Pheophytin a

• CAS: 603-17-8
• Catalog Number: ACM603178
• Category: Main Products
• Molecular Weight: 871.2
• Molecular Formula: C₅₅H₇₄N₄O₅
• Synonyms: PHEOPHYTIN A;,11s),4beta,21beta]]-;ramethyl-20-oxo-,3,7,11,15-tetramethyl-2-hexadecenylester,[3s-[3alpha(2e,7s;3,7,11,15-tetramethylhexadec-2-en-1-yl [3S-[3alpha(2E,7S*,11S*),4beta,21beta]]-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-9-vinylphorbine-3-propionate;PHENOPHYTINA;PHEOPHORBIDE A (SH);PHEOPHYTHIN A
• IUPAC Name: pheophytin a
• Canonical SMILES: CCC1=C2C=C3C(=C4C(=O)C(C(=C5C(C(C(=N5)C=C6C(=C(C(=CC(=C1C)N2)N6)C=C)C)C)CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C4=N3)C(=O)OC)C
• InChI Key: DQVGVYRSVYCJRR-HOIIHFJFSA-N
• EC Number: 210-031-3
• Exact Mass: 870.56600

Case Study

Study of excited states of pheophytin a

Parusel, Andreas BJ, and Stefan Grimme. The Journal of Physical Chemistry B 104.22 (2000): 5395-5398.

The first six excited states of pheophytin a and chlorophyll a with the phytyl chain replaced by hydrogen atoms were calculated by combining density functional theory and the multi-reference configuration interaction method (DFT/MRCI). The calculations accurately reproduce the experimental absorption energies and intensities. Four and three excited states were calculated in the visible region for pheophytin a and chlorophyll a, respectively. Therefore, the presence of more than two Q and Q electronic states in this energy range is predicted. These additional states have significant double excitation characteristics and cannot be explained in the four-boundary orbital model. Two strongly allowed states were calculated in the Soret region at 2.9 eV.
In the DFT/MRCI calculations, an energy cutoff of 0.8 hartree was used to select the most important configurations generated by single and double excitations from the 60 (pheophytin a) and 59 (chlorophyll a) reference configurations. The reference space was iteratively optimized by starting with a small CI calculation with four electrons in four orbitals and then including configurations as reference if the weight in the intermediate wave function was greater than 0.008. The number of configurational state functions considered in CI space was 9.2 × 10^5 for pheophytin a and 8.5 × 10^5 for chlorophyll a. The oscillator strengths were calculated in dipole length representation.

Routine method for determination of pheophytin a content in complexes

Eijckelhoff, Camiel, and Jan P. Dekker. Photosynthesis Research 52 (1997): 69-73.

The simplest method for determining the stoichiometry of chlorophyll a, pheophytin a and carotene in isolated PS II reaction center complexes is by analyzing the spectra of the pigments extracted in 80% acetone. Two different calculation methods are proposed using the extinction coefficients of the purified pigments in 80% acetone at different wavelengths. One of the methods also accounts for the possible presence of chlorophyll b. Comparison of the results with those of HPLC pigment analysis shows that these methods are suitable for routine determination of the pigment stoichiometry of isolated PS II reaction center complexes.
If the molar extinction coefficients of the three pigments at three different wavelengths are known, the concentrations c of the three pigments in the extract can be determined. Since for some preparations contamination with chlorophyll b cannot be completely excluded, an alternative method is proposed that includes this pigment. The extraction of PS II RC preparations from spinach in 80% acetone has been described in detail previously. Chlorophyll a, pheophytin a and carotene were obtained from such extracts with a purity > 99.9% by reversed-phase HPLC using 100% methanol as mobile phase. Peak fractions were collected, dried by flushing with nitrogen and redissolved in 80% acetone before recording their absorption spectra on a spectrophotometer. The spectra of chlorophyll a, chlorophyll b and -Car were normalized to the published extinction coefficients in 80% acetone, on the basis of which the extinction coefficients of these pigments in 80% acetone at all recorded wavelengths were obtained.

Pheophytin a extracted from edible green algae has potent anti-inflammatory activity

Okai, Yasuji, and Kiyoka Higashi-Okai.International Journal of Immunopharmacology 19.6 (1997): 355-358.

A chlorophyll-related compound, pheophytin a, was identified from edible green algae as a potent inhibitory substance that effectively inhibits genotoxin-induced gene expression in test bacteria. In the study, the anti-inflammatory effects of pheophytin a from edible green algae were analyzed by in vitro and in vivo experiments. 1. Using the cytochrome C reduction method, pheophytin a inhibited the production of superoxide anions (02) in mouse macrophages induced by 12O-tetradecanoylphorbol-13-acetate (TPA). 2. In the Boyden chamber assay, pheophytin a had an inhibitory effect on formyl Met-Leu-Phe (FMLP)-induced chemotaxis of human polymorphonuclear leukocytes (PMNs). 3. Pheophytin a had a significant inhibitory effect on TPA-induced inflammatory responses, such as ear edema formation in BALB/c mice.
The edible green algae was dried and fully chopped using an electric grinding device. A mixture of methanol and acetone (50:50, V/V) was added to the algae powder (10 ml/g powder) and transferred to a glass tube and stirred in the dark for one week. The mixture was centrifuged and evaporated using a rotary evaporator at room temperature. The extracts were spotted on the starting line of a silica gel thin layer chromatography plate in sequence and developed with a mixture of petroleum ether and acetone (70:30, V/V) for 15 minutes. The silica gel corresponding to the dark green color was recovered, transferred to a glass tube, and methanol was added to extract pheophytin a. The glass tube was stirred for 30 minutes and centrifuged at 5000×g for 15 minutes at 4°C. The supernatant fraction was concentrated and dried by a small vibration evaporator. To further purify pheophytin a, the dried pigment was dissolved with a mixture of hexane and ethyl acetate (3:1, V/V) and eluted using HPLC with the same hexane/ethyl acetate mixture at a flow rate of 1 min/ml. The purified product was recovered, dried and dissolved in an appropriate solvent for further experiments.

Pheophytin a inhibits inflammation by suppressing LPS-induced substances

Lin, Chun-Yu, et al.International Journal of Molecular Sciences 15.12 (2014): 22819-22834.

Inflammation is a serious health problem worldwide. Pheophytin a is a chlorophyll-related compound derived from green tea. Pretreatment with pheophytin was found to inhibit lipopolysaccharide (LPS)-induced nitrate oxidase (NO), prostaglandin E2 (PGE2), and interleukin-1β in RAW 264.7 macrophages. The expression levels of NO synthase 2 (NOS2) and cyclooxygenase 2 (COX-2) were suppressed at the transcriptional and translational levels by pretreatment with pheophytin a. Pheophytin a inhibited NOS2 promoter activity via extracellular signal-regulated kinase (ERK1/2), but not its mRNA stability. This inhibition was reversed by an ERK1/2 inhibitor (U0126). Pheophytin a reduces activation of signal transducer and activator of transcription 1 (STAT-1) but has no significant effect on activator protein 1 (AP-1) and nuclear factor κB (NF-κB).
RAW 264.7 cells were transferred to 2% fetal bovine serum for 3 hours for serum starvation (as activation). RAW 264.7 cells were then treated with the indicated concentrations of pheophytin a. Thirty minutes later, RAW 264.7 cells were stimulated with LPS (100 ng/mL). After three hours of LPS stimulation, cells were harvested to measure RNA expression levels. After six hours of LPS stimulation, cells were harvested to measure protein production.

Custom Q&A

What is the molecular formula of pheophytin a?

The molecular formula of pheophytin a is C55H74N4O5.

What are the synonyms for pheophytin a?

The synonyms for pheophytin a are PLU1CG1U91, CHEBI:44898, and chlorophyll a.

Where can pheophytin a be found in nature?

Pheophytin a is a natural product found in Trididemnum solidum, Saussurea medusa, and other organisms.

What is the molecular weight of pheophytin a?

The molecular weight of pheophytin a is 871.2 g/mol.

When was pheophytin a created?

Pheophytin a was created on January 15, 2019.

When was pheophytin a last modified?

Pheophytin a was last modified on October 21, 2023.

What is the IUPAC Name of pheophytin a?

The IUPAC Name of pheophytin a is methyl (3R,21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-22-[3-oxo-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enoxy]propyl]-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaene-3-carboxylate.

What is the InChI of pheophytin a?

The InChI of pheophytin a is InChI=1S/C55H74N4O5/c1-13-39-35(8)42-28-44-37(10)41(24-25-48(60)64-27-26-34(7)23-17-22-33(6)21-16-20-32(5)19-15-18-31(3)4)52(58-44)50-51(55(62)63-12)54(61)49-38(11)45(59-53(49)50)30-47-40(14-2)36(9)43(57-47)29-46(39)56-42/h13,26,28-33,37,41,51,58,61H,1,14-25,27H2,2-12H3/b34-26+,44-28?,46-29?,47-30?,52-50?/t32-,33-,37+,41+,51-/m1/s1.

What is the InChIKey of pheophytin a?

The InChIKey of pheophytin a is FDHFJXKRMIVNCQ-OSIZZBRKSA-N.

What is the Canonical SMILES of pheophytin a?

The Canonical SMILES of pheophytin a is CCC1=C(C2=NC1=CC3=C(C4=C(C(C(=C5C(C(C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)OCC=C(C)CCCC(C)CCCC(C)CCCC(C)C)C4=N3)C(=O)OC)O)C)C.