Polyacetylenes from Bidens bipinnata L. and their biological activities

doi:10.1016/j.phytol.2013.12.002

Phytochemistry Letters

Volume 7, February 2014, Pages 198-201

https://doi.org/10.1016/j.phytol.2013.12.002 Get rights and content

Highlights

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New polyacetylenes from Bidens bipinnata L. were isolated and identified.
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Six polyacetylenes were isolated in total and two are new.
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All the compounds exhibited anti-inflammatory activity in vitro.

Abstract

Two new polyacetylenes, (2S) (5E,11E)-tridecadiene-7,9-diyne-1,2,13-triol (1) and (6E,12E)-3-oxo-tetradecadiene-8,10-diyne-14-hydroxyl-1-O-β-d-glucopyranoside (2) along with four known polyacetylenes (3–6), were isolated from the whole plant of Bidens bipinnata L. Their structures were elucidated by spectroscopic data. All compounds were evaluated for their anti-inflammatory activities on lipopolysaccharide (LPS)-induced IL-1 and tumor necrosis factor (TNF-α) production in macrophage (RAW264.7) cells and cytotoxic activities on human cervical carcinoma (Hela), human hapetocelluar carcinoma (HepG-2), and human breast carcinoma (MCF-7) cell lines.

Graphical abstract

Introduction

The genus Bidens (Asteraceae: Heliantheae) comprises about 240 species with cosmopolitan distribution (Silva et al., 2011). It is used as anti-pyretic, anti-rheumatic and anti-hepatitis traditional medicine in many countries for a long history (Bo et al., 2012). The plants in this genus contain a variety of chemical compounds, such as flavonoids, sesquiterpene lactones and polyacetylenes. Pharmacy studies on Bidens have revealed its anti-liver fibrosis (Yuan et al., 2008), anti-diabetes (Chien et al., 2009) and anti-malaria activities (Oliveira et al., 2004).

Bidens bipinnata L. belongs to this genus and is wildly distributed in tropical and subtropical areas. In China, the whole herb has been used as folk medicine against various diseases, such as sore throat, chronic diarrhea, malaria, dysentery and acute nephritis (Yang et al., 2012). Our previous studies showed the extract of B. bipinnata exhibit anti-inflammatory activity in acute liver injury and liver fibrosis in rats (Yuan et al., 2008, Zhong et al., 2007). Further study on the extract of this plant led to the isolation of two new polyacetylenes, named (2S) (5E,11E)-tridecadiene-7,9-diyne-1,2,13-triol (1) and (6E,12E)-3-oxo-tetradecadiene-8,10-diyne-14-hydroxyl-1-O-β-d-glucopyranoside (2), together with four known compounds. Herein, we report their characterizations and biological activities.

Section snippets

Results and discussion

Compound 1 was obtained as a pale yellow powder, had a molecular formula of C₁₃H₁₆O₃ based on its HRTOF-MS. The IR absorptions of compound 1 demonstrated the presence of hydroxyl groups (3377 cm⁻¹), acetylenes (2129 cm⁻¹, 2204 cm⁻¹), olefinics (1623 cm⁻¹, 949 cm⁻¹). The ¹H NMR data exhibited two methylenes at δ 1.53 (2H, m, H-3) and δ 2.33 (2H, m, H-4), two oxygenated methylenes at δ 3.43 (2H, m, H-1) and δ 4.17 (2H, m, H-13), one oxygenated methine at δ 3.59 (1H, m, H-2), and four olefinic protons

General experimental procedures

Optical rotations were measured on OA PolAAr 3002 Polarimeter. UV spectra were recorded on Agilent 8450 spectrophotometer. IR spectra were recorded on Bio-Rad FTS-135 spectrometer. 1D and 2D NMR spectra were recorded on Bruker AM-400 and DRX-500 (400 MHz for ¹H NMR and 100 MHz for ¹³C NMR) spectrometer with TMS as internal standard. HRMS (ESI-TOF) was measured on Agilent 1260-6224. Column chromatography was performed on HPD-100 macroporous resin (BaoEn Chemical Co. Ltd., China), Sephadex LH-20

Acknowledgement

This project was supported by National Science and Technology Major Projects for “Major New Drugs Innovation and Development”, No. 2009ZX09102-386.

References (13)

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Anti-diabetic properties of three common Bidens pilosa variants in Taiwan
Phytochemistry
(2009)
M. Gerards et al.
Circular dichroism. XCIII. Determination of the absolute configuration of alcohols, olefins, epoxides, and ethers from the CD of their “in situ” complexes with [Rh₂(OCOCF₃)₄]
Tetrahedron: Asymmetry
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New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities
Carbohydr. Res.
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F.Q. Oliveira et al.
New evidences of antimalarial activity of Bidens pilosa roots extract correlated with polyacetylene and flavonoids
J. Ethnopharmacol.
(2004)
X.W. Yang et al.
Phenolics from Bidens bipinnata and their amylase inhibitory properties
Fitoterapia
(2012)
Y. Zhang et al.
Coreosides A–D, C14-polyacetylene glycosides from the capitula of Coreopsis tinctoria and its anti-inflammatory activity against COX-2
Fitoterapia
(2013)

There are more references available in the full text version of this article.

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A phytochemical investigation of Bidens procera L.C.Xu ex X.W.Zheng afforded two novel polyacetylenes, tridecane-2E-monoene-4,6,8-triyntylen-1,13-diol-12-O-β-glucoside (1) and tetradecane-2E,8E-diene-4,6-diyne-1,14-diol-13-O-β-glucoside (2), together with ten known compounds (3 − 12). Their chemical structures were elucidated by NMR and MS spectrums as well as the comparison of the published data. Furthermore, the chemotaxonomy of the yielded compounds was also discussed.
Bioactive polyacetylenes from Bidens pilosa L and their anti-inflammatory activity
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A new polyacetylenic glucoside together with three known compounds were isolated from the whole herb of Bidens pilosa L. The structure elucidation of these four compounds was employed by combining NMR and HR-MS data as 4-O-β-D-glucopyranosyloxy-1-hydroxy- 6-(E)-tetradecene-8,10,12-triyne (1), 3-O-β-D-glucopyranosyloxy-1-hydroxy-6-(E)-tetradec- ene-8,10,12-triyne (2), 2-O-β-D-glucopyranosyloxy-1-hydroxy-5-(E)-tetradecene-7,9,11-triy- ne (3) and icthyothereol acetate (4). Additionally, bioactivity study showed that these compounds have potential anti-inflammatory activity. This study has certain guiding significance for the development and utilisation of polyacetylene compounds in Bidens pilosa L.
In-vitro examination and isolation of antidiarrheal compounds using five bacterial strains from invasive species Bidens bipinnata L.
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Citation Excerpt :
The whole plant is used against malaria, sore throat, acute nephritis and dysentery. Pharmacological studies of this plant has been investigated before i.e. anti-arthritis (Shen et al. 2015) and antihepatoprotective activity (Wang et al. 2014). However its antibacterial activity is not well studied.
Bidens bipinnata is widely utilized medicinal plant for treatment of diseases like malaria, sore throat, acute nephritis and dysentery. However, despite its traditional uses Bidens bipinnata is not widely explored for its antimicrobial effect. Thus, the current study is aimed to form antimicrobial activity report of Bidens bipinnata extracts, along with isolation and evaluation of antibacterial activity of the isolated compounds through bioassay-guided purification. Hexane extract of its leaves has appeared to be most active thus it is exposed to automated column chromatography. Further purification using High-performance liquid chromatography has led to isolation of active peaks, identified by Gas Chromatography-mass spectrometry, as 16-Pregnenolone and 9-Octadecenoic acid (Z)-, methyl ester. Their antimicrobial activity was confirmed via broth dilution procedure on Staphylococcus aureus, 16-Pregnenolone revealed a strong antimicrobial activity with MIC₅₀ of 72 μg/mL whereas 9-Octadecenoic acid (Z)-, methyl ester display an MIC₅₀ of >250 μg/mL. Present study is the first report on isolation of these compounds from Bidens bipinnata.
Flavonoids-rich extract from Bidens bipinnata L. protects pancreatic β-cells against oxidative stress-induced apoptosis through intrinsic and extrinsic pathways
2021, Journal of Ethnopharmacology
Citation Excerpt :
For example, the crude drug “Ham-hong-chho” consisted of B. bipinnata, B. pilosa and B. chinensis has been used as a folk medicine to treat diabetes (Lin, 1992; Yang et al., 2012). More recent researches of B. bipinnata have indicated that its biological functions included antioxidant, anti-inflammatory, anti-cancer, antihypertensive, and hepato-protective effects (Bo et al., 2012; Wang et al., 2014; Yang et al., 2012; Yuan et al., 2008; Zahara et al., 2015; Zhong et al., 2007). Most previous reports showed that flavonoids have been regarded as one of the major anti-diabetic composition in B. bipinnata.
As a traditional Chinese medicinal, Bidens bipinnata L. has been used to treat many diseases with a long history in China. The anti-diabetic effects of extract from B. bipinnata have been demonstrated in the previous reports.
The protective effects of flavonoids-rich extract from B. bipinnata (BBTF) on cell damage induced by H₂O₂ in pancreatic β cell and its potential mechanisms were evaluated.
MTT, ROS production, nuclear staining and flow cytometry assays were adopted to determine the effects of BBTF on cell viability, production of ROS and cell apoptosis in H₂O₂-treated INS-1 cell. Cell apoptosis-related proteins expressions were detected by Western blot assay.
Pre-treatment of BBTF could significantly increase INS-1 cell viability, inhibit the production of intracellular ROS and reduced the characteristic features of cell apoptosis induced by H₂O₂ in INS-1 cells. The studies of the underlying mechanism showed that BBTF could regulate Bax and Bcl-2 proteins expressions, suppress the phosphorylation of JNK, ERK and p38, as well as down-regulate Fas and FasL proteins expressions induced by H₂O₂. The expressions of caspase-8, caspase-9 and caspase-3 were therefore decreased.
The results indicated that flavonoids-rich extract from B. bipinnata could be a natural agent in diabetic prevention and therapy.
Two new polyacetylene glucosides and a new caffeoyl derivative with angiogenic activity from Bidens parviflora Willd.
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Two new polyacetylene glucosides, (1) (10S)-tridecane-2E,12-diene-4,6,8-triyne-1-ol-10-O-β-D-glucopyranoside and (2) (12R)-tridecane-2E,8E-diene-4,6-diyne-1,14-diol-12-O-β-D-glucopyranoside, and a new caffeoyl derivative, (3) 4-O-acetyl-3-O-caffeoyl-2-C-methyl-D-erythronate, were isolated from the ethanol extract of the whole herb of Bidens parviflora Willd. The compound structures were confirmed by 1D and 2D NMR and HR-ESI-MS spectra and by comparison with literature data. In addition, the absolute configurations of compounds 1 and 2 were determined by circular dichroism (CD). The angiogenic activity of compounds 1∼3 was evaluated with an intersegmental vessel (ISV) zebrafish injury model induced by PTK787. Compounds 1 and 2 exhibited angiogenic activity at 25 μg/mL.
The role of pericarp in Bidens L. heterocarpy (Asteraceae)
2019, Flora: Morphology, Distribution, Functional Ecology of Plants
Citation Excerpt :
Precise identification of the compounds were not feasible due to the isomeric possibilities. The coumarins, esculin and escutelin isolated from B. bipinnata (Wang et al., 2014) have also been identified in B. pilosa (Sarg et al., 1991). Esculin (m/z = 341) was present in the central cypselae of B. frondosa, B. bipinnata and, B. subalternans as well as in the peripheral cypselae of B. subalternans.
Diaspore heteromorphism is a common reproductive strategy in Asteraceae. The genus Bidens L. contains some species with two or more types of cypselae in a single capitulum, with dicarpy being more frequently observed. Our work aims to address how the pericarp influences germination in heterocarpic species of Bidens. The species were assigned based on their morphophysiological features: dicarpic species included Bidens alba (L.) DC., B. aristosa (Michx.) Britton, B. bipinnata L., B. frondosa L., B. pilosa L., B. subalternans DC., and a polycarpic species included B. gardneri (Baker). We investigated the variation in cypselae via morphological measurements, pericarp anatomical analysis and secondary metabolites profile by high-performance liquid chromatography-mass spectrometry (HPLC-ESI⁺). The pericarp weight and the anatomical structures differed among the types of cypselae, but these differences cannot be assumed to represent a germination barrier. Nonetheless, principal component analysis indicated that the pericarp chemical composition varied among B. aristosa, B. bipinnata, B. pilosa, and B. subalternans. The analysis of metabolic profile of the pericarps revealed esculin, glycosylated flavonoids and nitrogenous compounds in all cypselae. Our work brings new evidence for understanding the way the pericarp influences the germination of heterocarpic species under anatomical and metabolomic frameworks. We discard the differential mechanical constraint as the main inducer of dicarpy for these Bidens species.

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Phytochemistry Letters

Highlights

Abstract

Graphical abstract

Introduction

Section snippets

Results and discussion

General experimental procedures

Acknowledgement

References (13)

Anti-diabetic properties of three common Bidens pilosa variants in Taiwan

Phytochemistry

Circular dichroism. XCIII. Determination of the absolute configuration of alcohols, olefins, epoxides, and ethers from the CD of their “in situ” complexes with [Rh₂(OCOCF₃)₄]

Tetrahedron: Asymmetry

New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities

Carbohydr. Res.

New evidences of antimalarial activity of Bidens pilosa roots extract correlated with polyacetylene and flavonoids

J. Ethnopharmacol.

Phenolics from Bidens bipinnata and their amylase inhibitory properties

Fitoterapia

Coreosides A–D, C14-polyacetylene glycosides from the capitula of Coreopsis tinctoria and its anti-inflammatory activity against COX-2

Fitoterapia

Cited by (17)

New polyacetylenes from Bidens procera

Bioactive polyacetylenes from Bidens pilosa L and their anti-inflammatory activity

In-vitro examination and isolation of antidiarrheal compounds using five bacterial strains from invasive species Bidens bipinnata L.

Flavonoids-rich extract from Bidens bipinnata L. protects pancreatic β-cells against oxidative stress-induced apoptosis through intrinsic and extrinsic pathways

Two new polyacetylene glucosides and a new caffeoyl derivative with angiogenic activity from Bidens parviflora Willd.

The role of pericarp in Bidens L. heterocarpy (Asteraceae)