A New Tocopherol Derivative and Cytotoxicity from the Leaves of Dalbergia velutina

Abstract

A new tocopherol derivative, named (+)-α-tocuspirone (1), along with eleven known compounds, including six tocopherol derivatives (2–7) and five triterpenes (8–12) were isolated from the leaves of Dalbergia velutina. Their structures were determined by spectroscopic analysis especially NMR spectroscopy. The absolute configurations of 1 and 2 were assigned by NOESY experiments and ECD calculations. All isolated compounds were evaluated for their cytotoxicity against five cancer cell lines (KB, HeLa S-3, HT-29, MCF-7 and HepG-2). Dioslupecin A (10) showed potent cytotoxicity against all the five cancer cell lines with IC₅₀ values in the range of 0.28–2.05 μM. In addition, caffeoxylupeol (12) showed potent cytotoxicity against KB cell with an IC₅₀ value of 2.28 μM.

Keywords

(+)-α-Tocuspirone Dalbergia velutina Leguminosae Cytotoxicity

References

Kaennakam

, Siripong

, Tip-pyang

(2015) Velucarpins A-C, three new pterocarpans and their cytotoxicity from the roots of Dalbergia velutina. Fitoterapia, 105, 165–168.

Kaennakam

, Siripong

, Tip-Pyang

(2016) Dalvelutinoside, a new isoflavone glycoside from the methanol extract of Dalbergia velutina roots. Natural Product Research, 30, 1493–1498.

Kaennakam

, Siripong

, Tip-pyang

(2017) Cytotoxicities of two new isoflavanes from the roots of Dalbergia velutina. Journal of Natural Medicines, 71, 310–314.

Lin

W.Y.

, Kuo

Y.H.

, Chang

Y.L.

, Teng

C.M.

, Wang

E.C.

, Ishikawa

(2003) Anti-platelet aggregation and chemical constituents from the rhizome of Gynura japonica. Planta Medica, 69, 757–764.

Chiang

Y.M.

, Kuo

Y.H.

(2003) Two novel α-tocopheroids from the aerial roots of Ficus microcarpa. Tetrahedron Letters, 44, 5125–5128.

Rosenau

, Habicher

W.D.

(1997) Novel tocopherol compounds. Part VII. γ-tocopherol-5-carboxylic acid. A novel route to γ-tocopherol. Synlett, 208–210.

Janiszowska

, Michalski

, Kasprzyk

(1976) Polyprenyl quinones and α-tocopherol in Calendula officinalis. Phytochemistry, 15, 125–127.

Vecchi

, Schmid

, Walther

, Gerber

(1981) Determination of the diastereomers of vitamin K1, HRC CC, Journal of High Resolution Chromatography, 4, 257–259.

Bolland

J.L.

, Hughes

(1949) The primary thermal oxidation product of squalene. Journal of the Chemical Society, 26, 492–497.

10.

Marner

F.J.

, Freyer

, Lex

(1991) Triterpenoids from gum mastic, the resin of Pistacia lentiscus. Phytochemistry, 30, 3709–3712.

11.

Kuo

Y.H.

, Chang

C.I.

, Li

S.Y.

, Chou

C.J.

, Chen

C.F.

, Kuo

Y.H.

(1997) Cytotoxic constituents from the stems of Diospyros maritima. Panta Medica, 63, 363–365.

12.

Chang

C.I.

, Kuo

Y.H.

(1998) Three new lupane-type triterpenes from Diospyros maritima. Chemical & Pharmaceutical Bulletin, 46, 1627–1629.

13.

Alvarenga

, Ferro

E.A.

(2000) A new lupane caffeoyl ester from Hippocratea volubilis. Fitoterapia, 71, 719–721.

14.

Ochi

, Takaishi

, Shibata

, Higuti

, Kataoka

(2005) Chemical constituents of Capsicum annuum L var. angulosum, and anti-Helicobacter pylori activity. Natural Medicines, 59, 76–84.

15.

Kuo

Y.H.

, Chang

C.I.

, Li

S.Y.

, Chou

, Chen

C.F.

, Lee

K.H.

(1997) Cytotoxic constituents from the stems of Diospyros maritima. Planta Medica, 63, 363–365.

16.

Kongkathip

, Kongkathip

, Siripong

, Sangma

, Luangkamin

, Niyomdecha

(2003) Potent antitumor activity of synthetic 1,2-naphthoquinones and 1,4-naphthoquinones. Bioorganic and Medicinal Chemistry, 11, 3179–3191.

17.

ISIS/Draw, MDL Information Systems, Inc., San Leandro, CA, USA, 2002.

18.

Frisch

M.J.

, Trucks

G.W.

, Schlegel

H.B.

, Scuseria

G.E.

, Robb

M.A.

, Cheeseman

J.R.

(2009) Gaussian 09, revision A.01. Wallingford, CT: Gaussian Inc.

19.

Bruhn

, Schaumlöffel

, Hemberger

, Bringmann

(2013) SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra. Chirality, 25, 243–249.

Supplementary Material

Please find the following supplemental material available below.

For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.

For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.

0.00 MB

0.97 MB