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CN-121990959-A - Rehmannia pigment compound, preparation method thereof and application thereof in additive

CN121990959ACN 121990959 ACN121990959 ACN 121990959ACN-121990959-A

Abstract

The application provides a rehmannia pigment compound shown in a formula (I), a stereoisomer thereof or a pharmaceutically acceptable salt thereof. The application also provides a preparation method of the rehmannia pigment compound, the stereoisomer or the pharmaceutically acceptable salt thereof and application of the rehmannia pigment compound, the stereoisomer or the pharmaceutically acceptable salt in additives. The rehmannia pigment compound provided by the application has a definite structure and no obvious toxicity to cells under the effective concentration, has good biological safety, and can be used as a multifunctional additive to be applied to the fields of foods, medicines or cosmetics.

Inventors

  • DING GANG
  • ZHONG LIWEN
  • CHEN LIN

Assignees

  • 中国医学科学院药用植物研究所

Dates

Publication Date
20260508
Application Date
20251231

Claims (10)

  1. 1. A rehmannia glutinosa dye compound of formula (I), a stereoisomer thereof, or a pharmaceutically acceptable salt thereof: ; Wherein, the R1, R2 and R5 are independently hydroxy, mercapto or amino; R3 is oxygen or sulfur; R4 is independently oxygen, sulfur or imino; the steric configurations of 5-C and 6-C are independently R or S; The double bond configuration of 9-C and 13-C is independently E or Z; Wherein brackets close to 13'-C are brackets a and brackets far from 13' -C are brackets b, the structural units in the brackets a and the structural units in the brackets b are independently optional structural units, a is 0 or 1, and b is 0 or 1; when a is 0, the structural units in the brackets a are absent, and when a is 1, the structural units in the brackets a are present; when b is 0, the structural units in the brackets of b are absent, and when b is 1, the structural units in the brackets of b are present.
  2. 2. The rehmannia-pigment compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof according to claim 1, wherein the compound is a compound having a structure represented by formula (i), formula (ii), formula (iii), formula (iv) or formula (v): ; ; ; ; in formula (i), the 9-C double bond is of formula E, the 13-C double bond is of formula E, and a is 0, b is 0; in formula (ii), the 9-C double bond is of formula Z, the 13-C double bond is of formula E, and a is 0, b is 0; in formula (iii), the 9-C double bond is of formula E, the 13-C double bond is of formula Z, and a is 0, b is 0; in formula (iv), the 9-C double bond is of formula E, the 13-C double bond is of formula E, and a is 1, b is 0; In formula (v), the 9-C double bond is of formula E, the 13-C double bond is of formula E, and a is 1, b is 1.
  3. 3. The rehmannia-pigment compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof according to claim 2, wherein the compound is a compound having a structure represented by formula (i-e), formula (ii-f), formula (iii-g), formula (iv-h) or formula (v-i): ; ; ; 。
  4. 4. the rehmannia-pigment compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof according to claim 1, wherein the stereoconfiguration of 5-C and 6-C is (5 r,6 r) or (5 s,6 r).
  5. 5. The rehmannia-pigment compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof according to claim 1, wherein the 9-C double bond is of formula Z and the 13-C double bond is of formula E.
  6. 6. The rehmannia pigment compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof according to claim 1 or 2, wherein R1, R2 are independently hydroxy or mercapto, R3 is oxygen, R4 is oxygen, and R5 is hydroxy.
  7. 7. The rehmannia-pigment compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof according to claim 1, wherein a is 0 and b is 0.
  8. 8.A process for preparing the rehmannia root pigment compound, stereoisomer thereof, or pharmaceutically acceptable salt thereof according to any one of claims 1 to 7, comprising the steps of: Carrying out normal phase chromatography on the crude rehmannia pigment product to obtain a primary purification component containing a target component; performing reverse phase chromatography on the primary purified component to obtain a further purified sub-component; subjecting the subfractions to size exclusion chromatography to obtain a secondary component; And (3) performing semi-preparative high performance liquid chromatography and/or preparative high performance liquid chromatography separation on the secondary component to obtain the rehmannia pigment compound.
  9. 9.An additive composition comprising a rehmannia root pigment compound, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as defined in any one of claims 1 to 7, and a pharmaceutically, pharmaceutically or cosmetically acceptable adjuvant.
  10. 10. Use of a rehmannia root pigment compound as defined in any one of claims 1 to 7, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, or an additive composition as defined in claim 9, in an additive.

Description

Rehmannia pigment compound, preparation method thereof and application thereof in additive Technical Field The application relates to the technical field of natural product chemistry and application, in particular to a rehmannia pigment compound, a preparation method thereof and application thereof in additives. Background With consumer increased health and safety awareness, additives derived from natural sources are becoming increasingly favored in the food, pharmaceutical and cosmetic industries to replace synthetic additives that present potential safety risks. Among the numerous natural additives, natural plant pigments are widely used due to their vivid color and biological origin. However, many natural pigments of the prior art are relatively single-acting, primarily as colorants, and lack a clear, scientifically proven additional bioactivity. For example, it has been disclosed in the prior art to prepare a mixture of natural pigments from rehmannia and use it as a colorant, but this technique yields only crude extracts of undefined composition, and specific chemical monomers therein have not been isolated and identified. Currently, the existing natural pigments are limited in variety, and in the fields of medicines, foods and cosmetics, the demands for natural additives which are safe, good in tinting strength and have biological activities (such as anti-inflammatory) are increasing. Disclosure of Invention The application aims to provide a novel rehmannia pigment compound, a stereoisomer or a pharmaceutically acceptable salt thereof, which has definite structure, safety, no toxicity and definite biological activity and can be used as an additive in medicines, foods or cosmetics. To achieve the above object, the present application provides a rehmannia pigment compound represented by the formula (I): Wherein R1, R2 and R5 are independently hydroxyl, mercapto or amino, R3 is oxygen or sulfur, R4 is independently oxygen, sulfur or imino, the stereoconfiguration of 5-C and 6-C is independently R or S, the double bond configuration of 9-C and 13-C is independently E or Z, in formula (I), brackets close to 13'-C are a brackets, brackets distant from 13' -C are b brackets, the structural unit in a brackets and the structural unit in b brackets are independently optional structural units, a is 0 or 1, b is 0 or 1, the structural unit in a brackets is absent when a is 0, the structural unit in a brackets is present when a is 1, the structural unit in b brackets is absent when b is 0, and the structural unit in b brackets is present when b is 1. The present example provides conjugated polyene carotenoid compounds (rehmannia pigment compounds) with completely new and clear structure, the chemical structures of which are fully confirmed by modern spectroscopy means, and the blank of the structure type compounds in the prior art is filled. The rehmannia pigment compound provided by the embodiment has both bright orange coloring performance and remarkable anti-inflammatory activity, and compared with the colorant with single function or the extract with unknown components in the prior art, the rehmannia pigment compound provided by the embodiment can be used as a multifunctional additive, and can provide additional health benefits for the product while providing color. In particular, the compound in this example has no significant toxicity to cells at an effective concentration, and is proved to have good biosafety, and is suitable for use as an additive in foods, medicines and cosmetics that are in direct contact with the human body. Further, the compound is a compound having a structure represented by formula (i), formula (ii), formula (iii), formula (iv) or formula (v): Wherein, the In formula (i), the 9-C double bond is of formula E, the 13-C double bond is of formula E, and a is 0, b is 0; in formula (ii), the 9-C double bond is of formula Z, the 13-C double bond is of formula E, and a is 0, b is 0; in formula (iii), the 9-C double bond is of formula E, the 13-C double bond is of formula Z, and a is 0, b is 0; in formula (iv), the 9-C double bond is of formula E, the 13-C double bond is of formula E, and a is 1, b is 0; In formula (v), the 9-C double bond is of formula E, the 13-C double bond is of formula E, and a is 1, b is 1. Further, the compound is a compound having a structure represented by formula (i-e), formula (ii-f), formula (iii-g), formula (iv-h) or formula (v-i): The structure of the specific compounds provided in this example, the compounds of the present application can be used as a multifunctional additive to provide additional health benefits to the product while providing color. In particular, the compound of the present application has no significant toxicity to cells at an effective concentration, and is proved to have good biosafety, and is suitable for use as an additive in foods, medicines and cosmetics which are in direct contact with the human body. Further, the stereo configuration