Not to be semantically confused with :
Uniquely identifiable characteristics
Distinguishing Feature : the strikingly variegated three-colour Ace-of-Spades leaves.
There is only one Genus (Houttuynia) in the Chameleon Family, and only one plant in the Houttuynia Genus, this one. It is found in both the un-variegated and the variegated Tricolor form shown here.
It is grown as a leaf vegetable in Vietnam, and has a fishy smell.
It has a great propensity for spreading wildly by runners, and is hard to eradicate once established, although brown-fingered gardeners should have no trouble at all. The Author's Chameleons have all died, or so he thinks. Paradoxically, it likes wettish soils in full sun. Somewhat strangely, given its spreading abilities, it is to be found growing wild only in the Isle of Man and just one other place (but not Anthony Gormley's Place).
The family that it inhabits obtains its name Saururaceae from the lizard-like tail that sticks up above the petals (Latin saurus - lizard).
The version shown here is a more common garden variety; the Tricolor variety. The wild variety has non-variegated green leaves and is able to spread more profusely.
Chameleon contains several cytotoxic alkaloids, amongst them
Aristolactam A and B,
Cepharadione B, Splendidine,
Piperolactam A, as well as the glycosides of flavonols
Afzerin, Quercitrin and Isoquercitrin and
When crushed between the fingers Chameleon, otherwise known as Fishplant, has a strong metallic or fishy smell, said to be due to the presence of 3-oxo-dodecanal but others have doubts about this. The two smells may be separate components, the fishy smell due to the extensive presence of pyridine alkaloids whilst the metallic smell is perhaps due to
1-octen-3-one), which only exhibits a metallic smell when it comes into contact with the skin but your Author cannot find evidence to support that Chameleon contains this ketone, although it does contain other longer aliphatic ketones such as
Decanoyl Aldehyde and
4-Tridecanone. MethylNonylKetone has a strong odour and is used as a cat, dog and insect repellent, although it is also used in perfumes. All three are used in perfumes.
FLAVONOL & ISOFLAVONOL GLYCOSIDES
Hyperin or Hyperoside (quercetin-3-O-β-galactoside) is a Glycosidic Flavonoid present in Chameleon. It is very similar to Astragalin, another example which is also based upon the flavonol Quercetin. Hyperin is present in the
Downy Birch and
Silver Birch trees, some species of Rhododendron, and in
Perforate St. John's Wort (
Hypericum perforatum), from which species it obtained its name.
Quercitrin and IsoQuercitrin are Flavonol Glycosides similar to Rutin which Chameleon also contains (as do many other plants). They are based on the Flavonol Quercetin, a polyphenolic plant anti-oxidant.
STRIGOLACTONES - plant growth hormones
5-DeOxy-Strigol is the pre-cursor to the Strigolactones produced within Chameleon.
Strigolactones are Plant Hormones which stimulate the growth of symbiotic mycorrhizal fungi. They also inhibit the formation of branches on established plants whilst at the same time promoting the germination of nearby seedlings. The seedlings then germinate and have more room around them allowing more sunlight to dance upon their fledgling leaves. These Strigolactones are produced within Chameleon itself and are derived from Carotenoids.
Sorgomol is another Strigolactone produced not only in Chameleon but also in Sorghum from which it derives its name. It is a potent germination stimulant for seeds of the root-parasitic weeds of
Great Millet (Sorghum bicolor) and is probably instrumental in the propensity for Chameleon to spread rampantly. One Strigolactone (not as far as the author knows produced by Chameleon) is called
Sorgolactone, which gets its name from the Sorghum plants it helps germinate. Another is (+)-Orobanchol (which is also not reportedly produced by Chameleon), presumably so-called from plants of the genus Orobanche (
Broomrapes) it helps germinate.
Strigone has been isolated from root extracts of Chameleon and is also a potent seed germination stimulant, depending upon the four possible stereoisometric arrangements of the compound, some of which will not be produced naturally.
Karrikins are structurally similar to Strigolactones, but much simpler. They are produced naturally in the smoke from forest fires when plant matter burns at high temperature and are much more effective plant hormones, helping seeds to germinate after a fire, than are the Strigolactones themselves.
Splendidine is an aporphine alkaloid contained within Chameleon which is structurally similar to Apomorphine and Isocordyline.
7-chloro-6-demethyl- cepharadione B is a most unusual alkaloid in the plant world; it contains an atom of chlorine and is thus technically an organo-chloride. Notice that it is based upon an aporphine alkaloid skeleton, like the Splendidine above. It is probably a plant metabolite.
There are not many naturally occurring organochlorides in the plant world, but there are some. [There are a great many more organochlorides within other kingdoms, such as micro-organisms, fungi, lichen, algae (especially blue-green and red-algae) and many sea inhabitants, including seaweed and many bottom-dwelling invertebrate sea creatures, since they are immersed in chlorine containing salts. About 3000 natural organochlorides have been found so far in this diverse group].
IN THE PLANT KINGDOM
Most organochlorides synthesized within plants are contained in compounds containing acetylenic (triple-bonds) such as in Acetylene, HC≡CH and
polyacetylenes (aka Polyynes), in
sesquiterpenoids and in compounds with 7-membered rings. In many instances the chlorine containing part is a chlorohydrin, R1-CHCl-CHOH-R2, and many will have been formed spontaneously from epoxides after attack by chloride ions or
Hydrochloric Acid HCl; the chlorohydrins then often fold up into ring structures or become modified in other ways.
Perhaps the most abundant organochloride in the plant world is that contained in one of the four auxin plant growth hormones, 4-chloro-indoleacetic acid, which is bio-synthesized in members of the Pea Family such as green peas, lentils, vetch, various beans and other peas. Alongside it is the non-chlorinated version, another auxin. The growth hormone function of the chlorinated version is 100-fold stronger than that of the normal version. However, it has been found to be far too strong to be of much use as a growth promoter in the plants that synthesize it: pea cuttings treated with it at first rooted profusely, but for seven days started producing large amounts of the gas ethylene, a senescence inducer and almost died, whereas normal non-chlorinated auxins only initiate production of ethylene for one day. It is theorised that the plant may produce chlorinated auxins which they use as the often observed (but so far un-identified) 'death hormone' produced by the seeds during their development which eventually kills the mother plant thereby giving the seedling a much better survival chance.
Control of the shape of leaves is accomplished by the concentration of auxins in certain areas encouraging higher growth whilst the concentration from locality to locality of anti-auxins reduces or inhibiting growth in other areas. By this means leaves can be made flat, cusped, crinkled, cup-shaped, lobed or have pointed ends, rounded ends, spines or teeth on the edge, etc.
The few organo-chlorides known in the plant world will be listed here:
Asian Bracket Fern, which contains several chlorinated pterosins, such as Pterosin F, and which are responsible for cattle poisoning. The non-chlorinated version, Pterosin B, which is also found in Bracken, is shown for comparison.
The Brazilian plant Vellozia bicolor, which contains some chlorinated di-terpenes.
Common Ragwort contains the highly toxic pyrrolizidine alkaloid Jaconine, an exceptionally toxic chlorinated alkaloid, which is based upon the less toxic non-chlorinated analogue, Jacoline, which is also one of the many pyrrolizidine alkaloids contained within Common Ragwort.
Doronicum macrophyllum contains another chlorinated alkaloid, Doronine.
Whilst Lolidine, another chlorinated alkaloid, is manufactured in Lolium cuneatum and Acutumine in Sinomenium acutum.
Saxalin is a chlorinated furocoumarin (based on psoralen) which is contained in several plants of the Carrot Family especially |
The aromatin chlorocarbon 1,2,3,4-tetrachlorobenzene is a major constituent of Needlerush oil which is obtained from the (non-native) rush Juncus roemarianus.
Japaneswe Lily Lilium maximowiczii produces several chlorophenolic fungicides at the site of infection when exposed to the pathogenic plant fungus Fusarium oxysporum.
Several Liverworts produce polymeric chlorinated phenols including a bisbenzyl, which contains six atoms of chlorine.
The Asian shrub Diospyros maritima manufactures both 3-chloro-plumbagin and 3-bromo-plumbagin. See Plumbagin. A chlorinated bi-plumbagin near-dimer called Chitranone, which crystallises in orange plates, is also manufactured within this plant.
Common Valerian is one of very few vascular plants that are capable of converting the inorganic chloride ion into organic chlorine. Others are
Yellow Star Thistle, Potato plants and many in the the Pea Family of plants. Potatoes, Corn, Lentils, Rice, Wheat, Mushrooms and Soybeans all manufacture several chlorinated benzodiazepines, including the commercial drug diazepam (Valium) and are to be found in mammalian brains as a direct result of eating these foodstuffs.
Halogens such as chlorine in organohalides increase lipophilicity and hence increase bioavailability. Halogens on benzene rings, for example, also block metabolism by deactivating the entire ring against metabolic oxidation. This may be some of the reasons why halogens are incorporated into some plant compounds. This, and their increased toxicity which the plants probably use to defend themselves from invading organisms.
A plant notorious for killing livestock is the West African plant Dichapetalum toxicarium which produces the highly toxic
FluoroAcetic Acid, which is widely used as a pesticide. These plants contain other fluorinated compounds, 18-Fluoro-Oleic acid, 16-Fluoro-Palmitic Acid and other fluorinated fatty acids. Organofluorides in the plant kingdom are extremely rare: only 12 have yet been identified in plants and none in plants known to grow wild in the UK. Of those, FluoroAcetate is the most common, followed by Fluorinated Fatty Acids (such as those mentioned above),
Threonine is an
Amino Acid found in mammals). OrganoFluorides are toxic; even more so than their OrganoChloride analogues.
The reader will also find references within this website to numerous other organochlorides found in plants which are not mentioned on this page. Look in the Subject Index on the right for 'OrganoChlorides', or for the full organochloride list on the Structural Formulae menu.