Abstract
In the present work, a novel cordycepic pigment was successfully isolated and identified from Cordyceps militaris, as well as named as cordycepene (C14H17N1O4), according to the long unsaturated conjugated polyene structural characteristic. Cordycepene is sensitive to light, high temperature (≥ 60 °C), and acidic condition (pH ≤ 3), but possesses high stability against metal ions, and under alkaline and neutral conditions. Cordycepene shows a comparable DPPH (1,1-diphenyl-2-picrylhydrazyl) radical-scavenging activity at higher concentration (≥ 2 mg/mL) to vitamin C. Cordycepene promotes the growth of HSF (human skin fibroblast cell) after incubation for 72 h, and has an ability to repair the UV light–treated HSF cells. In addition, cordycepene increases the antioxidant activity (SOD, superoxide dismutase; GSH-Px, glutathione peroxidase; CAT, catalase) and decreases MDA (malondialdehyde) level, indicating that cordycepene inhibits the photochemical senescence of HSF by enhancing the antioxidant defense system. The discovery of cordycepene can provide a basis for research on light incubation and the accumulation of yellow pigment (carotenoids) from C. militaris.
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References
Andrés-Bello A, Barreto-Palacios V, García-Segovia P, Mir-Bel J, Martínez-Monzó J (2013) Effect of pH on color and texture of food products. Food Eng Rev 5(3):158–170. https://doi.org/10.1007/s12393-013-9067-2
Chen C, Bau T, Bao HY (2013) Chemical composition analysis of cultured Cordyceps militaris. Food Sci 34(11):36–40. https://doi.org/10.7506/spkx1002-6630-201311009
Chen A, Wang Y, Shao Y, Huang B (2017) A Novel technique for rejuvenation of degenerated caterpillar medicinal mushroom, Cordyceps militaris (Ascomycetes), a valued Traditional Chinese Medicine. Int J Med Mushrooms 19:87–91. https://doi.org/10.1615/intjmedmushrooms.v19.i1.90
Chen BX, Wei T, Ye ZW, Yun F, Kang LZ, Tang HB, Guo LQ, Lin JF (2018) Efficient CRISPR-Cas9 gene disruption system in edible-medicinal mushroom Cordyceps militaris. Front Microbiol 9:1157. https://doi.org/10.3389/fmicb.2018.01157
Chiang SS, Liang ZC, Wang YC, Liang CH (2017) Effect of light-emitting diodes on the production of cordycepin, mannitol and adenosine in solid-state fermented rice by Cordyceps militaris. J Food Compos Anal 60:51–56. https://doi.org/10.1016/j.jfca.2017.03.007
Chung KT (2000) Mutagenicity and carcinogenicity of aromatic amines metabolically produced from azo dyes. J Environ Sci Health C 18:51–74. https://doi.org/10.1080/10590500009373515
Cui JD (2015) Biotechnological production and applications of Cordyceps militaris, a valued traditional Chinese medicine. Crit Rev Biotechnol 35(4):475–484. https://doi.org/10.3109/07388551.2014.900604
Detienne G, De Haes W, Mergan L, Edwards SL, Temmerman L, Van Bael S (2018) Beyond ROS clearance: peroxiredoxins in stress signaling and aging. Ageing Res Rev 44:33–48. https://doi.org/10.1016/j.arr.2018.03.005
Dong JZ, Liu MR, Lei C, Zheng XJ, Wang Y (2012) Effects of selenium and light wavelengths on liquid culture of Cordyceps militaris link. Appl Biochem Biotechnol 166(8):2030–2036. https://doi.org/10.1007/s12010-012-9628-5
Dong JZ, Wang SH, Ai XR, Yao L, Sun ZW, Lei C, Wang Y, Wang Q (2013) Composition and characterization of cordyxanthins from Cordyceps militaris fruit bodies. J Funct Foods 5(3):1450–1455. https://doi.org/10.1016/j.jff.2013.06.002
Fratianni A, Cinquanta L, Panfili G (2010) Degradation of carotenoids in orange juice during microwave heating. LWT Food Sci Technol 43(6):867–871. https://doi.org/10.1016/j.lwt.2010.01.011
González BS, Hernández-Rojas J, Bretón J, Gomez Llorente JM (2007) Global potential energy minima of (H2O)n clusters on graphite. J Phys Chem C 111(40):14862–14869. https://doi.org/10.1021/jp074249f
Kang HJ, Baik HW, Kim SJ, Lee SG, Ahn HY, Park JS, Park SJ, Jang EJ, Park SW, Choi JY, Sung JH, Lee SM (2015) Cordyceps militaris enhances cell-mediated immunity in healthy Korean men. J Med Food 18(10):1164–1172. https://doi.org/10.1089/jmf.2014.3350
Labuschagne CF, Brenkman AB (2013) Current methods in quantifying ROS and oxidative damage in Caenorhabditis elegans and other model organism of aging. Ageing Res Rev 12(4):918–930. https://doi.org/10.1016/j.arr.2013.09.003
Ley RD, Fourtanier A (1997) Sunscreen protection against ultraviolet radiation-induced pyrimidine dimers in mouse epidermal DNA. Photochem Photobiol 65(6):1007–1011. https://doi.org/10.1111/j.1751-1097.1997.tb07961.x
Li H, Rebmann E, Opstad CL, Schmid R, Sliwka HR, Partali V (2010) Synthesis of a highly unsaturated, stable hydroxy peroxide: a yellow blue color-changing carotenoid oxidation product with leuco dye properties. Eur J Org Chem 2010(24):4630–4636. https://doi.org/10.1002/ejoc.201000243
Liu F, Zhu ZY, Sun X, Gao H, Zhang YM (2017) The preparation of three selenium-containing Cordyceps militaris polysaccharides: characterization and anti-tumor activities. Int J Biol Macromol 99:196–204. https://doi.org/10.1016/j.ijbiomac.2017.02.064
Manivasagan P, Bharathiraja S, Santha Moorthy M, Mondal S, Seo H, Dae Lee K, Oh J (2018) Marine natural pigments as potential sources for therapeutic applications. Crit Rev Biotechnol 38(5):745–761. https://doi.org/10.1080/07388551.2017.1398713
Meneghin E, Volpato A, Cupellini L, Bolzonello L, Jurinovich S, Mascoli V, Carbonera D, Mennucci B, Collini E (2018) Coherence in carotenoid-to-chlorophyll energy transfer. Nat Commun 9:3160. https://doi.org/10.1038/s41467-018-05596-5
Moloney JN, Cotter TG (2018) ROS signalling in the biology of cancer. Semin Cell Dev Biol 80:50–64. https://doi.org/10.1016/j.semcdb.2017.05.023
Pérez-Rodríguez L (2009) Carotenoids in evolutionary ecology: re-evaluating the antioxidant role. BioEssays 31(10):1116–1126. https://doi.org/10.1002/bies.200900070
Ribeiro D, Freitas M, Silva AMS, Carvalho F, Fernandes E (2018) Antioxidant and pro-oxidant activities of carotenoids and their oxidation products. Food Chem Toxicol 120:681–699. https://doi.org/10.1016/j.fct.2018.07.060
Rodriguez-Amaya DB (2016) Natural food pigments and colorants. Curr Opin Food Sci 7:20–26. https://doi.org/10.1016/j.cofs.2015.08.004
Sanz A (2017) Mitochondrial ROS and ageing. Free Radic Biol Med 106:S9. https://doi.org/10.1016/j.freeradbiomed.2017.04.059
Snodderly DM, Brown PK, Delori FC, Auran JD (1984) The macular pigment. I. Absorbance spectra, localization, and discrimination from other yellow pigments in primate retinas. Investig Ophthalmol Vis Sci 25(6):660–673
Sung GH, Hywel-Jones NL, Sung JM, Luangsa-ard JJ, Shrestha B, Spatafora JW (2007) Phylogenetic classification of Cordyceps and the clavicipitaceous fungi. Stud Mycol 57:5–59. https://doi.org/10.3114/sim.2007.57.01
Tang J, Qian Z, Wu H (2018) Enhancing cordycepin production in liquid static cultivation of Cordyceps militaris by adding vegetable oils as the secondary carbon source. Bioresour Technol 268:60–67. https://doi.org/10.1016/j.biortech.2018.07.128
Wang F, Liu Q, Zhang J, Liu K, Li K, Liu G, Dong C (2018) Comparative transcriptome analysis between a spontaneous albino mutant and its sibling strain of Cordyceps militaris in response to light stress. Front Microbiol 9:1237. https://doi.org/10.3389/fmicb.2018.01237
Yan XT, Bao HY, Bau T (2010) Isolation and identification of one natural pigment from cultured Cordyceps militaris. Mycosystema 29(9):777–781. https://doi.org/10.13346/j.mycosystema.2010.05.018
Zepka LQ, Mercadante AZ (2009) Degradation compounds of carotenoids formed during heating of a simulated cashew apple juice. Food Chem 117:28–34. https://doi.org/10.1016/j.foodchem.2009.03.071
Zhang H, Yang YF, Zhou ZQ (2018) Phenolic and flavonoid contents of mandarin (Citrus reticulata Blanco) fruit tissues and their antioxidant capacity as evaluated by DPPH and ABTS methods. J Integr Agric 17:256–263. https://doi.org/10.1016/S2095-3119(17)61664-2
Funding
This work was supported by Technology Program of Guangdong Province and the Natural Science Foundation of Guangdong Province, (grant nos. 2014B020205003, 2016A030313404), and the National Natural Science Foundation of China (grant nos. 31572178, 31772273, 31801918).
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Tang, H., Chen, C., Zou, Y. et al. Purification and structural characterization of a novel natural pigment: cordycepene from edible and medicinal mushroom Cordyceps militaris. Appl Microbiol Biotechnol 103, 7943–7952 (2019). https://doi.org/10.1007/s00253-019-10101-z
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DOI: https://doi.org/10.1007/s00253-019-10101-z