Flindersia bourjotiana

[hairyplant]

I stumbled over an interesting description of a Flindersia spp. in the Hyland et al. Key to Australian Rainforest Plants. Under natural history notes for the tree Flindersia bourjotiana. It says:

"The bark of most Flindersia spp. Contains compounds of considerable chemical interest. This observation was imprinted on the author’s mind by a story told to him by some aboriginal forestry workers in the Kuranda area. The story goes something like this: “We found the sugar bag (native bee hive) and cut it out of the tree it was in. Rather than put it on the ground and get it contaminated with dirt and pebbles, we stripped the bark off a Silver Ash (Flindersia bourjotiana) and placed the sugar bag on the clean, inner surface of the freshly stripped bark. Later on when we had eaten the sugar bag we could see fairies floating through the rainforest.” Whether the hallucinations were induced by the exudates from the F. bourjotiana or from components of the sugar bag or from some completely unrelated source will never be know with certainty."

Anyone know of any other in vivo tests or more on effects?

[XipeTotec]

interesting find I look forward to hearing more about this one

[apothecary]

The leaf oils of the australian species of Flindersia (Rutaceae)

BROPHY Joseph J. ; GOLDSACK Robert J. ; FORSTER Paul I. ;

The leaf oils of the 15 Australian members of the genus Flindersia have been examined by GC and GC/MS. They produced, in the main, sesquiterpenic oils with very little monoterpene content. Flindersia maculosa and F. dissosperma contained significant amounts of the C12 hydrocarbons geijerene and pregeijerene together with methyl geranate, α-pinene, β-caryophyllene and bicyclogermacrene in the case of F. dissosperma and α-pinene, 1,8-cineole, β-caryophyllene and bicyclogermacrene in the case of F. maculosa. In F. acuminata and one chemotype of F. australis the principal components were bicyclogermacrene, guaiol, bulnesol; the second chemotype of F. australis contained β-caryophyllene and spathulenol as major components and lacked guaiol and bulnesol. The leaf oils of F. bennettiana, produced an oil rich in bicyclogermacrene, while in F. bourjotiana the principal component was β-caryophyllene. In F. brassiii the principal components were α-cadinol and δ-cadinene, while in F. brayleyana they were spathulenol and caryophyllene oxide. Flindersia collina gave an oil dominated by (E,E)-farnesol. The leaf oil of F. ifflaiana was dominated by β-caryophyllene, α-humulene and bicyclogermacrene, while that from F. laevicarpa was variable with major components being β-caryophyllene, germacrene D, bicyclogennacrene and elemol. Flindersia oppositifolia gave a variable oil with both mono- and sesquiterpenes in significant amounts, while F. pimenteliana gave an oil dominated either by β-caryophyllene and bicyclogermacrene or by α-pinene. The leaf oil from F. schottiana contained significant amounts of monoterpenes, with α-pinene or sabinene being the major component while that from F xanthoxyla was dominated by bicyclogermacrene, 8-cadinene and β-caryophyllene.

See highlighty bit.

Title: The Chemical Constituents of Australian Flindersia Species. IV. The Constituents of Flindersia bourjotiana F. Muell

Authors: Cannon, J. R., Hughes, G. K., Price, J. R., & Ritchie, E.

Journal: Australian Journal of Scientific Research, Series A: Physical Sciences, vol. 5, p.420

Bibliographic Code: 1952AuSRA...5..420C

http://adsabs.harvard.edu/full/1952AuSRA...5..420C (paper in image or pdf form, otherwise would replicate text here)

[Torsten]

I think the effect may lie more with the alkaloids in this species. Both skimmianine and flindersine are found in the bark. They are very closely related alkaloids and skimmianine is known to be a substantial serotonin antagonist. I think a bark alkaloid extract would be interesting.

[apothecary]

Cool. I didn't check out the second link too in depth mostly because I'm lazy but after Torts post I checked it out. It mentioned skimmianine and flindersamine, T, I assume flindersine == flindersamine?

So on this prompting I went and found some more papers... here's an interesting one:

http://www.ncbi.nlm.nih.gov/pubmed/3753096

Effect of skimmianine on animal behavior.

Cheng JT.

Skimmianine, a component of Rutaceae plants, was found to have a significant inhibitory effect on spontaneous motor activity, exploratory behavior, cataleptogenic activity, conditioned avoidance response and long-term isolation-induced fighting of animals. A mild antimethamphetamine activity was also observed. Its neuroleptic activity was less potent than that of chlorpromazine.

Antimethamphetamine eh...

http://www.ncbi.nlm.nih.gov/pubmed/2076049

Cardiovascular effect of skimmianine in rats.

Cheng JT, Chang SS, Chen IS.

Skimmianine, a general component contained in the plants of Rutaceae, was found to have a selective inhibitory effect on the 5-hydroxytryptamine-induced vasopressor responses of rats. A similar inhibitory action was also observed in the isolated atria. Moreover, skimmianine produced a nonspecific blockade of the cardiovascular functions at higher concentration.

http://www.blackwell-synergy.com/doi/abs/1...urnalCode=aap.1

Skimmianine and related furoquinolines function as antagonists of 5-hydroxytryptamine receptors in animals

# Juei-Tang Cheng11Department of Pharmacology, College of Medicine, National Cheng Kung University, Tainan City, Taiwan,

# Tzen Kwan Chang**Department of Neurology, The Hospital of China Medical College, Taichung City &

# Ih-Sheng Chent

1 Skimmianine, kokusaginine and confusameline, three furoquinolines extracted from the leaves of Evodia merrillii(Rutaceae), were investigated to characterize their selective effects on subtypes of 5-hydroxytryptamine (5-HT) receptors.

2 In the isolated membranes of rat cerebrocortex, using [3H]-5-HT and [3H]-ketanserin as radioligands, skimmianine and the two other furoquinolines displaced radioligand bindings in a concentration-dependent manner. Lower concentrations were required to affect [3H]-ketanserin binding than [3H]-5-HT binding in the order skimmianine > kokusaginine > confusameline.

3 Furoquinolines inhibited 5-HT-induced contraction mediated by 5-HT2 receptors in the presence of methiothepin in rat isolated aorta. Also, the combination of furoquinolines with ketanserin showed an additive antagonism.

4 These furoquinolines were inactive on the 5-carboxamidotryptamine-induced relaxation of guinea-pig ileum, a 5-HT1-mediated event. However, 5-HT-induced contraction via 5-HT2 receptors was reduced by these furoquinolines in a way similar to that in blood vessels.

5 The failure of these compounds to affect the 5-HT-induced Bezold–Jarisch-like reflex in anaesthetized rats, the major .5-HT3-mediated action, ruled out an action on 5-HT3 receptors.

6 The results obtained suggest that three furoquinoline alkaloids may act on 5-HT receptors in animals, more selectively to the 5-HT2 subtype, in the order of skimmianine > kokusaginine > confusameline.

So, not just serotonin, but 5-HT2 specifically. Very interesting....that's probably whats meant as anti-methamphetamine?

[Torsten]

T, I assume flindersine == flindersamine?

flindersine + 3 second memory = flindersamine ;)

[hairyplant]

Very interesting, thanks for the replies!

I have found mature individuals quite hard to find in the rainforest, I think mostly due to the targeting of this species during selective logging times. My search is continuing however...

[apothecary]

Hey hairy, this plant is supposedly planted all over campus at JCU Cairns.

[Entheo]

I think the effect may lie more with the alkaloids in this species. Both skimmianine and flindersine are found in the bark. They are very closely related alkaloids and skimmianine is known to be a substantial serotonin antagonist. I think a bark alkaloid extract would be interesting.

What about if it is Flindersia laevicarpa, which contains harmalan, hesperidin, flindercarpin-2, in the leaves (Picker et al., 1976) and flindercarpin-1, flindercarpin-2, and flindercarpin-3 along with flindersiachromone and 8-methoxyflindersiachromone in the bark.

Picker, K., Ritchie, E. & Taylor, W.C. 1976. The chemical constituents of Australian Flindersia species XXI. An examination of the bark and leaves of F. laevicarpa. Aust. J. Chem. 29, 2023-2036.