Pimarane diterpenes from the fungus Epicoccum sp. HS-1 associated with Apostichopus japonicus

Xia, Xuekui; Zhang, Jianye; Zhang, Yonggang; Fang, Wei; Liu, Xin; Jia, Airong; Liu, Changheng; Li, Wei; She, Zhigang; Lin, Yongcheng

doi:10.1016/j.bmcl.2012.01.055

Cited by 44 publications

(37 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…102 The ACs of 78, 79, and 80 were assigned by CD comparison with that of 77, whose structure and AC were determined by X-ray analysis, consistent with CD and NMR evidence. 102 The ACs of 78, 79, and 80 were assigned by CD comparison with that of 77, whose structure and AC were determined by X-ray analysis, consistent with CD and NMR evidence.…”

Section: Stereochemical Assigment Of Pimarane Diterpenessupporting

confidence: 53%

“…An ethyl acetate extract showed cytotoxicity against KB. 102 Aspergilone A (78) and the known compound 80 were moderately active against human epidermis carcinoma (KB) cells with IC 50 s of 3.5 and 3.86 μg/mL, respectively, and EC 50 s of 2.34 and 6.52 μg/mL were observed against multidrug resistant cells with high levels of P-glycoprotein (KBv200). The structures 78 to 80 were assigned by spectroscopic analysis, and their relative configuration by a combination of the results obtained from NOESY NMR spectra and the measurement of coupling constant values in the 1 H-NMR spectra.…”

Section: Epicoccum Spmentioning

confidence: 99%

See 1 more Smart Citation

Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity

et al. 2018

View full text Add to dashboard Cite

Plants and fungi are seemingly inexhaustible sources of interesting natural products with remarkable structural and biological diversity. One of the most important groups is the terpenes, ubiquitous natural products that are generated by 2 now well-established biosynthetic pathways: the older mevalonate and the more recently discovered 1-deoxyxylulose-5-phosphate. Among the diterpenes, the pimarane diterpenes are a very representative subgroup with several and interesting biological activities resulting from different functional group modifications. In this review, we outline the method of their structure determination, mainly spectroscopic results, their absolute configuration, and structure-activity relationships, were reported, as well as the mode of action for selected examples from plants, marine organisms, and fungi. The pimarane, isopimarane, and ent-pimarane diterpenes covered in this review have a wide range of biological activities including antimicrobial, antifungal, antiviral, phytotoxic, phytoalexin, cytotoxicity, and antispasmodic and relaxant effects.

show abstract

Section: Stereochemical Assigment Of Pimarane Diterpenessupporting

confidence: 53%

Section: Epicoccum Spmentioning

confidence: 99%

Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity

et al. 2018

View full text Add to dashboard Cite

show abstract

“…The IR spectrum ( Supplementary Material S22) showed the presence of hydroxy (3372 cm −1 ), and α , β ‐unsaturated ketone (1630 and 1604 cm −1 ) groups in 2 . The 1 H‐ and 13 C‐NMR spectral data ( Table , Supplementary Material S14 and S15) of 2 resembled those of 1 , which suggested that compound 2 possessed the same pimarane diterpene skeleton . Moreover, compared with the literature, the structure of 2 was very similar to that of compound libertellenone G, except for the methoxy ( δ (C) 60.6) instead of the H‐atom at C(14).…”

Section: Resultsmentioning

confidence: 58%

“…Since the two carbonyl carbons and eight olefinic carbons occupied six out of the nine degrees of unsaturation, the remaining three degrees of unsaturation indicated that compound 1 possessed a tricyclic system. Further structural information of 1 was deduced by its 2D‐NMR data (COSY, HMQC, and HMBC spectra) ( Supplementary Material S4, S5, and S6), which suggested the presence of pimarane diterpenoid structure . The COSY cross‐peaks ( Figure ) revealed connectivities of C(1) to C(2), C(11) to C(12), and C(15) to C(16).…”

Section: Resultsmentioning

confidence: 96%

Bioactive Pimarane Diterpenes from the Arctic Fungus Eutypella sp. D‐1

Wang

Sun

Wang

2018

Chemistry & Biodiversity

View full text Add to dashboard Cite

Two new pimarane diterpenes, libertellenone M (1) and libertellenone N (2), together with five known compounds were isolated from the culture extract of Eutypella sp. D-1 derived from high-latitude soil of the Arctic. The structures of these compounds were determined by spectroscopic data as well as experimental and calculated electronic circular dichroism (ECD) analysis. Antimicrobial and cytotoxic activities of the isolated compounds were evaluated. Compound 3 exhibited weak antibacterial activity against Escherichia coli, Bacillus subtilis, and Vibrio vulnificus, each with MIC values of 16 μg/mL. Compounds 2 and 3 showed moderate cytotoxic activity against K562 and MCF-7 cell lines with IC values of 7.67 and 9.57 μm, respectively.

show abstract

“…), is a fungicolous and mycoparasitic fungus, which is used as biocontrol agent for phytopathogens . Recently, chemical investigation of fungi of the genus Epicoccum resulted in the isolation of structurally diverse bioactive compounds, including polyketides, diketopiperazine alkaloids, and diterpenes which exhibited important biological activities . Remarkably, even the well known antitumor drug taxol, glycosylated flavonoids, and anthraquinones were reported from E. nigrum .…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Host Plant Flavonoids by the Fungal Endophyte Epicoccum nigrum

et al. 2019

View full text Add to dashboard Cite

Fermentation of the fungus Epicoccum nigrum isolated from leaves of Salix sp. on green lentil solid medium yielded the flavonol kaempferol (3) as well as two kaempferol O‐diglycosides (1 and 2) including the new compound 1. The fungal flavonoids bear strong structural similarities to kaempferol derivatives such as kaempferol O‐glycoside (4) being present in green lentils. Furthermore, feeding experiments were conducted by adding flavonoids (kaempferol and rutin) as precursors to solid rice media followed by HPLC and LC‐MS analyses. Fermentation of the fungus on flavonoid free solid rice medium afforded flavonoid free extracts indicating that the fungal flavonoids originate through hydrolytic cleavage of kaempferol glycosides such as 4 followed by glycosylation and acetylation. This study suggests that E. nigrum is capable of biotransformation reactions of plant derived flavonoids whereas de novo biosynthesis of flavonoids is less likely.

show abstract

Pimarane diterpenes from the fungus Epicoccum sp. HS-1 associated with Apostichopus japonicus

Cited by 44 publications

References 5 publications

Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity

Pimarane diterpenes: Natural source, stereochemical configuration, and biological activity

Bioactive Pimarane Diterpenes from the Arctic Fungus Eutypella sp. D‐1

Biotransformation of Host Plant Flavonoids by the Fungal Endophyte Epicoccum nigrum

Contact Info

Product

Resources

About