Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata

doi:10.1007/s13659-024-00430-6

Natural Products and Bioprospecting ›› 2024, Vol. 14 ›› Issue (3): 22-22.DOI: 10.1007/s13659-024-00430-6

• ORIGINAL ARTICLES • Previous Articles Next Articles

Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata

Shi-Hui Qin^1,2, Zhi-Lan Li¹, Liu Yang¹, Jiang-Miao Hu¹

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, China;
2 College of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012, China

Received:2023-11-22 Online:2024-06-14
Contact: Jiang-Miao Hu,E-mail:hujiangmiao@mail.kib.ac.cn
Supported by:
This work was supported by grants from Poverty alleviation through science and technology projects of Chinese Academy of Sciences (KFJ-FP-201905).

Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata

Shi-Hui Qin^1,2, Zhi-Lan Li¹, Liu Yang¹, Jiang-Miao Hu¹

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, China;
2 College of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012, China

通讯作者: Jiang-Miao Hu,E-mail:hujiangmiao@mail.kib.ac.cn
基金资助:
This work was supported by grants from Poverty alleviation through science and technology projects of Chinese Academy of Sciences (KFJ-FP-201905).

Abstract

Abstract: Based on the research progress and traditional usage with whole herbal of the TCM "Tianma", chemical studies herein on the flower branch of Gastrodia elata were carried out in-depth and got 13 compounds including the gastrodinols (1–4), the flavonoid morins (5–8, 11–12), together with the specialist mulberrofurans (9, 13) and gastrodiamide (10) for the first time from the species. The antibacterial and cholinesterase inhibitory activities were then evaluated and the results showed that compounds 5, 11, 12, 13 have good activity against anti-methicillin-resistant Staphylococcus aureus, and compounds 9, 13 had good acetylcholinesterase inhibitory activity. All these results provide new chemical composition for better understanding the traditional application of "Tianma" and for exploring new pharmacological ingredients.

Key words: Gastrodia elata, Orchidaceae, Gastrodinol, Isoprene-flavonoids, Mulberrofurans, Gastrodiamide

摘要： Based on the research progress and traditional usage with whole herbal of the TCM "Tianma", chemical studies herein on the flower branch of Gastrodia elata were carried out in-depth and got 13 compounds including the gastrodinols (1–4), the flavonoid morins (5–8, 11–12), together with the specialist mulberrofurans (9, 13) and gastrodiamide (10) for the first time from the species. The antibacterial and cholinesterase inhibitory activities were then evaluated and the results showed that compounds 5, 11, 12, 13 have good activity against anti-methicillin-resistant Staphylococcus aureus, and compounds 9, 13 had good acetylcholinesterase inhibitory activity. All these results provide new chemical composition for better understanding the traditional application of "Tianma" and for exploring new pharmacological ingredients.

关键词: Gastrodia elata, Orchidaceae, Gastrodinol, Isoprene-flavonoids, Mulberrofurans, Gastrodiamide

Shi-Hui Qin, Zhi-Lan Li, Liu Yang, Jiang-Miao Hu. Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata[J]. Natural Products and Bioprospecting, 2024, 14(3): 22-22.

Shi-Hui Qin, Zhi-Lan Li, Liu Yang, Jiang-Miao Hu. Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata[J]. 应用天然产物, 2024, 14(3): 22-22.

References

1. Duan H, Zhou YX, Wang DD, Yan WJ. Differences in volatile organic compounds in Rhizoma gastrodiae (Tian Ma) of different origins determined by HS-GC-IMS. Molecules. 2023;28(13):4883. https://doi.org/10.3390/molec ules2 81348 83.
2. Li Y, Xie M, Shao MS, Qu QC, Wei YQ, Zhao HJ, Ji XM, Wang SJ. Research progress on pharmacological activities and chemical constituents of last ten years on Gastrodia elata Blume. J Tradit Chin Med. 2017;35(12):2987–93. https://doi.org/10.13193/j.issn. 1673-7717. 2017. 12. 002.
3. Yang L, Jiang R, Li HH, Pan YP, Lu JJ, Zhang H, Shou JL, Shen JL, Hu JM. Three new compounds from the flower branch of Gastrodia elata Blume and anti-microbial activity. RSC Adv. 2020;10(25):14644–9. https://doi. org/10. 1039/D0RA0 0965B.
4. Lv YF, Ren FC, Kuang MT, Miao Y, Li ZL, Hu JM, Zhou J. Total synthesis of gastrodinol via photocatalytic 6π electrocyclization. Org Lett. 2020;22(17):6822–6. https://doi.org/10.1021/acs. orgle tt. 0c023 35.
5. Ren FC, Wang LX, Lv YF, Hu JM, Zhou J. Structure revision of four classes of prenylated aromatic natural products based on a rule for diagnostic ¹³C NMR chemical shifts. J Org Chem. 2021;86(16):10982–90. https://doi. org/10. 1021/acs. joc. 0c024 09.
6. Chen CC, Huang YL, Ou JC, Lin CF, Pan TM. Three new prenylflavones from Artocarpus altilis. J Nat Prod. 1993;56:1594–7. https://doi.org/10.1021/np500 99a021.
7. Ryu YB, Ha TJ, Curtis-Long MJ, Ryu HW, Gal SW, Park KH. Inhibitory effects on mushroom tyrosinase by flavones from the stem barks of Morus lhou (S.) Koidz. J Enzyme Inhib Med Chem. 2008;23(6):922–30. https://doi. org/10. 1080/14756 36070 18102 07.
8. Fukai T, Hano Y, Hirakura K, Nomura T, Uzawa J, Fukushima K. Structures of two natural hypotensive diels-alder type adducts, mulberrofurans F and G, from the cultivated mulberry tree (Morus lhou KOIDZ.). Chem Pharm Bull. 1985;33(8):3195–204. https://doi.org/10.1248/cpb. 33. 3195.
9. Darby EM, Trampari E, Siasat P, Gaya MS, Alav I, Webber MA, Blair JMA. Molecular mechanisms of antibiotic resistance revisited. Nat Rev Microbiol. 2023;21(5):280–95. https://doi.org/10.1038/s41579-022-00820-y.
10. Blaskovich MAT. Antibiotics special issue: challenges and opportunities in antibiotic discovery and development. ACS Infect Dis. 2020;6(6):1286–8. https://doi.org/10.1021/acsin fecdis. 0c003 31.
11. Bai L, Masukawa N, Yamaki M, Takagi S. Four stilbenoids from Pleione bulbocodioides. Phytochemistry. 1998;48(2):327–31. https://doi.org/10.1016/S0031-9422(97) 01110-2.
12. Tanaka T, Ohyama M, Kawasaka Y, Iinuma M. Tetrapterols A and B: novel flavonoid compounds from Sophora tetraptera. Tetrahedron Lett. 1994;35(48):9043–4. https://doi.org/10.1016/0040-4039(94) 88422-6.
13. Jeong SH, Ryu YB, Curtis-Long MJ, Ryu HW, Baek YS, Kang JE, Lee WS, Park KH. Tyrosinase inhibitory polyphenols from roots of Morus lhou. J Agric Food Chem. 2009;57(4):1195–203. https://doi.org/10.1021/jf803 3286.
14. Nomura T, Fukai T, Matsumoto J. Oxidative cyclization of morusin. J Heterocyclic Chem. 1980;17(4):641–6. https://doi.org/10.1002/jhet. 55701 70404.
15. Ma YF, Li XT, Zhang WJ, Ying XX, Stien D. A trace alkaloid, oleraisoindole A from Portulaca oleracea L. and its anticholinesterase effect. Nat Prod Res. 2021;35(2):350–3. https://doi.org/10.1080/14786 419. 2019. 16273 56.
16. Botta B, Vitali A, Menendez P, Misiti D, Monache DG. Prenylated flavonoids: pharmacology and biotechnology. Curr Med Chem. 2005;12(6):717–39. https://doi.org/10.2174/09298 67053 202241.
17. Ren FC, Liu L, Lv YF, Bai X, Kang QJ, Hu XJ, Zhuang HD, Yang L, Hu JM, Zhou J. Antibacterial prenylated p-hydroxybenzoic acid derivatives from Oberonia myosurus and identification of putative prenyltransferases. J Nat Prod. 2021;84(2):417–26. https://doi.org/10.1021/acs. jnatp rod. 0c011 01.

[1]	Yue-Hu Wang. Traditional Uses and Pharmacologically Active Constituents of Dendrobium Plants for Dermatological Disorders: A Review [J]. Natural Products and Bioprospecting, 2021, 11(5): 465-487.
[2]	Yanan Wang, Min Zhang, Xue Zhou, Chengbo Xu, Chenggen Zhu, Yuhe Yuan, Naihong Chen, Yongchun Yang, Qinglan Guo, Jiangong Shi. Insight into Medicinal Chemistry Behind Traditional Chinese Medicines: p-Hydroxybenzyl Alcohol-Derived Dimers and Trimers from Gastrodia elata [J]. Natural Products and Bioprospecting, 2021, 11(1): 31-50.
[3]	Cheng-Bo Xu, Qing-Lan Guo, Ya-Nan Wang, Sheng Lin, Cheng-Gen Zhu, Jian-Gong Shi. Gastrodin Derivatives from Gastrodia elata [J]. Natural Products and Bioprospecting, 2019, 9(6): 393-404.
[4]	Si-Yue Chen, Chang-An Geng, Yun-Bao Ma, Ji-Jun Chen. Melatonin Receptors Agonistic Activities of Phenols from Gastrodia elata [J]. Natural Products and Bioprospecting, 2019, 9(4): 297-302.
[5]	Cheng-Bo LI, Cong WANG, Wei-Wei FAN, Fa-Wu DONG, Feng-Qing XU, Qin-Li WAN, Huai-Rong LUO, Yu-Qing LIU, Jiang-Miao HU, Jun ZHOU. Chemical components of Dendrobium crepidatum and their neurite outgrowth enhancing activities [J]. Natural Products and Bioprospecting, 2013, 3(2): 70-73.

Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata

Gastrodinol derivatives and prenylated flavones from the flower branch of Gastrodia elata

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 5

Recommended Articles

Metrics

Comments