주목열매 추출물 구조분석 (Structure Determination of the Extractives from the Taxus Cuspidata Fruits)

서지정보

· 발행기관 : 한국목재공학회
· 수록지 정보 : 목재공학 / 41권 / 6호 / 566 ~ 575페이지
· 저자명 : 박세영, 최인규, 배영수

초록

주목열매에서 분리한 과육과 씨를 95% EtOH 용액을 사용하여 각각 1.15 kg과 0.94 kg을 유리 용기에 침지하여 추출하고, 농축된 추출용액을 용매의 극성에 따라 n-hexane, dichloromethane, ethyl acetate 및 수용성으로 순차 분획한 후, 동결건조하였다. 혼합물로부터 순수한 화합물을 분리하기 위하여 ethyl acetate 및 수용성 분획에 대하여 Sephadex-LH 20 칼럼크로마토그래피를 실시하였다. 단리된 화합물들의 구조는 flavan 화합물의 경우 1H-NMR, 13C-NMR 및 EI-MS 스펙트럼을 측정하였으며, 탄수화물은 보다 정확한 구조를 결정하기 위해 COSY, HSQC와 같은 2-D NMR과 LC/MS 스펙트럼을 이용하여 구조를 결정하였다. 또한 구성당 분석을 위해 acid hydrolysis, permethylation을 실시하여 구성당의 성분과 결합위치를 확인하였다. 위의 실험을 통하여 (+)-catechin (1), (-)-epicatechin (2), (+)-gallocatechin (3), (-)-epigallocatechin(4) 및 β-D-fructofuranose-(2→4)-O-β-D-glucopyranose(1→4)-O-α-D-glucopyranose-(1→2)-O-β-D-fructofuranose (5)의 구조를 결정하였다.

영어초록

The fruits of Taxus cuspidata were collected, divided into seeds and fruits, and extracted with95% EtOH. The extracts were evaporated under the reduced vacuum pressure, concentrated, then successively fractionated with a series of n-hexane, dichloromethane, ethyl acetate and water ona separatory funnel to get some freeze dried samples. A portion of the EtOAc (arils:1.65 g, seeds:1.04g) and H2O (arils:7 g, seeds:10 g) soluble samples were chromatographed on a Sephadex columnusing MeOH-H2O (1:1, 1:3, 1:5, v/v), EtOH-hexane (3:1, v/v) mixture and 100% H2O as eluting solventsto isolate pure compounds from the fractions. The isolates were developed by cellulose TLC usingt-BuOH-HOAc-H2O (TBA; 3:1:1, v/v/v) and 6% aqueous HOAc. Visualization was done underultraviolet light and by spraying the vanillin-HCl-EtOH reagent (4.8:12:480, v/v/v). followed byheating. The structures of the isolates were characterized by 1H- and 13C-NMR, DEPT, 2D-NMR,LC/MS and EI-MS spectra. In addition to the NMR and MS spectra, acid hydrolysis andpermethylation were used to determine the correct structure of the isolated sugar compound.
Their structures were elucidated as (+)-catechin (1), (-)-epicatechin (2), (+)-gallocatechin (3),(-)-epigallocatechin (4) and β-D-fructofuranose-(2→4)-O-β-D-glucopyranose(1→4)-O-α-D-glucopyranose(1→2)-O-β-D-fructofuranose (5) on the basis of the above experimental evidences.

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