VIETNAM NATIONAL UNIVERSITY HO CHI MINH CITY HO CHI MINH CITY UNIVERSITY OF TECHNOLOGY NGUYEN HUYNH HUONG THAO ENRICHMENT OF THE BIOACTIVE COMPONENTS FROM THE RESIDUE OF ROSEMARY (Rosmarinus officinalis L.) LEAF AFTER DISTILLATION BY USING MACROPOROUS RESIN Major: Chemical Engineering Major code: 8520301 MASTER THESIS HO CHI MINH CITY, JANUARY 2024 THIS THESIS IS COMPLETED AT HO CHI MINH CITY UNIVERSITY OF TECHNOLOGY – VNU-HCM Supervisor: Dr. Le Xuan Tien Examiner 1: Assoc. Mai Huynh Cang Examiner 2: Dr. Le Vu Ha This master’s thesis is defended at HCM City University of Technology, VNU- HCM City on 26th January 2024.
Master’s Thesis Committee: (Please write down full name and academic rank of each member of the Master’s Thesis Committee) 1. Nguyen Thi Phuong Phong (Committee Chair) 2. Mai Huynh Cang (Thesis Advisor 1) 3. Tong Thanh Danh (Committee Member) 4.
Le Vu Ha (Thesis Advisor 2) 5. Nguyen Dang Khoa (Committee Secretary) Approval of the Chair of Master’s Thesis Committee and Dean of Faculty of Chemical Engineering after the thesis being corrected (If any) CHAIR OF THESIS COMMITTEE DEAN OF FACULTY OF CHEMICAL ENGINEERING VIETNAM NATIONAL UNIVERSITY - HO CHI MINH CITY SOCIALIST REPUBLIC OF VIETNAM HO CHI MINH CITY UNIVERSITY OF TECHNOLOGY Independence – Freedom - Happiness THE TASK SHEET OF MASTER’S THESIS Full name: Nguyen Huynh Huong Thao Student ID: 2270014 Date of birth: 18th March 1999 Place of birth: Long An Major: Chemical engineering Major ID: I. THESIS TITLE (In Vietnamese): Làm giàu hoạt chất kháng oxy hoá từ bã chưng cất lá hương thảo (Rosmarinus officinalis L.) bằng nhựa hấp phụ. THESIS TITLE (In English): Enrichment of the bioactive components from the residue of rosemary (Rosmarinus officinalis L.) leaf after distillation by using macroporous resin.
TASKS AND CONTENTS: - Obtain the rosemary leaves’s residue after one hour of distillation, and evaluate the potential of reusing the residue extract. - Investigate the conditions of adsorption and desorption process to enhance the content of actives in residue extract by using macroporous resin. - Evaluate the antioxidant capacity of enriched extract in artificial sebum. THESIS START DAY: 6th February 2023 V.
THESIS COMPLETION DAY: 10th December 2023 VI. Le Xuan Tien Ho Chi Minh City, 26th January 2024 SUPERVISOR HEAD OF DEPARTMENT DEAN OF FACULTY OF CHEMICAL ENGINEERING ACKNOWLEDGEMENTS The process of scientific research over six years at the Ho Chi Minh University of Technology is marked by the distinguished pages of my master's thesis. Completing this thesis was not only my effort and dedication but also a journey filled with emotions alongside the collaborative atmosphere of Laboratory 401B2. I greatly appreciate Dr.
Le Xuan Tien - my dedicated mentor who guided me in the early days of research. He not only taught me diligently but also helped me build essential knowledge and develop comprehensive soft skills to break stereotypes about a master's degree. Simultaneously, my family has always been a strong support, spiritual support whenever I felt weary. The encouragement from my family provided the strength for me to continue on the chosen path.
A few lines of gratitude cannot describe the immense sacrifices of my parents, who always hoped to see their little daughter grow day by day and reach further in my career. Thanks to my grandmother and younger sister as well for taking care of every meal and sleep and always listening to me whenever I need. Next, I extend my thanks to two partners, Luu Bao Chau and Nguyen Anh Khoa, who accompanied me during the research process. I appreciate their efforts and collaboration in resolving challenging issues.
I wish them continued passion in their future endeavors. Furthermore, the suggestions from Minh Chau significantly contributed to improving the quality of my thesis. I appreciate the valuable time she spent supporting me in the research process. In addition to the direct support from teachers, family, and friends, I want to express my heartfelt thanks to Vo Minh Khai - a friend who was always by my side, providing moments of relaxation after the pressured research period.
Thank you for overcoming the distance to join me for meals, I hope our future times together will be beautiful. A few words cannot encapsulate everything, and I want to express my final thanks to those friends and companions who stood by me throughout this journey. iii I hope to keep my passion for Chemistry and contribute to the research efforts for future generations. Quá trình nghiên cứu khoa học hơn 6 năm tại ngôi trường Đại học Bách Khoa – ĐHQG TPHCM được đánh dấu bằng những trang luận văn thạc sĩ đầy danh giá.
Để hoàn thành bài luận văn này không chỉ là sự cố gắng và nỗ lực của riêng bản thân em, mà còn là cả một chặng đường đầy cảm xúc với tập thể phòng thí nghiệm 401B2. Em xin dành lời cảm ơn chân thành và sâu sắc nhất đến TS. Lê Xuân Tiến - người thầy tận tình chỉ dạy em trong những ngày đầu nghiên cứu. Đồng thời thầy là người giúp em xây dựng nền tảng kiến thức vững chắc, phát triển toàn diện các kĩ năng mềm để xoá tan định kiến về một thạc sĩ giấy từ lâu nay.
Song song đó, gia đình luôn là điểm tựa vững chắc, là hậu phương mỗi khi em mệt mỏi, chính những sự động viên không ngừng từ gia đình đã tiếp thêm cho em dũng khí bước tiếp trên con đường mình đã chọn. Vài dòng tâm thư không thể sánh được với sự hi sinh lớn lao của ba mẹ, những người luôn mong đứa con gái bé nhỏ từng ngày trưởng thành, tiến xa hơn trên con đường sự nghiệp. Cảm ơn ngoại và em gái, người luôn chăm chút từng bữa cơm, giấc ngủ và là nơi lắng nghe những trải lòng của em sau tháng ngày dài nghiên cứu. Tiếp đến là lời cảm ơn dành cho hai người em Lưu Bảo Châu và Nguyễn Anh Khoa đã đồng hành vùng em trong quá trình nghiên cứu.
Cảm ơn các em đã không kể công sức, lăn xả cùng chị giải quyết những vấn đề khó khăn, chúc các em tương lai sau này mãi giữ lòng nhiệt huyết như ban đầu. Bên cạnh đó, chính những lời góp ý chân thành từ chị Minh Châu đã giúp em hoàn thiện bản thảo luận văn tốt hơn, cảm ơn chị đã dành thời gian quí báu của mình hỗ trợ em trong quá trình nghiên cứu. Bên cạnh những sự hỗ trợ trực tiếp từ thầy cô, người thân và bạn bè, em muốn gửi lời cảm ơn chân thành đến bạn Võ Minh Khải - người bạn luôn bên cạnh em, mang đến những phút giây thư giãn sau khoảng thời gian nghiên cứu đầy áp lực. Cảm ơn bạn đã không ngại khoảng cách xa xôi sang đón mình đi ăn, mong rằng khoảng thời gian sau này của hai chúng ta mãi mãi tốt đẹp.
iv Đôi lời muốn nói không thể gói gọn trong vài trang giấy, em xin dành lời cảm ơn gửi đến những người bạn, người em đã luôn bên cạnh em trong suốt chặng đường qua. Bản thân em hi vọng chính mình luôn giữ lửa đam mê ngành Hoá, góp phần đóng góp vào công cuộc nghiên cứu cho thế hệ mai sau. Trân trọng cảm ơn. v ABSTRACT Rosemary (Rosmarinus officinalis L.) is known as a plant with a pleasant fragrance, and its essential oil is often extracted by steam distillation.
Additionally, the portion of polyphenols that are less volatile in rosemary residue is considered a rich source of antioxidant compounds. Therefore, the study aims to utilize rosemary residue to increase the content of carnosol and carnosic acid in the extract by using macroporous resin, serving the application of antioxidant properties in artificial sebum. The results showed that DM301 resin was suitable for the adsorption process, achieving an adsorption ratio of 82.52% for carnosol and 93.27% for carnosic acid. Regarding desorption, the thesis determined that 99.5% (v/v) ethanol was an effective type of solvent for removing target compounds from the DM301 resin surface, with a desorption time of 60 minutes and a resin: solvent ratio of 1:70 g/mL.
Under these conditions, desorption ratios were 88.49% for carnosol and 83.01% for carnosic acid. The research was examined the purity of carnosol in static desorption extract (32.99%) and gradient concentration extract (23. For carnosic acid, the purity in the gradient concentration extract (70.4 times higher than that in static desorption (15. Lastly, the concentration of the 400 ppm enriched extract (gradient concentration extract) exhibited a 3.5 times higher antioxidant capacity for artificial sebum compared to the RDR extract at the same concentration, with values of 45.47 mg MDA/kg sample and 154.22 mg MDA/kg sample, respectively.
vi THE COMMITMENT OF AUTHOR The thesis was carried out at Ho Chi Minh University of Technology and I declare that this is an original work. Under the guidance of Dr. Le Xuan Tien, the research results and conclusions in this thesis are honest and not copied from any source in any form. This work has yet to be submitted for any other award at any other university.
Nguyen Huynh Huong Thao vii LIST OF CONTENTS ABSTRACT. vi LIST OF FIGURES. xi LIST OF TABLES. xiii CHAPTER 1 : LITERATURE REVIEW.
AN OVERVIEW OF CARNOSIC ACID AND CARNOSOL:. Anti-inflammatory activity:. Anti-cancer activity:. MACROPOROUS ADSORPTION RESIN:.
Characteristics of macroporous resin:. The HPD – 100 resin:. The DM – 301 resin:. The XAD – 7HP resin:.
The potential applications of macroporous resins in the future:. AN OVERVIEW OF ACNE AND THE MECHANISM OF ACNE FORMATION ON THE SKIN:. SUMMARIZE THE FOREIGN AND DOMESTIC RESEARCH:. 21 viii CHAPTER 2 : EXPERIMENTAL.
OBJECTIVE AND RESEARCH CONTENT:. Method for measuring moisture content:. The extraction process of rosemary leaves:. Investigate the adsorption and desorption ratio of macroporous resins: 27 2.
The quantification method of target compounds in extract after adsorption in macroporous resin:. 33 CHAPTER 3 : RESULT & DISCUSSION. Distillation efficiency of rosemary essential oil by steam distillation method:. The extraction efficiency:.
The polyphenol content in dried rosemary leaves and RDR extract:. Investigation of factors affecting the adsorption capacity of macroporous resin:. Selection of the suitable solvents for dissolving rosemary extract:. Investigation of the adsorption capacity of three types of resins:.
Selecting the macroporous resin based on the content of carnosol and carnosic acid:. Investigation of factors affecting the desorption capability of the resin:59 3. Selection of desorption solvent:. Selecting the desorption time:.
Selection of desorption solvent volume:. Comparison of the carnosol and carnosic acid content in the initial extract and purified extract:. Enrichment of carnosol and carnosic acid by resin column:. Qualitative analysis by thin-layer chromatography (TLC):.
Quantification of the content of target compounds by HPLC:. Determine the TBARS value in artificial sebum:. 70 CHAPTER 4 : CONCLUSION AND DISCUSSION. 74 x LIST OF FIGURES Figure 1.1: Map of rosemary distribution in the world [98] .2: The shape of rosemary species .3: The structure of carnosic acid .4: Meat sample before and after metmyoglobin formation .5: The structure of carnosol .6: The shape of three macroporous resins .7: The components of sebum in pore .1: Rosemary dried leaves .2: Rosemary leaves after grinding .3: The extraction process of rosemary leaves .4: The procedure of calculating the adsorption .5: Carnosic acid standard calibration .6: Carnosol standard calibration .7: Gallic acid standard calibration .8: The reaction between MDA and TBA .9: The MDA calibration in artificial sebum.1: The main (a) and the secondary products (b) of steam distillation method from dried rosemary leaves .2: The comparison between the extraction efficiency of initial dried rosemary leaves and RDR extract .