Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China

doi:10.1007/s13659-022-00326-3

应用天然产物 ›› 2022, Vol. 12 ›› Issue (1): 1-14.DOI: 10.1007/s13659-022-00326-3

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Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China

Lu Zhang¹, Ping Yi², Hui Yan¹, Xiao-Nian Li¹, Meng-Yuan Xia¹, Jun Yang¹, Ji-Feng Luo¹, Yue-Qiu He³, Yue-Hu Wang¹

1 Key Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and 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;
2 Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 550014, People's Republic of China;
3 Faculty of Plant Protection, Yunnan Agricultural University, Kunming 650201, People's Republic of China

收稿日期:2021-12-21 修回日期:2022-01-09 出版日期:2022-02-24 发布日期:2022-03-12
通讯作者: Yue-Qiu He, Yue-Hu Wang
基金资助:
This study was supported by Beijing Sino-Science Aquilaria Technology Co., Ltd., Beijing, China (no. KET202101).

Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China

Lu Zhang¹, Ping Yi², Hui Yan¹, Xiao-Nian Li¹, Meng-Yuan Xia¹, Jun Yang¹, Ji-Feng Luo¹, Yue-Qiu He³, Yue-Hu Wang¹

1 Key Laboratory of Economic Plants and Biotechnology, Yunnan Key Laboratory for Wild Plant Resources, and 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;
2 Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 550014, People's Republic of China;
3 Faculty of Plant Protection, Yunnan Agricultural University, Kunming 650201, People's Republic of China

Received:2021-12-21 Revised:2022-01-09 Online:2022-02-24 Published:2022-03-12
Contact: Yue-Qiu He, Yue-Hu Wang
Supported by:
This study was supported by Beijing Sino-Science Aquilaria Technology Co., Ltd., Beijing, China (no. KET202101).

摘要/Abstract

摘要： Five new 2-(2-phenylethyl)chromone derivatives, (5S,6R,7R,8S,7'R)-7'-hydroxyagarotetrol (1), (5S,6R,7R,8S,7'S)-7'-hydroxyagarotetrol (2), (6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone (3), (6S,7S,8R)-2-(2-phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone (4), (5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone (5), three new sesquiterpenoids, (4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (6), (4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (7), and (4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (8), along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data, single-crystal X-ray diffraction analysis, and electronic circular dichroism (ECD) calculations. The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma (PC12) cell injury induced by corticosterone. At concentrations from 5 to 40 μM, compounds 4 and 6, agarotetrol (9), and 6-hydroxy-2-(2-phenylethyl)chromone (17) showed significant protective activities against corticosterone-induced PC12 cell injury (P<0.001).

关键词: Thymelaeaceae, Aquilaria sinensis, Sesquiterpenoids, 2-(2-Phenylethyl)chromones, Neuroprotective

Abstract: Five new 2-(2-phenylethyl)chromone derivatives, (5S,6R,7R,8S,7'R)-7'-hydroxyagarotetrol (1), (5S,6R,7R,8S,7'S)-7'-hydroxyagarotetrol (2), (6S,7S,8R)-2-[2-(4-methoxyphenyl)ethyl]-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone (3), (6S,7S,8R)-2-(2-phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydrochromone (4), (5S,6R,7S,8R)-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxychromonyl-6-oxy]chromone (5), three new sesquiterpenoids, (4S,5S,7S,8S,10S,13R)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (6), (4S,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (7), and (4R,5S,7S,8S,10S,13S)-7,8,13-trihydroxyrotunda-1,11-dien-3-one (8), along with 14 known compounds were isolated from the resinous heartwood of Aquilaria sinensis (Thymelaeaceae). The chemical structures of these new compounds were elucidated by 1D and 2D NMR and MS data, single-crystal X-ray diffraction analysis, and electronic circular dichroism (ECD) calculations. The neuroprotective activities of these isolates were evaluated using an in vitro model of rat adrenal pheochromocytoma (PC12) cell injury induced by corticosterone. At concentrations from 5 to 40 μM, compounds 4 and 6, agarotetrol (9), and 6-hydroxy-2-(2-phenylethyl)chromone (17) showed significant protective activities against corticosterone-induced PC12 cell injury (P<0.001).

Key words: Thymelaeaceae, Aquilaria sinensis, Sesquiterpenoids, 2-(2-Phenylethyl)chromones, Neuroprotective

Lu Zhang, Ping Yi, Hui Yan, Xiao-Nian Li, Meng-Yuan Xia, Jun Yang, Ji-Feng Luo, Yue-Qiu He, Yue-Hu Wang. Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China[J]. 应用天然产物, 2022, 12(1): 1-14.

参考文献

1. Editorial Board of Chinese Pharmacopoeia. Chinese Pharmacopoeia, vol. 1. Beijing:China Medical Science Press; 2020. p. 192-3.
2. Su J, Liu Z, Li R-C, Yang X-J. Literature research of traditional Chinese medicine prescription containing agilawood. China J Tradit Chin Med Pharm. 2017;32:1853-5.
3. Peng D, Wang C, Liu Y, Wei J. Research progress on the chemical constituents of Aquilariae Lignum Resinatum and their pharmacological activities. Chin J Mod Appl Pharm. 2021;38:358-65.
4. Gonçalves S, Mansinhos I, Romano A. Aromatic plants:a source of compounds with antioxidant and neuroprotective effects. In:Martin CR, Preedy VR, editors. Oxidative stress and dietary antioxidants in neurological diseases. Amsterdam:Elsevier; 2020. p. 155-73.
5. Wei S-Y, Hu D-B, Xia M-Y, Luo J-F, Yan H, Yang J-H, Wang Y-S, Wang Y-H. Sesquiterpenoids and 2-(2-phenylethyl)chromone derivatives from the resinous heartwood of Aquilaria sinensis. Nat Prod Bioprosp. 2021;11:545-55.
6. He Q, Hu D-B, Zhang L, Xia M-Y, Yan H, Li X-N, Luo J-F, Wang Y-S, Yang J-H, Wang Y-H. Neuroprotective compounds from the resinous heartwood of Aquilaria sinensis. Phytochemistry. 2021;181:112554.
7. Yoshii E, Koizumi T, Oribe T, Takeuchi F, Kubo K. The structure of agarotetrol, a novel highly oxygenated chromone from agarwood (jinko). Tetrahedron Lett. 1978;19:3921-4.
8. Shimada Y, Konishi T, Kiyosawa S, Nishi M, Miyahara K, Kawasaki T. Studies on the agalwood (Jinko). IV. Structures of 2-(2-phenylethyl) chromone derivatives, agarotetrol and isoagarotetrol. Chem Pharm Bull. 1986;34:2766-73.
9. Sugiyama T, Narukawa Y, Shibata S, Masui R, Kiuchi F. Three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone derivatives enantiomeric to agarotetrol from agarwood. J Nat Med. 2018;72:667-74.
10. Konishi T, Sugimoto A, Kiyosawa S, Fujiwara Y. Studies on the agalwood "Jinko". XII. Structures of pentahydroxy-2-(2-phenylethy)chromone derivatives. Chem Pharm Bull. 1992;40:778-9.
11. Xiang P, Mei W, Chen H, Kong F, Wang H, Liao G, Zhou L, Dai H. Four new bi-phenylethylchromones from artificial agarwood. Fitoterapia. 2017;120:61-6.
12. Zheng K-M, Zhang J-Q, Shen P-N, Zhuo C. Preparative isolation and purification of agarotetrol and 4'-methoxyagarotetrol from Aquilaria sinensis (Lour.) Gilg by high-speed counter-current chromatography. Chin Tradit Pat Med. 2011;33:96-9.
13. Konishi T, Iwagoe K, Sugimoto A, Kiyosawa S, Fujiwara Y, Shimada Y. Studies on agalwood (Jinko). X. Structures of 2-(2-phenylethyl)chromone derivatives. Chem Pharm Bull. 1991;39:207-9.
14. Iwagoe K, Kakae T, Konishi T, Kiyosawa S, Fujiwara Y, Shimada Y, Miyahara K, Kawasaki T. Studies on the agalwood (Jinko). VIII. Structures of bi-phenylethylchromone derivatives. Chem Pharm Bull. 1989;37:124-8.
15. Huo H-X, Zhu Z-X, Song Y-L, Shi S-P, Sun J, Sun H, Zhao Y-F, Zheng J, Ferreira D, Zjawiony JK, Tu P-F, Li J. Anti-inflammatory dimeric 2-(2-phenylethyl)chromones from the resinous wood of Aquilaria sinensis. J Nat Prod. 2017;81:543-53.
16. Shimada Y, Konishi T, Kiyosawa S. Studies on the agalwood (Jinko). VI. Structures of three 2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone derivatives, AH1A, AH2a and AH2b. Chem Pharm Bull. 1986;34:3033-7.
17. Yagura T, Ito M, Kiuchi F, Honda G, Shimada Y. Four new 2-(2-phenylethyl) chromone derivatives from withered wood of Aquilaria sinensis. Chem Pharm Bull. 2003;51:560-4.
18. Yang JS, Wang YL, Su YL. Studies on the chemical constituents of Aquilaria sinensis (Lour.) Gilg. V.:isolation and characterization of three 2-(2-phenylethyl)chromone derivatives. Acta Pharm Sin. 1989;24:678-83.
19. Iwagoe K, Konishi T, Kiyosawa S, Shimada Y, Miyahara K, Kawasaki T. The structures of AH₁₀ and AH₁₁, nobel bi-phenylethylchromones from agalwood. Chem Pharm Bull. 1986;34:4889-91.
20. Kitajima J, Ishikawa T, Tanaka Y, Ono M, Ito Y, Nohara T. Water-soluble constituents of fennel. V. Glycosides of aromatic compounds. Chem Pharm Bull. 1998;46:1587-90.
21. Gaussian 16 Citation, http://gaussian.com/citation/ (accessed on December 17, 2021).
22. SYBYL-X 2.1.1, Tripos International, 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA.
23. Bruhn T, Schaumlöffel A, Hemberger Y, Pecitelli G. SpecDis version 1.71, Berlin, Germany, 2017. http://specdis-software.jimdo.com.

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Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China

Five new 2-(2-phenylethyl)chromone derivatives and three new sesquiterpenoids from the heartwood of Aquilaria sinensis, an aromatic medicine in China

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