Chiang Mai Journal of Science

Quality Transfer Characteristics of Gardenia jasminoides Ellis in Xingnaojing Injection

1. INTRODUCTION

     XNJ is a traditional Chinese medicine preparation derived from the classical prescription “Angong Niuhuang Pill” and composed of musk, borneol, Radix Curcumae, and GJE [1-4]. This formulation is known for its therapeutic effects in reducing fever and toxins, promoting blood circulation, and enhancing cognitive function and alertness [5-9]. Clinically, XNJ is widely used in the management of stroke-induced coma, hemiplegia due to disrupted qi and blood flow, and cerebral vein stagnation [10-13]. It is also applied in conditions such as traumatic headaches, delirium, alcohol-induced neurological symptoms (e.g., headaches, vomiting, coma, convulsions), cerebral embolism, acute cerebral hemorrhage, craniocerebral trauma, and acute intoxication [14-17].
     Among its constituents, GJE serves as a critical ingredient in XNJ. Although the 2020 edition of the Chinese Pharmacopoeia designates geniposide as a quality control marker for GJE, the manufacturing process of XNJ involves steam distillation to extract volatile components from GJE and Radix Curcumae. This process minimizes non-volatile impurities, resulting in a final product whose pharmacological activity is largely attributed to its volatile constituents [18,19]. However, current national drug standards for XNJ lack validated, standardized markers to assess the contribution of GJE’s volatile components. This gap impedes accurate quality evaluation and potentially compromises product consistency [20-22]. Building upon our prior innovation in quality assessment methodologies for XNJ, a patented approach for evaluating GJE quality within this formulation has been established (Chinese Patent CN107907611B) [23]. To bridge this gap and specifically target volatile constituents, a method combining steam distillation with liquid-liquid extraction was developed to isolate and track potential markers throughout the manufacturing process. This approach facilitated the identification of a consistent and suitable volatile quality marker for GJE in XNJ. This study specifically focuses on the sesquiterpene derivative 4-methyleneisophorone. We demonstrate its consistent presence and traceability across critical stages—from the raw GJE material, through intermediate extracts generated during processing, to the final XNJ product. This compelling evidence positions 4-methyleneisophorone as a critical quality marker for GJE in the context of XNJ. Its quantifiable transfer characteristics provide a scientifically grounded means to monitor and ensure the consistency of GJE-derived active components throughout production. Consequently, this work significantly strengthens the quality control framework for both the botanical raw material and the finished traditional Chinese medicine injection, ensuring its pharmacological integrity from source to patient [24]. Although the core extraction methodology is protected under Chinese Patent CN107907611B, that patent primarily claims the method itself. This present study provides the first comprehensive application of this method to systematically track the transfer of a critical volatile marker, 4-methyleneisophorone, across the entire industrial production chain of XNJ—from raw material to finished product. This systematic validation and the resulting chemical data constitute the novel contribution of this work beyond the patent scope.
     To address this issue, there is a need to strengthen the quality control system of XNJ to ensure its safety, efficacy, and consistency in clinical applications. This study introduces a novel method combining steam distillation with liquid-liquid extraction to identify reliable chemical markers from GJE. GC-MS was used to analyze volatile components in both GJE and combined extracts of GJE and Radix Curcumae [25,26]. Two key sesquiterpene compounds—namely isophorone and 4-methyleneisophorone—were detected in both volatile oil extracts and XNJ samples. Among them, 4-methyleneisophorone was identified as a unique and consistent marker [27-29]. Its presence throughout the manufacturing process indicates that it can serve as a critical indicator for the quality evaluation of GJE, offering a foundation for a more robust quality assurance framework for XNJ [30-32].

2. MATERIALS AND METHODS

2.1 Materials
     The plant materials—GJE and Radix Curcumae—were authenticated by Prof. Lili Huang (Institute of Forest Medicinal Materials and Food, Jiangxi Academy of Forestry). GJE refers to the dried ripe fruits of GJE, and Radix Curcumae is derived from the tuberous roots of Curcuma wenyujin Y. H. Chen et C. Ling. XNJ was provided by Dali Pharmaceutical Co. Instrumentation included an Agilent 7890B GC-MS system equipped with an Agilent DB-23 MS capillary column (0.25 mm × 30 m, 0.25 μm film thickness). Reagents such as ethyl acetate, anhydrous sodium sulfate, petroleum ether, and n-hexane were all of analytical grade.

2.2 Preparation of GJE Volatile Oil Sample
     A total of 100 g of GJE powder (sieved through a 60-mesh screen) was placed in a 1 L round-bottom flask and mixed with distilled water (5–7 times the powder weight). Approximately 1–3 mL of ethyl acetate was added. A standard volatile oil extractor was assembled, and 20 mL of distilled water was added into the graduated collection chamber of the condenser. The mixture was gradually heated to boiling and kept at a gentle boil for 5–8 hours.
     After distillation, the ethyl acetate phase was collected in a 5 mL volumetric flask. The extractor was rinsed multiple times with ethyl acetate, and the rinsate was combined with the distillate to reach a final volume of 5 mL. A 2 mL aliquot was transferred into a 5 mL centrifuge tube, where 50 mg of anhydrous sodium sulfate was added to remove water. The dried solution was filtered through a 0.45 μm microporous membrane for GC-MS analysis. The sample preparation procedures were performed following the core principles outlined in Chinese Patent CN107907611B, which this study aims to validate and apply for quality marker tracking.

2.3 Preparation of GJE Steam Distillation Sample
     In the XNJ production process, 1500 mL of water was added to GJE and Radix Curcumae for steam distillation, resulting in 1000 mL of distillate. Musk was then introduced into the distillate, followed by an additional 250 mL of water for a second round of distillation, yielding another 1000 mL. Borneol was dissolved with 5 g of polysorbate 80, mixed into the distillate, then blended with 8 g of sodium chloride. After thorough mixing, the mixture was refrigerated overnight, filtered, filled, and sterilized.
     To assess GJE individually, 30 g of GJE powder (60-mesh) was distilled with 1500 mL of water. A total of 1000 mL of distillate was collected, then combined with 250 mL of water for a second distillation, again collecting 1000 mL. This was concentrated to 100 mL, then extracted three times with equal volumes of petroleum ether. The petroleum ether phase was evaporated under reduced pressure, and the residue was diluted to 1 mL with chromatographic-grade petroleum ether. The final solution was mixed thoroughly and filtered through a 0.45 μm membrane.

2.4 Preparation of XNJ Intermediate Sample
     Equal parts (30 g each) of pulverized and sieved (60-mesh) GJE and Radix Curcumae were combined with 1500 mL of distilled water and soaked for 12 hours. The mixture was then subjected to steam distillation. As the distillation commenced, 5 mL samples were collected at 15 and 30 minutes from the condenser outlet, followed by 5 mL samples every 30 minutes until the total volume reached 1000 mL.
     The distillate was concentrated to 100 mL and extracted 2–3 times with equal volumes of petroleum ether. The combined petroleum ether layers were concentrated under reduced pressure. The residue was dissolved in petroleum ether and diluted to 1 mL in a volumetric flask. The final solution was filtered through a 0.45 μm membrane.

2.5 Preparation of XNJ Final Product Sample
     A 10 mL sample of XNJ was extracted with an equal volume of low-polarity solvent 2–3 times. The combined extracts were concentrated under reduced pressure, re-dissolved in low-polarity solvent, and adjusted to 1 mL. The solution was thoroughly mixed and filtered through a 0.45 μm membrane.

2.6 GC-MS Analysis
     GC-MS was used to analyze the volatile oils from GJE, GJE compound extracts, and XNJ. The operating conditions are summarized in Table 1.

3. RESULTS AND DISCUSSION

3.1 Results
     Advancements in modern pharmaceutical manufacturing and analytical technologies have significantly reshaped the quality evaluation strategies for GJE. Techniques such as high-performance liquid chromatography (HPLC), ultra-high-performance liquid chromatography (UPLC), and chromatographic fingerprinting specific to traditional Chinese medicine have been systematically applied to strengthen quality control frameworks [33,34].
     A notable shift has occurred in the evaluation criteria for GJE, moving from a singular focus on geniposide quantification toward multi-component index analysis. Chromatographic fingerprinting was used to assess both the hydrophilic profile of GJE through HPLC and its volatile, lipophilic constituents via GC-MS. These profiles enabled comparative analysis of similarity coefficients among GJE samples collected from different geographical regions, providing insight into regional phytochemical diversity. In another study, the fingerprint profiles of GJE from different origins were evaluated based on the quantification of nine principal bioactive compounds [35,36].
     Peng Kaifeng’s extensive investigation further enriched this understanding by identifying 63 chemical constituents from GJE through advanced chromatographic methods. Structural elucidation was achieved using a combination of physical, chemical, and spectral techniques. Ensuring safety in clinical application remained a top priority; excessive concentrations of chemical constituents in herbal preparations may introduce new compounds or alter the pharmacokinetics upon administration. Therefore, stringent quality control measures are essential in regulating the active components of GJE and ensuring therapeutic consistency in traditional prescriptions [37].
     While the 2020 edition of the Chinese Pharmacopoeia includes geniposide as a quality marker for GJE, it does not cover the range of other pharmacologically active constituents present in classical formulations. This limited scope presents challenges in accurately evaluating GJE's role in such prescriptions. In the manufacturing process of XNJ, steam distillation is used to isolate volatile compounds, whereas geniposide, being non-volatile, is largely excluded. This distinction underscores the need to expand quality indicators beyond geniposide to better represent the contribution of GJE in formulations like XNJ and Angong Niuhuang pills.
     According to existing literature, several volatile components of GJE—such as β-isophorone, isophorone, 4-methyleneisophorone, (E,Z)-2,4-decadienal, and (E,E)-2,4-decadienal—have been identified through GC-MS analysis. Huang and colleagues applied ultraviolet spectroscopy to characterize nine major components in a single-step extraction of XNJ. Their findings, based on intermediate distillates of GJE and Radix Curcumae, confirmed that both isophorone and 4-methyleneisophorone originated exclusively from GJE—consistent with the current study's preliminary results.
     Notably, 4-methyleneisophorone was consistently detected in the volatile oil of GJE using GC-MS. This compound was also present in the steam distillation extract of GJE, in combined extracts with Curcuma wenyujin, and in the liquid-liquid extract of the final XNJ product. Its identification was supported by literature references, mass spectral database matching, and its prominence as Peak 1 in the GC-MS chromatogram (Figure 1).

3.2 Discussion
     Contemporary pharmacological studies have demonstrated that XNJ is capable of crossing the blood–brain barrier and exerting direct effects on the central nervous system. Post-administration, a marked reduction in blood–brain barrier permeability has been observed, along with therapeutic outcomes including neural regulation, neuroprotection, mitigation of cerebral edema, and improved microcirculation.
     Current quality control assessments for XNJ primarily focus on the final product, with particular attention to the levels of muscone, borneol, and sesquiterpenes derived from Radix Curcumae. While effective, these traditional chromatographic approaches often suffer from long extraction times and inconsistent batch-to-batch reproducibility. In contrast, the approach employed in this study offers several practical advantages: it is straightforward, cost-efficient, requires no pre-treatment, and enhances real-time visualization of the extraction process during industrial-scale production. The core extraction methodology referenced in this work has been formally protected under Chinese Patent CN107907611B. We are currently refining ancillary protocols to further optimize process standardization and validation parameters [38,39].
     The consistent detection of 4-methyleneisophorone throughout all production stages, as demonstrated in this study, serves as a successful practical validation of the patented method combining steam distillation with liquid-liquid extraction for its intended purpose of monitoring component transfer in complex traditional Chinese medicine injections. Therefore, while the patented method provides the technical framework, this research delivers the essential scientific validation and detailed analytical evidence required for its practical implementation in quality control. It confirms the method's robustness and identifies a specific, reliable chemical marker for monitoring GJE quality in XNJ, information not detailed in the patent.

4. CONCLUSIONS

     This study introduces a combined steam distillation–liquid-liquid extraction technique, followed by GC-MS analysis, to track the presence of 4-methyleneisophorone throughout the manufacturing pipeline. The compound was detected in GJE’s water extract, the intermediate products generated during extraction, and in the final XNJ formulation. These findings support its role as a reliable quality marker for GJE, offering a practical and scientifically grounded parameter to monitor the transfer and consistency of active constituents across the production stages. Ultimately, 4-methyleneisophorone emerges as a key indicator of GJE quality in the XNJ formulation. Its consistent presence from raw material to finished product reinforces its potential utility in refining quality control standards for traditional Chinese medicine injections. The focus of this study is on revealing the transfer characteristics of 4-methyleneisophorone. Its specific pharmacological and toxicological profiles require further investigation in future studies.
     Building on the foundation of the patented method and the chemical marker identified in this study, future work will focus on establishing quantitative thresholds for 4-methyleneisophorone in raw materials and intermediates to define actionable quality control standards. Furthermore, exploring the integration of this marker with rapid analytical techniques for online or at-line monitoring during production represents a promising direction for process analytical technology in traditional Chinese medicine manufacturing. Looking forward, the consistent transfer characteristics of 4-methyleneisophorone support its potential integration into formal quality control protocols. Specifically, its presence and concentration could be proposed as acceptance criteria for the GJE raw material and critical intermediates during production.
     This study, while providing a validated method and a reliable marker for the quality control of GJE in XNJ, also establishes a foundational dataset and a technical framework. It serves as a crucial prerequisite and supporting study for our ongoing research. Subsequent investigations will focus on developing quantitative assays based on 4-methyleneisophorone, conducting large-scale batch validation, and exploring the relationship between its transfer characteristics and pharmacological activity. These planned studies will form a comprehensive body of work, with the current manuscript representing the essential first step.

ACKNOWLEDGEMENTS

     The authors would like to express their gratitude to Dali Pharmaceutical Co. for providing the XNJ used in this study.

AUTHOR CONTRIBUTIONS

Pei Wu: Investigation, Formal analysis, Data curation, Writing - Original draft preparation, Writing - Reviewing and Editing. Jiajia Liu: Investigation, Methodology, Validation. Lei Zhang: Resources, Validation. Yu Ding: Software, Visualization. Lili Huang: Supervision, Writing - Reviewing and Editing. Lili Liu: Supervision, Project administration. Kangde Bao: Conceptualization, Resources, Supervision, Funding acquisition, Writing - Reviewing and Editing.

CONFLICT OF INTEREST STATEMENT

     The authors declare that they hold no competing interests.

DECLARATION OF GENERATIVE AI IN PREPARATION OF MANUSCRIPT

     During the preparation of this work, the authors used “DeepSeek” to improve the readability and language of the manuscript. After using this tool, the authors reviewed and edited the content as necessary and take full responsibility for the publication's content.

FUNDING

     This work was supported by Agreement on the Co-establishment of the National Technology Transfer Center of Zhejiang Sci-Tech University (Tongling) [grant number 25170018-V].

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