Peonidin

Peonidin
Names
	IUPAC name 2-(4-Hydroxy-3-methoxyphenyl)chromenylium-3,5,7-triol
Identifiers
CAS Number	134-01-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:75314 ;
ChEMBL	ChEMBL1277324 ;
ChemSpider	390370 ;
KEGG	C08726 ;
PubChem CID	441773;
UNII	D0O766G47B ;
	InChI InChI=1S/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1 Key: XFDQJKDGGOEYPI-UHFFFAOYSA-O ; InChI=1/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1 Key: XFDQJKDGGOEYPI-IKLDFBCSAN;
	SMILES Oc1cc2c(O)cc(O)cc2[o+]c1c3cc(OC)c(O)cc3;
Properties
Chemical formula	C16H13O6+
Molar mass	301.27 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Peonidin is an O-methylated anthocyanidin derived from Cyanidin, and a primary plant pigment. Peonidin gives purplish-red hues to flowers such as the peony, from which it takes its name, and roses. It is also present in some blue flowers, such as the morning glory.

The generic garden peony

Like most anthocyanidins, it is pH sensitive, and changes from red to blue as pH rises because anthocyanidins are highly conjugated chromophores. When the pH is changed, the extent of the conjugation (of the double bonds) is altered, which alters the wavelength of light energy absorbed by the molecule. (Natural anthocyanidins are most stable in a very low pH environment; at pH 8.0, most become colorless.) At pH 2.0, peonidin is cherry red; at 3.0 a strong yellowish pink; at 5.0 it is grape red-purple; and at 8.0 it becomes deep blue; unlike many anthocyanidins, however, it is stable at higher pH, and has been isolated as a blue colorant from the brilliant "Heavenly Blue" morning glory (Ipomoea tricolor Cav cv).

Because of its unusual color stability, a cafeyl-acylated buffered formulation of it has been patented for use as food coloring.

Peonidin, like many anthocyanidins, has shown potent inhibitory and apoptotic effects on cancer cells in vitro, notably metastatic human breast cancer cells.[1] A very large question, however, has been raised about anthocyanidins' penetration and retention in human cells in vivo, due to their rapid elimination from the human body.

By far the greatest dietary source of peonidin is raw cranberries, which contain 42 mg per 100 g of fruit. Blueberries, plums, grapes, and cherries also contain significant amounts, ranging from 5 to 12 mg/100 g. Only fresh fruit has been shown to contain significant peonidin; frozen blueberries have been shown to contain almost none. Peonidin has been found in concentrations of up to 40 mg per 100 g (cooked) of certain cultivars of purple fleshed sweet potatoes; the amount of peonidin varies greatly across cultivars.[2] It has also been isolated from raw black rice and black bananas.

The higher level of peonidin in fresh fruit corresponds to the rule of thumb that more natural fruit is healthier. Specifically, the amount of phenolic compounds in cranberries has been found to be inversely correlated with fruit size and crop yield.[3]

List of peonidin derivatives

Peonidin-3-O-glucoside, found in red onion

gollark: https://pastebin.com/RM13UGFaAt the top of this code file.

gollark: From the official docs.

gollark: "Features:- Fortunes/Dwarf Fortress output/Chuck Norris jokes on boot (wait, IS this a feature?)- (other) viruses (how do you get them in the first place? running random files like this?) cannot do anything particularly awful to your computer - uninterceptable (except by crashing the keyboard shortcut daemon, I guess) keyboard shortcuts allow easy wiping of the non-potatOS data so you can get back to whatever nonsense you do fast- Skynet (rednet-ish stuff over websocket to my server) and Lolcrypt (encoding data as lols and punctuation) built in for easy access!- Convenient OS-y APIs - add keyboard shortcuts, spawn background processes & do "multithreading"-ish stuff.- Great features for other idio- OS designers, like passwords and fake loading (est potatOS.stupidity.loading [time], est potatOS.stupidity.password [password]).- Digits of Tau available via a convenient command ("tau")- Potatoplex and Loading built in ("potatoplex"/"loading") (potatoplex has many undocumented options)!- Stack traces (yes, I did steal them from MBS)- Backdoors- er, remote debugging access (it's secured, via ECC signing on disks and websocket-only access requiring a key for the other one)- All this useless random junk can autoupdate (this is probably a backdoor)!- EZCopy allows you to easily install potatOS on another device, just by sticking it in the disk drive of any potatOS device!- fs.load and fs.dump - probably helpful somehow.- Blocks bad programs (like the "Webicity" browser).- Fully-featured process manager.- Can run in "hidden mode" where it's at least not obvious at a glance that potatOS is installed.- Convenient, simple uninstall with the "uninstall" command.- Turns on any networked potatOS computers!- Edits connected signs to use as ad displays.- A recycle bin.- An exorcise command, which is like delete but better.- Support for a wide variety of Lorem Ipsum."

gollark: You would need to get rid of the autoupdate capabilities of potatOS itself, or swap them to your own pastebins/github stuff, and then keep everything in line with the current versions.

gollark: Anyway, <@151391317740486657>, what you can do is fork potatOS and get rid of the bits you don't like, but that's also hard (less, though) and would be very difficult to keep updated.

References

Jung Yeon Kwon; Ki Won Lee; Haeng Jeon Hur; Hyong Joo Lee (2007). "Peonidin Inhibits Phorbol-Ester-Induced COX-2 Expression and Transformation in JB6 P+ Cells by Blocking Phosphorylation of ERK-1 and -2". Annals of the New York Academy of Sciences. 1095 (1): 513–520. doi:10.1196/annals.1397.055. PMID 17404064.
Van-Den Truong; Nigel Deighton; Roger T. Thompson; Roger F. McFeeters; Lisa O. Dean; Kenneth V. Pecota & G. Craig Yencho (2009). "Characterization of Anthocyanins and Anthocyanidins in Purple-Fleshed Sweetpotatoes by HPLC-DAD/ESI-MS/MS" (PDF). Journal of Agricultural and Food Chemistry. 58: 404–410. doi:10.1021/jf902799a. PMID 20017481. Archived from the original (PDF) on 2010-07-12.
N. Vorsa; J. Polashock; D. Cunningham; R. Roderick; A. Howell. "Evaluation Of Fruit Chemistry In Cranberry Germplasm: Potential For Breeding Varieties With Enhanced Health Constituents". ISHS Acta Horticulturae. 574: VII International Symposium on Vaccinium Culture.

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[1] Jung Yeon Kwon; Ki Won Lee; Haeng Jeon Hur; Hyong Joo Lee (2007). "Peonidin Inhibits Phorbol-Ester-Induced COX-2 Expression and Transformation in JB6 P+ Cells by Blocking Phosphorylation of ERK-1 and -2". Annals of the New York Academy of Sciences. 1095 (1): 513–520. doi:10.1196/annals.1397.055. PMID 17404064.

[2] Van-Den Truong; Nigel Deighton; Roger T. Thompson; Roger F. McFeeters; Lisa O. Dean; Kenneth V. Pecota & G. Craig Yencho (2009). "Characterization of Anthocyanins and Anthocyanidins in Purple-Fleshed Sweetpotatoes by HPLC-DAD/ESI-MS/MS" (PDF). Journal of Agricultural and Food Chemistry. 58: 404–410. doi:10.1021/jf902799a. PMID 20017481. Archived from the original (PDF) on 2010-07-12.

[3] N. Vorsa; J. Polashock; D. Cunningham; R. Roderick; A. Howell. "Evaluation Of Fruit Chemistry In Cranberry Germplasm: Potential For Breeding Varieties With Enhanced Health Constituents". ISHS Acta Horticulturae. 574: VII International Symposium on Vaccinium Culture.