1,2,3,4,6-펜타갈로일 포도당

1,2,3,4,6-Pentagalloyl glucose
1,2,3,4,6-펜타갈로일 포도당
Chemical structure of pentagalloyl glucose
이름
선호 IUPAC 이름
(2S,3R,4S,5R,6R)-6-{[(3,4,5-트리히드로xybenzoyl)oxy]메틸}옥산-2,3,4,5-테트라일 테트라키스(3,4,5-트리히드로xybenzoyl)
기타 이름
1,2,3,4,6-펜타-O-갈로일-β-D-글루코스
1,2,3,4,6-펜타키스-O-갈로일-베타-D-글루코스
베타-펜타-오-갈로일-글루코스
PGG
1,2,3,4,6-펜타-O-갈로일-베타-D-글루코스
식별자
3D 모델(JSmol)
체비
켐벨
켐스파이더
ECHA InfoCard 100.113.489 Edit this at Wikidata
펍켐 CID
유니
  • InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1 checkY
    키: QJINZEYHSMRWBK-NICIMHBISA-N checkY
  • C1=C(C=C(=C1O)O)O)C(=O)OC2C(C(C(C(O2)OC(=O)C3=CC(=C(=C3)O)O)O.OC(=O)C4=CC(=C(=C4)O)O)O)OC(=O)C5=CC(=C(=C)O)O)O)OC(=O)C6=CC(=C(=C6)O)o
특성.
C41H32O26
어금질량 940.681 g·190−1
달리 명시된 경우를 제외하고, 표준 상태(25°C [77°F], 100 kPa)의 재료에 대한 데이터가 제공된다.
☒ NVERIFI (?란checkY☒N?

1,2,3,4,6-펜타갈로일글루코스는 포도당의 펜타갈산 에스테르이다.갈로타닌이며 타라기타닌의 전구체다.[1]

펜타갈로일 포도당은 사람의 침전 α-아밀라아제를 포함한 [2]단백질을 침전시킬 수 있다.[3]

자연발생

1,2,3,4,6-펜타갈로일 포도당은 푸니카 그라나툼([4]포메그라나이트), 엘레오카르푸스 실베스트리스,[5] 루스 발티티티나(스타곤 수맥),[6] 파에오니아 질식사([7]페오니), 망기페라 인디카(망고), 부에아 마크로멜라 그리피스트리스(맵랑)에서 찾을 수 있다.[9]

생합성

효소 베타글루칼린-테트라키스글루코오스 O-갈로일루코아제는 1-O-갈로일-베타-D-글루코스와 1,2,3,6-테트라키스-O-갈로일-베타-D-글루코스를 사용하여 D-글루코오스, 펜타갈로일루코스를 생산한다.

신진대사

텔리매그랑딘 II는 산화성 탈수증과 두 갈로일 그룹의 결합에 의해 펜타갈로일 포도당으로 형성된다.

β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase is an enzyme found in the leaves of Rhus typhina that catalyzes the galloylation of 1,2,3,4,6-penta-O-galloyl-β-D-glucose to 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-β-d-glucose (hexa-galloylglucose).[6]

화학

펜타갈로일 포도당은 pH에 따라 산화 반응을 일으킬 수 있다.[10]

리서치

펜타갈로일 포도당은 항균, 항염증, 항탄성, 항당뇨증, 항산화제로 사용될 가능성이 있는 것으로 연구되어 왔다.[11]그것은 또한 방사선방제를 위해 연구되었다.[5]이 화합물은 혈관조직의[12] 엘라스틴과 콜라겐의 안정화를 돕고 동맥 ECM의 생체역학 특성을 회복시켜 준다.[13]또한, 펜타갈로일 포도당은 동맥 석회화를 감소시키고 복부 대동맥류의 동물 모델에서 세포외 기질 보존을 촉진하는 것을 돕는다.[14]마우스 C2C12 근래성형 세포를 사용한 시험관내 연구에서 PGG가 용량 의존적인 방식으로 활성산소종(ROS)과 매트릭스 메탈로테미나제-2(MMP-2) 발현을 낮추는 데 도움이 된다는 것이 밝혀졌다.[15]

참조

  1. ^ Cammann J, Denzel K, Schilling G, Gross GG (August 1989). "Biosynthesis of gallotannins: beta-glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose". Archives of Biochemistry and Biophysics. 273 (1): 58–63. doi:10.1016/0003-9861(89)90161-6. PMID 2757399.
  2. ^ Hagerman AE, Rice ME, Ritchard NT (1998). "Mechanisms of Protein Precipitation for Two Tannins, Pentagalloyl Glucose and Epicatechin16(4→8) Catechin (Procyanidin)". Journal of Agricultural and Food Chemistry. 46 (7): 2590–2595. doi:10.1021/jf971097k.
  3. ^ Gyémánt G, Zajácz A, Bécsi B, Ragunath C, Ramasubbu N, Erdodi F, Batta G, Kandra L (February 2009). "Evidence for pentagalloyl glucose binding to human salivary alpha-amylase through aromatic amino acid residues". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. 1794 (2): 291–6. doi:10.1016/j.bbapap.2008.10.012. PMID 19038368.
  4. ^ Tanaka T, Nonaka G, Nishioka I (1985). "Punicafolin, an ellagitannin from the leaves of Punica granatum". Phytochemistry. 24 (9): 2075. doi:10.1016/S0031-9422(00)83125-8.
  5. ^ a b Park E, Lee NH, Baik JS, Jee Y (August 2008). "Elaeocarpus sylvestris modulates gamma-ray-induced immunosuppression in mice: implications in radioprotection". Phytotherapy Research. 22 (8): 1046–51. doi:10.1002/ptr.2430. PMID 18570220. S2CID 44278609.
  6. ^ a b Niemetz R, Gross GG (1998). "Gallotannin biosynthesis: Purification of β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase from sumac leavesfn1fn1In honour of Professor G. H. Neil Towers' 75th birthday". Phytochemistry. 49 (2): 327. doi:10.1016/S0031-9422(98)00014-4.
  7. ^ Fujiwara H, Tabuchi M, Yamaguchi T, Iwasaki K, Furukawa K, Sekiguchi K, Ikarashi Y, Kudo Y, Higuchi M, Saido TC, Maeda S, Takashima A, Hara M, Yaegashi N, Kase Y, Arai H (June 2009). "A traditional medicinal herb Paeonia suffruticosa and its active constituent 1,2,3,4,6-penta-O-galloyl-beta-D-glucopyranose have potent anti-aggregation effects on Alzheimer's amyloid beta proteins in vitro and in vivo". Journal of Neurochemistry. 109 (6): 1648–57. doi:10.1111/j.1471-4159.2009.06069.x. PMID 19457098. S2CID 205620592.
  8. ^ Torres-León C, Rojas R, Aguilar C (2017). "Extraction of antioxidants from mango seedkernel: Optimization assisted by microwave". Food and Bioproducts Processing. 105: 188–196. doi:10.1016/j.fbp.2017.07.005.
  9. ^ Kantapan J, Paksee S, Chawapun P, Sangthong P, Dechsupa N (2020). "Pentagalloyl Glucose- and Ethyl Gallate-Rich Extract from Maprang Seeds Induce Apoptosis in MCF-7 Breast Cancer Cells through Mitochondria-Mediated Pathway". Evidence-Based Complementary and Alternative Medicine. 2020: 1–19. doi:10.1155/2020/5686029. PMC 7193289. PMID 32382295.
  10. ^ Chen Y, Hagerman AE (February 2005). "Reaction pH and protein affect the oxidation products of beta-pentagalloyl glucose". Free Radical Research. 39 (2): 117–24. doi:10.1080/10715760400013789. PMID 15763959. S2CID 85098105.
  11. ^ Torres-Leon C, Ventura-Sobrevilla J, Serna-Cock L, Ascacio-Valdes JA, Contreras-Esquivel J, Aguilar CN (2017). "Pentagalloylglucose (PGG): A valuable phenolic compound with functional properties". Journal of Functional Foods. 37: 176–189. doi:10.1016/j.jff.2017.07.045.
  12. ^ Patnaik SS, Simionescu DT, Goergen CJ, Hoyt K, Sirsi S, Finol EA (January 2019). "Pentagalloyl Glucose and Its Functional Role in Vascular Health: Biomechanics and Drug-Delivery Characteristics". Annals of Biomedical Engineering. 47 (1): 39–59. doi:10.1007/s10439-018-02145-5. PMC 6318003. PMID 30298373.
  13. ^ Patnaik, Sourav S.; Piskin, Senol; Pillalamarri, Narasimha Rao; Romero, Gabriela; Escobar, G. Patricia; Sprague, Eugene; Finol, Ender A. (2019-07-03). "Biomechanical Restoration Potential of Pentagalloyl Glucose after Arterial Extracellular Matrix Degeneration". Bioengineering. 6 (3): 58. doi:10.3390/bioengineering6030058. ISSN 2306-5354. PMC 6783915. PMID 31277241.
  14. ^ Anderson, Jennifer L.; Niedert, Elizabeth E.; Patnaik, Sourav S.; Tang, Renxiang; Holloway, Riley L.; Osteguin, Vangelina; Finol, Ender A.; Goergen, Craig J. (January 2021). "Animal Model Dependent Response to Pentagalloyl Glucose in Murine Abdominal Aortic Injury". Journal of Clinical Medicine. 10 (2): 219. doi:10.3390/jcm10020219. PMC 7827576. PMID 33435461.
  15. ^ Arnold, Frances; Muzzio, Nicolas; Patnaik, Sourav S.; Finol, Ender A.; Romero, Gabriela (2021-05-24). "Pentagalloyl Glucose-Laden Poly(lactide-co-glycolide) Nanoparticles for the Biomechanical Extracellular Matrix Stabilization of an In Vitro Abdominal Aortic Aneurysm Model". ACS Applied Materials & Interfaces. 13 (22): 25771–25782. doi:10.1021/acsami.1c05344. ISSN 1944-8252. PMID 34030437.