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Investigation of the germination promoting compounds in smoke. Gavin Flematti The University of Western Australia. Smoke. Emilio Ghisalberti (UWA) Kingsley Dixon (KPBG) Robert Trengove (Murdoch). Solving the bushfire germination mystery……. Smoke as a germination cue.

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Presentation Transcript
slide1
Investigation of the

germination promoting

compounds in smoke

Gavin Flematti

The University of Western Australia

Smoke

Emilio Ghisalberti (UWA)

Kingsley Dixon (KPBG)

Robert Trengove (Murdoch)

smoke as a germination cue
Smoke as a germination cue
  • In 1990, researchers in South Africa identified smoke as the key agent for stimulating germination of a threatened fynbos species Audouinia capitata (Bruniaceae)
  • Researchers at Kings Park and Botanic Garden (Western Australia) have since identified smoke as the key element for promoting the germination of many Australian native seeds
slide5
Smoke found to improve

seed germination of

many Australian native

species

slide7
Sites with smoke-stimulated germination of wild species

And the list of species includes…. lettuce, celery, parsley and others….

apparatus for generating plant derived smoke
Apparatus for generating Plant Derived Smoke

‘Smoke-water’

‘Aerosol Smoke’

slide9
Benefits for mining restoration

Lateritic nickel project

Mineral sands mining restoration - BUT… need 10 tonnes smoke water per hectare!

attempts to identify the active compound s
Attempts to identify the active compound(s)
  • Baldwin et al. (1994) identified 71 compounds and tested a total of 233
  • Dixon et al. (1997) identified a further 43 compounds
  • Researchers in South Africa (1995) and California (1997) have also identified compounds in smoke
  • Importantly, burning cellulose produces the active compound(s)
slide11
Stylidium affine

Lettuce (Grand Rapids)

Conostylis aculeata

The Needle in the Haystack - finding the chemical(s) in smoke responsible for germination

  • Bioassay - Test that uses a biological indicator for tracking the active components through separation steps
isolation of smoke compounds13
Isolation of Smoke Compounds

Smoke Water

Ether layer

Ether extract

Aqueous layer

isolation of smoke compounds14
Isolation of Smoke Compounds

Smoke Water

Ether extract

Ether

layer

Aqueous

layer

isolation of smoke compounds15
Isolation of Smoke Compounds

Smoke Water

Ether extract

Ether layer

NaHCO3 layer

NaHCO3 soluble

(stronger acids

- COOH)

isolation of smoke compounds16
Neutral fraction

(~35% by mass)

Isolation of Smoke Compounds

Smoke Water

Ether extract

Ether layer

NaHCO3 soluble

(stronger acids

- COOH)

NaOH soluble

(weaker acids

- phenols etc.)

NaOHlayer

-Activity found in the neutral fraction-

lots of chromatography
Lots of Chromatography!
  • Chromatography -

Physical method of

separating compounds

Mobile

phase

Stationary

phase

Classical Liquid

Chromatography

general separation scheme
C18 silica

Fraction 7

(Highest activity)

8 Fractions

Test for Activity

General separation scheme

Alumina

Neutral Fraction

15 Fractions

2 years later only 3 compounds
~ 2 years later…Only 3 Compounds!

UV recorded at 320nm

25% MeOH/water

3

2

1

  • All had molecular formula C8H6O3 (mw=150)
  • Separated and tested for activity
synthesis of the active compound 2
*”Karrikinolide”

*‘karrik’ – Aboriginal word for smoke, -olide indicates lactone

Synthesis of the active compound (2)
  • IUPAC name: 3-methyl-2H-furo[2,3-c]pyran-2-one (2)
  • Prepared in ~5% yield from Kojic acid (4)
slide29
Summary

First chemical identified from smoke that promotes germination

Novel structure – new to science

Devised a method of synthesis

Bioassay data demonstrating effect with species from Australia,

South Africa and North America

Potential uses in agriculture, horticulture, land restoration etc…

Compared with smoke water, karrikinolide operates

at < 1 g per hectare

slide30
Potent Germination Promoter

What other species…?

What other activity…?

Is there a better (simpler) synthesis…?

Are there active analogues…?

What is the mode of action…?

mode of action
LabelMode of Action??

Label = fluorescent

Questions ??

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