Cope Rearrangement into
Curzerene when its temperature is increased. The Cope Rearrangement involves the double bonds in 1,5-Dienes, which move into differing positions to become a tautomer of the original compound. Curzerene should be considered an artifact in Alexanders because it is produced in the heating of IsoFuranoDiene which is a natural component of Alexanders.
FuroScrobiculin B is another furano compound but this one has two 5-membered rings on each side of a 7-membered ring. FuroScrobiculin B is a
sesquiterpenoid which occurs in mushrooms belonging to the Basidiomycetes genus. Other than also occurring in this Lactarius scrobiculatus mushroom, from which it obviously derives its name, your Author has not been able to find anything else useful to know about this compound.
Curzerene is mentioned near the start of this secondary metamolites section. It is only shown here again to lump it with other similar sesquiterpenoids with two fused rings, apart from Germacrone where the cross-link is absent.
These latter two,
FuroScrobiculin B and Curzerene, look similar to
FuroCoumarins, but with certain obvious differences. But no FuroCoumarins are listed as occurring in Alexanders.
But no FuroCoumarins are listed as occurring in Alexanders.
Another source lists the main constituents of the essential oil from Alexanders as:
Curzerene 13.7% (an artefact of distilling IsoFuranoDiene),
Methyl-1-Benzyl-2-OxoCycloOctane Carboxylate 12.3%,
FuroScrobiculin B 3.2%,
IsoAromadendrene Oxide 1.7%,
Caryophyllene Oxide 0.4%,