Separation of six compounds from pigeon pea leaves by elution–extrusion counter‐current chromatography

Abstract

A valid and reliable method was established to separate six compounds from pigeon pea leaves via elution‐extrusion counter‐current chromatography. A solvent system composed of n‐hexane/methanol/formic acid aqueous solution with pH = 3 (10:6:4, v/v) was screened to achieve satisfactory isolation from the ethanol extract of pigeon pea leaves. Four compounds, 9.2 mg of compound 1 (96.8%), 3.2 mg of 2 (88.0%), 6.2 mg of 4 (94.2%) and 25.2 mg of 5 (94.2%), were obtained by conventional elution from 100 mg of the precipitation fraction, respectively. Two compounds, 14.4 mg of 3 (96.3%) and 28.1 mg of 6 (96.6%), with high K values were obtained by the subsequent extrusion procedure. The compounds 1–6 were identified as 3‐methoxy‐5‐(2‐phenylethenyl)‐phenol, pinostrobin chalcone, pinostrobin, 2‐hydroxy‐4‐methoxy‐6‐(2‐phenylvinyl)‐benzoic acid, longistylin C and cajaninstilbene acid by quadrupole time‐of‐flight mass spectrometry, and 1H and 13C NMR spectroscopy. The in vitro antiproliferation activities of compounds 1, 5 and 6 against human hepatoma cell were evaluated and the half‐maximum inhibitory concentrations were acquired.

Separation of five flavonoids with similar polarity from Caragana korshinskii Kom. by preparative high speed counter‐current chromatography with recycling and heart cut mode

“…Compared with traditional column chromatography, HSCCC has the advantages of large sample loading, high recovery, high efficiency, and easy scale‐up potential [5,6]. In addition, the various modes available to date, such as normal phase [7,8], reverse phase [9,10], gradient mode [11,12], recycling mode [13,14], pH Zone refining [15,16], extrusion [17], and dual‐mode [18], have made it widely used in the isolation and purification of active components from natural products. However, it is sometimes not easy to find a suitable solvent system, especially for compounds with a similar polarity, to perform an ideal separation.…”

Components identification and isomers differentiation in pigeon pea (Cajanus cajan L.) leaves by LC‐MS

“…Pinostrobin (96%), 3‐methoxy‐5‐(2‐phenylethenyl)‐phenol (97%), longistylin C (94%), 2‐hydroxy‐4‐methoxy‐6‐(2‐phenylvinyl)‐benzoic acid (94%), and cajanin stilbene acid (96%) were separated and purified in our laboratory. The structures were identified by Q‐TOF MS and NMR spectroscopy [14].…”

Pinostrobin attenuates azoxymethane-induced colorectal cytotoxicity in rats through augmentation of apoptotic Bax/Bcl-2 proteins and antioxidants

“…21 Notably, pinostrobin, as a natural flavonoid displayed inhibitory efficacy against numerous cancer cells including HeLa S3 and KBvin cells, 22 acute leukaemia cells 23 and colon cancer. 24 Pinostrobin (5-hydroxy-7-methoxy flavanone; PN) is a member of flavonoids and an ether (Figure 1) and a dietary bioflavonoid isolated from natural resources including plants, Pinus strobus, 4 Cajanus cajan (L.), 25 rhizomes of Boesenbergia rotunda 26 and finger root (Boesenbergia rotunda). 27 Numerous biological potentials exhibited by this flavanone including antioxidants, 28 anti-inflammatory, 29 augmentations of inflammatory cytokines (interleukin-1β, tumour necrosis factor (TNF)-α) 30 and anti-ulcerogenic actions.…”