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Myrrha – Moyao

  • Hildebert Wagner
  • Stefanie Püls
  • Talee Barghouti
  • Anton Staudinger
  • Dieter Melchart
Chapter

Abstract

Pharmacopoeia: [1]

Pharmacopoeia of the People’s Republic of China, English Edition Vol. I, 2010

Official drug: [1]

Myrrh is the dried resin collected from the trunk of Commiphora myrrha Engl. or Commiphora molmol Engl. (Fam. Burseraceae).

The drug is divided into natural myrrh and colloidal myrrh.

Origin: [2, 3, 4, 5, 6, 7, 8, 9]

Mainly in places such as Somalia and Ethiopia in north-eastern Africa, the southern Arabian Peninsula, India and China.

Description of the drugs: [1]

Natural myrrh

Irregular granular agglomerates, varying in size, the large one up to or more than 6 cm in diameter. Externally yellowish-brown or reddish-brown, the translucent part in brownish-black colour, covered with yellow dustlike powder. Texture hard and fragile, broken surface uneven, lusterless. With characteristic aromatic odour; taste bitter and slightly pungent.

Colloidal myrrh

Irregular pieces and grains, mostly agglutinated into lumps varying in size, the large one up to or more than 6 cm in diameter. Externally yellowish-brown to brown, opaque. Texture compact or loose. With characteristic aromatic odour; taste bitter and viscous.

Processing: [1]

Myrrha (processed with vinegar)

The clean Myrrha is stir-baked as described under the method for stir-baking with vinegar (Appendix II D) to lustrous on surface. To each 100 kg of Myrrha 5 kg of vinegar are added.

Medicinal use: [10]

In the western countries myrrh is used only as astringent tincture against inflammations of stomach and throat.

Toxicity: [10]

May cause nausea and vomiting, overdose may cause damage to the stomach, use of pills or capsules is recommended.

Effects and indications of Myrrha according to Traditional Chinese Medicine [1, 2, 3, 5, 10]

Taste:

Pungent, bitter, aromatic

Temperature:

Neutral

Channels entered:

Orbis hepaticus

Effects (functions):

To dissipate stasis to relive pain, disperse swelling and promote tissue regeneration.

Symptoms and indications:

Chest impediment and heart pain, pain in stomach duct, amenorrhea and dysmenorrhea, postpartum stasis and obstruction, abdominal pain caused by aggregation and accumulation, painful impediment caused by wind-dampness, injuries from falls and fights, swelling abscess, sore and ulcer.

Published Constituents

Furanosesquiterpenes : [2, 5, 6, 8, 9, 11, 12, 13, 14, 15, 16]

 

Germacrane-type

furanodien, furanodienon, 2-methoxyfuranodien, 5-acetoxy-2-methoxy-4,5-dihydrofuranodien-6-on

Eudesmene-type

furanoeudesma-1,3-diene, furanoeudesma-1,4-diene, lindestrene

Elemen-type

isofuranogermacren, curzerenone

Guajen-type

2-methoxyfuranoguaia-9-en-8-on

Sesquiterpenes : [6, 7, 8]

commiterpenes A-C; germacrene A,B,D; myrrhterpenoids K-N, curzerene, myrrhone

Resin : [5, 8, 12, 16]

α-,β-heerabol-myrrhol, heeraboresen, α-,β-,γ-commiphoric

acid, α-,β-heerabomyrrholic acid,

burseracin, 3-epi-α-amyrin, α-amyrenon, isolinalyl acetate,

β-eudesmol acetate, lupeone, 3-epi-lupenyl acetate,

campesterol, cholesterol, β-sitosterol

Essential oil : [4, 5, 6, 8, 10, 12, 16]

cuminaldehyde, cinnamaldehyde, m-cresol,

myrrholic acid, eugenol, α-pinene, β-elemene, limonene

Fig. 1 Formulae of the main compounds of Myrrha [8]

Reported pharmacology:

- lowers cholesterol [10]

- analgesic [10]

- antifungal/-bacterial/-microbial [9, 10, 11, 12, 16]

- astringent and disinfectant properties [10]

- promotes healing of wounds [10]

- stimulates gastrointestinal motility [10]

- cytotoxic [11, 12]

- anaesthetic [9, 11, 12, 16]

- anti-inflammatory [6, 11, 12]

- antioxidant [11]

- anti-schistosomal [6]

- antihyperglycemic [8, 9, 16]

- neuroprotective [7]

TLC Fingerprint Analysis

Drug samples

Origin

1

Myrrha praep. (roasted with rice wine vinegar)/without botanical assignment

Sample of commercial drug obtained from China Medica (origin: Kunming, Yunnan, China)

2

Myrrha/Commiphora myrrha

India

3

Myrrha/Commiphora myrrha

Ethiopia

4

Myrrha/Commiphoramolmol

Sample of commercial drug obtained from Cfm Oskar Tropitzsch GmbH (origin: Ethiopia)

Reference compounds of Fig. 2

Rf

T1

Furanoeudesma-1,3-diene

0.94

T2

Sudan IIIa

0.65

aused only as positive control

1. Extraction:

0.5 g powdered drug is shaken with 5 ml ethanol for 5 min.

 

The extract is filtered over Chromafil®, Type 0.20 μm and used for the TLC.

2. Reference compounds:

1.0 mg is dissolved in 1.0 ml methanol

3. Separation parameters:

 

 Plate:

HPTLC Silica gel 60 F254, Merck

 Applied amounts:

Myrrha extracts: each 10 μl

 

Reference compounds: each 8 μl

 Solvent system:

Toluene + ethyl acetate (18.6 + 1.4)

 Detection:

Anisaldehyde – Sulphuric acid reagent

0.5 ml anisaldehyde is mixed with 10 ml glacial acetic acid, followed by 85 ml methanol and 5 ml concentrated sulphuric acid, in that order.

The plate is sprayed with 10 ml, heated at 110 °C for 10 min, then evaluated in VIS.

Note: The reagent has only limited stability and is no longer useable when the colour has turned to red-violet.

Fig. 2 Thin layer chromatogram of the ethanol extracts of Myrrha, sprayed with Anisaldehyde – Sulphuric acid reagent (VIS)

4. Description:

The Commiphoramyrrha extracts 2 and 3 of different origin show a very homogeneous TLC-pattern of several pink zones with two violet zones at Rf = 0.25 and Rf = 0.29. Furanoeudesma-1,3-diene (T1) is not detectable.

The Myrrha praep. extract 1 differs only scarcely from the normal extracts but contains Furanoeudesma-1,3-diene (T1).

The Commiphoramolmol extract 4 differs from all other extracts by two distinct pink zones at Rf = 0.60 and Rf = 0.68 which might be derive from curzerenone and 2-methoxyfuranodien according to reference [4].

HPLC-Fingerprint Analysis [17]

1. Extraction:

0.5 g powdered drug is shaken with 5 ml ethanol for 5 min.

The extract is filtered over Chromafil®, Type 0.20 μm.

2. Injection volume:

Myrrha extracts: each 5 μl

3. HPLC – Parameter:

 

 Apparatus:

MERCK HITACHI D-6000 A Interface

MERCK HITACHI L-4500 A Diode Array Detector

MERCK HITACHI AS-2000 Autosampler

MERCK HITACHI L-6200 A Intelligent Pump

 Separation column:

LiChroCART® 250-4 LiChrospher® 60 RP select B (5 μm), Merck

 Precolumn:

LiChroCART® 4-4 LiChrospher® 60 RP select B (5 μm), Merck

 Solvent:

A: Water (Millipore Ultra Clear UV plus® filtered)

B: Acetonitrile (VWR)

 Gradient:

20% B for 5 min,

20–46% B in 25 min,

46–48% B in 15 min,

48–54% B in 5 min,

54–100% B in 15 min,

100% B for 7 min,

total runtime: 72 min

 Flow:

1.0 ml/min

 Detection:

210 nm

Retention times of the main peaks

Peak

Rt (min)

Compound

A

33.0–45.0

Mixtures of sesquiterpenoids

B

59.0–70.0

1

59.6

Furanoeudesma-1,3-diene

Fig. 3a HPLC-fingerprint analysis of the ethanol extract of Myrrha (sample 1)

Fig. 3b HPLC-fingerprint analysis of the ethanol extract of Myrrha (sample 3)

Fig. 3c HPLC-fingerprint analysis of the ethanol extract of Myrrha (sample 4)

Fig. 4 On line UV-spectra of peak 1 of Myrrha

4. Description of the HPLC-Figures

The HPLC-peak profiles of Myrrha extracts sample 1 and 3 are characterized by two peak ranges A and B between Rt = 33–45 (A) and Rt = 59–70 (B) with furanoeudesma-1,3-diene (1) which is only detectable in sample 1. Extract sample 4 (C. molmol) provides only two distinct peaks in the B range, with furanoeudesma-1,3-diene (1) as main constituent.

Conclusion

The authentication of Commiphora myrrha and C. molmol extracts are accurately possible by TLC and HPLC.

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Copyright information

© Springer International Publishing AG 2017

Authors and Affiliations

  • Hildebert Wagner
    • 1
  • Stefanie Püls
    • 2
  • Talee Barghouti
    • 2
  • Anton Staudinger
    • 3
  • Dieter Melchart
    • 4
  1. 1.LMU Munich Center of Pharma ResearchMunichGermany
  2. 2.Center of Pharma ResearchLMU Munich Center of Pharma ResearchMunichGermany
  3. 3.TCM-Klinik Bad KötztingBad KötztingGermany
  4. 4.Klinikum rechts der IsarKompetenzzentrum KomplementärmedMünchenGermany

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