Beshanzuamide A, an unprecedented prenylated indole alkaloid produced by <i>Aspergillus</i> sp. Y-2 from the critically endangered conifer <i>Abies beshanzuensis</i>

Zhu, Yuan-Xing; Ding, Wenxin; Hu, Jin‐Feng; Xiong, Juan; Li, Jiyang

doi:10.1039/d2ra01578a

Cited by 12 publications

(5 citation statements)

References 23 publications

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“…Y-2 obtained from Abies beshanzuensis , has an unprecedented prenylated indole alkaloid skeleton. 5 A biosynthetic pathway to beshanzuamide A 5 has been proposed. The structure of chevalinulin A 6 , a metabolite of the deep-sea cold-seep-derived fungus Aspergillus chevalieri CS-122, was established by X-ray analysis.…”

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confidence: 99%

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Hill

Sutherland

2022

Nat. Prod. Rep.

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confidence: 99%

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Hill

Sutherland

2022

Nat. Prod. Rep.

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“…Y-2 harbored on needles of Abies beshanzuensis led to the identification of a new compound, beshanzuamide A (98), together with five known isolates: 72, 85, 89, 91, and asperochramide A (99). None of the metabolites displayed any obvious activity against A549 or HeLa cells with IC 50 values beyond 50 µM [45].…”

Section: Diketopiperazine Alkaloidsmentioning

confidence: 94%

“…The endophytic fungus A. fumigatus LN-4 separated from the stem bark of Melia azedarach generated 24 natural products containing 24, 26, tryprostatin A (29), brevianamide F (30), fumitremorgin B (31), verruculogen (32), cyclotryprostatin B (33), cyclotryprostatin A (34), verruculogen TR-2 (35), 12β-hydroxy-13α-methoxyverruculogen TR-2 (36), and 12βhydroxyverruculogen TR-2 (37), fumitremorgin C (38), terezine D (39), and cyclo-(Pro-Gly) (40), cyclo-(Pro-Ala) (41), cyclo(D-Pro-L-Ala) (42), cyclo-(Pro-Ser) (43), cyclo-(Ser-trans-4-OH-Pro) (44), cyclo-(Leu-4-OH-Pro) (45), cyclo-(Alatrans-4-OH-Pro) (46), cyclo-(cis−OH-D-Pro-L-Phe) (47), cyclo-(Gly-Phe) (48), cyclo-(Pro-trans-4-OH-Pro) (49), and cyclo-(Gly-Ala) (50) [31]. Continuing research on the fungus A. fumigatus LN-4 using the one strain many compounds (OSMAC) method, compound 25, 12α-fumitremorgin C (51), and 18oxotryprostatin A (52) were also identified [32].…”

Section: Diketopiperazine Alkaloidsmentioning

confidence: 99%

Bioactive Alkaloids as Secondary Metabolites from Plant Endophytic Aspergillus Genus

Zhu,

Song,

Shen

et al. 2023

Molecules

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Alkaloids represent a large family of natural products with diverse structures and bioactivities. These compounds and their derivatives have been widely used in clinics to treat various diseases. The endophytic Aspergillus is a filamentous fungus renowned for its extraordinary ability to produce active natural products of high therapeutic value and economic importance. This review is the first to focus on Aspergillus-derived alkaloids. Through an extensive literature review and data analysis, 263 alkaloids are categorized according to their structural features into those containing cytochalasans, diketopiperazine alkaloids, quinazoline alkaloids, quinoline alkaloids, indole alkaloids, pyrrolidine alkaloids, and others. These metabolites exhibited diverse biological activities, such as antibacterial activity, cytotoxicity, anti-inflammatory activity, and α-glucosidase, ACE, and DPPH inhibitory activities. The bioactivity, structural diversity, and occurrence of these alkaloids are reviewed in detail.

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“…Li et al 112 characterised secondary metabolites from the fresh leaves of Pinus yunnanensis. Li et al 113 characterized beshanzuamide A, an indole alkaloid from the critically endangered conifer Abies beshanzuensis. Alam et al 114 reported on isolation, identification and DFT studies of two compounds from Bixa orellana.…”

Section: Nuclear Shielding Calculation In Natural Productsmentioning

confidence: 99%

Theory and computation of nuclear shielding

2023

Nuclear Magnetic Resonance

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This chapter continues earlier reviews of essential works on theoretical issues of nuclear magnetic shieldings published from 1 January to 31 December 2022. As previously, the chapter concentrates on theoretical calculations of nuclear shielding parameters and/or chemical shifts in case of free molecules in the gas phase and solution, and in some cases in the solid state using a periodic formulation. The nuclear shieldings in solution are mainly calculated using inexpensive polarizable continuum model of solvent (PCM). The use of discrete solvent molecules (in particular water and other polar solvents), which is essential for correct description of hydrogen bonding, is often omitted by numerous authors. Most calculations use a relatively simple and fast, but reliable density functional theory (DFT) combined with gauge-including atomic orbital (GIAO) approach. On the other hand, reports on prediction of nuclear magnetic shielding parameters using high level theoretical methods combined with large and flexible basis sets are not so common due to the enormous computational cost. In addition, correction of raw theoretical nuclear magnetic shieldings due to ro-vibration (zero-point vibration correction, ZPVC) and temperature corrections (TC), as well as implicit and explicit solvent effects and relativistic corrections are not often reported.

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Beshanzuamide A, an unprecedented prenylated indole alkaloid produced by Aspergillus sp. Y-2 from the critically endangered conifer Abies beshanzuensis

Abstract: A structurally unprecedented prenylated indole alkaloid, together with five known analogues, was isolated from an endophytic fungus associated with the endangered conifer Abies beshanzuensis.

Cited by 12 publications

References 23 publications

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Bioactive Alkaloids as Secondary Metabolites from Plant Endophytic Aspergillus Genus

Theory and computation of nuclear shielding

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