Langaside,a novel secoiridolactone glycoside derivative from Tachiadenus longiflorus Griseb. (Gentianaceae) formed by a [2+2] cycloaddition reaction |
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| Institution: | 1. Natural Products Research Group, Department of Chemistry, Faculty of Engineering and Physical Science, University of Surrey, Guildford GU2 7XH, United Kingdom;2. School of Chemistry and Physics, University of KwaZulu-Natal, Durban 4041, South Africa;3. Malaria Research Unit, Institut Pasteur de Madagascar, BP 1274, Antananarivo, 101, Madagascar;4. Centre for Toxicology, Faculty of Health and Medical Sciences, University of Surrey, Guildford GU2 7XH, United Kingdom;1. College of Bioengineering, Beijing Polytechnic, Beijing 100029, China;2. College of Pharmacy, Dalian Medical University, Dalian 116044, China;3. The Second Affiliated Hospital of Dalian Medical University, Dalian 116044, China;1. Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650031, PR China;2. Yunnan Academy of Tobacco Science, China Tobacco Yunnan Industrial Co., Ltd., Kunming 650106, PR China;1. State Key Laboratory of Organic–Inorganic Composites, Beijing University of Chemical Technology, 100029 Beijing, PR China;2. Institute of Chemical Sciences, Gomal University, Dera Ismail Khan, KP, Pakistan;1. Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, People''s Republic of China;2. JNU-HKUST Joint Laboratory for Neuroscience & Innovative Drug Research, Jinan University, Guangzhou 510632, People''s Republic of China;3. College of Pharmacy, Wannan Medical College, Wuhu 241000, People''s Republic of China;1. Faculty of Pharmacy, Umm Al-Qura University, Makka, Saudi Arabia;2. Faculty of Pharmacy (Girls), Al-Azhar University, Nasr-City, Cairo, Egypt;3. Faculty of Pharmacy, Egyptian-Russian University, Cairo, Egypt;4. National Organization for Drug Control and Research, Dokki, P.O. 29, Cairo, Egypt |
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| Abstract: | Langaside (1), a secoiridoid lactone glucoside possessing a novel skeleton formed by a 2 + 2] cycloaddition reaction between the secoiridolactone glucoside, 1,9-trans-9,5-cis-sweroside, and p-coumaric acid was isolated from the fruits and flowers of the Malagasy Tachiadenus longiflorus Griseb. (Gentianaceae), alongside another seven known compounds. The structure of langaside was established using HRESIMS, IR and NMR spectroscopy and comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Langaside was screened for its neuritogenic activity against SHSY-5Y cells and anticancer activity against the NCI59 human tumour cell panel but not found to be active. |
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| Keywords: | Langaside Secoiridolactone Sweroside Gentiopicrin SHSY-5Y cells |
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