The<sup>1</sup>H and<sup>13</sup>C NMR Spectra of the Abietadienoic Resin Acids

Landucci, Lawrence L.; Zinkel, Duane F.

doi:10.1515/hfsg.1991.45.5.341

Cited by 10 publications

(8 citation statements)

References 15 publications

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“…If the isopropyl group was attached with a double bond, the 15-H hydrogen spectrum shift of the isopropyl group was 2.4 ppm (e.g., compound 6, 12α-hydroxyabietic acid), and if the isopropyl group was attached with -OH, its chemical shift was 1.8 ppm (e.g., compound 3, 9α-13β-dihydroxyabiet-8( 14)-enoic acid). The literature corroborated this phenomenon [35].…”

Section: Discussionmentioning

confidence: 66%

Cytotoxicity Effect of Constituents of Pinus taiwanensis Hayata Twigs on B16-F10 Melanoma Cells

et al. 2022

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Pinus taiwanensis Hayata (Pinaceae) is an endemic plant in Taiwan. According to the Chinese Materia Medica Grand Dictionary, the Pinus species is mainly used to relieve pain, and eliminate pus and toxicity. In this study, nineteen compounds were isolated from the ethyl acetate layer of the ethanolic extract of P. taiwanensis Hayata twigs using bioassay-guided fractionation, and their anti-melanoma effects were investigated through a B16-F10 mouse melanoma cell model. The structures of the purified compounds were identified by 2D-NMR, MS, and IR, including 1 triterpenoid, 9 diterpenoids, 2 lignans, 4 phenolics, 1 phenylpropanoid, 1 flavonoid, and 1 steroid. Among them, compound 3 was found to be a new diterpene. Some of the compounds (2, 5, 6, 17, 18) showed moderate cytotoxicity effects. On the other hand, the anti-melanoma effect was no better than that from the original ethyl acetate layer. We presumed it resulted from the synergistic effect, although further experimentation needs to be performed.

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Section: Discussionmentioning

confidence: 66%

Cytotoxicity Effect of Constituents of Pinus taiwanensis Hayata Twigs on B16-F10 Melanoma Cells

et al. 2022

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“…All other signals were in agreement with those observed for abietane models. 14 In an attempt to cleave the side chain of the bicyclic intermediate 9, 6 we submitted it to a Baeyer-Villiger reaction induced by mCPBA. Two compounds were isolated from the crude reaction product and were spectroscopically characterized as the tetracyclic compounds 4 (50%) and 5 (33%), instead of the expected product 10 (Scheme 1).…”

Section: -C)mentioning

confidence: 99%

Chemical transformation of abietic acid to new chiral derivatives

Santos

Zukerman-Schpector

Imamura

2003

J. Braz. Chem. Soc.

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Neste trabalho descrevemos as reações de transformações químicas do anel C do ácido abiético (1a) com o objetivo de gerar novos síntons quirais. A partir do intermediário ceto-aldeído 9, obtido através da reação de ozonólise do abietato de metila (1b), foram sintetizados derivados bicíclicos tais como 14, 15 e 16 e um novo diterpeno tetracíclico 4. Foram também sintetizados, a partir 17, novos derivados contendo esqueleto abeo-abietano [6,6,5] tais como 19 e 20.Chemical transformations of the C-ring abietic acid (1a) for the preparation of some new chiral synthons are described. From the intermediate keto-aldehyde 9, readily available from 1b through the ozonide 2, the new tetracyclic diterpene 4 was synthesized. Additionally, from 13 and 17, previously prepared from 2, the bicyclic compounds 14, 15 and 16 and the derivatives containing the abeo-abietane [6,6,5] framework 19 and 20 were also synthesized.

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“…Conclusions can only be drawn regarding the compounds causing these signals. According to 2D-NMR simulations and literature data [ 32 ], a common extractive in spruce (abietic acid) has chemical shifts in the same region. It is therefore possible that these signals originate from extractives such as fatty acids and resin acids.…”

Section: Resultsmentioning

confidence: 99%

Comprehensive Analysis of Foulants in an Ultrafiltration Membrane Used for the Treatment of Bleach Plant Effluent in a Sulfite Pulp Mill

et al. 2021

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Fouling is a major obstacle in the introduction of membrane processes in new applications in the pulping industry. Due to the complex nature of the feed solutions, complementary analysis methods are usually needed to identify the substances involved. Four different methods were used for the comprehensive analysis of a membrane removed from an ultrafiltration plant treating alkaline bleach plant effluent in a sulfite pulp mill to identify the substances causing fouling. Magnesium was detected both on the membrane surface and in the nonwoven membrane backing and a small amount of polysaccharides was detected after acid hydrolysis of the fouled membrane. This study provides information on foulants, which can be used to improve processing conditions and cleaning protocols and thus the membrane performance in pulp mill separation processes. It also provides an overview of the usefulness of various analytical methods.

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The¹H and¹³C NMR Spectra of the Abietadienoic Resin Acids

Cited by 10 publications

References 15 publications

Cytotoxicity Effect of Constituents of Pinus taiwanensis Hayata Twigs on B16-F10 Melanoma Cells

Cytotoxicity Effect of Constituents of Pinus taiwanensis Hayata Twigs on B16-F10 Melanoma Cells

Chemical transformation of abietic acid to new chiral derivatives

Comprehensive Analysis of Foulants in an Ultrafiltration Membrane Used for the Treatment of Bleach Plant Effluent in a Sulfite Pulp Mill

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The1H and13C NMR Spectra of the Abietadienoic Resin Acids

Cited by 10 publications

References 15 publications

Cytotoxicity Effect of Constituents of Pinus taiwanensis Hayata Twigs on B16-F10 Melanoma Cells

Cytotoxicity Effect of Constituents of Pinus taiwanensis Hayata Twigs on B16-F10 Melanoma Cells

Chemical transformation of abietic acid to new chiral derivatives

Comprehensive Analysis of Foulants in an Ultrafiltration Membrane Used for the Treatment of Bleach Plant Effluent in a Sulfite Pulp Mill

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The¹H and¹³C NMR Spectra of the Abietadienoic Resin Acids