A New Limonoid from Chisocheton paniculatus Fruit Collected in Vietnam and Its NO Production Inhibitory Activity

Abstract

A new limonoid, 6α,7α-diacetoxy-3-oxo-24,25,26,27-tetranorapotirucalla-1,14,20(22)-trien-21,23-lactam (1), was isolated from the fruits of Chsocheton paniculatus Hiern collected in Vietnam, together with two known 5α,8α-epidioxysterols, (22E,24R)-5α,8α-epidioxy-24-methyl-cholesta-6,22-dien-3β-ol (2) and (22E,24R)-5α,8α-epidioxy-24-methyl-cholesta-6,9(11),22-trien-3β-ol (3) Their structures were elucidated by spectroscopic analyses, including D- and 2D-NMR and HRESIMS, and comparisons with the reported data in the literature. Compounds 1–3 exhibited the NO production inhibitory activities against the LPS stimulated BV2 cells with 69.0 ± 2.7 %, 69.5 ± 2.2 %, and 70.6 ± 1.6 %, at concentration of 20.0 μM, respectively.

Keywords

Chisocheton paniculatus Limonoid Tetranortriterpenoid NO inhibitor

References

Yang

M.H.

, Wang

J.S.

, Luo

J.G.

, Wang

X.B.

, Kong

L.Y.

(2009) Tetranortriterpenoids from Chisocheton paniculatus. Journal of Natural Products, 72, 2014–2018.

Shilpi

J.A.

, Saha

, Chong

S.L.

, Nahar

, Sarker

S.D.

, Awang

(2016) Advances in chemistry and bioactivity of the genus Chisocheton Blume. Chemistry & Biodiversity, 13, 483–503.

(a) Cortez

D.A.G.

, Fernandes

J.B.

, Vieira

P.C.

, Silva

MFGF

, Ferreira

A.G.

, Cass

Q.B.

, Pirani

J.R.

(1998) Meliacin butenolides from Trichilia estipulate. Phytochemistry, 49, 2493–2496; (b) Cheplogoi PK, Mulholland DA. (2003) Tetranortriterpenoid derivatives from Turraea parvifolia (Meliaceae). Phytochemistry, 62, 1173-1178; (c) Li JH, Li Y, An FL, Zhou MM, Luo J, Jian KL, Luo J, Kong LY. (2016) Limonoids with modified furan rings from root barks of Toona sinensis. Tetrahedron, 72, 7481-7487.

(a) Ioannou

, Abdel-Razik

A.F.

, Zervou

, Christofidis

, Alexi

, Vagias

, Alexis

M.N.

, Roussis

(2009) 5α,8α-Epidioxysterols from the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum: isolation and evaluation of their antiproliferative activity. Steroids, 74, 73–80; (b) Nowak R, Drozd M, Mendyk E, Lemieszek M, Krakowiak O, Kisiel W, Rzeski W, Szewczyk K. (2016) A new method for the isolation of ergosterol and peroxyergosterol as active compounds of Hygrophoropsis aurantiaca and in vitro antiproliferative activity of isolated ergosterol peroxide. Molecules, 21, 946.

Kiem

P.V.

, Cuong

L.C.V.

, Tai

B.H.

, Nhiem

N.X.

, Anh

H.L.

, Quang

T.H.

, Ngan

N.T.

, Oh

, Kim

Y.C.

(2016) New lignans from Antidesma hainanensis inhibit NO production in BV2 microglial cells. Chemical and Pharmaceutical Bulletin, 64, 1707–1712.

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

0.85 MB