Rubrenolide and rubrynolide: An alkene-alkyne pair from Nectandra rubra☆

Franca, Nidia C.; Gottlieb, Otto R.; Coxon, David T.

doi:10.1016/s0031-9422(00)86797-7

Cited by 28 publications

(13 citation statements)

References 2 publications

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“…2), indicated that a five-membered lactone moiety bearing side chains at C-2 (δ C 38.8) and C-4 (δ C 79.7) was present in the structure of 1. Detailed analysis of the remainder of the 1D-and 2D-NMR spectra revealed that 1 and rubrenolide (3) [6], a known polyketide-derived γ-lactone that was also isolated in this investigation, are closely related (l " Fig. 1).…”

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confidence: 64%

“…The initially assigned (2 S,4R,2S') configuration of rubrenolide was later shown to be (2 S,4R,2′R) instead through its total synthesis [8]. Although the 13 C NMR data of 3 agreed with those published for rubrenolide [6], information provided by the HMBC spectrum of the former revealed that the previously reported resonance values due to C-4 (δ 70.2) and C-2′ (δ 79.7) should be interchanged. This assumption was substantiated by long-range correlations observed from H-3 and H-5 to C-4, and from H-1′ and H-3′ to C-2′ in the HMBC spectrum of 3 (l " Fig.…”

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confidence: 73%

“…Therefore, the above data al- Letter THIEME lowed compound 2 to be determined as 2′,3′-diacetylrubrenolide, which is being reported for the first time as a natural product, yet it was formerly obtained by the acetylation of rubrenolide [6]. The 1 H and 13 C NMR spectral data of 2, not previously reported in the literature, are now presented in l " Table 1) and specific rotation value agreed with those reported for rubrenolide, a butyrolactone that has been previously obtained from only one Lauraceae species, Nectandra rubra (Mez) C. K. Allen (synonym Sextonia rubra (Mez) van der Werff) [6,7], and also by stereoselective syntheses [8,9] (l " Fig. 1).…”

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confidence: 94%

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Antiproliferative Butyrolactones from Mezilaurus crassiramea

et al. 2016

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Bioassay-guided fractionation of the ethanol extract from the leaves of Mezilaurus crassiramea, which was toxic to Artemia salina larvae, afforded 3′-acetylrubrenolide (1), 2′,3′-diacetylrubrenolide (2), and rubrenolide (3) from the active dichloromethane soluble fraction. Compound 1 is new, while 2 and 3 are first reported from a natural source and in the Mezilaurus genus, respectively. Compound 3 showed significant cytotoxicity against UACC-62, MCF-7, HT-29, and PC-3 human cancer cell lines, with GI 50 values ranging from 3.3 to 9.9 µg/mL, while 1 and 2 exhibited marginal activities against at least five of the six investigated cell lines. The structures of 1-3 were established on the basis of 1Dand 2D-nuclear magnetic resonance analyses, high-resolution electrospray ionization mass spectrometry data and specific optical rotation values.

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confidence: 64%

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confidence: 73%

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confidence: 94%

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Antiproliferative Butyrolactones from Mezilaurus crassiramea

et al. 2016

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“…In 1971, two γ-lactones, rubrynolide and rubrenolide, were isolated from the stem wood of S . rubra 21–23 , of which fungicidal and termicidal activities have been reported later, suggesting that these wood metabolites are likely responsible for S . rubra heartwood natural durability 24,25 .…”

Section: Introductionmentioning

confidence: 91%

Biosynthetic investigation of γ-lactones in Sextonia rubra wood using in situ TOF-SIMS MS/MS imaging to localize and characterize biosynthetic intermediates

Houël

Amusant

et al. 2019

Sci Rep

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Molecular analysis by parallel tandem mass spectrometry (MS/MS) imaging contributes to the in situ characterization of biosynthetic intermediates which is crucial for deciphering the metabolic pathways in living organisms. We report the first use of TOF-SIMS MS/MS imaging for the cellular localization and characterization of biosynthetic intermediates of bioactive γ-lactones rubrynolide and rubrenolide in the Amazonian tree Sextonia rubra (Lauraceae). Five γ-lactones, including previously reported rubrynolide and rubrenolide, were isolated using a conventional approach and their structural characterization and localization at a lateral resolution of ~400 nm was later achieved using TOF-SIMS MS/MS imaging analysis. 2D/3D MS imaging at subcellular level reveals that putative biosynthetic γ-lactones intermediates are localized in the same cell types (ray parenchyma cells and oil cells) as rubrynolide and rubrenolide. Consequently, a revised metabolic pathway of rubrynolide was proposed, which involves the reaction between 2-hydroxysuccinic acid and 3-oxotetradecanoic acid, contrary to previous studies suggesting a single polyketide precursor. Our results provide insights into plant metabolite production in wood tissues and, overall, demonstrate that combining high spatial resolution TOF-SIMS imaging and MS/MS structural characterization offers new opportunities for studying molecular and cellular biochemistry in plants.

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“…1 Many members of the Nectandra genus have been chemically investigated and they are mainly characterized by the occurrence of alkaloids, 5-10 lignans, [11][12][13] neolignans, [14][15][16][17] tetrahydrofuranoid lignans, 18 norlignans, 19 dehydrodieugenols 20 and γ-lactones. 21,22 The composition of several essential oils from N. angustifolia (syn. N. falcifolia), [23][24][25] N. coriacea, 26 N. elaiophora 27 and N. rigida 28 has been published.…”

Section: Introductionmentioning

confidence: 99%

Volatile compounds of Nectandra salicina (lauraceae) from Costa Rica and their cytotoxic activity on cell lines

Cicció¹,

Chaverri²,

Díaz³

2009

Quím. Nova

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Recebido em 1/8/08; aceito em 8/9/08; publicado na web em 5/2/09The chemical composition of the volatiles of Nectandra salicina growing wild in Costa Rica was determined by capillary GC/FID and GC/MS. Thirty-seven and forty-two compounds were identified in the leaf and branch oils respectively corresponding to about 92.6 and 86.2% of the total amount of the oils. The major components of the leaf oil were: atractylone (14.6%), viridiflorene (10.1%), α-pinene (9.4%), β-caryophyllene (7.2%), α-humulene (7.0%), δ-cadinene (6.1%), β-pinene (6.0%) and germacrene D (5.8%). The major components of the branch oil were: atractylone (21.1%), germacrene D (10.7%), viridiflorene (7.9%) and 7-epi-α-selinene (5.0%). When the oils were tested on different cell lines, all the LD 50 values were higher than 150 µg/mL, with values very similar for the leaf and branch oils. Low toxicity could be explained by antagonistic effects among the main compounds present in the oils.

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Rubrenolide and rubrynolide: An alkene-alkyne pair from Nectandra rubra☆

Cited by 28 publications

References 2 publications

Antiproliferative Butyrolactones from Mezilaurus crassiramea

Antiproliferative Butyrolactones from Mezilaurus crassiramea

Biosynthetic investigation of γ-lactones in Sextonia rubra wood using in situ TOF-SIMS MS/MS imaging to localize and characterize biosynthetic intermediates

Volatile compounds of Nectandra salicina (lauraceae) from Costa Rica and their cytotoxic activity on cell lines

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