Objective To study the chemical constituents of n-butanol fraction from ethanol extract of leaves of Cinnamomum cassia.
Methods The leaves of Cinnamomum cassia were extracted and concentrated to obtain an extract, which was separated and purified using separation techniques such as Silica gel column chromatography, Sephdex LH-20 column chromatography and semi-preparative HPLC. The structures were identified by spectroscopic analysis.
Results Six compounds were isolated from the leaves of Cinnamomum cassia, and identified as cinncassiol D1, vignaticol, (-)-(1R, 2R, 4S, 5R, 8S, 9S)-clovane-2,9,14-triol, (3S, 5R, 6R, 7E, 9S)-megastigman-7-ene-3,5,6,9-tetrol 3-O- β-D-glucopyranoside, tachioside and n-butyl-α-D-fructofuranoside.
Conclusion Compounds 2-6 are all isolated from Cinnamomum cassia for the first time.
1.中国药典 2020年版. 一部[S]. 2020: 91-92.
2.张笮晦, 童永清, 黄广智, 等. 肉桂叶化学成分及药理作用研究进展[J]. 广州化工, 2019, 47(1): 20-22. [Zhang ZM, Tong YQ, Huang GZ, et al. Research progress on chemical components and pharmacological activities of Cinnamomum cassia leaves[J]. Guangzhou Chemical Industry, 2019, 47(1): 20-22.] DOI: 10.3969/j.issn.1001-9677.2019.01.010.
3.曾俊芬, 朱虎成, 周忠泉. 肉桂皮及叶中木脂素类化学成分的研究[J]. 中国药师, 2017, 20(5): 781-784. [Zeng JF, Zhu HC, Zhou ZQ. Study on the lignans from barks and leaves of Cinnamomum cassia[J]. China Pharmacist, 2017, 20(5): 781-784.] DOI: 10.3969/j.issn.1008-049X.2017.05.002.
4.Zhou L, Tuo Y, Hao Y, et al. Cinnamomols A and B, immunostimulative diterpenoids with a new carbon skeleton from the leaves of Cinnamomum cassia[J]. Org Lett, 2017, 19(11): 3029-3032. DOI: 10.1021/acs.orglett.7b01323.
5.Zhou L, Zheng G, Li H, et al. Highly oxygenated isoryanodane diterpenoids from the leaves of Cinnamomum cassia and their immunomodulatory activities[J]. Phytochemistry, 2022, 196: 113077. DOI: 10.1016/j.phytochem.2021.113077.
6.Zhou L, Zheng GJ, Jin PF, et al. A new megastimane sesquiterpenoid from the leaves of Cinnamomum cassia[J]. J Asian Nat Prod Res, 2022, 24(9): 877-883. DOI: 10.1080/10286020.2021.1981872.
7.Shu PH, Wei XL, Xue YB, et al. Wilsonols A-L, megastigmane sesquiterpenoids from the leaves of Cinnamomum wilsonii[J]. J Nat Prod, 2013, 76(7): 1303-1312. DOI: 10.1021/np4002493.
8.Nohara T, Kashiwada Y, Murakami K, et al. Constituents of Cinnamomi cortex. V. structures of five novel diterpenes, cinncassiols D1, D1 glucoside, D2, D2 glucoside and D3[J]. Chem & Pharm Bull, 1981, 29(9): 2451-2459. DOI: 10.1248/cpb.29.2451.
9.Fraga BM, González-Coloma A, Gutiérrez C, et al. Insect antifeedant isoryanodane diterpenes from Persea indica[J]. J Nat Prod, 1997, 60(9): 880-883. DOI: 10.1021/np970167e.
10.Dong LP, Liu HY, Ni W, et al. Four new compounds from the leaves of Acer truncatum[J]. Chem Biodivers, 2006, 3(7): 791-798. DOI: 10.1002/cbdv.200690081.
11.Otsuka H, Hirata E, Shinzato T, et al. Stereochemistry of megastigmane glucosides from Glochidion zeylanicum and Alangium premnifolium[J]. Phytochemistry, 2003, 62(5): 763-768. DOI: 10.1016/S0031-9422(02)00614-3.
12.Jiang HB, Shao SY, Wei YZ, et al. Phenolic glycosides and indole alkaloids isolated from the roots and rhizomes of Clematis chinensis and their anti-inflammatory activity[J]. Phytochemistry, 2023, 215: 113832. DOI: 10.1016/j.phytochem.2023.113832.
13.Liu Y, Wu DD, Luo YM, et al. New sesquiterpenoid and aliphatic glycoside from the roots of Datura[J]. Phytochem Lett, 2022, 50: 15-20. DOI: 10.3760/cma.j.cn101379-20190915-00075.
14.Zeng J, Xue Y, Shu P, et al. Diterpenoids with immunosuppressive activities from Cinnamomum cassia[J]. J Nat Prod, 2014, 77(8): 1948-1954. DOI: 10.1021/np500465g.
15.Zhou H, Guoruoluo Y, Tuo Y, et al. Cassiabudanols A and B, immunostimulative diterpenoids with a cassiabudane carbon skeleton featuring a 3-oxatetracyclo [6.6.1.0(2,6).0(10,14)] pentadecane scaffold from Cassia buds[J]. Org Lett, 2019, 21(2): 549-553. DOI: 10.1021/acs.orglett.8b03883.
16.Zhang C, Fan L, Fan S, et al. Cinnamomum cassia presl: a review of its traditional uses, phytochemistry, pharmacology and toxicology[J]. Molecules, 2019, 24(19): 3473. DOI: 10.3390/molecules24193473.
17.Liu ST, Yang L, Zheng SW, et al. A review: the botany, ethnopharmacology, phytochemistry, pharmacology of Cinnamomi cortex[J]. RSC Advances, 2021, 11: 27461-27497. DOI: 10.1039/d1ra04965h.
18.Rao Z, Xu F, Wen T, et al. Protective effects of essential oils from Rimulus cinnamon on endotoxin poisoning mice[J]. Biomed Pharmacother, 2018, 101: 304. DOI: 10.1016/j.biopha.2018.02.092.
19.李富欣, 孙丹丹. 倍半萜类化合物生物活性研究进展[J]. 河南中医, 2024, 44(5): 797-803. [Li FX, Sun DD. Research progress of biological activity of sesquiterpene compounds[J]. Henan Traditional Chinese Medicine, 2024, 44(5): 797-803.] DOI: 10.16367/j.issn.1003-5028.2024.05.0147.
20.Lee IK, Kim KH, Lee SY, et al. Three new megastigmane glucopyranosides from the Cardamine komarovii[J]. Chem Pharm Bull, 2011, 59(6): 773-777. DOI: 10.1248/cpb.59.773.
21.卢闵, 饶佳丽, 郭瑜婕, 等. 天麻素药理活性及新制剂的研究进展[J]. 药品评价, 2023, 20(8): 916-920. [Lu M, Rao JL, Guo YJ. et al. Research progress on pharmacological activity and new preparation of gastrodin[J]. Drug Evaluation, 2023, 20(8): 916-920.] DOI: 10.19939/j.cnki.1672-2809.2023.08.02.
22.赵凯, 薛培凤, 屠鹏飞. 肉桂的化学成分及其生物活性研究进展[J]. 内蒙古医科大学学报, 2013, 35(1): 63-74. [Zhao K, Xue PF, Tu PF. Research progress on chemical constituents and pharmacological activities of Cinnamon (Cinnamomum cassia)[J]. Journal of Inner Mongolia Medical University, 2013, 35(1): 63-74.] DOI: 10.3969/j.issn.1004-2113.2013.01.013.