categoryZGallsAndRusts Galls And Rusts List 

ALEXANDERS

Smyrnium olusatrum

Carrot Family [Apiaceae]

month8mar month8march month8apr month8april month8may month8jun month8june

status
statusZarchaeophyte
 
flower
flower8yellow
 
inner
inner8green
 
morph
morph8hemizygo
 
petals
petalsZ5
 
type
typeZumbel
 
stem
stem8round
 
stem
stem8ribbed
 
smell
smell8myrrh smell8incense
myrrh

28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
Never very far away from the sea.


29th March 2011, Hilbre Island, West Kirkby, Wallasey. Photo: © RWD
In the first year, as in this photo, it is low and bushy with many leaves; in the second year it sprouts tall stems.


4th May 2005, Offas Dyke path, south of Prestatyn. Photo: © RWD
A stout, clump-forming plant to 1.5m high. Glossy dark-green leaves. Growing amidst the blue flowers of Green Alkanet.


21st April 2005, St. Helens Canal, Lancs. Photo: © RWD
The stems are solid and rigid. Flowers in large hemispherical umbels. (Because the leaves appear yellowish-green [rather than dark-glossy-green], this photo may be of a garden variety [but not of the S. perfoliatum species])


4th May 2005, Offas Dyke path, south of Prestatyn. Photo: © RWD
Flowers yellowish-green. The almost round leaves are in threes near the top of the plant, but pinnate lower down.


29th March 2011, Hilbre Island, West Kirkby, Wallasey. Photo: © RWD
Petals are cream coloured.


28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
The umbel is compound consisting of an umbel of umbellets. Stem slightly ridged.


28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
The umbel of umbellets from beneath. The umbels have between 4 and 15 hairless rays between 3 and 4cm long. The peduncle (the stem below the umbel) is usually longer than the rays. Bracts and bracteoles are usually few, small or sometimes absent - as here.


28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
Flowers have two central yellowish-green fused spheres. One sphere has two petals, the other 3 petals, making a hemizygomorphic flower rather than one with radial symmetry.


28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
The anthers have white pollen. The two yellow fused spheres will eventually be at the top of the fruit.


9th June 2016, Llandudno Junction, North Wales Coast. Photo: © RWD
This must be the terminal umbel, which had both male and hermaphrodite/bisexual flowers on. It has now turned to fruit and it is obvious that the male flowers were the shorter central umbellets and the female flowers those umbellets on the periphery, for only they have been fertilised and become fruit (the male flowers are incapable of bearing fruit). But, the central portion of each hermaphroditic umbellet also has a shorter and smaller set of male flowers.


9th June 2016, Llandudno Junction, North Wales Coast. Photo: © RWD
The remains of the male flowers in the centre. In the top right corner can also be seen fewer male flowers in the centre of the outer umbellets.


28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
Fruits mid-green at first will turn black when ripe. They are very smooth looking compared to many other umbellifer fruits. The two fused spheres have been truncated at the bottom and are now at the top of the fruits, with two short projections curving-outwards.


28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
The fruits have six concave but smooth sides and are (roughly) flattened ovals in outline. They are 7 to 8mm long. There are 3 prominent ridges on each of the two fruits, with a pale green carpophore atop each, where the two short styles are parallel at first before bending away from each other and eventually ending up appressed to the sides of the fruit.


16th June 2009, Little Orme, North Wales Coast. Photo: © RWD
The fruits look like two that are conjoined. Each fruit contains two black seeds.


29th March 2011, Hilbre Island, West Kirkby, Wallasey. Photo: © RWD
Lower leaves are bi-pinnate, with each branch having either usually 3 (sometimes 5) wide and coarsely toothed leaflets.


29th March 2011, Hilbre Island, West Kirkby, Wallasey. Photo: © RWD
Teeth are curved and pointed.


28th May 2012, Little Orme, North Wales Coast. Photo: © RWD
Upper stem leaves are trefoil.




A RUST FUNGUS

Puccinia smyrnia
 Galls and Rusts Menu

30th April 2019, near the promenade, Leasowe, Wirral Photo: © RWD
Puccinia smyrnia is a rust fungus which infects Alexanders, causing yellow galls as seen in the two photos, either on the stems or the leaves, or both. The galls may become thickened or distorted with the galls bearing the aecia of the fungus, which often appear cup-shaped when magnified, so are called cluster-cups. The acia distribute aeciospores on the wind which germinate as soon as they land on a suitable host plant.


30th April 2019, near the promenade, Leasowe, Wirral Photo: © RWD
The rust creates a small raised dais on the upper surface, with sometimes a depression in the centre (the spot SW of centre best shows that feature.


30th April 2019, near the promenade, Leasowe, Wirral Photo: © RWD
Later in the year large brown telia develop on the undersides of the leaf which in winter scatter their teleospores on the wind to infect other plants. Puccinia smyrnia is highly specific to Alexanders. This is an enlarged portion of stem section of the underside of the infected leaf in the photo above this one. Each raised dais on the upper surface results in a larger outward bulge on the underside, each of which has several pustules, some broken open releasing their orange-yellow teleospores, some of which have splattered themselves over a small area (especially on the one just north of dead-centre).

Both the raised large veins and the net-veins (which are in a darker green shade) are also visible.


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 Alexaders (Smyrnium perfoliatum) is found (as well as Alexanders). At only 60cm (1m maximum) it 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 Parsley and 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.

MONOTERPENOIDS

CUMINALDEHYDE


The brown fruit contains an essential oil, CuminAldehyde, (aka Cuminal) which has an odour reminiscent of the spice cumin (which also contains cuminal), its main aroma compound. Cuminal is another name for Cuminaldehyde / Cumaldehyde or 4-isopropylbenzaldehyde, which is contained in the essential oils of Myrrh, Eucalyptus, Cassia, Cumin and some other plants. Cuminaldehyde is related to Cumene (isoPropylBenzene) which is not a component of Cumin (nor of Alexanders).

Phellandral is a Menthane Monoterpenoid of the para-Menthane (aka 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 1,8-Cineole). [The ortho-Menthanes and meta-Menthanes are much rarer].



α-Terpinolene 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 γ-Elemene.



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 Lindestrine and 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.


α-Cadinol and 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, α-Guaiene and 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 lactarane 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: Sabinene 27.1%, Curzerene 13.7% (an artefact of distilling IsoFuranoDiene), Methyl-1-Benzyl-2-OxoCycloOctane Carboxylate 12.3%, α-Pinene 7.2%, Cryptone 7.1%, β-Pinene 5.7%, FuroScrobiculin B 3.2%, TriCosane 2.7%, Phellandral 2.1%, 2,4-DiCycloHexylButen-3-yne 2.0%, IsoAromadendrene Oxide 1.7%, δ-Cadinol 1.5%, Germacrone 0.9%, Cuminal 0.9%, β-Guaiene 0.8%, β-Elemenone 0.6%, Linalool 0.6%, δ-Cadinene 0.6%, α-Terpinolene 0.5%, α-Cadinol 0.5%, 1,5-Epoxysalvial-4(14)-ene 0.4%, Caryophyllene Oxide 0.4%,


  Smyrnium olusatrum  ⇐ Global Aspect ⇒ Apiaceae  

Distribution
 family8Carrot family8Apiaceae

 BSBI maps
genus8Smyrnium
Smyrnium
(Alexanders)

ALEXANDERS

Smyrnium olusatrum

Carrot Family [Apiaceae]