Isolation, Identification, and Biotransformation of Teadenol A from Solid State Fermentation of Pu-erh Tea and In Vitro Antioxidant Activity
Abstract
:1. Introduction
2. Experimental Section
2.1. PET Fermentation and Sample Collection
2.2. Determination of Constituents in Tea Samples
2.3. Extraction and Isolation of 1
2.4. Structure Elucidation of 1
2.5. In Vitro Antioxidant Activity Assays
2.6. Screening of Compound 1 Producing Microbes
2.7. Determination of Compounds in Commercial PFPT Samples
2.8. Statistical Analyses
2.9. Nucleotide Sequence Accession Numbers
3. Results and Discussion
3.1. Isolation and Identification of Compound 1
3.2. Isolation and Identification of Fungal and Bacterial Strains
3.3. Determination of Teadenol A in Commercial PFPT
3.4. Bioactivity of Teadenol A
Acknowledgments
Author Contributions
Conflict of Interest
Abbreviations
C | (+)-catechin |
CAF | Caffeine |
EC | (−)-epicatechin |
ECG | (−)-epicatechin 3-O-gallate |
EGC | (−)-epigallocatechin |
EGCG | (−)-epigallocatechin 3-O-gallate |
GA | gallic acid |
GG | 1,4,6-tri-O-galloyl-β-D-glucose |
HPLC | high-performance liquid chromatography |
NA | Nutrient Agar |
NFPT | non-fermented Pu-erh tea |
PET | Pu-erh tea |
PFPT | Post-fermented Pu-erh tea |
RBMA | Rose Bengal Medium Agar |
SSF | solid state fermentation |
TB | theabrownin |
TF | theaflavin |
TR | thearubigin |
UPLC-MS/MS | ultra-performance liquid chromatography tandem mass spectrometry |
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No. | PFPT Name | GA | EGC | C | CA | EC | EGCG | GG | ECG | Teaden-ol A |
---|---|---|---|---|---|---|---|---|---|---|
Mean Content (mg/g) (n = 6) | ||||||||||
1 | Jijin ziyin | 39.16 ± 1.1 | 10.85 ± 0.3 | 8.46 ± 0.5 | 39.35 ± 0.1 | 1.80 ± 0.0 | 22.47 ± 0.0 | 10.39 ± 0.0 | 9.52 ± 0.0 | 0.25 ± 0.0 |
2 | Zichun | 53.56 ± 2.1 | 9.02 ± 0.1 | 5.35 ± 0.1 | 46.06 ± 0.9 | 1.37 ± 0.1 | 18.48 ± 0.3 | 9.09 ± 0.3 | 4.57 ± 0.1 | 0.20 ± 0.0 |
3 | Shunde Jijin | 121.81 ± 1.6 | 25.06 ± 0.8 | 15.9 ± 0.5 | 52.87 ± 0.6 | 5.02 ± 0.1 | 43.39 ± 1.4 | 13.91 ± 0.4 | 1.90 ± 0.1 | 1.15 ± 0.0 |
4 | Gongting pu-er | 13.23 ± 0.1 | 1.52 ± 0.0 | 0.59 ± 0.2 | 34.88 ± 0.4 | 0.35 ± 0.1 | 0.32 ± 0.0 | 0.20 ± 0.0 | 0.67 ± 0.1 | 0.17 ± 0.0 |
5 | Nanye repaocha | 11.62 ± 0.8 | 4.60 ± 0.1 | 1.85 ± 0.1 | 30.29 ± 0.8 | 2.34 ± 0.2 | 1.68 ± 0.2 | 0.46 ± 0.1 | 1.25 ± 0.1 | 0.40 ± 0.0 |
6 | Mabang | 1.55 ± 0.1 | 3.67 ± 0.3 | 1.51 ± 0.1 | 12.17 ± 0.2 | 1.01 ± 0.3 | 0.72 ± 0.0 | 0.47 ± 0.1 | 0.60 ± 0.1 | 1.00 ± 0.2 |
7 | Huilong shengtaiqizibing | 124.50 ± 1.1 | 12.24 ± 0.0 | 11.23 ± 0.0 | 55.70 ± 0.0 | 2.74 ± 0.0 | 4.29 ± 0.1 | 1.23 ± 0.0 | 7.87 ± 0.0 | 1.43 ± 0.1 |
8 | Pinzang bing | 6.33 ± 0.2 | 3.80 ± 0.5 | 1.18 ± 0.2 | 36.78 ± 0.5 | 1.18 ± 0.4 | 0.98 ± 0.5 | 0.26 ± 0.1 | 0.19 ± 0.0 | 1.18 ± 0.2 |
9 | Menghai qizibing | 8.09 ± 0.1 | 6.93 ± 0.0 | 2.14 ± 0.0 | 32.24 ± 0.1 | 2.23 ± 0.0 | 0.91 ± 0.0 | 0.54 ± 0.0 | 1.37 ± 0.2 | 1.17 ± 0.2 |
10 | Lizhi hong | 22.80 ± 0.5 | 54.64 ± 1.0 | 26.16 ± 0.6 | 55.83 ± 0.6 | 1.60 ± 0.0 | 78.07 ± 0.3 | 20.12 ± 1.0 | 10.78 ± 0.5 | 1.28 ± 0.0 |
11 | Nannuo yihao | 4.30 ± 0.5 | 1.50 ± 0.2 | 0.61 ± 0.1 | 30.31 ± 0.5 | 0.34 ± 0.1 | 0.25 ± 0.0 | 0.69 ± 0.1 | 0.47 ± 0.0 | 5.03 ± 0.2 |
12 | Nanfangjiamu paka | 21.62 ± 1.2 | 11.18 ± 1.1 | 2.41 ± 0.1 | 40.45 ± 0.9 | 2.91 ± 0.2 | 1.74 ± 0.1 | 0.59 ± 0.1 | 1.86 ± 0.1 | 1.25 ± 0.2 |
13 | Puxiuqizibing | 23.96 ± 1.6 | 9.98 ± 0.1 | 7.65 ± 0.2 | 34.12 ± 0.1 | 1.15 ± 0.1 | 17.34 ± 0.1 | 8.46 ± 0.1 | 1.61 ± 0.1 | 3.15 ± 0.3 |
14 | Menghaitie bing | 18.11 ± 0.4 | 3.59 ± 0.1 | 2.15 ± 0.2 | 36.04 ± 0.1 | 0.47 ± 0.0 | 8.34 ± 0.1 | 3.76 ± 0.0 | 1.75 ± 0.1 | 6.20 ± 0.3 |
15 | Xiangyupu-er | 60.02 ± 49.5 | 3.27 ± 0.0 | 3.99 ± 0.2 | 44.66 ± 0.1 | 0.54 ± 0.0 | 12.30 ± 0.0 | 6.23 ± 0.1 | 3.16 ± 0.1 | 4.10 ± 0.0 |
16 | Nannuoyihao (shucha) | 33.78 ± 0.4 | 4.82 ± 0.2 | 3.50 ± 0.4 | 50.99 ± 1.5 | 1.18 ± 0.1 | 15.81 ± 0.6 | 6.99 ± 0.1 | 3.72 ± 0.5 | 8.15 ± 0.1 |
17 | Qingyungongma-o | 44.34 ± 1.6 | 6.94 ± 0.6 | 2.91 ± 0.1 | 37.88 ± 1.9 | 1.04 ± 0.1 | 13.34 ± 0.9 | 6.69 ± 0.1 | 2.13 ± 0.3 | 4.38 ± 0.1 |
18 | Chunqiaomuch | 32.90 ± 0.4 | 9.92 ± 0.5 | 7.55 ± 0.1 | 43.67 ± 1.2 | 1.73 ± 0.0 | 17.83 ± 0.4 | 7.20 ± 0.1 | 4.31 ± 0.4 | 1.31 ± 0.0 |
19 | Banzhangwang | 22.80 ± 0.5 | 6.86 ± 0.1 | 4.58 ± 0.4 | 40.77 ± 0.6 | 1.60 ± 0.0 | 18.82 ± 0.5 | 9.65 ± 0.6 | 5.96 ± 0.2 | 7.44 ± 0.3 |
20 | Daixiangyubing | 36.82 ± 1.6 | 9.00 ± 0.2 | 5.13 ± 0.1 | 52.79 ± 0.5 | 1.73 ± 0.1 | 24.49 ± 0.9 | 13.53 ± 0.2 | 5.00 ± 0.3 | 1.28 ± 0.1 |
21 | Lanxiangguiqi | 20.67 ± 0.6 | 9.49 ± 0.6 | 6.83 ± 0.6 | 53.14 ± 1.2 | 1.18 ± 0.0 | 21.65 ± 0.5 | 10.52 ± 1.6 | 2.05 ± 0.1 | 5.93 ± 0.0 |
22 | Pu-er sancha | 11.75 ± 0.2 | 1.90 ± 0.0 | 0.42 ± 0.0 | 32.52 ± 0.0 | 0.62 ± 0.0 | 0.33 ± 0.0 | 0.15 ± 0.0 | 1.25 ± 0.9 | 6.98 ± 0.4 |
Position | δC | δH | HMBC (1H–13C) | NOE (1H–1H) |
---|---|---|---|---|
2 | 73.5 | 4.52 (1H, s) | C-13, 14, 15 | H-3, 4, 13, 15 |
3 | 72.9 | 4.39 (1H, m) | - | - |
4 | 25.4 | 2.85 (1H, dd, J = 4.8, 17.4 Hz) | C-5, 10 | H-2, 3 |
3.02 (1H, dd, J = 1.8, 17.4 Hz) | C-2, 3, 5, 10 | H-2, 3 | ||
5 | 157.8 | - | - | - |
6 | 96.7 | 5.91 (1H, d, J = 2.4) | C-5, 8, 10 | H-8 |
7 | 157.9 | |||
8 | 95.9 | 5.78 (1H, d, J = 2.4) | C-6, 9, 10 | H-6 |
9 | 156.6 | - | - | - |
10 | 99.3 | - | - | - |
12 | 148.1 | - | - | - |
13 | 109.8 | 6.51 (1H, s) | C-2, 12, 16 | H-2, 15 |
14 | 139.3 | - | - | - |
15 | 116.6 | 5.19 (1H, s) | C-2, 13 | H-13 |
16 | 168.3 | 5.27 (1H, s) | C-2, 13 | H-13 |
No. | Isolates (GenBank Accession No.) | Length (bp) | Results of EzTaxon | |
---|---|---|---|---|
Closest Match (GenBank Accession No.) | Similarity (%) | |||
1 | 1-3-b-5 (KR149614) | 1373 | Achromobacter xylosoxidans DSM 10346(T) (Y14908) | 99.854 |
2 | 2-3-b-2 (KR149617) | 1365 | Achromobacter xylosoxidans NBRC 15126(T) (CP006958) | 99.93 |
3 | 1-1-b-5 (KR149606) | 1385 | Bacillus amyloliquefaciens subsp. plantarum FZB42(T) (CP000560) | 99.928 |
4 | 3-3-b-3 (KR149598) | 1345 | Bordetella avium 197N (AM167904) | 99.18 |
5 | 1-1-b-3 (KR149624) | 1385 | Enterobacter asburiae JCM 6051(T) (AB004744) | 99.35 |
6 | 1-1-b-4 (KR149608) | 1375 | Enterobacter asburiae JCM 6051(T) (AB004744) | 99.345 |
7 | 1-1-b-6 (KR149611) | 1367 | Enterobacter asburiae JCM 6051(T) (AB004744) | 99.415 |
8 | 1-2-b-1 (KR149610) | 1376 | Enterobacter hormaechei ATCC 49162(T) (AFHR01000079) | 99.345 |
9 | 2-4-b-4 (KR149622) | 1298 | Microbacterium sediminis YLB-01(T) (HQ219727) | 98.54 |
10 | 1-4-b-7 (KR149612) | 1322 | Ochrobactrum pseudintermedium ADV31(T) (DQ365921) | 99.849 |
11 | 2-3-b-5 (KR149618) | 1323 | Ochrobactrum pseudintermedium ADV31(T) DQ365921 | 99.697 |
12 | 1-1-b-8 (KR149609) | 1384 | Pantoea dispersa LMG 2603(T) (DQ504305) | 100 |
13 | 3-3-b-2 (KR149596) | 1373 | Pseudomonas aeruginosa JCM 5962(T) (BAMA01000316) | 99.93 |
14 | 3-4-b-2 (KR149600) | 1370 | Pseudomonas aeruginosa JCM 5962(T) (BAMA01000316) | 99.93 |
15 | 3-4-b-1 (KR149599) | 1375 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.854 |
16 | 3-5-b-5 (KR149604) | 1363 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.853 |
17 | 1-4-b-9 (KR149607) | 1376 | P seudomonas aeruginosa LMG 1242(T) (Z76651) | 99.854 |
18 | 1-5-b-2-1 (KR149613) | 1372 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.854 |
19 | 1-4-b-1 (KR149615) | 1371 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.854 |
20 | 1-3-b-2 (KR149616) | 1379 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.855 |
21 | 2-4-b-1 (KR149619) | 1369 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.854 |
22 | 2-4-b-2 (KR149620) | 1330 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.85 |
23 | 2-4-b-5 (KR149623) | 1387 | Pseudomonas aeruginosa LMG 1242(T) (Z76651) | 99.856 |
24 | 3-3-b-4 (KR149597) | 1377 | Pseudomonas beteli ATCC 19861(T) (AB021406) | 99.564 |
25 | 3-5-b-2 (KR149602) | 1358 | Pseudomonas plecoglossicida FPC951(T) (AB009457) | 99.853 |
26 | 3-4-b-5 (KR149601) | 1368 | Sphingobacterium thalpophilum DSM 11723(T) (AJ438177) | 99.415 |
27 | 2-4-b-3 (KR149621) | 1373 | Sphingobacterium thalpophilum DSM 11723(T) (AJ438177) | 99.854 |
28 | 2-5-b-1 (KR149605) | 1356 | Staphylococcus sciuri subsp. sciuri DSM 20345(T) (AJ421446) | 100 |
29 | 3-5-b-4 (KR149603) | 1385 | Staphylococcus sciuri subsp. sciuri DSM 20345(T) (AJ421446) | 100 |
30 | 1-5-f-10 (KR149625) | 506 | Acremonium falciforme (DQ094533) | 99.33 |
31 | y-2-b-2 (KR149637) | 546 | Aspergillus fumigatus_1 (AF455542) | 100 |
32 | 3-2-f-4(KR149634) | 534 | Aspergillus fumigatus_1 (JN226940) | 100 |
33 | 2-5-f-1 (KR149635) | 545 | Aspergillus fumigatus_1 (JN226940) | 100 |
34 | 2-1-f-1 (KR14964) | 542 | Aspergillus niger_1 (EF660199) | 99.8 |
35 | y-2-f-4 (KR149644) | 531 | Aspergillus niger_1 (EF660199) | 99.6 |
36 | 2-4-f-2 (KR149630) | 529 | Aspergillus niger_1 (EU821308) | 100 |
37 | 3-1-f-4(KR149642) | 529 | Aspergillus niger_1 (EU821308) | 100 |
38 | 1-5-f-15 (KR149631) | 547 | Aspergillus sclerotiorum_1 (GQ398087) | 100 |
39 | y-2-f-7 (KR149626) | 504 | Aspergillus sydowii_1 JN986787 | 100 |
40 | 2-5-f-4 (KR149638) | 554 | Aspergillus tamarii_1 (KC621084) | 100 |
41 | 3-5-f-1 (KR149640) | 553 | Aspergillus tamarii_2 (DQ411548) | 100 |
42 | 1-4-f-9 (KR149628) | 529 | Aspergillus tamarii_2 (EU021614) | 100 |
43 | 2-4-f-4 (KR149636) | 538 | Aspergillus tamarii_2 (EU021614) | 100 |
44 | 3-2-f-1 ( KR149627) | 537 | Aspergillus tubingensis (EU821292) | 100 |
45 | 3-1-f-2 (KR149633) | 538 | Aspergillus tubingensis (EU821292) | 100 |
46 | y-2-b-1 (KR149641) | 533 | Aspergillus tubingensis (EU821292) | 100 |
47 | 3-5-f-2 (KR149632) | 510 | Earliella scabrosa_2 (EU661875) | 98.88 |
48 | 1-5-f-9 (KR149639) | 706 | Lichtheimia corymbifera_9 (FJ719392) | 100 |
49 | 2-2-f-3 (KR149629) | 635 | Rhizopus microsporus_1 (AF115729) | 100 |
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Su, X.-q.; Zhang, G.-j.; Ma, Y.; Chen, M.; Chen, S.-h.; Duan, S.-m.; Wan, J.-q.; Hashimoto, F.; Lv, H.-p.; Li, J.-h.; et al. Isolation, Identification, and Biotransformation of Teadenol A from Solid State Fermentation of Pu-erh Tea and In Vitro Antioxidant Activity. Appl. Sci. 2016, 6, 161. https://doi.org/10.3390/app6060161
Su X-q, Zhang G-j, Ma Y, Chen M, Chen S-h, Duan S-m, Wan J-q, Hashimoto F, Lv H-p, Li J-h, et al. Isolation, Identification, and Biotransformation of Teadenol A from Solid State Fermentation of Pu-erh Tea and In Vitro Antioxidant Activity. Applied Sciences. 2016; 6(6):161. https://doi.org/10.3390/app6060161
Chicago/Turabian StyleSu, Xiao-qin, Gao-ju Zhang, Yan Ma, Mao Chen, Sheng-hu Chen, Shuang-mei Duan, Jin-qiong Wan, Fumio Hashimoto, Hai-peng Lv, Jia-hua Li, and et al. 2016. "Isolation, Identification, and Biotransformation of Teadenol A from Solid State Fermentation of Pu-erh Tea and In Vitro Antioxidant Activity" Applied Sciences 6, no. 6: 161. https://doi.org/10.3390/app6060161