crude oil pah constitution, degradation pathway and associated ... · incomplete combustion of...

INTERNATIONAL JOURNAL OF ENVIRONMENTAL SCIENCES Volume 1, No 7, 2011

© 2011 Kumar Arun et al., licensee IPA- Open access - Distributed under Creative Commons Attribution License 2.0

Research article ISSN 0976 – 4402

Received on March, 2011 Published on April 2011 1427

Crude oil PAH constitution, degradation pathway and associated

bioremediation microflora: an overview

Kumar Arun1, Munjal Ashok

1, Sawhney Rajesh

2

1- Department of Bioscience and Biotechnology, Banasthali Vidyapith, Banasthali, Rajasthan

(India)-304022

2- Department of Microbiology, Bhojia Institute of Life Sciences, Budh, Baddi. Distt.

Solan,Himachal Pradesh (India)-173205

[email protected]

doi:10.6088/ijessi.00107020004

ABSTRACT

Crude oil, a dark sticky liquid, is a complex mixture of varying molecular weight which is

used for the preparation of petroleum products. Crude oil contains more than 30 parent

polyaromatic hydrocarbons (PAHs). The U.S.EPA has designated 16 PAH compounds

(naphthalene, acenaphthylene, acenaphthene, fluorene, phenenthrene, anthracene,

fluoranthene, pyrene, benz[a]anthracene, chrysene, benzo[b]fluoranthene,

benzo[k]fluoranthene, benzo[a]pyrene, dibenz[a, h]anthracene, benzo[g, h, i]perylene, and

indeno[1,2,3-cd]pyrene) as priority pollutants. PAHs are one of the most widespread organic

pollutants and potentially health hazard. Besides other environmental components, they are

also found in foods (cereals, oils, fats, vegetables, cooked meat). They are

carcinogenic , mutagenic , and teratogenic . Thus, key focus is to eliminate these hazardous

pollutants from the environment. The present review highlights the presence of various PAHs

in the crude oil, key metabolic pathway for the degradation and the associated microbial

degraders. The current approach to bioremediation uses various bacterial and fungal genera

under aerobic or anaerobic conditions to directly target the specific PAH. However, there is

need to explore newer approaches to design an efficient, effective and ecofriendly

bioremediation tool. The dearomatization of crude oil might be a useful comprehensive

approach and one shot solution to multiple PAH population.

Keywords: Crude oil, PAHs, Bioremediation, Phytoremediation, Rhizoremediation

1 Introduction

Crude oil is a complex mixture of varying molecular weight hydrocarbons and other organic

compounds found beneath the earth's surface. It is a dark sticky fluid naturally-occurring in

certain rock formations. Crude oil contains carbon and hydrogen, with or without non-

metallic elements such as oxygen and sulfur. It is highly flammable and generates energy. Its

derivative i.e. natural gas, is an excellent fuel. The term "Petroleum" has been used as a

synonym to crude oil. This term was first used in the treatise “De Natura Fossilium”

published in 1546 by the German mineralogist Georg Bauer (Bauer-Georg et al., 1955).

1.1 Origin, constitution and use

Crude oil is the product of heating of ancient organic materials over geological period. It is

formed from pyrolysis of hydrocarbon, in a variety of reactions, mostly endothermic at high

mailto:[email protected]

http://en.wikipedia.org/wiki/Hydrocarbon

http://en.wikipedia.org/wiki/Organic_compound



http://en.wikipedia.org/wiki/Earth

http://en.wikipedia.org/wiki/Germany

http://en.wikipedia.org/wiki/Georg_Bauer

http://en.wikipedia.org/wiki/Diagenesis


http://en.wikipedia.org/wiki/Geologic_time_scale


http://en.wikipedia.org/wiki/Endothermic

Crude oil PAH constitution, degradation pathway and associated bioremediation microflora: an overview

Kumar Arun, Munjal Ashok, Sawhney Rajesh

International Journal of Environmental Sciences Volume 1 No.7, 2011 1428

temperature and/or pressure. Crude oil reserves were formed from the preserved remains

of prehistoric zooplankton and algae, which had settled to a sea or lake bottom in large

quantities under anoxic conditions. On the other hand, the remains of prehistoric terrestrial

plants led to form coal. During the formation of crude oil, diagenesis followed catagenesis.

The studies documented that over a period, the organic matter mixed with the mud and got

buried under heavy layers of sediments resulting in generation of high levels

of heat and pressure (diagenesis). This process transformed the organic matter into a waxy

material known as kerogen, followed by its further conversion to liquid and gaseous

hydrocarbons (catagenesis). The change from kerogen to natural gas through oil is a

temperature dependent event. Sometimes the oil formed at extreme depths migrates and is

entrapped at shallower depths. eg. Athabasca oil sands.

The crude oil is a heterogeneous entity, composed of hydrocarbon chains of varied lengths. It

contains hundreds of different hydrocarbon compounds such as

paraffins, naphthenes, aromatics as well as organic sulfur compounds, organic nitrogen

compounds and oxygen containing hydrocarbons (phenols). Crude oils generally lack in

olefins (Gary et al., 1984). The most common distillations of petroleum are fuels. Fuels

generally include, ethane and other short-chain alkanes, diesel fuel (petrodiesel), fuel oils,

gasoline (petrol), jet fuel, kerosene, liquefied petroleum gas (LPG). The following table-1

depicts various fuels with their use.

Table 1: Different distillations of Petroleum (Fuels) and their use.

S. No. Fuel/ Derivatives Uses

1 Alkenes (Olefins) Manufacture of plastics or other compounds

2 Lubricants Synthesis of light machine oils, motor oils

and greases, as viscosity stabilizers

3 Wax Used in the packaging of frozen foods

4 Petroleum coke

(asphalt)

Used in carbon products or as solid fuel, Paraffin

wax, Aromatic petrochemicals as precursors in

other chemical synthesis.

5 Paraffin wax & aromatic

petrochemicals

As precursor in chemical production

The different fractions of the crude oil, produced exhibit boiling point ranges, instead of a

single boiling point eg. a crude oil fractionator produces an overhead fraction called

"naphtha". This fraction becomes a gasoline component after it is further processed through a

catalytic hydrodesulfurizer and a catalytic reformer into molecules having higher octane

rating value (Nelson, 1958; and Gary et al., 1984).

1.2 Variety of PAHs in crude oil

PAHs, commonly termed as poly-aromatic hydrocarbons or polynuclear aromatic

hydrocarbons, are chemical compounds that consist of fused aromatic rings and do not

contain heteroatoms or carry substituents (Fetzer, 2000). The natural crude oil contains

significant amounts of polycyclic aromatic hydrocarbons (PAHs) that arise from chemical

conversion of natural product molecules, like steroids, to aromatic hydrocarbons. PAHs are

http://en.wikipedia.org/wiki/Prehistory

http://en.wikipedia.org/wiki/Zooplankton

http://en.wikipedia.org/wiki/Algae

http://en.wikipedia.org/wiki/Anoxic_sea_water

http://en.wikipedia.org/wiki/Terrestrial_plant



http://en.wikipedia.org/wiki/Coal

http://en.wikipedia.org/wiki/Mud

http://en.wikipedia.org/wiki/Sediment

http://en.wikipedia.org/wiki/Heat

http://en.wikipedia.org/wiki/Pressure

http://en.wikipedia.org/wiki/Catagenesis_(geology)

http://en.wikipedia.org/wiki/Athabasca_Oil_Sands



http://en.wikipedia.org/wiki/Paraffin

http://en.wikipedia.org/wiki/Naphthene

http://en.wikipedia.org/wiki/Aromatic

http://en.wikipedia.org/wiki/Category:Organosulfur_compounds

http://en.wikipedia.org/wiki/Category:Organonitrogen_compounds



http://en.wikipedia.org/wiki/Oxygen

http://en.wikipedia.org/wiki/Phenols

http://en.wikipedia.org/wiki/Olefin

http://en.wikipedia.org/wiki/Petroleum_distillation

http://en.wikipedia.org/wiki/Fuel

http://en.wikipedia.org/wiki/Ethane

http://en.wikipedia.org/wiki/Alkanes

http://en.wikipedia.org/wiki/Diesel_fuel

http://en.wikipedia.org/wiki/Fuel_oil

http://en.wikipedia.org/wiki/Gasoline

http://en.wikipedia.org/wiki/Jet_fuel

http://en.wikipedia.org/wiki/Liquefied_petroleum_gas

http://en.wikipedia.org/wiki/Alkenes

http://en.wikipedia.org/wiki/Plastics

http://en.wikipedia.org/wiki/Lubricant

http://en.wikipedia.org/wiki/Motor_oil

http://en.wikipedia.org/wiki/Grease_(lubricant)

http://en.wikipedia.org/wiki/Viscosity

http://en.wikipedia.org/wiki/Wax

http://en.wikipedia.org/wiki/Frozen_food

http://en.wikipedia.org/wiki/Petroleum_coke

http://en.wikipedia.org/wiki/Paraffin_wax




http://en.wikipedia.org/wiki/Petrochemical

http://en.wikipedia.org/wiki/Chemical

http://en.wikipedia.org/wiki/Naphtha

http://en.wikipedia.org/wiki/Hydrodesulfurizer

http://en.wikipedia.org/wiki/Catalytic_reformer

http://en.wikipedia.org/wiki/Octane_rating



http://en.wikipedia.org/wiki/Chemical_compound


http://en.wikipedia.org/wiki/Simple_aromatic_ring

http://en.wikipedia.org/wiki/Heteroatom

http://en.wikipedia.org/wiki/Substituent




also found in processed fossil fuels, tar and various edible oils (Glenn, 1995). It is described

that the distributions of PAHs with respect to the relative amounts of individual PAHs and

that of the isomers produced, determine the type of combustion and acts as the indicators of

the burning history.

The simplest PAHs are phenanthrene and anthracene (International Union on Pure and

Applied Chemistry (IUPAC). Benzene and naphthalene have been formally excluded from

the list of PAHs. However, they are chemically related to PAHs and referred to as

monoaromatic or diaromatics.

The literature documents that the number of aromatic rings determine the type of PAHs. The

number in PAH may vary from 4 to 7, with 5 or 6 ringed PAH being more common. PAHs

composed only of six-membered rings are called alternant PAHs. Certain alternant PAHs,

lacking in complete benzene ring, are called "benzenoid" PAHs. The figure-1 and table-2

enlists different PAHs constituents of crude oil.

PAHs are classified as small and large depending on the presence of number of rings. The

“small” PAHs contain up to six fused aromatic rings where as “large” PAHs contain more

than six aromatic rings.

PAHs have characteristic UV absorbance spectra with many bands each unique for each ring

structure. Thus, each isomer has a different UV absorbance spectrum (200nm-400nm). This

helps in the identification of PAHs. Most of the PAHs are also fluorescent. The extended pi-

electron electronic structures of PAHs lead to these spectra, as well as to certain large PAHs

also exhibiting semi-conducting and other behaviors.

Polycyclic aromatic hydrocarbons are lipophilic. The larger compounds are less water-

soluble and less volatile. These properties gives PAHs, it’s a place in the environment,

primarily in soil, sediment and oily substances. However, they are also a component of

concern in particulate matter suspended in air.

PAHs, the aromatic compounds, exhibit varying degree of aromaticity for each ring segment.

Clar's rule, given by Erich Clar in 1964 explains that benzene-like moieties are the most

important for the characterization of the properties of PAHs (Kim et al., 2003). The degree of

aromacity determines its level of reactivity.

http://en.wikipedia.org/wiki/Tar

http://en.wikipedia.org/wiki/Isomer

http://en.wikipedia.org/wiki/Naphthalene

http://en.wikipedia.org/wiki/Ultraviolet-visible_spectroscopy

http://en.wikipedia.org/wiki/Fluorescent

http://en.wikipedia.org/wiki/Semiconductor

http://en.wikipedia.org/wiki/Lipophilic

http://en.wikipedia.org/wiki/Volatility_(chemistry)

http://en.wikipedia.org/wiki/Soil

http://en.wikipedia.org/wiki/Particulate_matter

http://en.wikipedia.org/wiki/Aromaticity




Figure 1: Radial depiction showing parent polyaromatic hydrocarbons present in

crude oil.

Ova

Pya

Hec

Hep

Trp

Cor

Rub

Hex

Hep

Tpl

Pec

Pen

Per

Per

Pic

Ple Npc

Chr Pyr

Tpl

Aca

Acp

Flt

Ant

Phr

Phe

Flu

Ach

sIn

aIn

Bip

Hep

Azu

Nap

Ind Pen




Table 2: Parent Polyaromatic hydrocarbons present in crude oil.

S.N. Radial

Depiction for

PAH

PAH Name PAH structure Molecular

formula

1. Pen Pentalene

C8H6

2. Ind Indene

C9H8

3. Nap Naphthalene

C10H8

4. Azu Azulene

C10H8

5. Hep Heptalene

C12H10

6. Bip Biphenylene

C12H8

7. aIn as-Indacene

C12H8

8. sIn s-Indacene

C12H8

9. Can Acenaphthylene

C12H8

10. Flu Fluorene

C13H10

11. Phe Phenalene

C13H10

12. Phr Phenanthrene

C14H10

13. Ant Anthracene

C14H10

14. Flt Fluoranthene

C16H10

15. Acp Acephenanthrylene

C16H10

16. Aca Aceanthrylene

C16H10

17. Tpl Triphenylene

C18H12

18. Pyr Pyrene

C16H10




19. Chr Chrysene

C18H12

20. Npc Naphthacene

C18H12

21. Ple Pleiadene

C18H12

22. Per Perylene

C20H12

23. Pic Picene

C22H14

24. Pen Pentaphene

C22H14

25. Pec Pentacene

C22H14

26. Tpl Tetraphenylene

C24H16

27. Hep Hexaphene

C26H16

28. Hex Hexacene

C26H16

29. Rub Rubicene

C26H14

30. Cor Coronene

C24H12

31. Trp Trinaphthylene

C30H18

32. Hep Heptaphene

C30H18

33. Hec Heptacene

C30H18

34. Pya Pyranthrene

C30H16

35. Ova Ovalene

C32H14

The United States Environmental Protection Agency (USEPA) has designated 16 PAHs

compounds as priority pollutants (Table-3). They are naphthalene, acenaphthylene,

acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene,

chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenz[a,

h]anthracene, benzo[g, h, i]perylene, and indeno[1,2,3-cd]pyrene. These priority PAHs are

generally targeted for measurement in environmental samples.




Table 3: The U.S. EPA has designated 16 PAH compounds.

Naphthalene Acenaphthylene

Acenaphthene

Phenanthrene

Anthracene Benz[a,h]

anthracene

Benz[a] anthracene Chrysene

Pyrene

Benzo[a]pyrene Indeno[1,2,3-cd]

pyrene

Benzo[g, h, i]

perylene

Fluorene

Fluoranthene

Benzo[k] fluoranthene

Benzo[b]

fluoranthene

2. PAHs and Human health

PAHs are one of the most widespread organic pollutants and potentially health hazard. In

addition to their presence in fossil fuels they are also formed by

incomplete combustion of carbon-containing fuels such as wood, coal, diesel, fat, tobacco,

or incense. They have been identified as carcinogenic, mutagenic, and teratogenic. PAHs are

also found in foods. Studies have shown that most food intake of PAHs comes from cereals,

oils and fats. Smaller intakes come from vegetables and cooked meats (Larsson et al., 1983;

and Agency for toxic substances and disease registry 1996, European Commission, 2002).

The toxicity of PAHs is dependent on its structure and the isomers may exhibit variable

toxicity. Benzo[a]pyrene, is the first chemical carcinogen to be discovered. It is one of the

constituent found in cigarette smoke. The EPA has classified seven PAH compounds as

probable human carcinogens: benz[a]anthracene, benzo[a]pyrene, benzo[b]fluoranthene,

benzo[k]fluoranthene, chrysene, dibenz[a,h]anthracene, and indeno[1,2,3-cd]pyrene. Besides

these, Benzo[j]fluoranthene, benzo[ghi]perylene, coronene, and ovalene are known

for carcinogenic, mutagenic and teratogenic properties (Luch, 2005).

http://en.wikipedia.org/wiki/Phenanthrene

http://en.wikipedia.org/wiki/Chrysene

http://en.wikipedia.org/wiki/Pyrene

http://en.wikipedia.org/wiki/Benzopyrene

http://en.wikipedia.org/wiki/Combustion

http://en.wikipedia.org/wiki/Carbon

http://en.wikipedia.org/wiki/Wood

http://en.wikipedia.org/wiki/Coal

http://en.wikipedia.org/wiki/Diesel_fuel

http://en.wikipedia.org/wiki/Fat

http://en.wikipedia.org/wiki/Tobacco

http://en.wikipedia.org/wiki/Incense

http://en.wikipedia.org/wiki/Carcinogen

http://en.wikipedia.org/wiki/Mutagen

http://en.wikipedia.org/wiki/Teratogen

http://en.wikipedia.org/wiki/Benzopyrene

http://en.wikipedia.org/wiki/Chemicals_in_a_cigarette

http://en.wikipedia.org/wiki/Perylene

http://en.wikipedia.org/wiki/Coronene

http://en.wikipedia.org/wiki/Ovalene

http://en.wikipedia.org/wiki/Carcinogen

http://en.wikipedia.org/wiki/Mutagen

http://en.wikipedia.org/wiki/Teratogen




3. Bioremoval strategies for PAHs

Microorganisms degrade PAHs either via metabolism or co-metabolism. Co-metabolism is

especially relevant for the degradation of mixtures of PAHs. Both aerobic and anaerobic

metabolism exist for PAH degradation. However aerobic pathways, their kinetics and

enzymatic and genetic regulation is well documented. The present focus is on aerobic

metabolism of PAHs The metabolic pathways, the degradation kinetics and the enzymatic

and genetic regulation are well understood (Wirtz et al., 1981; Digiovanni, 1992; Goyal and

Zylstra, 1997).

The literature cites four types of aromatic metabolism (Fuchs, 2008):

a) Aerobic Metabolism

b) Hybrid type aerobic metabolism

c) Reductive aromatic metabolism

d) Reductive metabolism in anaerobes

The flow chart exhibits the aerobic metabolic pathway of degradation for anthracene, as a

model compound (Fig 2).

The aerobic aromatic metabolism is characterized by the extensive use of molecular oxygen

as co-substrate for oxygenases that introduce hydroxyl groups and cleave the aromatic ring.

The aerobic PAH catabolism is mediated by the enzymatic activity of

dioxygenase/monooxygenase. It incorporates atoms of molecular oxygen into the aromatic

nucleus and as a result aromatic ring is oxidized (Digiovanni, 1992; Auger et al., 1995; Goyal

et al., 1997,). On the basis of the substituents on the original molecule, two hydroxyl groups

may be positioned either ortho (catechol and protocatechuate) or para to each other (gentisate

and homogentisate). The cis-dihydrodiols that are formed in this reaction are further oxidized

to the aromatic dihydroxy compounds (catechols). These compounds are further oxidized

through the ortho or meta cleavage pathways (Denome et al., 1993; Baboshin et al 2008).

Finally, the reactions culminate into synthesis of the precursors of TCA cycle (tricarboxylic

acid) intermediates. The degradation of all PAHs is carried out by this common scheme.

However, its known that the number of aromatic rings govern the kinetic efficiency of the

pathway and the type of reaction intermediates produced.

Hybrid type aerobic metabolism is used by facultative aerobes eg. aerobic metabolism of

benzoate, phenylacetate, and anthranilate. This pathways uses coenzyme A thioesters of the

substrates and do not require oxygen for ring cleavage. An oxygenase/reductase leads to

dearomatization of the ring.




Anthracene

Naphthalene 1, 2-dioxygenase

Cis-1, 2-Dihydroanthracene-1, 2-diol

Cis-1, 2-dihydrodihydroxy-naphthalene

dehydrogenase

Anthracene-1, 2-diol

Anthracene-1,2-diol-1,2-

dioxygenase

Anthracene-1, 2-diol-

1, 2-dioxygenase

3-[(Z)-2-carboxyvinyl]-2-naphthoate

4-(2-hydroxynaph-3-yl)-2-oxobut-3-enoate

4-(2-hydroxynaph-3-yl)-2-oxobut-3-enoate

hydratase-aldolase

6, 7-Benzocoumarin

3-Hydroxy-2-naphthoate

3-hydroxy-2-naphthoate

hydroxylase

2, 3-Dihydroxy-naphthalene

Phthalate

Figure 2: Aerobic oxidation of polyaromatic hydrocarbon (model compound anthracene).

In the presence of oxygen, facultative aerobes and phototrophs use a reductive aromatic

metabolism. The reduction of the aromatic ring of benzoyl-coenzyme A is catalyzed by




benzoyl-coenzyme A reductase. This reduction is led by the hydrolysis of 2 ATP molecules.

It has been documented that a little characterized benzoyl-coenzyme A reductase operates in

strict anaerobe as they can not afford the costly ATP-dependent ring reduction (Georg, 2008).

Both fungi and bacteria are involved in biodegradation of PAHs (Table 4 & 5).

Table 4: Bacterial genera involved in PAHs degradation

Bacterial species strain PAHs References

Achromobacter sp. NCW Carbazole Guo et al., 2008

Alcaligenes denitrificans Fluoranthene Weissenfels et al., 1990

Arthrobacter sp. F101 Fluorene Casellas et al., 1997

Arthrobacter sp. P1-1 Phenanthrene, Carbazole,

Dibenzothiophene Seo et al., 2006

Arthrobacter sulphureus RKJ4 Phenanthrene Samanta et al., 1999

Acidovorax delafieldii P4-1 Phenanthrene Samanta et al., 1999

Bacillus cereus P21 Pyrene Kazunga et al., 2000

Bacillus subtilis BMT4i

(MTCC9447)

Benzo[a]pyrene Lily et al., 2009

Brevibacterium sp.HL4 Phenanthrene Samanta et al., 1999

Burkholderia sp.S3702, RP007,

2A-12TNFYE-5, BS3770

Phenanthrene Kang et al., 2003,

Balashova et al., 1999,

Laurie et al., 1999

Burkholderia sp. C3 Phenanthrene Seo et al., 2006

Burkholderia cepacia BU-3 Phenanthrene

Pyrene, Naphthalene

Kim et al., 2003

Burkholderia xenovorans

LB400

Benzoate, Biphenyl Denef et al., 2005

Chryseobacterium sp. NCY Carbazole Guo et al., 2008

Cycloclasticus sp. P1 Pyrene Wang et al., 2008

Geobacillus sp. Napthalene, Phenanthrene,

Fluorene Bubians et al., 2007

Geobacillus stearothermophilus

“AAP7919”

Anthracene Kumar et al., 2011

Janibacter sp. YY-1 Phenanthrene, Fluorene,

Anthracene, Dibenzofuran,

Dibenzo-p-dioxin,

Dibenzothiophene

Yamazoe et al., 2004

Marinobacter NCE312 Naphthalene Hedlund et al., 2001

Mycobacterium sp.PYR, Benzo[a]pyrene Cheung et al., 2001,

Grosser et al., 1991

Mycobacterium sp. JS14 Fluoranthene Lee et al., 2007

Mycobacterium sp. 6PY1, KR2,

AP1

Pyrene Rehmann et al., 1998,

Vila et al., 2001,

Krivobok et al., 2003

Mycobacterium sp. RJGII-135 Benzo[a]pyrene, Schneider et al., 1996




Benz[a]anthracene

Pyrene

Mycobacterium sp.PYR-1,

LB501T

Pyrene, Phenanthrene,

Fluoranthene, Anthracene Mody et al., 2001,

Kelley et al., 1993,

Sepic et al., 1998,

Ramirez et al., 2001,

Van et al., 2003

Mycobacterium sp. CH1, BG1,

BB1, KR20

Pyrene, Phenanthrene, Fluorene Boldrin et al., 1993,

Rehmann et al., 2001

Mycobacterium flavescens Pyrene, Fluoranthene Dean-Ross et al., 2002,

Dean-Ross et al., 1996

Mycobacterium vanbaalenii

PYR-1

Phenanthrene

Pyrene,

Dimethylbenz[a]anthracene

Kim et al., 2005,

Moody et al., 2003

Mycobacterium sp. KMS Pyrene Miller et al., 2004

Nocardioides aromaticivorans

IC177

Carbazole Inoue et al., 2006

Pasteurella sp. IFA Fluoranthene Sepic 1999

Polaromonas

naphthalenivorans CJ2

Naphthalene Pumphrey et al., 2007

Pseudomonas sp. C18, PP2,

DLC-P11

Phenanthrene, Naphthalene Denome et al., 1993,

Prabhu et al., 2003

Pseudomonas sp. BT1d 3-hydroxy-2-

formylbenzothiophene Bressler et al., 2001

Pseudomonas sp. HH69 Dibenzofuran Fortnagel et al., 1990

Pseudomonas sp. CA10 Chlorinated dibenzo-p-dioxin,

Carbazole Habe et al., 2001

Pseudomonas sp. NCIB 9816-4 Fluorene, Dibenzofuran,

Dibenzothiophene Resnick et al., 1996

Pseudomonas sp. F274 Fluorene Grifoll et al., 1994

Pseudomonas paucimobilis Phenanthrene Weissenfels et al., 1990

Pseudomonas vesicularis

OUS82

Fluorene Weissenfels et al., 1990

Pseudomonas putida P16,

BS3701, BS3750, BS590-P,

BS202-P1

Phenanthrene, Naphthalene Kiyohara et al., 1994,

Balashova et al., 1999

Pseudomonas fluorescens

BS3760

Phenanthrene, Benz[a]anthracene,

Chrysene Balashova et al., 1999

Pseudomonas stutzeri P15 Pyrene Kazunga et al., 2000




Pseudomonas saccharophilia Pyrene Kazunga et al., 2000

Pseudomonas aeruginosa Phenanthrene Romero et al., 1998

Ralstonia sp. SBUG 290, U2 Naphthalene, Dibenzofuran Becher et al., 2000,

Zhou et al., 2002

Rhodanobacter sp. BPC-1 Benzo[a]pyrene Kanaly et al., 2002

Rhodococcus sp. Pyrene, Fluoranthene Dean-Ross et al., 2002,

Walter et al., 1991

Rhodococcus sp. WU-K2R Benzothiophene,

Naphthothiophene Kirimura et al., 2002

Rhodococcus erythropolis I-19 Alkylated dibenzothiophene Folsom et al., 1999

Rhodococcus erythropolis D-1 Dibenzothiophene Matsubara et al., 2001

Staphylococcus sp. PN/Y Phenanthrene Mallick et al., 2007

Stenotrophomonas maltophilia

VUN 10,010

Benzo[a]pyrene

Pyrene, Fluoranthene

Boonchan et al., 1998

Stenotrophomonas maltophilia

VUN 10,003

Pyrene, Fluoranthene,

Benz[a]anthracene Juhasz et al., 2000

Sphingomonas yanoikuyae R1 Pyrene Kazunga et al., 2000

Sphingomonas yanoikuyae

JAR02

Benzo[a]pyrene Rentz et al., 2008

Sphingomonas sp.P2, LB126 Phenanthrene, Fluoranthene,

Fluorene, Anthracene Pinyakong et al., 2003,

Van et al., 2003,

Pinyakong et al., 2000

Sphingomonas sp. Dibenzofuran, Carbazole,

Dibenzothiophene Gai et al., 2007

Sphingomonas paucimobilis

EPA505

Phenanthrene, Fluoranthene,

Anthracene, Naphthalene Story et al., 2001,

Mueller et al., 1990

Sphingomonas wittichii RW1 Chlorinated dibenzo-p-dioxin Nam et al., 2006

Sphingomonas sp. KS14 Phenanthrene, Naphthalene Cho et al., 2001

Terrabacter sp.DBF63 Fluorene, Dibenzofuran,

Chlorinated dibenzo-p-dioxin,

Chlorinated dibenzothophene

Habe et al., 2004, Habe

et al., 2001, Habe et al.,

2002

Xanthamonas sp. Benzo[a]pyrene

Pyrene, Carbazole

Grosser et al., 1991

White rot fungi often prepare aromatic compounds for ring cleavage by first converting them

to quinones. The initial oxidation of anthracene (to 9,10-anthraquinone), benzo[a]pyrene

(Haemmerli, et al., 1986) and several other PAHs is catalyzed by lignin peroxidases

from Phanerochaete chrysporium, Bjerkandera sp. strain BOS55 (Field, J.A. et al., Enzyme

and Micro. Tech. 18:300-308, 1996) and other white rot fungi. Manganese peroxidases,

another family of lignin degrading peroxidases produced by white rot fungi, can also oxidize

anthracene (Eibes et al., 1986). Laccases, copper-containing enzymes that are also involved

in lignin degradation by Trametes versicolor, have also been shown to oxidize anthracene

(Collins et al., 1986). Not all white rot fungi produce laccases. P. chrysosporium can

completely mineralize anthracene. It cleaves 9,10-anthraquinone to phthalate and, here

http://www.ncbi.nlm.nih.gov/pubmed/3700421






proposed, catechol, though o-benzoquinone or aliphatic compounds are also possible

(Hammel et al., 1991).

Table 5: Fungal genera capable of degrading PAHs.

Name of Fungus PAH Reference

Phanerochaete chrysporium Anthracene Field et al.,1996

Bjerkandera sp. strain

BOS55

Anthracene Field, et al.,1996

Trametes versicolor Anthracene Collins et al., 1986

Cunninghamella

elegansoxidizes

Anthracene Cernigilia, 1997

P. chrysosporium Anthracene Hammel et al., 1991

Aspergillus flavus Benzo[a]pyrene Romero et al., 2010

Paecilomyces farinosus Benzo[a]pyrene Romero et al., 2010

Different technologies such as biostimulation, bioaugmentation, bioaccumulation,

biosorption, phytoremediation and rhizoremediation are the key focus of present

bioremediation strategies.

4. Conclusion

Crude oil contains variety of PAHs, which are known pollutants and potential health hazards.

Besides other approaches, dearomatization of crude oil might be a direct hit to target and curb

the PAH pollution. Voluminous researches have evolved different bioremediation tools in the

form of efficient bacteria and fungi as potential degraders. The metabolism involved in

degradation pathways is also well understood. The present day developments and newer

approaches primarily focus to target the specific PAHs. However, development of precise,

effective and composite technology to treat the complex mixtures is still a matter of concern.

Acknowledgement

We are thankful to Professor Aditya Shastri for kindly extending “Banasthali Centre for

Education and Research in Basic Science” sanctioned under CURIE (Consolidation of

University Research for Innovation and Excellence in Women University) program of

department gratefully acknowledged. The authors are indebted to Bhojia Charitable Trust for

Science Research and Social Welfare for providing adequate facilities to prepare this

manuscript.

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