Photochemical decomposition of alkannin/shikonin enantiomers

Hui Wen Cheng; Fu An Chen; Hsing Chu Hsu; Chau Yang Chen

doi:10.1016/0378-5173(94)00367-E

Photochemical decomposition of alkannin/shikonin enantiomers

Hui Wen Cheng, Fu An Chen, Hsing Chu Hsu, Chau Yang Chen

Research output: Contribution to journal › Article › peer-review

30 Citations (Scopus)

Abstract

Alkannin/shikonin ((±)-5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone), isolated from Macrotomia euchroma, is sensitive to light exposure. A chloroform solution of alkannin/shikonin was exposed to sunlight for 1 month. The major photolytic product, a newly discovered naphthoquinone derivative, was isolated by adsorption chromatography. The chemical structure of the purified photolytic product was identified by NMR, MS and FTIR techniques to be (-)-5,8-dihydroxy-2-(1-hydroxy-3-oxo-4-methyl-4-pentenyl)-1,4-naphthoquinone, indicating that a photo-oxidation reaction had occurred.

Original language	English
Pages (from-to)	137-144
Number of pages	8
Journal	International Journal of Pharmaceutics
Volume	120
Issue number	2
DOIs	https://doi.org/10.1016/0378-5173(94)00367-E
Publication status	Published - Jun 30 1995

Keywords

Alkannin/shikonin
Macrotomia euchroma
Photochemical decomposition
Photodegradation

ASJC Scopus subject areas

Pharmaceutical Science

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10.1016/0378-5173(94)00367-E

Cite this

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title = "Photochemical decomposition of alkannin/shikonin enantiomers",

abstract = "Alkannin/shikonin ((±)-5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone), isolated from Macrotomia euchroma, is sensitive to light exposure. A chloroform solution of alkannin/shikonin was exposed to sunlight for 1 month. The major photolytic product, a newly discovered naphthoquinone derivative, was isolated by adsorption chromatography. The chemical structure of the purified photolytic product was identified by NMR, MS and FTIR techniques to be (-)-5,8-dihydroxy-2-(1-hydroxy-3-oxo-4-methyl-4-pentenyl)-1,4-naphthoquinone, indicating that a photo-oxidation reaction had occurred.",

keywords = "Alkannin/shikonin, Macrotomia euchroma, Photochemical decomposition, Photodegradation",

author = "Cheng, {Hui Wen} and Chen, {Fu An} and Hsu, {Hsing Chu} and Chen, {Chau Yang}",

year = "1995",

month = jun,

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doi = "10.1016/0378-5173(94)00367-E",

language = "English",

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journal = "International Journal of Pharmaceutics",

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publisher = "Elsevier",

number = "2",

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TY - JOUR

T1 - Photochemical decomposition of alkannin/shikonin enantiomers

AU - Cheng, Hui Wen

AU - Chen, Fu An

AU - Hsu, Hsing Chu

AU - Chen, Chau Yang

PY - 1995/6/30

Y1 - 1995/6/30

N2 - Alkannin/shikonin ((±)-5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone), isolated from Macrotomia euchroma, is sensitive to light exposure. A chloroform solution of alkannin/shikonin was exposed to sunlight for 1 month. The major photolytic product, a newly discovered naphthoquinone derivative, was isolated by adsorption chromatography. The chemical structure of the purified photolytic product was identified by NMR, MS and FTIR techniques to be (-)-5,8-dihydroxy-2-(1-hydroxy-3-oxo-4-methyl-4-pentenyl)-1,4-naphthoquinone, indicating that a photo-oxidation reaction had occurred.

AB - Alkannin/shikonin ((±)-5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone), isolated from Macrotomia euchroma, is sensitive to light exposure. A chloroform solution of alkannin/shikonin was exposed to sunlight for 1 month. The major photolytic product, a newly discovered naphthoquinone derivative, was isolated by adsorption chromatography. The chemical structure of the purified photolytic product was identified by NMR, MS and FTIR techniques to be (-)-5,8-dihydroxy-2-(1-hydroxy-3-oxo-4-methyl-4-pentenyl)-1,4-naphthoquinone, indicating that a photo-oxidation reaction had occurred.

KW - Alkannin/shikonin

KW - Macrotomia euchroma

KW - Photochemical decomposition

KW - Photodegradation

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U2 - 10.1016/0378-5173(94)00367-E

DO - 10.1016/0378-5173(94)00367-E

M3 - Article

AN - SCOPUS:0029076830

SN - 0378-5173

VL - 120

SP - 137

EP - 144

JO - International Journal of Pharmaceutics

JF - International Journal of Pharmaceutics

IS - 2

ER -

Photochemical decomposition of alkannin/shikonin enantiomers

Abstract

Keywords

ASJC Scopus subject areas

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