Jump to content
The Corroboree
Auxin

Planty fluorene derivative?

Recommended Posts

Some years back, just in passing, I saw the structure of a fluorene derivative substituted at the methylene bridge cited as a constituent of whatever medicinal plant I was investigating at the time. I only noted it at the time because I played with fluorene and fluorenone in college.

Fluorene:

200px-Fluorene.svg.png

What the hell plant was it? :lol:

(I'm asking because of the discovery of a group of synthetic cancer specific apoptosis inducing BAX activator compounds recently discovered [Link] [Patent with pics] I swear I saw a relevant looking natural analog at some point and I'm curious if the plant has traditional use against cancer)

  • Like 2

Share this post


Link to post
Share on other sites

And, no, it wasnt gibberellic acid :wink:

Share this post


Link to post
Share on other sites

Some harmala alkaloids (like harmaline, harmane, harmine etc) look a bit like that with a N at the bridge.

Was it Syrian Rue, B.Caapi or Tribulus Terrestris?

Edited by einseins

Share this post


Link to post
Share on other sites

Nope, wasnt a ß-carboline, there was definitely a carbon there.

Tho, since the substituent connected to that spot can be a nitrogen and do the cancer fighting thing with the nitrogen just 1 space removed from the ß-carboline position I wonder if harmine was tested for the BAX activity. Harmine is known to have an anti-proliferative and pro-apoptotic effect on cancer.

Its too bad that when they throw the whole library of 300,000 compounds at something we cant see all of the raw data. Positive hits are discounted for reasons that wouldnt bother me, like not being patentable or being hallucinogenic.

  • Like 1

Share this post


Link to post
Share on other sites

Cytisus is the plant they base Chantix/Champix off of but not that shape but Chantix is close in shape but cystine is not. Just giving ideas I am sure I can find it Monday if no one found it.

Share this post


Link to post
Share on other sites

I wish I knew more chemistry, I love the research posts here and have based some of my own work on the responses people have given purely from interest and passion

Every time there is a sexy research post on SAB, another tinfoil hat explodes

  • Like 4

Share this post


Link to post
Share on other sites

you'd think there would be a database - like with all the *omics

Edited by Dreamwalker.

Share this post


Link to post
Share on other sites

I expect the pharmaceutical giants have such a critter. Pop in some structure bit, cross reference to activity or receptor affinity, and the database squirts out a list. I wish things like that would show up on piratebay. If there was just 1 awesome database leaked for every hundred midget pornos....

  • Like 3

Share this post


Link to post
Share on other sites

I ran it through SciFi nder, lots of hits for growth regulators like morphactins. Bioremediation (I guess referring to fluorene as a PAH pollutant). Some stuff on CB2 and 5-HT receptors, but seemed to all be synthetic rather than plant based. And the anti-cancer stuff.

Ring any bells? If you can narrow it down a bit it would help, fluorenes are used for a lot of things. I need keywords dammit!

I can do a partial chemical structure search, but you'll have to narrow it down. I ran unsubstituted fluorene, it gets a lot of hits as a substructure, as you would expect. Can you remember the nature of the substituent? Was it a heteroatom? Quarternary carbon site at the bridge? Bulky, acidic, some sort of amine?

Edited by Alice

Share this post


Link to post
Share on other sites
I need keywords dammit!

:lol:

I remember it was substituted at carbon 9 with a carbon chain, I think one with heteroatoms (O or N) on it somewhere, but the bit that connected to carbon 9 was a carbon with carbon(s) attached. It was substituted somewhere other than carbon 9 as well but I cant remember specifics.

SciFi nder sounds fun.

Edited by Auxin

Share this post


Link to post
Share on other sites

OK cool, I don't think I can narrow it down. They're pretty much all substituted at C9 with some sort of alkyl chain. Anyway, if you remember the compound be sure to post it, I'm intrigued :)

Share this post


Link to post
Share on other sites

A number of fluoren-9-one natural products, including dengibsin, dengibsinin, and dendroflorin, have been reported to occur in the Asiatic orchid Dendrobium gibsonii Lindley (Figure 1.) [1, 2]

post-5043-0-58411200-1414641297_thumb.jp

Dendrobium chrysanthum contains 2,4,7-trihydroxy-5-methoxy-9-fluorenone and 2,4,7-trihydroxy-1,5-dimethoxy-9-fluorenone amongst other derivatives [a, b, full text]

Tripterygium wilfordii contains [3]:

post-5043-0-23665900-1414643099_thumb.jp

... it was substituted at carbon 9 with a carbon chain, I think one with heteroatoms (O or N) on it somewhere, but the bit that connected to carbon 9 was a carbon with carbon(s) attached. It was substituted somewhere other than carbon 9 as well but I cant remember specifics.

Cant find anything to that exact description but I'll keep looking.

Ehretia microphylla contains Microphyllone [4]:

75872-69-4.gif

Closest I can find is Selaginella pulvinata which contains PDE4 inhibiting compounds [5]:

ol-2013-03282f_0006.gif

post-5043-0-58411200-1414641297_thumb.jpg

post-5043-0-23665900-1414643099_thumb.jpg

Edited by Alchemica
  • Like 1

Share this post


Link to post
Share on other sites

Wow, I'd seen references in journal abstracts to the fluorenones in Dendrobium gibsonii but I didnt log in to see the structures. That dengibsinin is a sexy one, reminds me of the bioactivated antioxidant flavones and lignans.

Selaginpulvilin A looks like a bad girl, must be why vilin is in the name

Liberty_Spikes_by_Snowvalley.jpg

Share this post


Link to post
Share on other sites

Slightly similar, though not likely it, are the canthins like canthin-6-one

Share this post


Link to post
Share on other sites

Matrine is a sexy critter. I've toyed with the thought of growing Sophora flavescens before, the whole plant is usually better than the isolated alkaloids except in some heart conditions. Hopefully not a plant I'd actually need tho.

Share this post


Link to post
Share on other sites

You may not ever need it but could be helpful to grow incase someone else wants it. If I don't have room for new plants I go to libraries and community centers and offer to decorate. Just make sure you do plant some neat looking things. This year I plan on growing the non somniferum poppies at a library nearby and at the end of the season I will collect the seeds and some plant material. Well that is just one of my plans sometimes I like to decorate chain link fences with Ipomea and I will try some decorating with Passiflora as well but I am not so convinced it can become self sustaining in my climate.

Share this post


Link to post
Share on other sites

Oh yeah, I know that one. I learned about it at 13 when I saw Vinca rosea in a book on legal highs :lol:

I never tried it tho, those alks are too hardcore- theyre real chemo drugs with all the associated implications of hair loss and explosive vomiting, loss of immune function, etc.

If I were ever desperate enough to go in for chemo I'd let the doctors administer that stuff but I'd look into preparatory prolonged fasting. Theres some interesting research being done there. Apparently going on a 0 calorie starvation fast for 3 days before the chemo (and obviously fasting while sick on chemo) shuts down the healthy immune cells as much as possible, protecting them from the chemo, but the cancer still acts like a drunken college student and so gets killed by the chemo. On top of that, research shows that prolonged fasting effectively 'de-ages' the immune system both in the efficiency of individual immune cells and restoring proper ratios between immune cell types (which go off balance with age). Cool stuff.

Prolonged Fasting Reduces IGF-1/PKA to Promote Hematopoietic-Stem-Cell-Based Regeneration and Reverse Immunosuppression

Reduced levels of IGF-I mediate differential protection of normal and cancer cells in response to fasting and improve chemotherapeutic index

Share this post


Link to post
Share on other sites

I do remember learning of a sea plant or animal which had amazing properties to treat many forms of cancer. I know that it was located in a small cove in one part of the world but was extinct within less than a decade of it's discovery.

It is a faint memory but we only were told about it briefly we did not study it at all.

This is one alkaloid I am studying very closely. http://en.wikipedia.org/wiki/Halofuginone

It may have practical applications in treating auto-immune diseases and that is of great interest to me, It may also have some use treating tumors. It is very exciting and a great start to modulating specific T cells.

Edited by doxneed2c-me

Share this post


Link to post
Share on other sites

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now

×