New <i>p</i>-terphenyl and benzoquinone metabolites from the bioluminescent mushroom <i>Neonothopanus nambi</i>

Sangsopha, Watchara; Lekphrom, Ratsami; Schevenels, Florian; Saksirirat, Weerasak; Bua-art, Sureeporn; Kanokmedhakul, Kwanjai; Kanokmedhakul, Somdej

doi:10.1080/14786419.2019.1578763

Cited by 9 publications

(7 citation statements)

References 14 publications

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“…The structural diversity of the natural p-terphenyls mainly resulted from the variation of the ring B, the number and the position of hydroxy groups, and the changes of the phenol to quinone functions. Approximately 230 natural p-terphenyls have been identified from the year 1877 to 2018 (Li et al 2018;Liu 2006), and this number is growing every year (Kalansuriya et al 2019;Kalvo et al 2018;Lin et al 2019;Lu et al 2019;Narmani et al 2019;Ren et al 2018;Sangsopha et al 2019;Song et al 2019;Wang et al 2019b;Xu et al 2018). Our present work isolated and identified a new p-terphenyl alcohol with a dibenzofuran moiety from the marine sponge-derived fungus A. candidus OUCMDZ-1051, as well as nine known p-terphenyl alcohols.…”

Section: Resultsmentioning

confidence: 99%

p-Terphenyl alcohols from a marine sponge-derived fungus, Aspergillus candidus OUCMDZ-1051

Wang

Zhou

et al. 2020

Mar Life Sci Technol

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In order to discover structurally new and bioactive compounds from marine life, we studied the secondary metabolites of the marine-derived fungi associated with a marine sponge (XS-3) from the Xisha islands. As a result, 4-O-methylcandidusin A (1), a new p-terphenyl alcohol, along with nine known analogs (2-10), were isolated and identified from the marine spongederived fungus Aspergillus candidus OUCMDZ-1051. The structures of these compounds were determined by analyzing spectroscopic data, especially 1D and 2D NMR. The new compound 1 selectively inhibited the growth of the MDA-MB-468, BT474 and A431 human cancer cell lines with the IC 50 values of 1.84, 6.05 and 0.98 μmol/L, respectively. Compound 1 also displayed a selective antimicrobial activity against Escherichia coli with an MIC value of 27.3 μmol/L. The results indicated 4-O-methylcandidusin A (1) as a potential lead in the new drug discovery for triple negative breast cancer, invasive ductal breast cancer and epidermoid cancer. The antimicrobial metabolites also evidenced a clue for chemical defense of sponges by their associated microorganisms.

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Section: Resultsmentioning

confidence: 99%

p-Terphenyl alcohols from a marine sponge-derived fungus, Aspergillus candidus OUCMDZ-1051

Wang

Zhou

et al. 2020

Mar Life Sci Technol

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“…In addition, the NMR data of 2 were very similar those of nambiscalarane (8), with slight differences arising from the substitution of the hydroxy group at C-11 by a malonate. NOESY correlations (Figure 3) between H-11β/H 3 -21/H 3 -22/H 3 -23 and H-6β/H-7β/H 3 -19/H 3 -21/H 3 -22, as well as the large 1 H-1 H coupling constants between H-6/H-7 (11.2 Hz) and H-11/H-12 (11.2 Hz) indicated that the relative configuration of compound 2 was identical to that of compound 1. The absolute configuration of compound 2 was established through comparison of calculated and experimental ECD curves.…”

Section: Structural Characterization Of the New Compoundsmentioning

confidence: 97%

“…The luminescent mushroom Neonothopanus nambi belongs to the Omphalotaceae family. It is known as 'Hed Ruang Sang Sirin-ratsami' or 'Sirin-ratsami mushroom' in Thai [1]. Previous agricultural studies have shown that N. nambi can induce systemic resistance against root-knot nematodes such as Meloidogyne incognita in tomato plants [2,3].…”

Section: Introductionmentioning

confidence: 99%

“…N. nambi produces diverse secondary metabolites that seemed to greatly vary in nature based on the conditions of its culture (Figure S1 and Table S1). Our previous work showed that potato dextrose broth led to the production of sesquiterpenoids (and dimers) as well as terphenyls and benzoquinones [1,4]. Yeast malt agar conditions led to the isolation of more diverse secondary metabolites.…”

Section: Introductionmentioning

confidence: 99%

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Scalarane Sesterterpenoids with Antibacterial and Anti-Proliferative Activities from the Mushroom Neonothopanus nambi

Wisetsai

Lekphrom

Bua-art³

et al. 2021

Molecules

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Seven undescribed scalarane sesterterpenoids, nambiscalaranes B–H (1–7), together with two known compounds, nambiscalarane (8) and aurisin A (9) were isolated from the cultured mycelium of the luminescent mushroom Neonothopanus nambi. Their structures were elucidated by thorough analysis of their 1D and 2D NMR spectroscopic data. The absolute configurations of 1–8 were determined by electronic circular dichroism (ECD) calculations and optical rotation measurements. The isolated sesterterpenoids were evaluated against A549, HT29, HeLa, and HCT-116 cancer cell lines, and against five bacterial strains. Compounds 3, 5, and 7 showed strong cytotoxicity against HCT-116 cell line, with IC50 values ranging from 13.41 to 16.53 µM, and showed no cytotoxicity towards Vero cells. Moreover, compound 8 inhibited the growth of Bacillus subtilis with a MIC value of 8 µg/mL, which was equivalent to the MIC value of the standard kanamycin.

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“…Metabolites isolated from species of the genus Aspergillus have continually attracted the interest of pharmacologists due to their broad array of biological activities and their structural diversity (Wang et al, 2017). p-Terphenyl derivatives have been reported with diverse biological activities, such as neuraminidase inhibitory (Guo et al, 2012), α-glucosidase inhibitory (Zhang et al, 2018), antioxidant (Yen et al, 2001, cytotoxic (Cai et al, 2011;Sangsopha et al, 2019;Yurchenko et al, 2017), antibacterial (Yan et al, 2017, and immunosuppressive activities (Ivanets et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

A new p-terphenyl derivative from the insect-derived fungus Aspergillus candidus Bdf-2 and the synergistic effects of terphenyllin

Shan

Wang

et al. 2020

PeerJ

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A new p-terphenyl derivative 4″-deoxy-2′-methoxyterphenyllin (1), along with six known p-terphenyl derivatives (2–7), a known flavonoid derivative dechlorochlorflavonin (8) and a known fellutanine A (9), were isolated from the insect-derived strain of the fungus Aspergillus candidus Bdf-2, associated with Blaptica dubia. The structure of 1 was established by the analysis of the 1D and 2D NMR and HR-ESI-MS spectra. Compounds 1–9 were evaluated for antibacterial activities against Staphylococcus aureus ATCC29213, Escherichia coli ATCC25922 and Ralstonia solanacearum, and for antioxidant activities. Synergistic effects of compound 2 with the other compounds were also investigated. As a result, compound 6 displayed the best antibacterial activities in all single compound with MIC value of 32 µg/mL against S. aureus ATCC29213 and R. solanacearum, respectively. However, no antibacterial effect against E. coli ATCC25922 was detected from any single compound. The combination of 2 + 6 exhibited obvious synergistic effect against S. aureus ATCC29213 and the MIC value was 4 µg/mL. Compound 6 also showed the best antioxidant activity as a single compound with an IC50 value of 17.62 µg/mL. Combinations of 5 + 6, 2 + 4 + 5 and 2 + 4 + 5 + 6 displayed synergistic effect and their antioxidant activities were better than that of any single compound.

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New p-terphenyl and benzoquinone metabolites from the bioluminescent mushroom Neonothopanus nambi

Cited by 9 publications

References 14 publications

p-Terphenyl alcohols from a marine sponge-derived fungus, Aspergillus candidus OUCMDZ-1051

p-Terphenyl alcohols from a marine sponge-derived fungus, Aspergillus candidus OUCMDZ-1051

Scalarane Sesterterpenoids with Antibacterial and Anti-Proliferative Activities from the Mushroom Neonothopanus nambi

A new p-terphenyl derivative from the insect-derived fungus Aspergillus candidus Bdf-2 and the synergistic effects of terphenyllin

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