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MindMap Gallery Natural Medicinal Chemistry Phenylpropanoids

Natural Medicinal Chemistry Phenylpropanoids

This is a mind map about natural medicinal chemistry phenylpropanoids. These compounds are widely found in plants and have important physiological activities, such as anti-tumor, anti-inflammatory, antibacterial and immunomodulatory effects.

Edited at 2024-01-16 20:33:08

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Natural Medicinal Chemistry Phenylpropanoids

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Outline

phenylpropanoids

Definition and classification of phenylpropanoids

definition

A compound composed of a benzene ring and three straight-chain carbon units (C6-C3)

Classification

Phenylpropionic acid, coumarin, lignans

Biosynthetic pathway (cinnamic acid pathway)

phenylpropionic acid

definition

Basic structure: phenolic hydroxyl-substituted aromatic carboxylic acid

Important phenylpropionic acid

Chlorogenic acid

Antibacterial and choleretic, found in Yincheng, honeysuckle, and Ganoderma lucidum

Rosmarinic acid

Stop diarrhea

Danshensu

Treat coronary heart disease

Extraction and Separation

Features: It has certain water solubility and is often mixed with phenolic acids and flavonoid glycosides.

Extraction method: decoction method, heating reflux method; ultrasonic extraction method, microwave extraction method

Extraction of chlorogenic acid from honeysuckle

Extraction: water extraction and alcohol precipitation method

Water extract → Concentrate to 1:1 → Add 95% EtOH to 75%

Refining: Macroporous resin method

Adjust the water extract to pH 3.0 in HCl → filter → put the filtrate on a macroporous resin column Water → 10% → 45%EtOH → EtOH elution, collect the 45%EtOH fraction Concentrate to paste → add 95% EtOH to >80% → let stand and filter → take the supernatant

Lignans

Definition: A natural product formed by the oxidative polymerization of phenylpropanoid, usually a dimer, and a few trimers and tetramers.

Classification: neolignans, norlignans, heterolignans

Common types

Physical and chemical properties: properties; solubility: free - lipophilic, glycoside - increased solubility; basically non-volatile; most are optically active

Extraction and Separation

Extraction: Less polar solvents, such as ethanol and acetone

Separation: chromatography, solvent extraction, fractional precipitation, recrystallization. Commonly used chromogenic reagents for lignan thin-layer chromatography are: antimony trichloride reagent and 5% phosphomolybdic acid ethanol solution. Lignans are easily resinified during solvent extraction and separation.

coumarin

mother nucleus

Umbeliferolide is the mother core of coumarin; there is often an oxygen-containing functional group at position 7 of the mother core

Classification

simple coumarin

Only the benzene ring has substitutions (hydroxyl, alkoxy, phenyl, isopentene)

C3, C6, and C8 positions have high electronegativity and are easy to alkylate.

Furanocoumarins

The 6, 8-isopentenyl group on the coumarin core is often cyclized with the ortho-position phenolic hydroxyl group (7-hydroxyl group) → furan or pyran ring

6-replaces: linear type, 8-replaces: angular type

Pyran coumarin

Other coumarins

Refers to coumarins with substituents on the α-pyrone ring

biological activity

Low concentrations can stimulate plant germination and growth; high concentrations can inhibit

Photosensitivity: can cause skin pigmentation

Antibacterial and antiviral effects: Cnidium monnieri and Angelica sinensis root can inhibit hepatitis B surface antigen

Smooth muscle relaxant: Artemisinolide from Artemisia vulgaris

anticoagulant effect

Hepatotoxicity

Physical and chemical properties

physical properties

Free: sublimable, volatile, blue fluorescent under UV, and soluble in alkaline water because of its phenolic hydroxyl group. Glycoside: increased water solubility, non-volatile

chemical properties

alkaline hydrolysis reaction

Difficulty of reaction

The electron-donating conjugation effect of 7-OCH3 makes it difficult for carbonyl C to accept the nucleophilic reaction of OH-, so it is difficult to react; 7-OH forms a salt in alkali solution, and the electron-donating effect is ↑, making it more difficult to react; Coumarin>7 -Methoxycoumarin>7-Hydroxycoumarin

3,4-C=C isomerization: long-term heating or high concentration of alkali will convert from cis to trans

Coumarin with special structure

For example, those with >C=O, >C=C<, or epoxy structures at the appropriate position of the C-8 substituent can associate and add to the newly generated phenolic OH from hydrolysis. After acidification, it will hinder the lactone. Restoration of o-hydroxycinnamic acid

color reaction

Iron hydroxamate reaction (identification of lactone)

Under alkaline conditions, coumarin opens the lactone ring, condenses with hydroxylamine hydrochloride to form hydroxamic acid, and complexes with iron ions under acidic conditions to form iron hydroxamate (red)

Gibbs reaction and Emerson reaction

Reaction conditions: There must be free phenolic hydroxyl groups and no substitution at the para position; for coumarin, no substitution at the 6-position, alkaline hydrolysis reagent

Gibbs reaction reagent: 2,6-dichloro(bromo)benzoquinone chlorimine • blue

Emerson's reaction reagent: aminoantipirin and potassium ferricyanide • red

Extraction and Separation

Sublimation, steam distillation

According to the volatility of coumarin, it is suitable for extracting coumarin with stable chemical properties.

Alkali extraction and acid precipitation

According to the alkaline hydrolysis reaction, coumarin with a special structure will not be able to cyclize (there is a carbonyl group, double bond, and epoxy structure at the C-8 position)

Solvent extraction method

System solvent extraction method for initial separation, column chromatography and TCL for further extraction and separation.

Spectral characteristics

Mother core (when there is no oxygen-containing functional group): 274nm (benzene ring), 311nm (α-pyrone); when there is an oxygen-containing substituent: red shift

fluorescence

-OH at C-7 position: fluorescence is enhanced; etherification at C-7 position: fluorescence is weakened

Generally, it has a strong molecular ion peak, and the most common fragment ion peak in the mass spectrum is the loss of a series of CO.

1H-NMR

Active H shift of COOH: 12-13Hz; ph-OH: 9～10Hz; carbon-carbon double bond: trans: (large) 17-18Hz, cis: 10-12Hz; coupling constant of benzene ring ortho pair: ortho 7-8Hz, between 1-3Hz, against 0-1Hz

coumarin core

Chemical shift: H-4, 5, 7>H-3, 6, 8 (due to the electron-withdrawing effect of the lactone carbonyl group, the electron cloud density decreases and the chemical shift value increases); H-4max, H-3min

Remote Coupling: H-4 and H-8

hydroxyl substitution

Forcing effect and NOE effect

Forced position effect: When there is a substituent at position 4 or 5, the chemical shift of H at the other position increases and the chemical shift of C decreases.

NOE effect: distance <3A, increase ≥2% (when positions 4 and 5 have different protons, the peak height of the other position will increase after irradiation)

13C-NMR

C-C:30(10-30); C-O:60; C with two O:90; C=C:120; C=C-O:150; C=O:200 (ketone carbonyl), C=O:160 (ester carbonyl)

When there is OR substitution: attached carbon: 30, ortho carbon: -13, para carbon: -8