Nat Prod Sci.  2019 Sep;25(3):244-247. 10.20307/nps.2019.25.3.244.

Flavestin K, An Isoprenylated Stilbene from the Leaves of Macaranga recurvata Gage

• Tjahjandarie TS
• Tanjung M
• Saputri RD
• Nadar PB
• Aldin MF
• EvaMarliana
• Permadi A

• KMID: 2459967
• DOI: http://doi.org/10.20307/nps.2019.25.3.244

Abstract

A new isoprenylated stilbene, flavestinK (1) together with two known isoprenylated stilbenes, flavestin B (2), flavestin G (3), and two isoprenilated flavanones, 4-O-methyl-8-isoprenylnaringenin (4) and 8-isoprenyl-5,7-dihydroxyflavanone (5) were isolated from the leaves of Macaranga recurvata Gage. All of the structures have been determined based on HRESIMS, 1D and 2D NMR spectral data. All of the isolated compounds were evaluated for their cytotoxicity against three human cancer cells (HeLa, T47D and WiDr). Compound 1 showed higher activity than doxorubicin against HeLa cells with ICâ‚…â‚€ value of 13.1 µg/mL.

Keyword

Flavestin K; Stilbene; Macaranga recurvata; Cytotoxicity

MeSH Terms

Doxorubicin
Euphorbiaceae*
Flavanones
HeLa Cells
Humans
Stilbenes
Doxorubicin
Flavanones
Stilbenes

Figure

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  Fig. 1 Stilbenes and flavonoids 1 – 5 isolated from the leaves of M. recurvata.

• 

  Fig. 2 Selected HMBC correlations for flavestin K (1).

Reference

1. Syah YM, Ghisalberti EL. Nat Prod Commun. 2010; 5:219–222.

2. Kamarozaman AS, Ahmat N, Isa SNM, Hafiz ZZ, Adenan MI, Yusof MIM, Azmin NFN, Latip J. Phytochem Lett. 2019; 30:174–180.

3. Yang DS, Wei JG, Peng WB, Wang SM, Sun C, Yang YP, Liu KC, Li XL. Fitoterapia. 2014; 99:261–266.

4. Tanjung M, Hakim EH, Syah YM. Chem Nat Compd. 2017; 53:215–218.

5. Tanjung M, Hakim EH, Elfahmi , Latip J, Syah YM. Nat Prod Commun. 2012; 7:1309–1310.

6. Kusano G, Koguchi S, Shibano M, Takahashi K, Okada Y, Coskun M, Ozgen U, Erdurak CS, Okuyama T. Nat Med. 2002; 56:129–135.

7. Marliana E, Tjahjandarie TS, Tanjung M. Der Pharm Lett. 2015; 7:153–156.

8. Dong X, Liu Y, Yan J, Jiang C, Chen J, Liu T, Hu Y. Bioorg Med Chem. 2008; 16:8151–8160.

9. Saputri RD, Tjahjandarie TS, Tanjung M. Nat Prod Sci. 2018; 24:155–158.

10. Tanjung M, Rachmadiarti F, Saputri RD, Tjahjandarie TS. Nat Prod Res. 2018; 32:1062–1067.

11. Mah SH, Ee GCL, Teh SS, Sukari MA. Nat Prod Res. 2015; 29:98–101.

12. Sigmond J, Backus HHJ, Wouters D, Temmink OH, Jansen G, Peters GJ. Biochem Pharmacol. 2003; 66:431–438.

13. Lee SK, Lee HJ, Min HY, Park EJ, Le KM, Ahn YH, Cho YJ, Pyee JH. Fitoterapia. 2005; 76:258–260.

14. Tanjung M, Juliawaty LD;, Syah YM. Fitoterapia. 2018; 126:74–77.

15. Pailee P, Sangpetsiripan S, Mahidol C, Ruchirawat S, Prachyawarakorn V. Tetrahedron. 2015; 71:5562–5571.

16. Marliana E, Astuti W, Kosala K, Hairani R, Tjahjandarie TS, Tanjung M. Asian J Chem. 2018; 30:795–798.