Prenylated flavonoids from the fruits of Sinopodophyllum emodi and their cytotoxic activities

Abstract

Thirteen new prenylated flavonoids, sinoflavonoids C-O (1-13), were isolated from the fruits of Sinopodophyllum emodi together with eleven known analogues (14-24). Their structures were elucidated on the basis of spectroscopic evidence. The cytotoxic activities of all isolated compounds were evaluated against MCF-7 and HepG2 cell lines. By the preliminary structure-activity relationships, it was first discovered that the simple, non-prenylated 5,7,3 0 ,4 0 -tetrahydroxyflavonol analogues (22 and 23) showed higher cytotoxic activities than the corresponding prenylated ones (1-2, 4-21, and 3 and 24).Compound 22 exhibited the most potent cytotoxicity against MCF-7 and HepG2 cell lines with IC 50 values of 3.14 and 2.08 mM, respectively.

Labdane Diterpenes from the Fruits of Sinopodophyllum emodi

“…Chinese herbal medicines produce a wide variety of secondary metabolites, which can be exploited as potential anticancer agents. Previous chemical investigations on S. emodi revealed the presence of aryltetralin lactone and tetrahydrofuranoid lignans [2,3,7,8,10], flavonoids [1,6,9,11,20], steroids [21], and phenolics [22]. Cytotoxic activities of some isolated S. emodi constituents have been shown in various cancer cell lines.…”

“…Sinolignan C displayed cytotoxicity against the KB cell line and was more cytotoxic than etoposide [12]. 3-Methoxyquercetin showed cytotoxicity against the MCF-7 and HepG2 cell lines, with IC 50 values of 3.14 and 2.08 μM, respectively [11]. All of the isolated labdane diterpenoids were evaluated for cytotoxic activities against the MCF-7 and HepG2 cell lines (Table 3).…”

“…Previous phytochemical and pharmacological investigations revealed that S. emodi is particularly rich in aryltetralin lactone lignans and prenylated flavonoids, and has attracted wide attention due to their cytotoxic properties [1,2,3,6,7,8,9]. In our search for cytotoxic natural products, we previously reported the isolation, identification and cytotoxic activity of aryltetralin lactone and tetrahydrofuranoid lignans, and prenylated flavonoids from S. emodi [10,11,12]. In a further examination of the fruits of this plant, two new labdane diterpenes, sinoditerpene A ( 1 ) and B ( 2 ), were obtained together with two known analogues 3 and 4 (Figure 1).…”

Synthesis of prenylated flavonols and their potents as estrogen receptor modulator

“…8-Prenyl substitution also enhances the bioavailability of quercetin in different tissues in vivo 5 . Prenylated flavonoids possess a wide variety of bioactivities, such as estrogenic activity, immunomodulatory activity, anticancer activity and antioxidant activity 6 , 7 .…”

Preparative Isolation of Two Prenylated Biflavonoids from the Roots and Rhizomes of Sinopodophyllum emodi by Sephadex LH-20 Column and High-Speed Counter-Current Chromatography

“…Its roots and rhizomes have been used for the treatment of certain cancer, various verrucosis [1], constipation, parasitosis [3], rheumatoid ache [4], and pyogenic infection of skin tissue [5]. Previous chemical investigations on S. emodi revealed the presence of bioactive aryltetralin [1,3,4,5,6,7,8] and tetrahydrofuranoid lignans [9], flavonoids [2,10,11,12], steroids [13], and phenolics [14]. Although flavonoids have been the research focus of this plant [2,10,11,12], the biflavonoids, podoverines B, C (Figure 1), were found firstly in the genus Sinopodophyllum .…”