| Original Article |
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Uncarialines A-E, new alkaloids from Uncaria rhynchophylla and their anticoagulant activity |
| Ke-Pu Huang1,2, Li-Li Xu2, Sheng Li2, Yin-Ling Wei2, Lian Yang2, Xiao-Jiang Hao2, Hong-Ping He1, Yu Zhang2 |
1. School of Chinese Materia Medica, Yunnan University of Chinese Medicine, Kunming, 650500, People's Republic of China;
2. 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 |
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Abstract Uncarialines A-E (1-5), five undescribed monoterpene indole alkaloids, together with five known analogues were obtained from the stems of Uncaria rhynchophylla. Alkaloids 1-3 were unique 3,4-seco-tricyclic alkaloids with a 6/5/10 ring system, while 4 and 5 possessed a rare rearranged scaffold originated from corynantheine-type alkaloids with C-2/C-7 oxidation. Their structures were characterized by a comprehensive analysis of MS, NMR, and ECD. Their effects on blood clotting times of human plasma were evaluated and alkaloid 5 had a slight prolongation effect on both thrombin time and activated partial thromboplastin time (p<0.001).
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| Keywords
Uncaria rhynchophylla
Monoterpene indole alkaloids
Uncarialines A-E
Anticoagulant activity
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| Fund:This work was financially supported by Yunnan Applied Basic Research Projects (No. 202301AS070057), National Key R&D Program of China (No. 2022YFF1100301), and Yunnan Revitalization Talents Support Plan-Young Talent Project (to Y. Zhang). |
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Corresponding Authors:
Hong-Ping He,E-mail:hehongping@yahoo.com;Yu Zhang,E-mail:zhangyu@mail.kib.ac.cn
E-mail: hehongping@yahoo.com;zhangyu@mail.kib.ac.cn
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Issue Date: 18 May 2023
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1 Ndagijimana A, Wang XM, Pan GX, Zhang F, Feng H, Olaleye O. A review on indole alkaloids isolated from Uncaria rhynchophylla and their pharmacological studies. Fitoterapia. 2013;86:35-47.
2 Zhang Y, Bai X, Yuwen HS, Guo LL, Liu JW, Hao XJ. Alkaloids from Tabernaemontana divaricata combined with fluconazole to overcome fluconazole resistance in Candida albicans. Bioorg Chem. 2021;107:104515.
3 Zhang Y, Yuan YX, Goto M, Guo LL, Li XN, Morris-Natschke SL, Lee KH, Hao XJ. Taburnaemines A-I, cytotoxic vobasinyl-iboga-type bisindole alkaloids from Tabernaemontana corymbosa. J Nat Prod. 2018;81:562-71.
4 Faisal S, Badshah SL, Kubra B, Emwas AH, Jaremko M. Alkaloids as potential antivirals. A comprehensive review. Nat Prod Bioprospect. 2023;13:4.
5 Sun SF, Zhong HJ, Zhao YL, Ma XY, Luo JB, Zhu L, Zhang YT, Wang WX, Luo XD, Geng JW. Indole alkaloids of Alstonia scholaris (L.) R. Br. alleviated nonalcoholic fatty liver disease in mice fed with high-fat diet. Nat Prod Bioprospect. 2022;12:14.
6 Zhang Q, Zhao JJ, Xu J, Feng F, Qu W. Medicinal uses, phytochemistry and pharmacology of the genus Uncaria. J Ethnopharmacol. 2015;173:48-80.
7 Horie S, Yano S, Aimi N, Sakai S, Watanabe K. Effects of hirsutine, an antihypertensive indole alkaloid from Uncaria rhynchophylla, on intracellular calcium in rat thoracic aorta. Life Sci. 1992;50:491-8.
8 Zou L, Lu FY, Lin B, Zhou Y, Liu TT, Sun Y. Stability of alkaloids during drying process and their effect on anticoagulating activity of Uncariae Ramulus Cum Uncis. J Anal Methods Chem. 2019;2019:7895152.
9 Sakti AS, Nityasa AR, Saputri FC. Effect of Uncaria gambir and Uncaria sclerophylla on pulmonary-thromboembolism mice. Phcog J. 2020;12:192-6.
10 Gao L, Kong X, Wu W, Feng Z, Zhi H, Zhang Z, Long H, Lei M, Hou J, Wu W. Dissecting the regulation of arachidonic acid metabolites by Uncaria rhynchophylla (Miq). Miq. in spontaneously hypertensive rats and the predictive target sEH in the anti-hypertensive effect based on metabolomics and molecular docking. Front Pharmacol. 2022;13:909631.
11 Lu JH, Tan JQ, Durairajan SSK, Liu LF, Zhang ZH, Ma L, Shen HM, Chan HE, Li M. Isorhynchophylline, a natural alkaloid, promotes the degradation of alpha-synuclein in neuronal cells via inducing autophagy. Autophagy. 2012;8:98-108.
12 Azevedo BC, Morel LJF, Carmona F, Cunha TM, Contini SHT, Delprete PG, Ramalho FS, Crevelin E, Bertoni BW, França SC. Aqueous extracts from Uncaria tomentosa (Willd. ex Schult.) DC. reduce bronchial hyperresponsiveness and inflammation in a murine model of asthma. J Ethnopharmacol. 2018;218:76-89.
13 Sakakibara I, Terabayashi S, Kubo M, Higuchi M, Komatsu Y, Okada M, Taki K, Kamei J. Effect on locomotion of indole alkaloids from the hooks of Uncaria plants. Phytomedicine. 1999;6:163-8.
14 Qin N, Lu X, Liu Y, Qiao Y, Qu W, Feng F, Sun H. Recent research progress of Uncaria spp. based on alkaloids:phytochemistry, pharmacology and structural chemistry. Eur J Med Chem. 2021;210:112960.
15 Zhou HF, Li WY, Peng LY, Li XN, Zuo ZL, Zhao QS. Rhynchines A-E:Cav3.1 calcium channel blockers from Uncaria rhynchophylla. Org Lett. 2021;23:9463-7.
16 Xu Y, Wang R, Hou T, Li H, Han Y, Li Y, Xu L, Lu S, Liu L, Cheng J. Uncariphyllin A-J, indole alkaloids from Uncaria rhynchophylla as antagonists of dopamine D2 and Mu opioid receptors. Bioorg Chem. 2023;130:106257.
17 Yu ZL, Bai R, Zhou JJ, Huang HL, Zhao WY, Huo XK, Yang YH, Luan ZL, Zhang BJ, Sun CP. Uncarialins J-M from Uncaria rhynchophylla and their anti-depression mechanism in unpredictable chronic mild stress-induced mice via activating 5-HT1A receptor. Chin J Chem. 2021;39:1331-43.
18 Guo Q, Si X, Shi Y, Yang H, Liu X, Liang H, Tu P, Zhang Q. Glucoconjugated monoterpene indole alkaloids from Uncaria rhynchophylla. J Nat Prod. 2019;82:3288-301.
19 Guo Q, Yang H, Liu X, Si X, Liang H, Tu P, Zhang Q. New zwitterionic monoterpene indole alkaloids from Uncaria rhynchophylla. Fitoterapia. 2018;127:47-55.
20 Liang JH, Luan ZL, Tian XG, Zhao WY, Wang YL, Sun CP, Huo XK, Deng S, Zhang BJ, Zhang ZJ. Uncarialins A-I, monoterpenoid indole alkaloids from Uncaria rhynchophylla as natural agonists of the 5-HT1A receptor. J Nat Prod. 2019;82:3302-10.
21 Wenkert E, Cochran D, Hagaman E, Schell F, Neuss N, Katner A, Potier P, Kan C, Plat M, Koch M. Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. XIX. Aspidosperma alkaloids. J Am Chem Soc. 1973;95:4990-5.
22 Lim KH, Sim KM, Tan GH, Kam TS. Four tetracyclic oxindole alkaloids and a taberpsychine derivative from a Malayan Tabernaemontana. Phytochemistry. 2009;70:1182-6.
23 Cao XF, Wang JS, Wang XB, Luo J, Wang HY, Kong LY. Monoterpene indole alkaloids from the stem bark of Mitragyna diversifolia and their acetylcholine esterase inhibitory effects. Phytochemistry. 2013;96:389-96.
24 Ponglux D, Wongseripipatana S, Takayama H, Kikuchi M, Kurihara M, Kitajima M, Aimi N, Sakai SI. A new indole alkaloid, 7α-hydroxy-7H-mitragynine, from Mitragyna speciosa in thailand. Planta Med. 1994;60:580-1.
25 Kitajima M, Ohara S, Kogure N. New indole alkaloids from Melodinus henryi. Heterocycles. 2012;85:1949-59.
26 Kolodziejczyk-Czepas J, Ponczek M, Sady-Janczak M, Pilarski R, Bukowska B. Extracts from Uncaria tomentosa as antiplatelet agents and thrombin inhibitors-the in vitro and in silico study. J Ethnopharmacol. 2021;267:113494. |
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