Production of Aloesin

The Aloe Ferox plant grows in the wild. The leaves are harvested so as to protect the growth of the plant, i.e. renewable plant source. Aloe Ferox has a higher percentage of Aloesin compared with the Aloe Vera species. Aloesin is extracted from the sap of the Aloe Ferox leaf. It is isolated as a powder which is >95% pure (HPLC). Aloe Ferox, a plant species prevalent in South Africa, and found predominantly in the Eastern and Western Cape, grows in the wild, free of chemicals, pesticides and herbicides.

The aloe bitter sap comprises of aloin , aloesin, aloeresin- the composition of which varies dependent on the botanical source of material.  The sap may be subjected to chemical or enzymatic hydrolysis in converting aloeresin to aloesin and p-coumaric acid.  The amount of Aloesin available for extraction is therefore increased and the extraction of Aoesin is made easier and less costly.  Isolation of the crude aloesin is done by removal with suitable solvents.  Purification of the crude aloesin is by by recrystallisation in solvents

The complete Aloesin production process is described in patent  number WO 2006/097811 A1, granted to the CSIR:  Method for converting Aloeresin to Aloesin.

 

Aloesin production:  Extraction from Bitter Sap

After the Aloe Verox leaves are harvested, the bitter sap is transferred to the production facility.  Here the Aloesin is isolated by repeated solvent extractions, crystallizations and purification until a pure white powder is crystalised.  The speciation and purity is presented in the typical certificate of analysis here under.

Production facility

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Specification and Certificate of Analysis

TYPICAL CERTIFICATE OF ANALYSIS

 

 PRODUCT:                                      Aloesin

DESCRIPTION:                               2-acetonyl-8-b-D-glucopyranosyl-7-hydroxy-5-methylchromone

PRODUCT CODE:                    Development Product

BATCH NUMBER:                         B7-1

 

 

ANALYSIS

SPECIFICATION

RESULTS

Colour and appearance

White to off-white powder Off-white powder

Purity by HPLC (dry basis)

Not less than 90 % 98.0 %
Anthraquinone by HPLC None detected Pass
Moisture Not more than 5 % Pass

Storage Conditions:   Please store below 25°C in the dark

 

 

 

TECHNICAL SPECIFICATIONS

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Aloesin

(2-acetonyl-8-glucopyranosyl-7-hydroxy-5-methylchromone)

 

Physical/Chemical Properties

Molecular Formula          =             C19H22O9

Molecular Weight            =             394 g/mol

Melting point                     =             142-144°C with sintering

UV (MeOH) lmax               =             216,250,254,298

[a]25D + 59.2°

IR (KBr) nmax                       =             3300,1715,1662,1596 cm-1

Solubility:            Freely soluble in water and polar organic solvents, especially alcohols.

Stability:               Store in dark at room temperature.  Photo-catalyzed degradation observed, especially in solution.  Resistant to thermal denaturation and mild acid hydrolysis (100°C in 2M HCI-EtOH (1:1) for 1.5 hours).

 

Biological Properties

  1. Non-competitive inhibitor of tyrosinase enzyme responsible for melanin pigment formation in human skin (Yagi et al., 1987)
  2. Hepatoprotective factor: stimulates cell proliferation in vitro and in vivo (Univera Pharmaceuticals, Inc.)

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