Diterpenoids from the needles and twigs of the cultivated endangered pine Pinus kwangtungensis and their PTP1B inhibitory effects |
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| Affiliation: | 1. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, PR China;2. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, PR China;1. Key Laboratory of Modern Preparation of TCM, Jiangxi University of Traditional Chinese Medicine, Ministry of Education, Nanchang 330004, China;2. Jiangxi Pharmaceutical School, Nanchang 330004, China;1. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai, 201203, PR China;2. Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA, 19104-6323, United States;3. CAS Key Laboratory of Receptor Research, Shanghai Institute of Material Medica, Chinese Academy of Sciences, No. 555 Zuchongzhi Road, Shanghai, 201203, PR China;1. Institute of Agricultural and Environmental Sciences, Estonian University of Life Sciences, Kreutzwaldi 1, Tartu 51014, Estonia;2. Department of Biology, University of Louisville, Louisville, KY 40292, USA;3. Institute of Technical and Natural Sciences Research-Development of “Aurel Vlaicu” University, 2 Elena Dragoi St., Arad 310330, Romania;4. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan;5. Ecological Chemistry Group, Department of Chemistry, KTH, Royal Institute of Technology, 100 44 Stockholm, Sweden;6. Institute of Technology, University of Tartu, Nooruse 1, Tartu 50411, Estonia;7. Estonian Academy of Sciences, Kohtu 6, 10130 Tallinn, Estonia;1. Department of Natural Products Chemistry, School of Pharmacy, Fudan University, No. 826 Zhangheng Road, Shanghai 201203, PR China;2. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, No. 555 Zuchongzhi Road, Shanghai 201203, PR China;3. Institute of Bioengineering and Nanotechnology, 31 Biopolis Way, The Nanos 138669, Singapore;1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, PR China;2. University of Chinese Academy of Sciences, Beijing 10039, PR China |
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| Abstract: | Pinus kwangtungensis is an endangered pine species native to China. In the present study, 15 diterpenoids including three new labdane-type analogs were isolated and characterized during a pioneer phytochemical investigation on a mass-limited sample of the needles and twigs of this plant, which is growing in a Cantonese garden. The new structures, (4S,5R,9S,10R)-6-oxo-labd-7,13-dien-16,15- olid-19-oic acid (1), 15(S)-n-butoxypinusolidic acid (2), and β-d-glucopyranosyl- (4S,5R,9S,10R)-labda-8(17),13-dien-15,16-olid-19-oate (3), were established by extensive spectroscopic methods and some chemical transformations. Among the isolates, lambertianic acid (10) and cassipourol (15) showed inhibitory activities against human protein tyrosine phosphatase 1 B (PTP1B), a target for the treatment of type-II diabetes and obesity, with IC50 values of 25.5 and 11.2 μM, respectively. |
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| Keywords: | Pinaceae Endangered plant Diterpenoids PTP1B inhibition |
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