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sandalwood

quandong and the grandisine type delta opioid agonists

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I have been interested in the Elaeocarpus grandis tree for some time...

after reading specific chemistry about selected species...focusing on compounds of the grandisine types that have varying levels of potency as delta opioid agonists...

one of the more potent analogs, should occur in elaeocarpus grandis.

I was lucky enough to have a freind send me leaf and seed sample.

elaeocarpus ganitrus is also known as rudraksha tree...

this tree has ornamental value....and I think the leaves and fruits and seeds are also used in ayurvedic and folk tradition medicine.

the seeds of e. ganitrus are known as rudraksha seeds...and they are used as mala beads, and as jewelry, magic talismans etc within hindu religion/culture.

the seeds can have from 1 to 32 or more segments....

the most common is the 5 "mukhi" or 5 segment seed.....the rarer the seed, the more the cost...some rudraksha seeds can be priced into the thousands of dollars for just a few seeds.

so my interest in e. grandis was also in the ornamental and bead direction as well as possible source for grandisine alkaliods.

the seed of e. grandis, while not as fine, small, and intricate as the rudraksha seed, definitely has bead potential...I have never seen this seed in any western bead stores...and rarely see rudraksha seeds for that matter either....the potential that the seed could be used for decoration is a good one...especially if the seeds were well weathered naturally.

if anyone knows of any traditional use of Elaeocarpus grandis leaf let me know...it would be very interesting if that is so.

the potential of grandisine mu opioid active analogs is not my area of knowledge.

but even delta opioid agonist compounds are interesting.

I have several seeds...around 10...and I am interested in busting up one of them, and trying to get some to germinate...

the rudraksha plant has been tested to show sedative, anti bacterial, and analgesic activity....

as for e. grandis, I have only read that it is possible the alkaloids might have analgesic action in animals and humans...so the research into the opioid activity is basically only on the cellular level for now.

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whats the tie in with quandong?........found some fresh santalum acuminata fruit last week.

t s t .

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well, the tie in is...

Elaeocarpus grandis - Blue Quandong

is that elaeocarpus grandis is also known as the the blue quandong....

perhaps there are more than one type of "quandong"?

it seems so, that santalum acuminata is known as desert quandong, or native peach...

today I looked up a website that shows pictures of carved quandong seeds...

and they are considerably different from the elaeocarpus grandis seeds that I sourced (if the person correctly identified it!)

looking into some photos of the two different species seeds I can tell that the santalum quandong seed is rounded, looking actually similiar to a rudraksha seed, but without as much of a topographical feature as the rudra...

comparing e. grandis seeds to s. acuminata...the grandis seeds have much more topographical feature...they are most common 5 segment seeds...just like the rudra..

they are very close to certian types of rudraksha seeds actually,just bigger.

a freind saw some of my rudra malas, and excitedly showed me banyan tree seeds from the big island...they were similiar to e. grandis seeds too, but much larger, and without a fine. tight, jewelry quality shell.......

but the e. grandis seeds are jewelry quality...these seeds are friggin hard...if you dont have the right tools to deal with them...they will bust your tools...

even the difference between rudraksha beads is so different that I believe that different elaeocarpus tree species are used to source bead materials, either that or the genetic diversity between trees of the same species accounts for the differences.

Java rudra beads are worth the most....I dont have any java beads though I dont think.

most rudra beads are about 1/4 the size of the standard e grandis seed...but there are very large rudra beads as well....108 bead count mala's of these large rudra beads are very long....you will see the large, large seeds on mostly sadhus...

is it possible that other species of elaeocarpus are used for the bead industry in India/Nepal? if so e. grandis seeds might have some potential value.

a person could drill through the centers...put them on a rod....and the grind down the high parts of the seed and have a very wicked looking surface for a handle for a knife, tool, letter opener.....

they could be ground into squares....different shapes. the seeds even have a hole on the tops of them that work great for a starter hole...actually, a needle can be pushed almost into the center of the stone...so drilling through these seeds is not going to be as much work as going through the whole stone.

elaeocarpus grandis, from what I could tell in the report specifically researching the grandisine alkaloids, is the one that contains the highest amounts of the purported most potent agonist at the delta receptor...and that would be grandisine F...

so when I was asking my freind about locality of this species, he reportedly has one in his yard.

he collected seed and leaf material for me.

so I am hoping that the material might contain grandisine F...

in the meantime, I am trying to find a ayurvedic extract of the elaeocarpus ganitrus (sphearicus) AKA rudraksha tree....as I know that currently this tree is consumed for various health issues.

growing the rudraksha tree in the right environement would be very interesting...when they would start to fruit, a person could experience the fun of going through the fruits for the seeds with low or high numbers of segments....

if a person could potentially induce certian variation of segments...say find a feed/treatment/shock for the plant that might help create multi segment seeds above the 10 segment mark, that person might have a good thing on their hands...

paying 50$ for a 11-14 segment thing retail would be a good deal.

having a 108 seed mala with all 1 segments would be worth thousands...

having a "siddha" mala with various numbers of different high segment beads cost into the thousands...up to the ten thousand mark and above for extremely large/complex ones.....

if an interesting compound can be sourced from e. grandis. of course that would be great. I am just wondering if the leaf material is consumed by many animals.? or if there is any human usage of the tree beyond just eating the fruits?

whats the tie in with quandong?........found some fresh santalum acuminata fruit last week.

t s t .

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fascinating! I have spent hours just looking at the blue seeds on the rainforest floor wondering if they might be interesting beyond their stunning visual effect. I will definitely collect some next time I see them - which will probably not be till mid summer or so.

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nice torsten...maybe you could harvest fallen leaf material as well.

does anyone know if the desert quandong, the santalum acuminata tree, has similiar aroma as the sandalwood tree?

if so, it could be a nice source of limited incense material as well as carveable stone/pit...

I wouldnt mind getting some of these desert quandong seeds as well...some of the carved beads I have seen a photo of made of that stone looked really nice.

fascinating! I have spent hours just looking at the blue seeds on the rainforest floor wondering if they might be interesting beyond their stunning visual effect. I will definitely collect some next time I see them - which will probably not be till mid summer or so.

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nice torsten...maybe you could harvest fallen leaf material as well.

does anyone know if the desert quandong, the santalum acuminata tree, has similiar aroma as the sandalwood tree?

if so, it could be a nice source of limited incense material as well as carveable stone/pit...

I wouldnt mind getting some of these desert quandong seeds as well...some of the carved beads I have seen a photo of made of that stone looked really nice.

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Great find Sandalwood,

According to the link below Elaeocarpus grandis is now known as Elaeocarpus angustifolius.

http://www.anbg.gov.au/cgi-bin/apni?taxon_id=61757

Oddly enough one of the 'Rudraksha' sites stated it was the seeds of E. angustfolius, another E. sphaericus? (no references)

http://www.rudraksha-mahima.com/rudraksha.htm

For anyone else interested here is the report I think Sandalwood was talking about

Anthony R. Carroll,*† Garrie Arumugan,† Ronald J. Quinn,† Joanne Redburn,† Gordon Guymer,‡ and Paul Grimshaw‡ - Griffith University

J. Org. Chem., 2005, 70 (5), pp 1889–1892

http://www4.gu.edu.au:8080/adt-root/upload....160928/public/

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adt logo

Australian Digital Theses Program

Thesis Details

Title Chemical Investigations of the Alkaloids from the Plants of the Family Elaeocarpaceae

Author Katavic, Peter L

Institution Griffith University

Date 2006

Abstract

A phytochemical survey to detect alkaloids was performed on extracts of 339 discrete plants parts from a total of 77 species from five genera of Elaeocarpaceae, including 30 species from Queensland, 38 from PNG, and nine from China. An alkaloid detecting reagent, bismuth (III) tetraiodide (Dragendorff's reagent) was used in a preliminary test for alkaloids, with positive ESIMS used to confirm the presence of alkaloids. A total of 35 extracts of various plant parts produced positive results with Dragendorff's reagent. Positive ESIMS detected alkaloids in only 13 of these extracts. Bismuth (III) tetraiodide was demonstrated to produce false positive results with the new non-alkaloidal poly-oxygenated compounds 112 and 113, which were purified from the extract of Sloanea tieghemii. Two new alkaloid producing species, Elaeocarpus habbeniensis, and E. fuscoides were detected from the survey. These species were chemically investigated for the first time. Two other previously investigated species, E. grandis and Peripentadenia mearsii, were also studied.

A total of 16 alkaloids, 11 of which are new, were purified from the extracts of these four species. The novel pyrrolidine alkaloids habbenine (114) and peripentonine (123), were isolated from the leaves of E. habbeniensis and Peripentadenia mearsii, respectively. Both of these compounds were purified as inseparable mixtures of diastereomers. The new pyrrolidine alkaloid mearsamine 1 (124), and the novel amino alkaloid mearsamine 2 (125), were also purified from the leaves of P. mearsii. The known pyrrolidine alkaloid peripentadenine (81), was purified from the bark of P. mearsii. Peripentonine (123) was reduced to peripentadenine (81) upon reaction with Pd/C.

Four aromatic indolizidine alkaloids were isolated from the extract of the leaves of E. fuscoides. One new compound, elaeocarpenine (122), was isolated from this New Guinean plant. Three known Elaeocarpus alkaloids, isoelaeocarpicine (62), elaeocarpine (60) and isoelaeocarpine (61) were also purified from E. fuscoides. Elaeocarpenine (122) was demonstrated to produce the epimeric compounds elaeocarpine and isoelaeocarpine via reaction with ammonia.

The chemical investigation of the Queensland plant E. grandis by two separate purification procedures was performed. An SCX/C18 isolation protocol was used to purify the new indolizidine alkaloids grandisine C (127), D (126), and E (128), in conjunction with the known tetracyclic indolizidine isoelaeocarpiline (63). The second purification of E. grandis was achieved with the use of ammonia in an acid/base partitioning protocol. Grandisine F (129) and G (130), and compounds 131a and b were purified by this procedure, as were 63, 126 and 127. Grandisine F and G were proposed to be ammonia adducts of grandisine D (126). Compound 131a and b were isolated as a mixture of diastereomers. The reduction of grandisine D (126) with Pd/C yielded a mixture of isoelaeocarpine (61) and elaeocarpine (60), whereas the reduction of isoelaeocarpiline (63) produced isoelaeocarpine (61).

All of the alkaloids isolated from the Elaeocarpaceae, except grandisine E (128) and 131a and b, were evaluated for binding affinity against the human δ opioid receptor. Every compound except mearsamine 2 (125) possessed a binding affinity of less than 100 μM. The most active compounds were grandisine F (129), D (126), C (127), elaeocarpenine (122), isoelaeocarpine (61), isoelaeocarpiline (63) and peripentadenine (81). The IC50 values for these compounds were 1.55, 1.65, 14.6, 2.74, 13.6, 9.86 and 11.4 &muM, respectively. The SAR of the active compounds was compared. These observations indicated that the indolizidine alkaloids were more active than the pyrrolidine alkaloids, and a phenol or ketone at position C-12 of the indolizidine alkaloids produced better binding affinity. All of these alkaloids, except 129, were proposed to interact with two of the three binding domains of the δ opioid receptor. Grandisine F (129) was proposed to have a different mode of action than the other alkaloids in the series.

Synthetic modifications to isoelaeocarpine (61) and peripentadenine (81) were investigated in an attempt to incorporate an extra aromatic group into these molecules. An extra aromatic group was proposed to provide increased binding affinity to the δ opioid receptor by interaction with the third binding domain of the receptor. Two different aromatic amines were successfully attached to peripentadenine (81) by a reductive amination reaction using NaBH(OAc)3 and a titanium catalyst. The reductive amination of the ketone in isoelaecarpine (61) with various amines and NaBH(OAc)3 or NaBH4 proved unsuccessful.

Thesis 01Front.pdf (298.1 Kb)

02Whole.pdf (3716.0 Kb)

Webhumans Copyright 2002 Griffith University Disclaimer

http://www4.gu.edu.au:8080/adt-root/public...0928/index.html

t s t .

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"if an interesting compound can be sourced from e. grandis. of course that would be great. I am just wondering if the leaf material is consumed by many animals.? or if there is any human usage of the tree beyond just eating the fruits?"

I think the leaves are not eaten at all by much except maybe the odd larvea during times of drought, they are left alone by most creatures

However i think that the wood from large trees may be used occassionaly in cabinet making, , i spoke to a cabinet making friend and he confirmed that!! ( cool) , although not that often, possibility of further use in the future as in its local area its quite a strong growing tree.

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Swamp Wallabies (Wallabia bicolor) feed voraciously on the leaves of planted Blue Quandongs.

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Thinking about buying some leaf material for bioassay ... anyone's got an idea about the dosage?

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I have purchased some leaf material for a bioassay. Has anyone tried this plant before? What's a good starting dose? best RoA?

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bump?

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I have a beauty in my front yard, I planted it (E.grandis). I reckon it will finally flower this year and drop it's ornamental blue fruits all up the front path, a nice finishing touch to the native tropical look.

The way to germinate Elaeocarpus is to put them in a damp sack out in the garden for 6 months. When they are ready they will start to pop and you can move the seeds over in a community pot to finish germinating.

Ive seen a couple species in PNG too. How might one experiment with this plant? Eat? Chew? Tea? smoke?

I'll give it a go. Could it be poisonous?

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Hi Sandlewood,

Here in s/e QLD we get 5 species of Elaeocarpus that I know of.

Elaeocarpus eumundi; Eumundi Quandong (rainforest)

Elaeocarpus grandis; Blue Quandong (rainforest)

Elaeocarpus kirtonii; White Quandong (rainforest)

Elaeocarpus obovatus; Hard Quandong (rainforest)

Elaeocarpus reticulatus; Blueberry Ash (eucalypt/rainforest)

Sorry but don't know anything about the alkaloids of any of these species.

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