(+)- and (−)-Spiroreticulatine, A Pair of Unusual Spiro Bisheterocyclic Quinoline-imidazole Alkaloids from the South China Sea Sponge <i>Fascaplysinopsis reticulata</i>

Wang, Qi; Tang, Xiangming; Luo, Xiangchao; Voogd, Nicole J. de; Li, Pinglin; Li, Guoqiang

doi:10.1021/acs.orglett.5b01503

Cited by 51 publications

(49 citation statements)

References 25 publications

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“…The unique scaffold of this natural alkaloid could lead to novel molecular probes to study p300/HIF‐1α interactions and the role these proteins play in tumor response to low oxygen conditions or new therapeutic anticancer lead compounds that could disrupt critical protein–protein binding events. During the same year, novel bisheterocyclic quinolineimidazole alkaloids (+)‐ and (−)‐spiroreticulatine ( 77 , 78 ) (Figure ) from Fascaplysinopsis reticulate were inactive against K562, A549, Hela, or Jurkat tumor cell lines, but inhibited IL‐2 production in a dose‐dependent manner …”

Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

152

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To follow-up on our prior Part I review, this Part II review summarizes and provides updated literature on novel quinoline and quinazoline alkaloids isolated during the period of 2009-2016, together with the biological activity and the mechanisms of action of these classes of natural products. Over 200 molecules with a broad range of biological activities, including antitumor, antiparasitic and insecticidal, antibacterial and antifungal, cardioprotective, antiviral, anti-inflammatory, hepatoprotective, antioxidant, anti-asthma, antitussive, and other activities, are discussed. This survey should provide new clues or possibilities for the discovery of new and better drugs from the original naturally occurring quinoline and quinazoline alkaloids.

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Section: Biological Activities Of Quinoline and Quinazoline Alkaloidsmentioning

confidence: 99%

Biologically active quinoline and quinazoline alkaloids part II

Shang

Morris‐Natschke

Yang

et al. 2018

Medicinal Research Reviews

152

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“…[8] [11] Previous investigations on the sponge Agelas nakamurai mainly focused on the species collected from Okinawa, [5] [11] [19] Indonesia, [17] [20] Papua New Guinean, [21] and Kuchinoerabu-jima Island. In the course of our search for bioactive substances from marine organisms in the South China Sea, [10] [23] we investigated extracts of the sponge 1 These authors contributed equally to this work. In the course of our search for bioactive substances from marine organisms in the South China Sea, [10] [23] we investigated extracts of the sponge 1 These authors contributed equally to this work.…”

Section: Introductionmentioning

confidence: 99%

“…[22] And there were no report on the South China Sea sponge A. nakamurai. In the course of our search for bioactive substances from marine organisms in the South China Sea, [10] [23] we investigated extracts of the sponge 1 These authors contributed equally to this work.…”

Section: Introductionmentioning

confidence: 99%

Pyrrole Derivatives and Diterpene Alkaloids from the South China Sea Sponge Agelas nakamurai

Chu

Tang

Qin

et al. 2017

Chemistry & Biodiversity

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Two pairs of new non-brominated racematic pyrrole derivatives, (±)-nakamurine D (1) and (±)-nakamurine E (2), two new diterpene alkaloids, isoagelasine C (16) and isoagelasidine B (21), together with 13 known pyrrole derivatives ((±)-3 - 15), five known diterpene alkaloids (17 - 20, 22) were isolated from the South China Sea sponge Agelas nakamurai. The racemic mixtures, compounds 1 - 4, were resolved into four pairs of enantiomers, (+)-1 and (-)-1, (+)-2 and (-)-2, (+)-3 and (-)-3, and (+)-4 and (-)-4, by chiral HPLC. The structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses, quantum chemical calculations, quantitative measurements of molar rotations, application of van't Hoff's principle of optical superposition, and comparison with the literature data. The NMR and MS data of compound 3 are reported for the first time, as the structure was listed in SciFinder Scholar with no associated reference. These non-brominated pyrrole derivatives were found in this species for the first time. Compound 18 showed valuable cytotoxicities against HL-60, K562, and HCT-116 cell lines with IC values of 12.4, 16.0, and 19.8 μm, respectively. Compounds 16 - 19, 21, and 22 showed potent antifungal activities against Candida albicans with MIC values ranging from 0.59 to 4.69 μg/ml. Compounds 16 - 19 exhibited moderate antibacterial activities against Proteusbacillus vulgaris (MIC values ranging from 9.38 to 18.75 μg/ml).

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“…A new type of spirocyclic derivative, pestaloficin A ( 240 ) was reported by Yin and co‐workers . Spiroreticulatine ( 241 ) is a spiro quinoline‐imidazole alkaloid derived from sponge, which exhibit inhibitory activity on IL‐2 production . Leonurusoleanolides ( 242 ) are spirocyclic triterpenoids isolated from Leonurus japonicus fruit and showed potent cytotoxic activity against human cancer cell lines (Figure ) …”

Section: Spirocyclesmentioning

confidence: 99%

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

Kotha

Meshram

Dommaraju

2018

The Chemical Record

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In this perspective, we summarize new synthetic approaches for the construction of various polycyclic compounds involving ring-closing metathesis as a key step. In this regard, we used ring-closing metathesis in combination with other popular reactions like Suzuki-Miyaura coupling, Claisen rearrangement, Fischer indolization, Grignard addition, Diels-Alder reaction, and [2+2] cycloaddition reaction etc. To this end, a variety of functional molecules such as α-amino acids, cyclophanes, heterocycles, propellanes, spirocycles, and macrocycles have been prepared. The strategies developed and the molecules prepared here play a key role in designing new materials and also act as lead compounds in drug design. The strategies and tactics developed here are useful to design polycycles, macrocycles, and heterocycles of diverse ring systems.

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(+)- and (−)-Spiroreticulatine, A Pair of Unusual Spiro Bisheterocyclic Quinoline-imidazole Alkaloids from the South China Sea Sponge Fascaplysinopsis reticulata

Cited by 51 publications

References 25 publications

Biologically active quinoline and quinazoline alkaloids part II

Biologically active quinoline and quinazoline alkaloids part II

Pyrrole Derivatives and Diterpene Alkaloids from the South China Sea Sponge Agelas nakamurai

Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring‐Closing Metathesis

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