<i>Securinega</i> Alkaloids from the Twigs of <i>Securinega suffruticosa</i> and Their Biological Activities

Park, Kyoung-Jin; Kim, Chung Sub; Khan, Zahra; Oh, Joonseok; Kim, Sun Yeou; Choi, Sang Un; Lee, Kang Ro

doi:10.1021/acs.jnatprod.9b00142

Cited by 43 publications

(48 citation statements)

References 27 publications

(53 reference statements)

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“…Thus, DP4+ probability analysis was used to indicate the relative configuration at C-6 and C-10. This method was used to assign the relative configurations of organic molecules employing GIAO (gauge-independent atomic orbital) NMR shift calculations [17,18]. Based on a DP4+ protocol [19], both proton and carbon data of four possible isomers were calculated, and the results were analyzed with the experimental values.…”

Section: Structure Elucidation Of the New Compoundsmentioning

confidence: 99%

Three New Sesquiterpenoids from the Algal-Derived Fungus Penicillium chermesinum EN-480

Yang

et al. 2020

Marine Drugs

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Secondary metabolites obtained from marine-derived fungi are rich sources of drug candidates. Three new sesquiterpenoids, chermesiterpenoids A–C (1–3), along with four known alkaloids (4–7), were isolated and identified from the marine red algal-derived fungus Penicillium chermesinum EN-480. The structures of these new sesquiterpenoids were elucidated using detailed analysis of the NMR data and their relative configurations were elucidated using nuclear overhauser effect spectroscopy (NOESY) spectra as well as gauge-independent atomic orbital (GIAO) NMR shift calculations and DP4+ probability analysis. Their absolute configurations were determined using electronic circular dichroism (ECD) calculations and modified Mosher’s method. Compounds 2 and 3 exhibited potent activities against human and aquatic pathogenic bacteria and plant pathogenic fungi.

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Section: Structure Elucidation Of the New Compoundsmentioning

confidence: 99%

Three New Sesquiterpenoids from the Algal-Derived Fungus Penicillium chermesinum EN-480

Yang

et al. 2020

Marine Drugs

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“…S. Suffruticosa is a deciduous shrub belonging to the Euphorbiaceae family that has extremely strong adaptability and can endure cold, drought, and barren conditions, i.e., sandy soil [3]. S. suffruticosa grows approximately 1-2 m in height and has clusters, twigs, and treeshaped expansion.…”

Section: Introductionmentioning

confidence: 99%

Diversity and antimicrobial activity of endophytic fungi isolated from Securinega suffruticosa in the Yellow River Delta

Yao

et al. 2020

PLoS ONE

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Securinega suffruticosa (Pall.) Rehd is an excellent natural secondary shrub in the Shell Islands of Yellow River Delta. The roots of S. suffruticosa have high medicinal value and are used to treat diseases, such as neurasthenia and infant malnutrition. Any organism that is isolated from this species is of immense interest due to its potential novel bioactive compounds. In this research, the distribution and diversity of culturable endophytic fungi in S. suffruticosa were studied, and the endophytic fungi with antimicrobial activity were screened. A total of 420 endophytic fungi isolates were obtained from the S. suffruticosa grown in Shell Islands, from which 20 genera and 35 species were identified through morphological and internal transcribed spacer (ITS) sequence analyses. Chaetomium, Fusarium, Cladosporium, and Ceratobasidium were the dominant genera. The high species richness S (42), Margalef index D 0 (5.6289), Shannon-Wiener index H 0 (3.1000), Simpson diversity index D s (0.9459), PIE index (0.8670), and evenness Pielou index J (0.8719) and a low dominant index λ (0.0541) indicated the high diversity of endophytic fungi in S. suffruticosa, the various species of endophytic fungi with obvious tissue specificity. The inhibition percentages of the 12 species of such endophytic fungi against Colletotrichum siamense were 3.6%-26.3%. C. globosum, Fusarium sp.3, and C. ramotenellum had a high antibacterial activity against Enterococcus faecalis, Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus. The Minimum Inhibitory Concentration (MIC) and the Minimum Bactericidal Concentration (MBC) were between 0.5 mg/mL and 2 mg/mL. Alkaloid content detection indicated that endophytic fungi had a high alkaloid content, whereas the alkaloid contents of C. globosum and Fusarium sp.3 reached 0.231% and 0.170%, respectively. Members belonging to the endophytic fungal community in the S. suffruticosa of Shell Islands that may be used as antagonists and antibacterial agents for future biotechnology applications were identified for the first time.

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“…Its enantiomer, (+)‐phyllantidine ( 1 ), was isolated in 1992 from the leaves of Breynia coronata . Phyllantidine possesses a unique oxazabicyclo[3.3.1]nonane structure and exhibits leishmanicidal activity and anti‐inflammatory properties . Interestingly, Flueggeacosine B ( 11 ), a heterodimer of phyllantidine ( 1 ) and a novel securinega alkaloid fragment containing a azabicyclo[3.2.1]octane system, was isolated recently in 2018 from the roots of Flueggea suffruticosa and displays potent neuronal differentiation activity …”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of (±)‐Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen‐Oxygen Bonds

et al. 2020

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The development of a concise total synthesis of (±)‐phyllantidine (1), a member of the securinega family of alkaloids containing an unusual oxazabicyclo[3.3.1]nonane core, is described. The synthesis employs a unique synthetic strategy featuring the ring expansion of a substituted cyclopentanone to a cyclic hydroxamic acid as a key step that allows facile installation of the embedded nitrogen‐oxygen (N−O) bond. The optimization of this sequence to effect the desired regiochemical outcome and its mechanistic underpinnings were assessed both computationally and experimentally. This synthetic approach also features an early‐stage diastereoselective aldol reaction to assemble the substituted cyclopentanone, a mild reduction of an amide intermediate without N−O bond cleavage, and the rapid assembly of the butenolide found in (1) via use of the Bestmann ylide.

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Securinega Alkaloids from the Twigs of Securinega suffruticosa and Their Biological Activities

Cited by 43 publications

References 27 publications

Three New Sesquiterpenoids from the Algal-Derived Fungus Penicillium chermesinum EN-480

Three New Sesquiterpenoids from the Algal-Derived Fungus Penicillium chermesinum EN-480

Diversity and antimicrobial activity of endophytic fungi isolated from Securinega suffruticosa in the Yellow River Delta

Total Synthesis of (±)‐Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen‐Oxygen Bonds

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