Natural Borneol Recycling from &lt;i&gt;Cinnamomum camphor&lt;/i&gt; chvar. &lt;i&gt;Borneol&lt;/i&gt; Oil Residue by Fractional Distillation and Recrystallization

Chen, Xiao‐Yong; Zhao, Xin; Zeng, HF; Xie, JH; Xl, Chen; Y, Liang; Wu, QD; Su, ZR; Hf, Wang; Lai, XP

doi:10.4314/tjpr.v13i9.12

Cited by 9 publications

(5 citation statements)

References 8 publications

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“…The content of borneol was 70.0% while camphor was 27.6%. Camphor and borneol were both bicyclic monoterpenoids and had similar characters, resulting in the difficulty of completely separating them by traditional methods or laborious and time‐consuming work needed.…”

Section: Resultsmentioning

confidence: 99%

“…Even though they had similar bioactivities, camphor should be used more carefully because of their differences in poisoning . The refining of borneol and camphor was usually achieved by recrystallization or sublimation from the hydro‐distillation of essential oils, by which high pure products were difficult to prepare or laborious and time‐consuming work was needed . Due to the similar characters of components in essential oils, it was a challenge work to prepare camphor and borneol with high purity in bulk.…”

Section: Introductionmentioning

confidence: 99%

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Gram‐scale separation of borneol and camphor fromCinnamomum camphora(L.) Presl by continuous counter‐current chromatography

Yang

Guo

Han

et al. 2018

Separation Science Plus

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Borneol and camphor are well known bicyclic monoterpenoids and have been widely used in food, senior aromatic spices and folk medicine in China, India and Japan for more than 2000 years. Although they can be obtained by recrystallization or sublimation, it is still a challenge to prepare high‐purity borneol and camphor with high yields. In this study, we introduce a new continuous counter‐current chromatography method for the gram‐scale preparation of borneol and camphor from Cinnamomum camphora (L.) Presl using heptane/ethyl acetate/methanol/water quaternary solvent system and heptane/methanol/water ternary solvent system. Compared to the heptane/ethyl acetate/methanol/water solvent system, the heptane/methanol/water solvent system was found to possess higher loading capacity, and the heptane/methanol/water (10:7:3, v/v/v) solvent system was found to be the optimal solvent system for the separation of the distillation products of C. camphora. As a result, borneol and camphor were well obtained in a one‐step separation with a purity of over 99.9%. In addition, continuous injections method using “on demand” solvent system formulation was used to improve the separation efficiency and reduce solvent consumption, whose results indicated that counter‐current chromatography was a powerful and efficient tool to obtain borneol and camphor with high purity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Gram‐scale separation of borneol and camphor fromCinnamomum camphora(L.) Presl by continuous counter‐current chromatography

Yang

Guo

Han

et al. 2018

Separation Science Plus

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“…The HPLC was used to detect the absorption of GFT after treatment with GFT (40 μM), NBNPs (400 μM), or NB (400 μM) in combination with GFT (40 μM). The chromatographic conditions for GC–MS were set as follows: a BD-1701 (30 m × 0.25 mm×0.25 μm) quartz capillary column, 99.999% helium (1 mL/min), an injection volume of 1 μL, with an initial temperature of 80 °C remaining for 1 min, and then the temperature programming from 80 to 230 °C at a rate of 15 °C/min, while the MS conditions are as follows: an electricity energy of 70 eV, with a full scanning mode to scan a range of 30–450 m / z . , The detection conditions for HPLC were set as follows: a UV–vis detection wavelength of 332 nm, a chromatographic column (4.6 × 250 mm) made in the USA, methanol/water (70:30, v/v, 1 mL/min) as a mobile phase, and an injection volume of 10 μL.…”

Section: Methodsmentioning

confidence: 99%

Engineering EHD1-Targeted Natural Borneol Nanoemulsion Potentiates Therapeutic Efficacy of Gefitinib against Nonsmall Lung Cancer

Yuan

Huang

Chan

et al. 2020

ACS Appl. Mater. Interfaces

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Despite the effective targeting of the epidermal growth factor receptor (EGFR), the use of gefitinib (GFT) for nonsmall cell lung cancer (NSCLC) treatment meets a failure because of the insufficient drug accumulation in the tumor region. Therefore, developing chemosensitizers of GFT with synergistic therapeutic effects is urgently needed for advanced cancer therapy. Herein, a natural chemosensitizer, natural borneol (NB), is reformulated as an oil-in-water nanoemulsion to enhance its solubility, distribution, and to ultimately increase the therapeutic index with GFT. The nanolization of NB (NBNPs) displays stronger targeted delivery and cytotoxicity than NB by selectively identifying eight specific protein targets in A549 NSCLC cells as revealed by the proteomic studies. Consistently, NBNPs realize stronger chemosensitization effects than NB with GFT by effectively regulating EGFR/EHD1-mediated apoptosis in A549 NSCLC cells. Owing to the satisfying synergistic effect between NBNPs and GFT, the combined therapy not only enhances the anticancer ability of GFT against NSCLC proliferation but also avoids heavy double toxicity in vivo. This finding demonstrates the effective synergism between NBNPs and GFT with clear mechanistic investigation and is expected to extend the application of NBNPs as a novel chemosensitizer for advanced cancer chemotherapy.

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“…[32] Pure 10 possesses desirable properties like anti-inflammatory, pain relieving and anticoagulating effects, while its diastereomer isoborneol 19 exhibits toxic effects in higher concentrations. [33,34] Enzymatic synthesis of 10 from renewable pinene 1/2 offers a novel route for selective and straightforward one-step production of this valuable compound.…”

Section: Switching Rearrangement Pathways By Single-point Mutationsmentioning

confidence: 99%

Controlling Monoterpene Isomerization by Guiding Challenging Carbocation Rearrangement Reactions in Engineered Squalene‐Hopene Cyclases

Ludwig,

Curado‐Carballada,

Hammer

et al. 2024

Angewandte Chemie

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The interconversion of monoterpenes is facilitated by a complex network of carbocation rearrangement pathways. Controlling these isomerization pathways is challenging when using common Brønsted and Lewis acid catalysts, which often produce product mixtures that are difficult to separate. In contrast, natural monoterpene cyclases exhibit high control over the carbocation rearrangement reactions but are reliant on phosphorylated substrates. In this study, we present engineered squalene‐hopene cyclases from Alicyclobacillus acidocaldarius (AacSHC) that catalyze the challenging isomerization of monoterpenes with unprecedented precision. Starting from a promiscuous isomerization of (+)‐β‐pinene, we first demonstrate noticeable shifts in the product distribution solely by introducing single point mutations. Furthermore, we showcase the tuneable cation steering by enhancing (+)‐borneol selectivity from 1% to >90% (>99% de) aided by iterative saturation mutagenesis. Our combined experimental and computational data suggests that the reorganization of key aromatic residues leads to the restructuring of the water network that facilitates the selective termination of the secondary isobornyl cation. This work expands our mechanistic understanding of carbocation rearrangements and sets the stage for target‐oriented skeletal reorganization of broadly abundant terpenes.

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Natural Borneol Recycling from <i>Cinnamomum camphor</i> chvar. <i>Borneol</i> Oil Residue by Fractional Distillation and Recrystallization

Cited by 9 publications

References 8 publications

Gram‐scale separation of borneol and camphor fromCinnamomum camphora(L.) Presl by continuous counter‐current chromatography

Gram‐scale separation of borneol and camphor fromCinnamomum camphora(L.) Presl by continuous counter‐current chromatography

Engineering EHD1-Targeted Natural Borneol Nanoemulsion Potentiates Therapeutic Efficacy of Gefitinib against Nonsmall Lung Cancer

Controlling Monoterpene Isomerization by Guiding Challenging Carbocation Rearrangement Reactions in Engineered Squalene‐Hopene Cyclases

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