Plant Biology Fall 2009

Mary Berecka
Atropa belladonna (Belladonna or Deadly Nightshade)

family Solanaceae

contains tropane alkaloids : atropine, hyoscine (scopolamine), and hyoscyamine.

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Andrew Byler
According to the famous botanist G.L. Stebbins (Flowering Plants: Evolution Above The Species Level, 1974), other species of Acacia growing in the same region of Central America (including A. chiapensis and A. macrantha) produce alkaloids, but grow much more slowly and live in drier areas than A. cornigera. Apparently these other species of Acacia pay the price for their alkaloid defense system in terms of a slower growth rate, which enables them to compete only in the drier regions where the growth of competing vegetation is also slower and less vigorous. The ability of A. cornigera to enter more moist, lush vegetation areas is apparently related to its evolution of another defense system that depends on a little hymenopteran helpmate rather than the production of bitter alkaloids.

The "swollen-thorn" acacias of Central America are truly remarkable trees. In the wild, their enlarged, hollowed-out stipular spines are occupied by fiercely biting-stinging ants that protect them from browsing herbivores and epiphytic plants that might shade them out. The swollen thorns are not galls, they are not produced in response to chemical or physical stimuli from invasive insects imbedded in their tissues. The amazing thorns are genetically-programmed structures that are formed with or without the presence of symbiotic ants. On wild trees they are inhabited by colonies of Pseudomyrmex ferruginea, very aggressive ants with a painful sting. Disturbed ants release an alarm pheromone and rush out of their thorn "barracks" in great numbers. According to Daniel Janzen (Costa Rican Natural History, 1983), livestock can apparently smell the pheromone and avoid these acacias day and night. Getting stung in the mouth and tongue is an effective deterrent to browsing on the tender foliage. In addition to protecting A. collinsii from leaf-cutting ants and other unwanted herbivores, the ants also clear away invasive seedlings around the base of the tree that might overgrow it and block out vital sunlight. According to Daniel Janzen (Smithsonian Contributions to Botany Number 13, 1974), the Central American swollen-thorn acacias lack the chemical defenses of most other acacias to discourage ravaging insect predators and competition, and symbiotic ants have taken over this vital role. The acacias reward their ant helpmates with thorn "condos" to live in, carbohydrate-rich nectar from glands on the leaf stalks, and nourishing, protein-lipid morsels called Beltian bodies on the leaflet tips. There is no known function for Beltian bodies, except to provide food for symbiotic ants.

Prior to settling on a thorn acacia, the winged virgin queen ant goes on a mating flight to the highest treetop or nearby hill. Here she gets inseminated by a winged male and then hunts for an acacia in which to lay her eggs. [This "hilltopping" phenomenon also occurs in San Diego County, California, where sexually mature adult male and female butterflies fly upslope to a rendezvous point at the summit!] The queen ant cuts an entrance hole into a green thorn, hollows it out, and then deposits her eggs. Subsequent entrance holes are cut by the new generations of worker ants. All this astonishing, complicated behavior has evolved in a tree that for some reason doesn't synthesize alkaloids.

Katherine D'Ovidio

Mexican morning glory (Turbina corymbosa) also known as Rivea corymbosa or Ipomoea burmanni

The infamous white-flowered Mexican morning glory, called oloiuqui, was used by Aztec priests in and intoxicating drink for religious worship. These seeds contain a lysergic acid alkaloid called ergine (d-lysergic acid amide), better known as "natural" LSD. The more potent synthetic LSD is d-lysergic acid diethylamide with two additional ethyl groups (C2H5). Before it was discovered in morning glories, ergine was only known from ergot (Claviceps purpurea), a rust fungus that infects grains. Psychoactive alkaloids, such as ergine and psilocybin contain the indole structure, a double carbon-nitrogen ring also found in the natural neurotransmitter serotonin. These alkaloids may interfere or compete with the action of serotonin in the brain, causing psychedelic visions, delusions and hallucinations.

see links for pictures and sources:

en.wikipedia.org/wiki/Turbina_corymbosa

waynesword.palomar.edu/mornglor.htm#turbinab.gif

waynesword.palomar.edu/ww0703.htm#Morning%20Glory

Geoffrey Ivison
Kratom (Mitragyna speciosa) is a tree native to the swamps of Asia and Africa (Babu et al. 2008). It grows from 15 to 50ft in height. It forms opposite shoots, and has thick parallel venation on the leaves, which are broad and taper to points (see picture at left). It has yellow flowers that grow in clusters, and winged seeds. It is ingested for its effects as both a stimulant and a sedative, and has also been used to treat pain and opium withdrawal symptoms. At lower doses it has a more euphoric and stimulant effect, while at higher doses it has a more sedative and opiate like effect. Traditionally its leaves are chewed to produce the desired psychoactive effects, although it can also be smoked, brewed as a tea, or made into an extract (Erowid).

Kratom contains at least 20 different alkaloids, but two have been identified as being primarily responsible for its psychoactive effects: mitragynine and 7-hydroxymitragynine. Both mitragynine and 7-hydroxymytraginine bind to mu-opioid receptors, which have been identified as mediating analgesia and euphoria, and also explain the plant’s effect as an aid to opiate cessation. Animal studies also show that mitragynine may stimulate adrenergic receptors, explaining the plant’s stimulant activity. It is currently still unclear as to why the plant acts as a stimulant at lower doses, while its opiate affects predominate in higher doses (Babu et al. 2008). 7-Hydroxymitragynine has been demonstrated to have approximately 46 times the affinity for mu-opioid receptors of mitragynine (and indeed 13 times the affinity of morphine). However, it is present in most varieties of the plant at 1/30th the concentration of mitragynine. It is also important to note that samples of the plant collected from different regions had fairly largely different amounts of alkaloids, suggesting that there may be important geographical variation in the plant (Takayama 2004).

Works Cited Babu, Kavita M., Christopher R. McCurdy, and Edward W. Boyer. "Opioid receptors and legal highs: Salvia divinorum and Kratom Opioid receptors." Clinical Toxicology 46 (2008): 146-52. Erowid. "Kratom Vault: Basics." Erowid. 29 Oct. 2008. Web. 05 Nov. 2009. &lt;http://www.erowid.org/plants/kratom/kratom_basics.shtml&gt;. Takayama, Hiromitsu. "Chemistry and Pharmacology of Analgesic Indole Alkaloids from the Rubiaceious Plant, Mitragyna speciosa." Chem. Pham. Bull. 52.8 (2004): 916-28.

Hannah Haskell


Pawpaw (Asimina) Alkaloids: Seeds - asiminine Bark - analobine

Susan Pickering
Tomato (Solanum 'lycopersicum)'

Native to South America

Alkaloids:

-Solanine (poisonous)

-Solanidine: steroid alkaloid; the nucleus (i.e. aglycone) for two important glycoalkaloids, solanine and chaconine

-Tomatine: a glycoalkaloid; its aglycone is tomatidine

The leaves, stems, and green unripe fruit of the tomato plant, as a member of the plant genus Solanum (nightshade), contain the poison solanine, which is toxic to humans and animals. (wikipedia - tomatoes)

http://www.ansci.cornell.edu/plants/toxicagents/steroid.html

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William Romey
I'm going to study Psychotria viridis, a plant from which DMT is sythesized. DMT, from what I've read so far, is about as potent as alkaloids get, in addition to being interesting with regards to its cultural usage and legality in the United States. http://en.wikipedia.org/wiki/Dimethyltryptamine http://en.wikipedia.org/wiki/Psychotria_viridis

[Molly Smith[[Image:Cacao tree.jpg|left|211x317px|Theobroma Cacao]]]
Theobroma Cacao and its Alkaloids 11/6/09

Theobroma Cacao (more commonly known simply as cacao) is a small evergreen tree native to South America. It is of the sterculiaceae family. Cacao was first cultivated by Aztecs. It is used to make cocoa, chocolate, and all related products. Theobroma, when translated, means “food of the gods.” The Cacao tree grows in tropical climates and requires nutrient-rich soil. It is an undergrowth tree and prefers shade. It produces small, light pink flowers directly on its trunk in clusters, which are pollinated by tiny flies. The fruit (also termed the Cacao pod) is oval-shaped and can range in size between 3x4” to 6x12.” The fruit contains 20 to 60 seeds and is yellow or orange in color when ripe. Cacao contains theobromine, caffeine, phenylethylamine, and seratonin. Cacao is the only plant from the Theobroma genus to be commercially used. (Angela Sotelo 1991). In order to make cocoa the pods are harvested from the Cacao plant and fermented by naturally occurring bacteria in order to get rid of their bitter flavor. Then they are cured and roasted. The resulting kernels (called nibs) are then often sold commercially for a variety of uses (CEE 2009). Out of the alkaloids found in cacao, theobromine is the one found in greatest quantity. The presence of theobromine and caffeine have been stated as a reason for addictions to chocolate, known as “chocoholism.” However, their addictive effects in the relatively small quantities found in chocolate may have been grossly overestimated. (Hendrik Smit et al 2004). In a study done in 2004 Smit et al found theobromine and caffeine (given in amounts found in an average bar of dark chocolate) to have noticeable psychopharmacological effects including increased energy and reaction time. At that time, there had been no direct test of the psychoactive effects’ role in the popularity of chocolate. Theobromine is a metabolite of caffeine and is found nearly exclusively in products made from Theobroma Cacao. Dark chocolate contains approximately 240-520 milligrams of theobromine per 50-gram portion. In addition to the pods, the leaves of Cacao also contain alkaloids. Alkaloids have been found to be most prevelant in cacao leaves during the early stages of leaf development. The alkaloid in highest concetration is theobromine, followed by caffeine. Over 75% of alkaloids disappeared with further leaf development (Yoko Koyama et al 2003). However, substantial amounts of theobromine have been detected in the seeds of adult cacao plants (Howell Edwards et al 2005). Phenethylamine and seratonin both affect the mental state of humans as well, and humans have been shown to have an elevated level of phenethylamine in their systems when stressed (M.A. Paulos, et al. 1982).

Yoko Koyama et al Plant Physiology &amp; Biochemistry; Nov2003, Vol. 41 Issue 11/12, p977, 8p

Howell Edwards et al. Analytica Chimica Acta; May2005, Vol. 538 Issue 1/2, p175-180, 6p

Robin, Raizel. Canadian Business, 2/17/2003, Vol. 76 Issue 3, p61, 2p.

Columbia Electronic Encyclopedia, 6th Edition; 1/1/2009, p1-1, 1p.

Hendrik J. Smit. Rachel J. Blackburn Reinforcing effects of caffeine and theobromine as found in chocolate 17 March 2005

Cacao(Theobroma cacao L.)

Tree Treacy
Coca (Erythroxylum coca Lam.)

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