Preparative isolation of cordycepin, N 6 -(2-hydroxyethyl)-adenosine and adenosine from Cordyceps militaris by macroporous resin and purification by recycling high-speed counter-current chromatography

Zhang, Zhong; Tudi, Tuernisan; Liu, Yanfang; Zhou, Shuai; Feng, Naixing; Yang, Yan; Tang, Chuanhong; Tang, Qingjiu; Zhang, Jingsong

doi:10.1016/j.jchromb.2016.08.025

Cited by 23 publications

(17 citation statements)

References 39 publications

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“…In the present study, we isolated cordycepin from the fruiting body of C. militaris. Compared with the previous study that isolated cordycepin from the fruiting body of C. militaris [31] by high-speed countercurrent chromatography, our method is more simple and provides a higher yield.…”

Section: Discussionmentioning

confidence: 91%

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

et al. 2019

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There is currently much interest in finding new phytochemicals among plants and fungi as nature-based alternatives to replace problematic herbicides such as glyphosate, which are preferentially used in agricultural production n. We discovered striking herbicidal potency in Cordyceps militaris (L.) and identified cordycepin as its principal plant growth inhibitor. Cordycepin obtained as an ethyl acetate extract was subjected to column chromatography and evaluated for its bioassay-guided phytotoxic capacity against Raphanus sativus (radish), showing a maximum inhibition on germination and growth of radish (IC50 = 0.052–0.078 mg/mL). Gas chromatography-mass spectrometry (GC-MS) (m/z: 251.2) and liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) ([M + Na]+ m/z: 274.1; [M + H]+ m/z: 252.1) analyses confirmed cordycepin as the major component of the tested column fraction (55.38%). At 0.04 mg/mL, cordycepin showed 3.8–5.9- and 3.3–3.7-fold greater inhibition of the germination and growth of radish than benzoic acid (BA) and glyphosate, respectively. Compared with BA, isolated cordycepin reduced plant chlorophyll and carotenoid contents (2.0–9.5 -fold), while proline, total phenolic and total flavonoid contents were increased 1.2–1.8-fold. Finally, cordycepin promoted electrolyte leakage and malondialdehyde accumulation in radish aerial parts. Thus, cordycepin successfully isolated from Cordyceps militaris is a highly potent plant growth inhibitor with pending worldwide patent and may become a potential plant-based novel alternative to the disputed glyphosate.

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Section: Discussionmentioning

confidence: 91%

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

et al. 2019

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“…Both HEA and cordycepin (3ʹ-deoxyadenosine) are main components of Cordyceps species and are also analogues of adenosine. The antitumor effect of cordycepin has been widely reported, but studies on HEA antineoplastic activity are relatively few [ 6 , 23 , 24 ]. Previous studies have shown that EEC has an antitumor effect, and HEA is one of the main components of EEC, but no in-depth study has been conducted [ 13 ].…”

Section: Discussionmentioning

confidence: 99%

“…As one of the main biological components of Cordyceps species, N6-(2-Hydroxyethyl)-adenosine (HEA) was first isolated from Cordyceps and Isaria species in 1983 (structure is shown in Figure 1 ). The separation and preparation of HEA have been reported [ 6 , 7 ]. Pharmacological studies found that HEA possesses antihyperglycemic, kidney protective, antioxidant, sedative, anti-inflammatory, and myocardium protective effects and interacts with human serum albumin [ 8 , 9 , 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

N6-(2-hydroxyethyl)-Adenosine Induces Apoptosis via ER Stress and Autophagy of Gastric Carcinoma Cells In Vitro and In Vivo

Xie

Yang

et al. 2020

IJMS

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Gastric cancer is the most common malignant tumor of the digestive tract and is great challenge in clinical treatment. N6-(2-Hydroxyethyl)-adenosine (HEA), widely present in various fungi, is a natural adenosine derivative with many biological and pharmacological activities. Here, we assessed the antineoplastic effect of HEA on gastric carcinoma. HEA exerted cytotoxic effects against gastric carcinoma cells (SGC-7901 and AGS) in a dose and time-dependent manner. Additionally, we found that HEA induced reactive oxygen species production and mitochondrial membrane potential depolarization. Moreover, it could trigger caspase-dependent apoptosis, promoting intracellular Ca2+-related endoplasmic reticulum (ER) stress and autophagy. On the other hand, HEA could significantly inhibit the growth of transplanted tumors in nude mice and induce apoptosis of tumor tissues cells in vivo. In conclusion, HEA induced apoptosis of gastric carcinoma cells in vitro and in vivo, demonstrating that HEA is a potential chemotherapeutic agent for gastric carcinoma.

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“…Content of HEA in I. cicadae mycelia cultured in barley was higher than those cultured in other substrates (Ke and Lee 2016). C. militaris mycelia and fruiting bodies produce HEA (Zhu et al 2013; Zhang et al 2016), as does I. tenuipes grown under submerged culture conditions (Liu et al 2012; Lei et al 2014). It was reported that the amount of HEA in Ophiocordyceps sinensis (Berk.)…”

Section: Introductionmentioning

confidence: 99%

Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus

Liu

Wang

et al. 2017

Mycology

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N6-(2-Hydroxyethyl)-adenosine (HEA), which was the first calcium antagonist derived from biological sources, has been intensively investigated because of its ability to inhibit tumour cell proliferation, restrain inflammation, protect kidneys and function as a sedative and insecticide. Up to now, the production of HEA has been detected only in a few species such as Cordyceps pruinosa, C. militaris and Isaria tenuipes. Here, we found a new HEA-producing fungus, which was identified as Beauveria bassiana based on morphological and phylogenetic characteristics. The HEA production was verified by reversed-phase high-performance liquid chromatography/mass spectrometry in this fungus. Moreover, HEA was also detected in the mycelia of two other B. bassiana strains from different origins, but not in the culture medium of all tested B. bassiana strains. The maximum production of HEA (0.8483 ± 0.0439 mg/g mycelia dry weight) was achieved on day 7. The fungal biomass and kinetics of HEA production exhibited similar trends over the duration of the culture period. This is the first report describing HEA production in B. bassiana, which suggests that this fungal strain may have new applications as a source of HEA.

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Preparative isolation of cordycepin, N 6 -(2-hydroxyethyl)-adenosine and adenosine from Cordyceps militaris by macroporous resin and purification by recycling high-speed counter-current chromatography

Cited by 23 publications

References 39 publications

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

N6-(2-hydroxyethyl)-Adenosine Induces Apoptosis via ER Stress and Autophagy of Gastric Carcinoma Cells In Vitro and In Vivo

Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus

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Preparative isolation of cordycepin, N 6 -(2-hydroxyethyl)-adenosine and adenosine from Cordyceps militaris by macroporous resin and purification by recycling high-speed counter-current chromatography

Cited by 23 publications

References 39 publications

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

Cordycepin Isolated from Cordyceps militaris: Its Newly Discovered Herbicidal Property and Potential Plant-Based Novel Alternative to Glyphosate

N6-(2-hydroxyethyl)-Adenosine Induces Apoptosis via ER Stress and Autophagy of Gastric Carcinoma Cells In Vitro and In Vivo

Beauveria bassiana: a new N6-(2-hydroxyethyl)-adenosine–producing fungus

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Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus