“Betalain”的意思、由来-开放百科全书

Betalains are a class of red and yellow indole-derived pigments found in plants of the Caryophyllales, where they replace anthocyanin pigments. Betalains also occur in some higher order fungi.^[1] They are most often noticeable in the petals of flowers, but may color the fruits, leaves, stems, and roots of plants that contain them. They include pigments such as those found in beets.

Description

The name "betalain" comes from the Latin name of the common beet (Beta vulgaris), from which betalains were first extracted. The deep red color of beets, bougainvillea, amaranth, and many cacti results from the presence of betalain pigments.^[2] The particular shades of red to purple are distinctive and unlike that of anthocyanin pigments found in most plants.

Chemistry

It was once thought that betalains were related to anthocyanins, the reddish pigments found in most plants. Both betalains and anthocyanins are water-soluble pigments found in the vacuoles of plant cells. However, betalains are structurally and chemically unlike anthocyanins and the two have never been found in the same plant together.^[6]^[7] For example, betalains contain nitrogen whereas anthocyanins do not.^[2]

It is now known that betalains are aromatic indole derivatives synthesized from tyrosine. They are not related chemically to the anthocyanins and are not even flavonoids.^[8] Each betalain is a glycoside, and consists of a sugar and a colored portion. Their synthesis is promoted by light.^[3]

The most heavily studied betalain is betanin, also called beetroot red after the fact that it may be extracted from red beet roots. Betanin is a glucoside, and hydrolyzes into the sugar glucose and betanidin.^[2] It is used as a food coloring agent, and the color is sensitive to pH. Other betalains known to occur in beets are isobetanin, probetanin, and neobetanin. The color and antioxidant capacity of betanin and indicaxanthin (betaxanthin derived of L-proline) are affected by dielectric microwave heating.^[9] Addition of TFE (2,2,2-trifluoroethanol) is reported to improve the hydrolytic stability of some betalains in aqueous solution.^[10] Furthermore, a betanin-europium(III) complex has been used to detect calcium dipicolinate in bacterial spores, including Bacillus anthracis and B. cereus.^[11]

Other important betacyanins are amaranthine and isoamaranthine, isolated from species of Amaranthus.

Taxonomic significance

Betalain pigments occur only in the Caryophyllales and some Basidiomycota (mushrooms),^[12] for instance Hygrophoraceae (waxcaps).^[13] Where they occur in plants, they sometimes coexist with anthoxanthins (yellow to orange flavonoids), but never occur in plant species with anthocyanins.^[14]

Among the flowering plant order Caryophyllales, most members produce betalains and lack anthocyanins. Of all the families in the Caryophyllales, only the Caryophyllaceae (carnation family) and Molluginaceae produce anthocyanins instead of betalains.^[12] The limited distribution of betalains among plants is a synapomorphy for the Caryophyllales, though their production has been lost in two families.

Economic uses

Betanin is commercially used as a natural food dye. It can cause beeturia (red urine) and red feces in some people who are unable to break it down. The interest of the food industry in betalains has grown since they were identified by in vitro methods as antioxidants,^[15] which may protect against oxidation of low-density lipoproteins.^[16]

Semisynthetic derivatives

Betanin extracted from the red beet^[17] was used as starting material for the semisynthesis of an artificial betalainic coumarin, which was applied as a fluorescent probe for the live-cell imaging of Plasmodium-infected erythrocytes.^[18]

See also

References

1. ^{{cite journal |vauthors= Strack D, Vogt T, Schliemann W |title= Recent advances in betalain research |journal= Phytochemistry |volume= 62 |issue= 3 |pages= 247–69 |date= February 2003 |pmid= 12620337 |doi= 10.1016/S0031-9422(02)00564-2 |url= http://linkinghub.elsevier.com/retrieve/pii/S0031942202005642 }}
2. ^¹²{{cite book |last= Robinson |first= Trevor | name-list-format = vanc |year=1963 |title=The Organic Constituents of Higher Plants |page=292 |location= Minneapolis |publisher= Burgess Publishing }}
3. ^¹{{cite book |last= Salisbury |first= Frank B. | first2 = Cleon W. | last2 = Ross | name-list-format = vanc |year=1991 |title=Plant Physiology |edition=4th |pages=325–326 |location= Belmont, California |publisher= Wadsworth Publishing |isbn=978-0-534-15162-1 }}
4. ^{{cite journal |last= Kimler |first= L. M. | name-list-format = vanc |year=1975 |title=Betanin, the red beet pigment, as an antifungal agent |journal= Botanical Society of America, Abstracts of Papers |volume= 36 }}
5. ^{{cite journal | vauthors = Gandía-Herrero F, García-Carmona F, Escribano J | title = Botany: floral fluorescence effect | journal = Nature | volume = 437 | issue = 7057 | pages = 334 | year = 2005 | pmid = 16163341 | doi = 10.1038/437334a | bibcode = 2005Natur.437..334G }}
6. ^{{cite book |title=Colorants |last=Francis |first=F.J. | name-list-format = vanc |year=1999 |publisher=Egan Press |isbn=978-1-891127-00-7}}
7. ^{{cite journal |last= Stafford |first= Helen A. | name-list-format = vanc |title= Anthocyanins and betalains: evolution of the mutually exclusive pathways |journal= Plant Science |volume= 101 |issue= 2 |pages= 91–98 |year= 1994 |issn= 0168-9452 |url=http://www.sciencedirect.com/science/article/pii/0168945294902445 |doi= 10.1016/0168-9452(94)90244-5 |accessdate= 20 May 2013 |postscript= {{inconsistent citations}} }}
8. ^{{cite book |last= Raven |first= Peter H. | first2 = Ray F. | last2 = Evert | first3 = Susan E. | last3 = Eichhorn | name-list-format = vanc |year=2004 |title=Biology of Plants |edition=7th |page=465 |location= New York |publisher= W. H. Freeman and Company |isbn=978-0-7167-1007-3 }}
9. ^{{cite journal | vauthors = Gonçalves LC, Di Genova BM, Dörr FA, Pinto E, Bastos EL |display-authors=3 | title = Effect of dielectric microwave heating on the color and antiradical capacity of betanin | journal = Journal of Food Engineering | volume = 118 | issue = 1 | pages = 49–55 | year = 2013 | doi = 10.1016/j.jfoodeng.2013.03.022}}
10. ^{{cite journal | vauthors = Bartoloni FH, Gonçalves LC, Rodrigues AC, Dörr FA, Pinto E, Bastos EL |display-authors=3 | year = 2013 | title = Photophysics and hydrolytic stability of betalains in aqueous trifluoroethanol | journal = Monatshefte für Chemie - Chemical Monthly | volume = 144 | pages = 567–571 | doi = 10.1007/s00706-012-0883-5 | issue = 4}}
11. ^{{cite journal | vauthors = Gonçalves LC, Da Silva SM, DeRose PC, Ando RA, Bastos EL |display-authors=3 | title = Beetroot-pigment-derived colorimetric sensor for detection of calcium dipicolinate in bacterial spores | journal = PLOS One | volume = 8 | issue = 9 | pages = e73701 | year = 2013 | pmid = 24019934 | pmc = 3760816 | doi = 10.1371/journal.pone.0073701 | bibcode = 2013PLoSO...873701G }}
12. ^¹{{cite book |last= Cronquist |first= Arthur | name-list-format = vanc |year=1981 |title=An Integrated System of Classification of Flowering Plants |pages=235–9 |location= New York |publisher= Columbia University Press |isbn=978-0-231-03880-5 }}
13. ^{{Cite journal|last=Lodge|first=D. Jean|last2=Padamsee|first2=Mahajabeen|last3=Matheny|first3=P. Brandon|last4=Aime|first4=M. Catherine|last5=Cantrell|first5=Sharon A.|last6=Boertmann|first6=David|last7=Kovalenko|first7=Alexander|last8=Vizzini|first8=Alfredo|last9=Dentinger|first9=Bryn T. M.|display-authors=3|date=2013-10-06|title=Molecular phylogeny, morphology, pigment chemistry and ecology in Hygrophoraceae (Agaricales)|journal=Fungal Diversity|language=en|volume=64|issue=1|pages=1–99|doi=10.1007/s13225-013-0259-0|issn=1560-2745}}
14. ^{{cite journal | last=Stafford | first=Helen A. | title=Anthocyanins and betalains: evolution of the mutually exclusive pathways (Review)| journal=Plant Science| volume=101 | issue=2 | year=1994 | issn=0168-9452 | doi=10.1016/0168-9452(94)90244-5 | pages=91–98|url=https://kundoc.com/pdf-anthocyanins-and-betalains-evolution-of-the-mutually-exclusive-pathways-.html}}
15. ^{{cite journal | vauthors = Escribano J, Pedreño MA, García-Carmona F, Muñoz R | year = 1998 | title = Characterization of the antiradical activity of betalains from Beta vulgaris L. roots | journal = Phytochem. Anal. | volume = 9 | pages = 124–7 | doi = 10.1002/(SICI)1099-1565(199805/06)9:3<124::AID-PCA401>3.0.CO;2-0 | issue = 3 }}
16. ^{{cite journal | vauthors = Tesoriere L, Allegra M, Butera D, Livrea MA | title = Absorption, excretion, and distribution of dietary antioxidant betalains in LDLs: potential health effects of betalains in humans | journal = The American Journal of Clinical Nutrition | volume = 80 | issue = 4 | pages = 941–5 | date = October 2004 | pmid = 15447903 | url = http://www.ajcn.org/cgi/content/abstract/80/4/941 | doi = 10.1093/ajcn/80.4.941 }}
17. ^{{cite journal | vauthors = Gonçalves LC, Trassi MA, Lopes NB, Dörr FA, Santos MT, Baader WJ, Oliveira Bastos EL |display-authors=3 | year = 2012 | title = A comparative study of the purification of betanin | journal = Food Chem. | volume = 131 | pages = 231–238 | doi = 10.1016/j.foodchem.2011.08.067}}
18. ^{{cite journal | vauthors = Gonçalves LC, Tonelli RR, Bagnaresi P, Mortara RA, Ferreira AG, Bastos EL |display-authors=3 | title = A nature-inspired betalainic probe for live-cell imaging of Plasmodium-infected erythrocytes | journal = PLOS One | volume = 8 | issue = 1 | pages = e53874 | year = 2013 | pmid = 23342028 | pmc = 3547039 | doi = 10.1371/journal.pone.0053874 | editor1-last = Sauer | bibcode = 2013PLoSO...853874G | editor1-first = Markus }}