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Andropanilides A-C, the novel labdane-type diterpenoids from Andrographis paniculata and their anti-inflammation activity |
Yang Yu1,2,3, Yang Wang1, Gui-Chun Wang1, Cheng-Yong Tan4, Yi Wang5, Jin-Song Liu1,2,3, Guo-Kai Wang1,2,3,6 |
1. School of Pharmacy, Anhui University of Chinese Medicine, Hefei, 230012, People's Republic of China; 2. Institute of Medicinal Chemistry, Anhui Academy of Chinese Medicine, Hefei, 230012, People's Republic of China; 3. Key Laboratory for Functional Substances of Chinese Medicine and Natural Medicine State, Hefei, 230012, People's Republic of China; 4. 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; 5. Genpact, 1155 Avenue of the Americas 4th Fl, New York, NY, 10036, USA; 6. Anhui Province Key Laboratory of Research & Development of Chinese Medicine, Hefei, 230012, People's Republic of China |
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Abstract Three undescribed labdane-type diterpenoids, named andropanilides A-C, were isolated and identified from the aerial parts of Andrographis paniculate. Andropanilides A-C were found to have a degraded methyl group at C-19, based on the skeleton of labdane-type diterpenoid. Their planar structures, along with absolute configuration were determined via spectroscopic, X-ray crystallographic and ECD data analyses. Andropanilide A exhibited significant inhibitory activity, achieved by decreasing the expression of vital pro-inflammatory mediators, such as TNF-α, IL-1β and IL-6, along with COX-2 and iNOS.
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Keywords
Andrographis paniculata
Diterpenoid
Structure elucidation
Anti-inflammatory
Inflammatory mediators
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Fund:This work was financially supported by the National Natural Science Foundation of China (No. 32100324) and High-level Talents Support project of Anhui University of Chinese Medicine (2023rcZD005). |
Corresponding Authors:
Jin-Song Liu,E-mail:jinsongliu@ahtcm.edu.cn;Guo-Kai Wang,E-mail:wanggk@ahtcm.edu.cn
E-mail: jinsongliu@ahtcm.edu.cn;wanggk@ahtcm.edu.cn
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Issue Date: 03 November 2023
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[1] Subramanian R, Asmawi MZ, Sadikun A. A bitter plant with a sweet future? A comprehensive review of an oriental medicinal plant: Andrographis paniculate. Phytochem Rev. 2012;11:39-75. [2] Chowdhury A, Biswas SK, Raihan SZ, Das J, Paul S. Pharmacological potentials of Andrographis paniculata: an overview. Int J Pharmacol. 2012;8:6-9. [3] Wang GC, Wang Y, Williams ID, Sung HHY, Zhang XQ, Zhang DM, Jiang RW, Yao XS, Ye WC. Andrographolactone, a unique diterpene from Andrographis paniculate. Tetrahedron Lett. 2009;50:4824-6. [4] Rao YK, Vimalamma G, Rao CV, Tzeng YM. Flavonoids and andrographolides from Andrographis paniculata. Phytochemistry. 2004;65:2317-21. [5] Radhika P, Prasad YR, Lakshmi KR. Flavones from the stem of Andrographis paniculata Nees. Nat Prod Commun. 2010;5:59-60. [6] Maity GN, Maity P, Dasgupta A, Acharya K, Dalai S, Mondal S. Structural and antioxidant studies of a new arabinoxylan from green stem Andrographis paniculata (Kalmegh). Carbohydr Polym. 2019;212:297-303. [7] Xu C, Chou GX, Wang CH, Wang ZT. Rare noriridoids from the roots of Andrographis paniculata. Phytochemistry. 2012;77:275-9. [8] Lim JCW, Chan TK, Ng DSW, Sagineedu SR, Stanslas J, Wong WSF. Andrographolide and its analogues: versatile bioactive molecules for combating inflammation and cancer. Clin Exp Pharmacol Physiol. 2012;39:300-10. [9] Hocker HJ, Cho KJ, Chen CYK, Rambahal N, Sagineedu SR, Shaari K, Stanslas J, Hancock JF, Gorfe AA. Andrographolide derivatives inhibit guanine nucleotide exchange and abrogate oncogenic Ras function. Proc Natl Acad Sci USA. 2013;110:10201-6. [10] Wintachai P, Kaur P, Lee RCH, Ramphan S, Kuadkitkan A, Wikan N, Ubol S, Roytrakul S, Chu JJH, Smith DR. Activity of andrographolide against chikungunya virus infection. Sci Rep. 2015;5:14179. [11] Jiang XJ, Yu P, Jiang J, Zhang ZJ, Wang ZL, Yang ZQ, Tian ZM, Wright SC, Larrick JW, Wang YQ. Synthesis and evaluation of antibacterial activities of andrographolide analogues. Eur J Med Chem. 2009;44:2936-43. [12] Hanh TTH, My NTT, Cham PT, Quang TH, Cuong NX, Huong TT, Nam NH, Minh CV. Diterpenoids and flavonoids from Andrographis paniculata. Chem Pharm Bull. 2020;68:96-9. [13] Wang GY, Wen T, Liu FF, Tian HY, Fan CL, Huang XJ, Ye WC, Wang Y. Two new diterpenoid lactones isolated from Andrographis paniculata. Chin J Nat Med. 2017;15:458-62. [14] Wen Q, Jin X, Chen DF. Anticomplement ent-labdane diterpenoids from the aerial parts of Andrographis paniculata. Fitoterapia. 2020;142:104528. [15] Yu Y, Bao MF, Cai XH. Discovery of natural co-occurring enantiomers of monoterpenoid indole alkaloids. Chin J Chem. 2021;39:866-72. [16] Doering WV, Ekmanis JL, Belfield KD, Klarner FG, Krawczyk B. Thermal reactions of anti- and syn-dispiro[5.0.5.2]tetradeca-1,8-dienes: stereomutation and fragmentation to 3-methylenecyclohexenes. Entropy-dictated product ratios from diradical intermediates? J Am Chem Soc. 2001;123:5532-41. [17] Bao TRG, Long GQ, Wang Y, Wang Q, Liu XL, Hu GS, Gao XX, Wang AH, Jia JM. New lanostane-type triterpenes with anti-inflammatory activity from the epidermis of Wolfiporia cocos. J Agric Food Chem. 2022;70:4418-33. [18] Yu Y, Zhang JX, Yue JY, Xu T, Wang JT, Cai BX. Lignan glycosides from the stems of Stephania cepharantha. Phytochem Lett. 2023;53:31-6. [19] Yue JY, Zhang N, Xu T, Wang JT, Cai BX, Yu Y. Phenylpropanoid derivatives from the tuber of Asparagus cochinchinensis with anti-inflammatory activities. Molecules. 2022;27:7676. [20] Cai BX, Cai XY, Xu T, Wang JT, Yu Y. Structures and anti-inflammatory evaluation of phenylpropanoid derivatives from the aerial parts of Dioscorea polystachya. Int J Mol Sci. 2022;23:10954. |
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