Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima |
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| Affiliation: | 1. Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University, 601# Huangpu Avenue West, Guangzhou 510632, People’s Republic of China;2. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Jinan University, 601# Huangpu Avenue West, Guangzhou 510632, People’s Republic of China;3. School of Life Sciences, The Chinese University of Hong Kong, Shatin, Hong Kong, People’s Republic of China;1. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, PR China;2. Joint Laboratory for Neuroscience & Innovative Drug Research, Jinan University, Guangzhou 510632, PR China;3. State Key Laboratory of Quality Research in Chinese Medicine and Institute of Chinese Medical Sciences, University of Macau, Macao;1. Dipartimento di Scienze del Farmaco, Università di Padova, Padova, Italy;2. Dipartimento di Salute della Donna e del Bambino – SDB, Laboratorio di Oncoematologia, Università di Padova, Padova, Italy;3. Scuola di Scienze del Farmaco e dei Prodotti della Salute, Università di Camerino, Camerino, Italy;4. Dipartimento di Biologia Ambientale, Università “La Sapienza” Roma, Italy;1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People’s Republic of China;2. University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China;1. Department of Microbiology and Immunology, Montana State University, Bozeman, MT 59717, United States;2. International Research and Production Holding “Phytochemistry”, Karaganda 100009, Kazakhstan;1. School of Pharmacy, Sungkyunkwan University, Suwon, Gyeonggi-do 16419, Republic of Korea;2. College of Pharmacy, Kyungsung University, Busan 48434, Republic of Korea;3. Division of Life Sciences, Korea Polar Research Institute, KIOST, Incheon 21990, Republic of Korea;4. School of Chemical Engineering, Sungkyunkwan University, Suwon, Gyeonggi-do 16419, Republic of Korea;5. Department of Medicine, Dankook University, Cheonan, Chungnam 31116, Republic of Korea;1. Department of Oral and Maxillofacial Surgery, Dokkyo Medical University School of Medicine, 880 Kitakobayashi, Mibu, Shimo-Tsuga, Tochigi 321-0293, Japan;2. Section of Dentistry, and Oral and Maxillofacial Surgery, Sano Kosei General Hospital, 1728 Horigome-cho, Sano, Tochigi 327-8511, Japan;3. Section of Dentistry, and Oral and Maxillofacial Surgery, Kamma Memorial Hospital, 2-5 Ooguro-cho, Nasushiobara, Tochigi 373-0033, Japan |
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| Abstract: | Pseudoguaianolide sesquiterpene lactones minimolides A (1), B (2), C (3) and D (4) and two guaianolide sesquiterpene lactones minimolides E (5) and F (6), along with seven known ones (7–13), were isolated from the supercritical fluid extract of Centipeda minima. The structures of these compounds were elucidated by extensive spectroscopic methods (IR, UV, HRESIMS, 1D-NMR and 2D-NMR), and the complete structure and stereochemistry of 1 was further confirmed by X-ray diffraction analysis. Compounds 1, 5–8, 11 and 13 displayed inhibitory activity against human nasopharyngeal cancer cells (CNE) with IC50 values ranging from 1.1 to 20.3 μM. Compound 13 containing both α-methylene-γ-lactone and α, β-unsaturated cyclopentenone moieties exhibited even stronger inhibitory activity than that of cisplatin (positive control) through cell cycle arrest at G2/M phase. Isolation of six sesquiterpene lactones from Centipeda minima highlighted the potential of supercritical fluid extraction for enrichment of minor constituents for phytochemical study. |
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