New Monoterpenoid Indoles with Osteoclast Activities from

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Dec 24

PMID 34946539

Citations 4

Authors

Xin Wei

Rui Guo

Xiao Wang

Jia-Jun Liang

Hao-Fei Yu

Cai-Feng Ding

Ting-Ting Feng

Li-Yan Zhang

Xia Liu

Xin-Yue Hu

Ying Zhou

Affiliations

Soon will be listed here.

Abstract

The well-known toxic medicine is widely and historically used to treat bone fracture and skin ulcers by the folk people of China. Two new monoterpenoid indole alkaloids, gelselegandines D and E, together with the known analogue gelegamine A were isolated from . Their structures were elucidated by means of spectroscopic techniques and quantum chemical calculations. All isolated compounds were tested for the effects on RANKL-induced osteoclast formation. Interestingly, gelselegandine E and gelegamine A, respectively, showed significant promoting and inhibitory activities on osteoclastogenesis, while gelselegandine D had no activity under the same concentration. This work suggested the different configurations for the carbons near the C-19/20 oxygen rings of the isolated compounds may be the key active groups on osteoclast formation and provided the evidence for the rationality as the traditional treatment for bone-related diseases of .

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References

Jin G, Su Y, Liu M, Xu Y, Yang J, Liao K . Medicinal plants of the genus Gelsemium (Gelsemiaceae, Gentianales)--a review of their phytochemistry, pharmacology, toxicology and traditional use. J Ethnopharmacol. 2014; 152(1):33-52. DOI: 10.1016/j.jep.2014.01.003. View

Ti Y, Wang R, Zhao J . [Mechanism of osteoclast in bone resorption]. Zhongguo Gu Shang. 2014; 27(6):529-32. View

de Villiers T, Gass M, Haines C, Hall J, Lobo R, Pierroz D . Global consensus statement on menopausal hormone therapy. Climacteric. 2013; 16(2):203-4. DOI: 10.3109/13697137.2013.771520. View

Chen H, Zhao Z, Cheng G, Zhao K, Han K, Zhou L . Immunosuppressive Nor-isopimarane Diterpenes from Cultures of the Fungicolous Fungus HFG1018. J Nat Prod. 2020; 83(2):401-412. DOI: 10.1021/acs.jnatprod.9b00889. View

Xu Y, Yang L, Liao S, Cao P, Wu B, Hu H . Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans. J Nat Prod. 2015; 78(7):1511-7. DOI: 10.1021/np5009619. View

Li F, Liu L, Liu Y, Wang J, Yang M, Khan A . HRESIMS-guided isolation of aspidosperma-scandine type bisindole alkaloids from Melodinus cochinchinensis and their anti-inflammatory and cytotoxic activities. Phytochemistry. 2021; 184:112673. DOI: 10.1016/j.phytochem.2021.112673. View

Adomaityte J, Farooq M, Qayyum R . Effect of raloxifene therapy on venous thromboembolism in postmenopausal women. A meta-analysis. Thromb Haemost. 2008; 99(2):338-42. View

Riggs B, Khosla S, Melton 3rd L . Sex steroids and the construction and conservation of the adult skeleton. Endocr Rev. 2002; 23(3):279-302. DOI: 10.1210/edrv.23.3.0465. View

Wei X, Dai Z, Yang J, Khan A, Yu H, Zhao Y . Unprecedented sugar bridged bisindoles selective inhibiting glioma stem cells. Bioorg Med Chem. 2018; 26(8):1776-1783. DOI: 10.1016/j.bmc.2018.02.024. View

10.

OBoyle N, Vandermeersch T, Flynn C, Maguire A, Hutchison G . Confab - Systematic generation of diverse low-energy conformers. J Cheminform. 2011; 3:8. PMC: 3073927. DOI: 10.1186/1758-2946-3-8. View

11.

Lodewyk M, Siebert M, Tantillo D . Computational prediction of 1H and 13C chemical shifts: a useful tool for natural product, mechanistic, and synthetic organic chemistry. Chem Rev. 2011; 112(3):1839-62. DOI: 10.1021/cr200106v. View

12.

Hu J, Nishishita K, Sakai E, Yoshida H, Kato Y, Tsukuba T . Berberine inhibits RANKL-induced osteoclast formation and survival through suppressing the NF-kappaB and Akt pathways. Eur J Pharmacol. 2007; 580(1-2):70-9. DOI: 10.1016/j.ejphar.2007.11.013. View

13.

Wang Z, Jiang M, Khan A, Cai S, Li X, Liu J . Epigynumgenane-type pregnane glycosides from Epigynum cochinchinensis and their immunosuppressive activity. Phytochemistry. 2019; 168:112127. DOI: 10.1016/j.phytochem.2019.112127. View

14.

Wei X, Huang X, Zhang L, Hu X, Zhang W, Zhou Y . New oxindole alkaloids with selective osteoclast inhibitory activity from . Nat Prod Res. 2021; 36(10):2630-2636. DOI: 10.1080/14786419.2021.1913589. View