New Stilbene, Benzofuran, and Coumarin Glycosides from Morus alba

Abstract

Five new compounds, including three new stilbene-derived glycosides, one novel arylbenzofuran derivative, and one new coumarin glycoside, along with ten known compounds were isolated from the H 2 O extract of the bark of Morus alba L. The new compounds were assigned to the structures of 4'-O-b- (5) by spectroscopic means, and acid and enzymatic hydrolyses. Three compounds, 2'- (8), and 6,7-dihydroxycoumarin 7-(6-O-a-rhamnopyranosyl-b-d-glucopyranoside) (9), were found for the first time in Morus alba.Introduction. -Morus alba L. (Moraceae) is widely distributed in the Anhui, Hunan, and Shanxi provinces in China. Its root bark is extensively used as an antitussive and antiasthmatic agent [1] in traditional Chinese medicines. Although many compounds such as stilbenes, flavonoids, benzofuran derivatives, and coumarins have been identified in Morus alba [2 -6], there have been few reports on its pharmacological properties. In our previous study, we investigated the absorbed constituents in rats following oral administration of the H 2 O extract of the bark of Morus alba [7] [8], and several stilbene derivatives were identified in the plasma, urine, and bile of rats. Further pharmacological studies showed that mulberroside A, a major stilbene constituent in the H 2 O extract, displayed a significant antitussive and antiasthmatic effect in animals [9]. In our ongoing search for the bioactive constituents from the H 2 O extract of Morus alba L., a systematic investigation on the chemical constituents of water extract of Morus alba was carried out, and resulted in the isolation of eight stilbene glycosides, three arylbenzofuran derivatives, and four coumarin glycosides. This article reports the isolation and structural elucidation of the three new stilbene glycosides 1 -3 1 ), the novel arylbenzofuran derivative 4, and the new coumarin glycoside 5. Ten known compounds were identified as mulberroside A (6)

Isoprenylated flavonoids from the root bark of Morus alba and their hepatoprotective and neuroprotective activities

“…The root bark, named Sang-BaiPi, has been used for treating diabetes, relieving asthma, and protecting the liver (Ahn 2012). Phytochemical studies on Sang-Bai-Pi extracts resulted in the isolation of phenolic compounds including isoprenylated flavonoids (Jiang et al 2003), Diels-Alder type adducts (Hano et al 1988), triterpenoids (Jung et al 2014), coumarins (Piao et al 2009), benzofurans (Piao et al 2009), and stilbenes (Piao et al 2009), which were reported to show anti-oxidant , tyrosinase inhibitory (Lee et al 2004), anti-inflammatory (Yang et al 2011), anti-hepatitis B virus (Geng et al 2012), anti-cancer (Dat et al 2010), and antimicrobial (Naik et al 2015) activities. The EtOAc soluble Electronic supplementary material The online version of this article (doi:10.1007/s12272-015-0613-8) contains supplementary material, which is available to authorized users.…”

New hydroxy fatty acid from the root bark of Morus alba L.

“…The root barks of mulberry trees are named ''SangBai-Pi'' and are used for a variety of medicinal purposes, primarily in South Asia. Previously, many phytochemical compounds such as flavonoids, Diels-Alder type adducts, coumarins, stilbenes, and triterpenoids (Hano et al 1988;Piao et al 2009;Jung et al 2014) have been isolated from the root bark of M. alba. These compounds have been reported to show anti-oxidant, anti-inflammatory, anticancer, and anti-microbial activities (Dat et al 2010;Yang et al 2011;Yang and Lee 2012;Naik et al 2015).…”

Two new phenolic constituents from the root bark of Morus alba L. and their cardioprotective activity

“…Furthermore, extracts of M. alba were shown to be potent antioxidants and prevented doxorubicin cardiotoxicity (Wattanapitayakul et al 2005). In this paper, we depicted the isolation and identification of a new biphenyl-furocoumarin, named morescoumarin A (1), a new prenylated flavanone, named morflavanone A (2), and five known compounds, moracin M (3) (Zhang et al 2009), moracin M-3′-O-β-D-glucopyranoside (4) (Basnet et al 1993), moracin M-6-O-β-D-glucopyranoside (5) (Piao et al 2009), mulberroside F (6) (Hano et al 1997). Structures of new compounds were characterised by 1 H NMR, 13 C NMR, 2D NMR, HR-ESI-MS and CD data.…”