Dibenzocyclooctadiene Lignans and Lanostane Derivatives from the Roots ofKadsura coccineaand their Protective Effects on Primary Rat Hepatocyte Injury Induced byt-Butyl Hydroperoxide

Abstract

A new dibenzocyclooctadiene lignan, acetylepigomisin R ( 1), and a new 3,4-seco-lanostane-type triterpene, seco-coccinic acid F ( 2), along with three known dibenzocyclooctadiene lignans, isovaleroylbinankadsurin A ( 3), kadsuralignan J ( 4), and binankadsurin A ( 5), and one lanostane-type triterpene, 20( R),24( E)-3-oxo-9 beta-lanosta-7,24-dien-26-oic acid ( 6), were isolated from the methanol extract of the Kadsura coccinea roots. Their structures were elucidated on the basis of spectroscopic evidence including ESI-MS, HR-EI-MS, 1D and 2D NMR. The protective effects of these compounds were evaluated in primary cultured rat hepatocytes intoxicated with 1.2 mM T-butyl hydroperoxide. Compounds 1, 3, and 5 showed protective effects with ED (50) values of 135.7, 26.1, and 79.3 microM, respectively.

Lignans from the roots of Kadsura coccinea and their inhibitory activities on LPS-induced NO production

“…The roots of K. coccinea have been an ethnomedicine used for the treatment of cancer, dermatosis, gastroenteric disorders, rheumatoid arthritis and relieving pain (Hu et al, 1999). Previous phytochemical investigations on K. coccinea revealed the main presence of lignans (Hu et al, 2012;Gao et al, 2012;Li et al, 2006Li et al, , 2007 and triterpenoids (Gao et al, 2008a;Li et al, 2008;Liang et al, 2012;Song et al, 2010;Wang et al, 2008Wang et al, , 2012 in this plant, which showed the antiproliferative , anti-hepatitis (Ban et al, 2009) and NO inhibitory activities (Li et al, 2007(Li et al, , 2006. In our continuous survey on the chemical composition of Chinese folk medicines and medicinal plants (Xu et al, 2012;Wang et al, 2013), three new lignans, 14-O-demethyl polysperlignan D (1), kadsurindutin E (16), coccilignan A (17), and fifteen known lignan compounds (2-15 and 18) (Fig.…”

Depigmentation Effect of Kadsuralignan F on Melan-A Murine Melanocytes and Human Skin Equivalents

“…Previous reports have shown various effects of lignans on skin: macelignan inhibited PAR-2 melanosome transfer in keratinocytes [25]; licarin E regulated MMP-1; and procollagen I was expressed in fibroblasts [26]. Kadsuralignans were isolated from K. coccinea , and their biological effects were reported, such as nitric oxide inhibition [18] and protection on t-butyl hydroperoxide-induced primary rat hepatocyte injury [27]. In this study, we first identify the anti-melanogenic effect, followed by the molecular mechanism of kadsuralignan F (Figure 1), a kadsuralignan.…”

Dibenzylbutane‐ and Butyrolactone‐type Lignans as Apoptosis Inducers in Human Hepatoma HuH‐7 Cells

“…Lignans are an important group of naturally occurring plant phenols derived from dimerization of phenylpropane units (C 6 C 3 ), which are linked by a bond between C‐8 and C‐8' of their side chains. They display a wide range of biological activities that go from cytotoxic (Chen et al ., ), chemopreventive (Takaba et al ., ; Pusztai et al ., ), antioxidant (Chin et al ., ), antibacterial (Zhang et al ., ), antifungal (Park et al ., ), to apoptosis induction (Matsumoto et al ., ), enzyme inhibition (Lee et al ., ), hepatoprotection (Ban et al ., ) and anti‐HIV activity (Xiao et al ., ). In recent years there has been growing interest in the study of lignans because some of them exhibit a remarkable antineoplastic activity.…”