Hawaiienols A–D, Highly Oxygenated <i>p</i>-Terphenyls from an Insect-Associated Fungus, <i>Paraconiothyrium hawaiiense</i>

Ren, Fengxia; Chen, Shenxi; Zhang, Yang; Zhu, Shuaiming; Xiao, Junhai; Liu, Xingzhong; Su, Rui‐Bin; Che, Yongsheng

doi:10.1021/acs.jnatprod.8b00106

Cited by 20 publications

(9 citation statements)

References 57 publications

(37 reference statements)

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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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“…Hawaiienol A (191) possesses a unique 4,7-dioxatricyclo [3.2.1.0 3,6 ]octane moiety in its p-terphenyl skeleton and showed significant activity against SH-SY5Y cells, with an IC 50 value of 9.3 μmol/L while hawaiienols B-D (192-194) did not show detectable activity at 50 μmol/L (Supplementary Fig. S2) (Ren et al 2018).…”

Section: P-terphenyls Of Other Groupsmentioning

confidence: 99%

Structural diversity and biological activity of natural p-terphenyls

Zhou

Zhu

Che

et al. 2021

Mar Life Sci Technol

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p-Terphenyls are aromatic compounds consisting of a central benzene ring substituted with two phenyl groups, and they are mainly isolated from terrestrial and marine organisms. The central ring of p-Terphenyls is usually modified into more oxidized forms, e.g., para quinone and phenols. In some cases, additional ring systems were observed on the terphenyl-type core structure or between two benzene moieties. p-Terphenyls have been reported to have cytotoxic, antimicrobial, antioxidant and α-glucosidase inhibitory effects. In this review, we will mainly summarize the structural diversity and biological activity of naturally occurring p-Terphenyls referring to the research works published before.

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“…The carbon skeletons usually bear oxygen functions including hydroxy, methoxy, and ester groups, mostly at C-3, C-4, C-3", or/and C-4" [1,2]. Recently, there has been a growing number of new types of p-terphenyls discovered, e.g., the allantonaphthofurans [20] and hawaiienols [21]. p-Terphenyls are also attractive because of their broad bioactivities such as cytotoxic, antimicrobial, antioxidant, and α-glucosidase inhibitory effects [1,8,22,23].…”

Section: Introductionmentioning

confidence: 99%

Polyhydroxy p-Terphenyls from a Mangrove Endophytic Fungus Aspergillus candidus LDJ-5

et al. 2021

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Six undescribed polyhydroxy p-terphenyls, namely asperterphenyllins A–F, were isolated from an endophytic fungus Aspergillus candidus LDJ-5. Their structures were determined by NMR and MS data. Differing from the previously reported p-terphenyls, asperterphenyllin A represents the first p-terphenyl dimer connected by a C-C bond. Asperterphenyllin A displayed anti-influenza virus A (H1N1) activity and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC50 values of 53 μM and 21 μM, respectively. The anti-influenza virus A (H1N1) activity and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity of p-terphenyls are reported for the first time. Asperterphenyllin G exhibited cytotoxicity against nine cell lines with IC50 values ranging from 0.4 to 1.7 μM. Asperterphenyllin C showed antimicrobial activity against Proteus species with a MIC value of 19 μg/mL.

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Hawaiienols A–D, Highly Oxygenated p-Terphenyls from an Insect-Associated Fungus, Paraconiothyrium hawaiiense

Cited by 20 publications

References 57 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

Structural diversity and biological activity of natural p-terphenyls

Polyhydroxy p-Terphenyls from a Mangrove Endophytic Fungus Aspergillus candidus LDJ-5

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