Isolation, Bioactivity, and Production of ortho-Hydroxydaidzein and ortho-Hydroxygenistein
Abstract
:1. Introduction
2. Isolation of OHD and OHG
3. Bioactivity of OHD and OHG
3.1. Anticancer-Related Bioactivity
3.2. Antimelanogenesis-Related Bioactivity
3.3. Other Bioactivity
4. Production of OHD and OHG
5. Conclusions
Acknowledgments
Conflicts of Interest
References
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Sources | Name | Microorganisms | Products | Ref. |
---|---|---|---|---|
Plants | Orobus tuberuosus | --- a | 3′-OHG | [22] |
Calophyllum polyanthum | --- | 3′-OHG | [23] | |
Erycibe expansa | --- | 3′-OHG | [24] | |
Eclipta prostrata | --- | 3′-OHG | [25] | |
Sophora japonica | --- | 3′-OHG | [26] | |
Machaerium villosum | --- | 3′-OHD | [29] | |
Dalbergia odorifera | --- | 3′-OHD | [30] | |
Styphnolobium japponicum | --- | 3′-OHD | [31] | |
Soybean Foods | Indonesian Tempeh | Rhizopus and other bacteria | 6-OHD, 8-OHD, 3′-OHG | [27,32] |
Japanese Soybean koji | A. saitoi | 8-OHD, 8-OHG, 6-OHD | [33,34] | |
Japanese Miso | A. oryzae | 8-OHD, 8-OHG, 6-OHD, 3′-OHD | [35–38] | |
Chinese Douchi | A. oryzae | 6-OHD, 8-OHD, 3′-OHD, 8-OHG | [39] | |
Korean Doenjang | diverse fungi and bacteria | 6-OHD, 8-OHD, 3′-OHD | [40] | |
Microbial Fermentation Broth | --- | A. niger | 8-OHG, 3′-OHG | [28] |
--- | Streptomyces sp. | 8-OHD, 3′-OHD | [43,44] | |
--- | Micrococcus sp. or Arthrobacter sp. | 6-OHG | [45] | |
--- | P. productus | 6-OHG | [46] |
Classification | Compound | Bioactivity | Ref. |
---|---|---|---|
Anticancer-Related Activity | 3′-OHG | Antiproliferative activity toward T47D tumorigenic breast epithelial cells; | [52,53] |
8-OHD | Increases life span against S180 bearing mice; | [43] | |
Suppression of MDR in Caco-2 colon adenocarcinoma cells; | [58] | ||
8-OHG | Antimutagenesis activity; | [36] | |
Antiproliferative activity toward HL-60 promyelocytic leukemia cells; | [35] | ||
6-OHD | Suppression of HCT-116 colon cancer cell proliferation in vitro and in vivo; | [54] | |
3′-OHD | Suppression of EGF receptor-positive skin cancer cell proliferation in vitro and in vivo; | [55,56] | |
Suppression of MDR transporters; | [57] | ||
Antimelanogenesis- Related Activity | 6-OHD | Competitive tyrosinase inhibitor; | [60] |
8-OHD | Irreversible tyrosinase inhibitor; | [61,62] | |
Antimelanogenesis activity in human volunteers; | [63] | ||
8-OHG | Irreversible tyrosinase inhibitor; | [61,62] | |
3′-OHD | Antimelanogenesis activity in human skin equivalents; | [64,65] | |
Potent autophage inducer; | [67] | ||
Other Bioactivities | 3′-OHG | HIV-1 integrase inhibitor; | [25] |
Antiinflammatory activity; | [68] | ||
Hepatoprotective activity; | [24] | ||
6-OHG | Hepatoprotective activity; | [46] | |
8-OHD | Aldose reductase inhibitor; | [69] | |
6-OHD | Suppression on adipogenesis of 3T3-L1 preadipocytes; | [70] | |
Promoting differentiation of 3T3-L1 preadipocytes; | [71] | ||
Antitrypanosomal activity | [72] | ||
3′-OHD | Antitrypanosomal activity; | [72,73] | |
Improving atopic dermatitis symptoms; | [74] |
Monooxygenase name | Monooxygenase sources | Recombinant hosts | Products | Yield (mg/L) | Ref. |
---|---|---|---|---|---|
CYP107H1 a | B. subtilis | E. coli | 3′-OHD | <0.1 | [75] |
Nfa33880 a | N. farcinica | E. coli | 8-OHD 6-OHD | 0.76 0.56 | [76] |
CYP154 a | N. farcinica | E. coli | 3′-OHD | 0.99 | [77] |
CYP102D1 b | S. avermitilis | E. coli | 8-OHD 6-OHD | 2.42 1.18 | [78] |
CYP105D7 c | S. avermitilis | S. avermitilis | 3′-OHD | 9.3 | [79] |
CYP105D7 a | S. avermitilis | S. avermitilis | 3′-OHD | 37.5 | [80] |
CYP107Y1 a | S. avermitilis | S. avermitilis | 3′-OHG | 6.75 | [21] |
Sam5 | S. espanaensis | E. coli | 3′-OHD | 75 | [82] |
CYP57B3 a | A. oryzae | S. cerevisiae | 3′-OHG | N.D. d | [16] |
CYP57B3 c | A. oryzae | P. pastoris | 6-OHD | 9.1 | [87] |
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Chang, T.-S. Isolation, Bioactivity, and Production of ortho-Hydroxydaidzein and ortho-Hydroxygenistein. Int. J. Mol. Sci. 2014, 15, 5699-5716. https://doi.org/10.3390/ijms15045699
Chang T-S. Isolation, Bioactivity, and Production of ortho-Hydroxydaidzein and ortho-Hydroxygenistein. International Journal of Molecular Sciences. 2014; 15(4):5699-5716. https://doi.org/10.3390/ijms15045699
Chicago/Turabian StyleChang, Te-Sheng. 2014. "Isolation, Bioactivity, and Production of ortho-Hydroxydaidzein and ortho-Hydroxygenistein" International Journal of Molecular Sciences 15, no. 4: 5699-5716. https://doi.org/10.3390/ijms15045699