Prenylated C6–C3 compounds with molecular diversity from the roots of Illicium oligandrum

Ma, Shuang‐Gang; Tang, Wen-Zhao; Liu, Yuxi; Hu, Youcai; Yu, Shi‐Shan; Zhang, Yi; Chen, Xiaoguang; Qu, Jing; Ren, Jinhong; Liu, Yun‐Bao; Xu, Song; Liu, Jing; Liu, Yuan-Yan; Li, Yong; Lü, Hai-Ning; Wu, Xianfu

doi:10.1016/j.phytochem.2010.10.021

Cited by 36 publications

(14 citation statements)

References 21 publications

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“…Recently, two spirooliganones A and B isolated from the plant showed antiviral activity [7]. As a part of our continuing study on antiviral constituents from I. oligandrum, two new sesquiterpenes, oligandrin (1) and oligandric acid (2), together with three known ones, tashironin A (3), tashironin (4), and oplodiol (5), were isolated from the CHCl 3 fraction of the roots of I. oligandrum. The structures of new compounds were determined based on 1D and 2D NMR experiments and X-ray diffraction.…”

Section: Introductionmentioning

confidence: 99%

“…Compound 2 is the first example of chamipinene-type sesquiterpene possessing a 6/4/6 tricyclic system from the genus Illicium. The obtained compounds (1)(2)(3)(4)(5) were evaluated for their antiviral activity in vitro. Herein, we report the isolation and structure elucidation of new sesquiterpenes (1 -2) and antiviral activity of 1 -5 ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

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Sesquiterpenes from the roots ofIllicium oligandrum

Lü

Ma²,

Liu

et al. 2015

Journal of Asian Natural Products Research

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Two new sesquiterpenes, oligandrin (1) and oligandric acid (2), together with three analogues, tashironin A (3), tashironin (4), and oplodiol (5), were isolated from the roots of Illicium oligandrum. The structures of new compounds were determined based on 1D and 2D NMR experiments and X-ray diffraction. Compound 1 represents a presumed biosynthetic precursor of seco-prezizaane sesquiterpenes which consists of a novel 6/6/5 tricarbocyclic skeleton. Compound 2 is the first example of chamipinene-type sesquiterpene possessing a 6/4/6 tricyclic system from the genus Illicium. Compounds 1-5 were evaluated in vitro for their activity against coxsackie virus B3 (CVB3), influenza virus A/Hanfang/359/95 (H3N2), and influenza virus A/FM/1/47 (H1N1). Compound 1 showed selective antiviral activity against CVB3 with IC50 value of 11.11 μM.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sesquiterpenes from the roots ofIllicium oligandrum

Lü

Ma²,

Liu

et al. 2015

Journal of Asian Natural Products Research

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“…The genus Illicium (family Illiciaceae) contains sesquiterpenes, neolignans and prenylated C 6 –C 3 compounds, featuring neurotropic or neurotoxic activities (Moriyama et al , ; Tang et al , ; Zhu et al , ; Ma et al , ). Illicium simonsii Maxim.…”

Section: Introductionmentioning

confidence: 99%

Reversal Effects of Components from the Fruits of Illicium simonsii on Human Adriamycin‐resistant MCF‐7 and 5‐Fluorouracil‐resistant Bel7402 Cells

Wei

Wang

Kong

2011

Phytotherapy Research

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Twenty-one compounds including seven characteristic sesquiterpene lactones were isolated from Illicium simonsii and screened in vitro for their potential to restore the sensitivity of Adriamycin (ADR) resistant breast cancer cells (MCF-7/ADR) and 5-fluorouracil-resistant hepatocellular carcinoma cells (Bel7402/5-FU) to ADR and 5-fluorouracil, respectively. These compounds were found to be non-toxic to a panel of tumour cell lines: human breast cancer cells (MCF-7), cervical cancer cells (HeLa), hepatic liver carcinoma cells (HepG-2, Bel7402) and gastric carcinoma cells (BGC-823, SGC-7901). Five compounds showed an obvious decrease in the IC(50) of doxorubicin in MCF-7/ADR and four compounds sensitized Bel7402/5-FU to 5-fluorouracil at non-toxic concentrations. The relationship between the structure of these non-cytotoxic substances and their multidrug-resistant (MDR) reversal abilities was investigated by principal component analysis (PCA) of the reversing fold (RF) values of these compounds and their calculated molecular descriptors of the tested substances. No correlations were found between the reversal potencies of these compounds to the two MDR cells. Compounds with lower polarity generally had stronger sensitizing ability to the P-glycoprotein (Pgp) overexpressed MCF-7/ADR cells. On the other hand, higher hydrophilic compounds seemed to exhibit a stronger reversal effect to the MDR-associated protein (MRP) overexpressed Bel7402/5-FU cell line. Our findings favoured further investigations on the active substances and the underlying mechanisms.

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“…Species of the genus Illicium L (Illiciaceae) are characterized by a variety of structurally unique sesquiterpenes such as seco-prezizaane-type [1][2][3], anislactone, and allo-cedrane sesquiterpenes [4][5][6], some of which were found to exhibit intriguing neurotrophic activities [7][8][9]. In our previous studies, we investigated the chemical constituents of I. oligandrum [10][11][12], I. simonsii [13], I. difengpi [14], and I. dunnianum [15]. As a result, sesquiterpenes [10,15], prenylated C 6 -C 3 compounds [10,11,13], and neolignan glycosides [12,14] with various biological activities were isolated from these plants.…”

mentioning

confidence: 99%

“…In our previous studies, we investigated the chemical constituents of I. oligandrum [10][11][12], I. simonsii [13], I. difengpi [14], and I. dunnianum [15]. As a result, sesquiterpenes [10,15], prenylated C 6 -C 3 compounds [10,11,13], and neolignan glycosides [12,14] with various biological activities were isolated from these plants. I. henryi is a toxic shrub, primarily distributed throughout Southern China and is used for the treatment of rheumatism [16].…”

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confidence: 99%

Novel Sesquiterpenoid Glycosides and Sesquiterpenes from the Roots of Illicium henryi

et al. 2013

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Seven new sesquiterpenoid glycosides, consisting of one thapsan-type (1), two capnellane-type (2 and 3), four floridanolide sesquiterpene glycosides (4-7), and one new azulene-type sesquiterpene (8), along with six known sesquiterpenes (9-14) were isolated from the roots of Illicium henryi. The structures of 1-8 were elucidated by extensive spectroscopic analyses and chemical methods. The absolute configurations of 1, 2, and 8 were determined based on Rh2(OCOCF3)4-induced CD, Mo2(OAc)4-induced CD data, and calculated electronic circular dichroism (ECD), respectively. Compound 1 was found to exhibit weak neurotoxicant activity.

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Prenylated C6–C3 compounds with molecular diversity from the roots of Illicium oligandrum

Cited by 36 publications

References 21 publications

Sesquiterpenes from the roots ofIllicium oligandrum

Sesquiterpenes from the roots ofIllicium oligandrum

Reversal Effects of Components from the Fruits of Illicium simonsii on Human Adriamycin‐resistant MCF‐7 and 5‐Fluorouracil‐resistant Bel7402 Cells

Novel Sesquiterpenoid Glycosides and Sesquiterpenes from the Roots of Illicium henryi

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