Crystal Structures and Cytotoxicity of Ent-Kaurane-Type Diterpenoids from Two Aspilia Species

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2018 Dec 7

PMID 30518152

Citations 5

Authors

Souaibou Yaouba

Arto Valkonen

Paolo Coghi

Jiaying Gao

Eric M Guantai

Solomon Derese

Vincent K W Wong

Mate Erdelyi

Abiy Yenesew

Affiliations

Soon will be listed here.

Abstract

A phytochemical investigation of the roots of led to the isolation of -kaurane-type diterpenoids and additional phytochemicals (⁻). The structures of the isolated compounds were elucidated based on Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analyses. The absolute configurations of seven of the -kaurane-type diterpenoids (⁻, and ) were determined by single crystal X-ray diffraction studies. Eleven of the compounds were also isolated from the roots and the aerial parts of . The literature NMR assignments for compounds and were revised. In a cytotoxicity assay, 12α-methoxy--kaur-9(11),16-dien-19-oic acid () (IC = 27.3 ± 1.9 µM) and 9β-hydroxy-15α-angeloyloxy--kaur-16-en-19-oic acid () (IC = 24.7 ± 2.8 µM) were the most cytotoxic against the hepatocellular carcinoma (Hep-G2) cell line, while 15α-angeloyloxy-16β,17-epoxy--kauran-19-oic acid () (IC = 30.7 ± 1.7 µM) was the most cytotoxic against adenocarcinomic human alveolar basal epithelial (A549) cells.

Citing Articles

Network pharmacology, molecular docking, and in vitro study on Aspilia pluriseta against prostate cancer.

Okpako I, Ngonga F, Kyama C, Njeru S BMC Complement Med Ther. 2024; 24(1):338.

PMID: 39304868 PMC: 11416023. DOI: 10.1186/s12906-024-04642-8.

Synthesis and Coordination Properties of a Water-Soluble Material by Cross-Linking Low Molecular Weight Polyethyleneimine with Armed Cyclotriveratrilene.

Ng Y, Coghi P, Ng J, Ali F, Wong V, Coluccini C Polymers (Basel). 2021; 13(23).

PMID: 34883636 PMC: 8659696. DOI: 10.3390/polym13234133.

In vitro cytotoxicity of Aspilia pluriseta Schweinf. extract fractions.

Njeru S, Muema J BMC Res Notes. 2021; 14(1):57.

PMID: 33563333 PMC: 7871548. DOI: 10.1186/s13104-021-05472-4.

Antimicrobial activity, phytochemical characterization and gas chromatography-mass spectrometry analysis of Schweinf. extracts.

Njeru S, Muema J Heliyon. 2020; 6(10):e05195.

PMID: 33083626 PMC: 7551365. DOI: 10.1016/j.heliyon.2020.e05195.

Biological Activities of Two Major Copaiba Diterpenoids and Their Semi-synthetic Derivatives.

Cicek S, Wenzel-Storjohann A, Girreser U, Tasdemir D Rev Bras Farmacogn. 2020; 30(1):18-27.

PMID: 32431465 PMC: 7222050. DOI: 10.1007/s43450-020-00002-y.

References

Duan H, Takaishi Y, Momota H, Ohmoto Y, Taki T, Jia Y . Immunosuppressive diterpenoids from Tripterygium wilfordii. J Nat Prod. 1999; 62(11):1522-5. DOI: 10.1021/np9902183. View

Tincusi B, Jimenez I, Bazzocchi I, Moujir L, Mamani Z, Barroso J . Antimicrobial terpenoids from the oleoresin of the Peruvian medicinal plant Copaifera paupera. Planta Med. 2002; 68(9):808-12. DOI: 10.1055/s-2002-34399. View

Muller S, Tirapelli C, de Oliveira A, Murillo R, Castro V, Merfort I . Studies of ent-kaurane diterpenes from Oyedaea verbesinoides for their inhibitory activity on vascular smooth muscle contraction. Phytochemistry. 2003; 63(4):391-6. DOI: 10.1016/s0031-9422(03)00073-6. View

Page J, Balza F, Nishida T, Towers G . Biologically active diterpenes from Aspilia mossambicensis, a chimpanzee medicinal plant. Phytochemistry. 1992; 31(10):3437-9. DOI: 10.1016/0031-9422(92)83702-z. View

Lee I, Jin W, Zhang X, Manh Hung T, Song K, Seong Y . Cytotoxic and COX-2 inhibitory constituents from the aerial parts of Aralia cordata. Arch Pharm Res. 2006; 29(7):548-55. DOI: 10.1007/BF02969263. View

Dias J, Gao H . 13C nuclear magnetic resonance data of lanosterol derivatives--profiling the steric topology of the steroid skeleton via substituent effects on its 13C NMR. Spectrochim Acta A Mol Biomol Spectrosc. 2009; 74(5):1064-71. DOI: 10.1016/j.saa.2009.09.005. View

Sebisubi F, Odyek O, Anokbonggo W, Ogwal-Okeng J, Carcache-Blanco E, Ma C . Antimalarial activity of Aspilia pruliseta, a medicinal plant from Uganda. Planta Med. 2010; 76(16):1870-3. DOI: 10.1055/s-0030-1250028. View

Wafo P, Kamdem R, Ali Z, Anjum S, Begum A, Oluyemisi O . Kaurane-type diterpenoids from Chromoleana odorata, their X-ray diffraction studies and potent α-glucosidase inhibition of 16-kauren-19-oic acid. Fitoterapia. 2011; 82(4):642-6. DOI: 10.1016/j.fitote.2011.02.003. View

Wong V, Zhang M, Zhou H, Ching Lam K, Chan P, Law C . Saikosaponin-d Enhances the Anticancer Potency of TNF-α via Overcoming Its Undesirable Response of Activating NF-Kappa B Signalling in Cancer Cells. Evid Based Complement Alternat Med. 2013; 2013:745295. PMC: 3610377. DOI: 10.1155/2013/745295. View

10.

Sheldrick G . SHELXT - integrated space-group and crystal-structure determination. Acta Crystallogr A Found Adv. 2014; 71(Pt 1):3-8. PMC: 4283466. DOI: 10.1107/S2053273314026370. View

11.

Sheldrick G . Crystal structure refinement with SHELXL. Acta Crystallogr C Struct Chem. 2015; 71(Pt 1):3-8. PMC: 4294323. DOI: 10.1107/S2053229614024218. View

12.

El Marsni Z, Torres A, Varela R, Molinillo J, Casas L, Mantell C . Isolation of Bioactive Compounds from Sunflower Leaves (Helianthus annuus L.) Extracted with Supercritical Carbon Dioxide. J Agric Food Chem. 2015; 63(28):6410-21. DOI: 10.1021/acs.jafc.5b02261. View

13.

Zhou Y, Yang B, Liu Z, Jiang Y, Liu Y, Fu L . Cytotoxicity of Triterpenes from Green Walnut Husks of Juglans mandshurica Maxim in HepG-2 Cancer Cells. Molecules. 2015; 20(10):19252-62. PMC: 6331897. DOI: 10.3390/molecules201019252. View

14.

Souza J, Chang M, Brito D, Farias K, Damasceno-Junior G, Turatti I . Antimicrobial activity of Aspilia latissima (Asteraceae). Braz J Microbiol. 2015; 46(4):1103-10. PMC: 4704628. DOI: 10.1590/S1517-838246420131281. View

15.

Huang W, Liang Y, Wang J, Li G, Wang G, Li Y . Anti-angiogenic activity and mechanism of kaurane diterpenoids from Wedelia chinensis. Phytomedicine. 2016; 23(3):283-92. DOI: 10.1016/j.phymed.2015.12.021. View

16.

Li S, Ding J, Li Y, Hao X, Li S . Antimicrobial Diterpenoids of Wedelia trilobata (L.) Hitchc. Molecules. 2016; 21(4):457. PMC: 6272858. DOI: 10.3390/molecules21040457. View

17.

Cai C, Zhang Y, Yang D, Hao X, Li S . Two new kaurane-type diterpenoids from Wedelia chinensis (Osbeck.) Merr. Nat Prod Res. 2017; 31(21):2531-2536. DOI: 10.1080/14786419.2017.1317775. View

18.

Arciniegas A, Perez-Castorena A, Melendez-Aguirre M, Avila J, Maria Garcia-Bores A, Villasenor J . Chemical Composition and Antimicrobial Activity of Ageratina deltoidea. Chem Biodivers. 2018; 15(3):e1700529. DOI: 10.1002/cbdv.201700529. View

19.

Pupier M, Nuzillard J, Wist J, Schlorer N, Kuhn S, Erdelyi M . NMReDATA, a standard to report the NMR assignment and parameters of organic compounds. Magn Reson Chem. 2018; 56(8):703-715. PMC: 6226248. DOI: 10.1002/mrc.4737. View