Biotransformations of monoterpenoids by Spodoptera litura are reviewed. Various substrates used for the transformations are included in this review of the literature for the period 1996–2006. The metabolism of monoterpenoids in S. litura may involve the following transformation; 1) position specific hydroxylation of Me or CH2 group; 2) formation of allylic alcohol by hydroxylation; 3) C=C epoxidation followed by hydration to a vicinal diol; 4) oxidation of a primary alcohol to a carboxylic acid.
PasseriterCM, WilsonJ, AndersenR, IsmanMB. (2004) Metabolism of thymol and trans-anethole in larvae of Spodoptera litura and Trichoplusia ni (Lepidptera: Noctuidae). Journal of Agricultural and Food Chemistry, 52, 2549–2551.
2.
MiyazawaM, MurataT. (2000) Biotransformation of β-myrcene by the larvae of common cutworm (Spodoptera litura), Journal of Agricultural and Food Chemistry, 48, 123–125.
3.
IshidaT, AsakawaY, TakemotoT, ArataniT. (1981) Biotransformation of α-pinane, β-pinane, pinane, 3-caren, caren, myrcene, and p-cymen in rabbits. Journal of Pharmaceutical Sciences, 70, 406–415.
4.
YamazakiY, HayashiY, HoriN, MikamiY. (1988) Microbial conversion of β-myrcene by Aspergillus niger.Agricultural and Biological Chemistry, 52, 2921–2922.
5.
MiyazawaM, MurataT. (2001) Biotransformation of (-)-dihydromyrcenol and (-)-dihydromyrcenyl acetate by the larvae of common cutworm (Spodoptera litura). Journal of Oleo Science, 50, 921–925.
6.
MiyazawaM, AkazawaS, SakaiH, NankaiH. (2000) Biotransformation of (-)-dihydromyrcenyl acetate using the plant parasitic fungus Glomerella cingulata as a biocatalyst. Journal of Agricultural and Food Chemistry, 48, 4826–4829.
7.
TakechiH, MiyazawaM. (2006) Biotransformation of geraniol by the larvae of common cutworm (Spodoptera litura). Journal of Oleo Science, 55, 143–149.
8.
HamadaH, YasumuneH, FuchikamiY, HirataT, SattlerI, HowardJW, ScottAI. (1997) Biotransformation of geraniol, nerol and (+)- and (-)-carvone by suspension cultured cells of Catharanthus roseus.Phytochemistry, 44, 615–621.
9.
FigueiredoAC, AlmendraMJ, BarrosoJG, SchefferJJC. (1996) Biotransformaion of monoterpenes and sesquiterpenes by cell suspension cultures of Achillea millefolium L. ssp. millefolium. Biotechnology Letters, 18, 863–868.
10.
CorbierB, EhretC. (1988) Biotransformation of monoterpenoids by cultured cells of Rosa centifolia.Developments in Food Science, 18, 731–741.
11.
ItokawaH, TakeyaK, MihashiS. (1977) Biotransformation of cannabinoid precursors and related alcohols by suspension cultures of callus induced from Cannabis sativa L. Chemical and Pharmaceutical Bulletin, 25, 1941–1946.
12.
TakeyaK, ItokawaH. (1977) Stereochemistry in oxidation of allylic alcohols by cell-free system of callus induced from Cannabis sativa L. Chemical and Pharmaceutical Bulletin, 25, 1947–1951.
13.
CarriereF, GilG, ChagrardieffP. (1989) Biotransformation of geraniol by photoautotrophic, photomixotrophic and heterotrophic plant cell suspensions. Phytochemistry, 28, 1087–1090.
14.
GboladeAA, LockwoodGB. (1989) Selective biotransformation of monoterpenoids by cell suspensions of Petroselinum crispum.Zeitschrift fuer Naturforschung, C: Journal of Biosciences, 44, 1066–1068.
15.
ZhuW, AsghariG, LockwoodGB. (2000) Factors affecting volatile terpene and non-terpene biotransformation products in plant cell cultures. Fitoterapia, 71, 501–506.
16.
EverittZM, LockwoodGB. (1992) Biotransformation of geraniol by agitating and immobilized cultures of Anethum graveolens.Fitoterapia, 63, 534–536.
17.
GuardiolaJ, CanovasM, IborraJL. (1996) Modelling of the biotransformation from geraniol to nerol by freely suspended and immobilized grape (Vitis vinifera) cells. Progress in Biotechnology, 11, 349–354.
18.
GuardiolaJ, IcorraJL, RodenasL, CanovasM. (1996) Biotransformation from geraniol and nerol by immobilized grapevine cells (V. vinifera). Applied Biochemistry and Biotechnology, 56, 169–180.
19.
ChatterjeeT. (2004) Biotransformation of geraniol by Rhodococcus sp. Strain GR3. Biotechnology and Applied Biochemistry, 39, 303–306.
20.
SeubertW, RembergerU. (1963) Studies on the bacterial degradation of isoprenoid compounds. II. The role of carbon dioxide. Biochemische Zeitschrift, 338, 245–246.
21.
MadyasthaKM. (1984) Microbial transformations of acyclic monoterpenes. Proceedings - Indian Academy of Sciences, Chemical Sciences, 93, 677–686.
22.
CantwellSG, LauEP, WattDS, FallRR. (1978) Biodegradation of acyclic isoprenoids by Pseudomonas species. Journal of Bacteriology, 135, 324–333.
23.
MadyasthaKM, BhattacharyyavPK, VaidyanathanCS. (1977) Metabolism of a monoterpene alcohol, linalool, by a soil pseudomonad. Canadian Journal of Microbiology, 23, 230–239.
24.
ChadhaA, MadyasthaKM. (1984) Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes. Xenobiotica, 14, 365–374.
25.
AbrahamWR, KieslichK, RengH, StumpfB. (1984) Formation and production of 1,2-trans-glycols from various monoterpenes with 1-menthane skeletons by microbial transformation with Diplodia gossypina.European Congress for Biotechnology.1, 245–248.
26.
MiyazawaM, WadaT, KameokaH. (1998) Biotransformation of (+)-and (-)-limonene by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 46, 300–303.
27.
CarmanRM, GreenfieldKL, RobinsonWT. (1986) Halogenated terpenoids. XXII Uroterpenol. The C8 stereochemistry, Australian Journal of Chemistry, 39, 21–30.
28.
DhavalikarRS, BhattacharyyaPK. (1966) Microbiological transformation of terpenes. VIII. Fermentation of limonene by a soil pseudomonad. Indian Journal of Biochemistry, 3, 144–157.
29.
DhavalikarRS, RangachariPN. (1966) Microbiological transformations of terpenes. IX. Pathways of degradation of limonene in a soil pseudomonad. Indian Journal of Biochemistry, 3, 158–164.
30.
DhereSG, DhavalikarRS. (1970) Microbial transformations of terpenoids: limonene. Science and Culture, 36, 292.
31.
MukherjeeBB, KraidmanG, MillID. (1973) Synthesis of glycols by microbial transformation of some monocyclic terpenes. Applied Microbiology, 25, 447–453.
32.
BowenER. (1976) Potential by-products from microbial transformation of d-limonene. Proceedings of the Florida State Horticultural Society, 88, 304–308.
33.
DeviJR, BhattacharyyaPK. (1977) Microbiological transformations of terpenes. Part XXIV. Pathways of degradation of linalool, geraniol, nerol and limonene by Pseudomonas incognita (linalool strain). Indian Journal of Biochemistry & Biophysics, 14, 288–291.
34.
AbrahamWR, KieslichK, RengH, StumpfB. (1984) Formation and production of 1,2-trans-glycols from various monoterpenes with 1-menthene skeletons by microbial transformation with Diplodia gossypina.European Congress for Biotechnology 3rd, 1, 245–248.
35.
AbrahamWR, StumpfB, KieslichK. (1986) Microbial transformations of terpenoids with 1-p-menthene skeleton. Applied Microbiology and Biotechnology, 24, 24–30.
36.
CadwalladerKR, BraddockRJ, ParishME, HigginsDP. (1989) Bioconversion of (+)-limonene by Pseudomonas gladioli.Journal of Food Science, 54, 1241–1245.
37.
DeviJR, BhattacharyyaPK. (1977) Microbiological transformations of terpenes. Part XXIV. Pathways of degradation of linalool geraniol, nerol and limonene by Pseudomonas incognita (linalool strain). Indian Journal of Biochemistry & Biophysics, 14, 359–363.
38.
NomaY, YamasakiS, AsakawaY. (1992) Biotransformation of limonene and related compounds by Aspergillus cellulosae.Phytochemistry, 31, 2725–2727.
39.
IgimiH, NshimuraM, KodamaR, IdeH. (1974) Metabolism of d-limonene (p-mentha-1,2-diene). I. Absorption, distribution, and excretion of d-limonene in rats. Xenobiotica, 4, 77–84.
40.
KodamaR, NodaK, IdeH. (1974) Metabolism of d-limonene (p-mentha-1,8-diene). II. Metabolic fate of d-limonene in rabbits. Xenobiotica, 4, 85–95.
41.
KodamaR, YanoT, FurukawaK, NodaK, IdeH. (1976) Studies on the metabolism of d-limonene (p-mentha-1,8-diene). IV. Isolation and characterization of new metabolites and species differences in metabolism. Xenobiotica, 6, 377–389.
42.
ReganJW, BjeldanesLF. (1976) Metabolism of (+)-limonene in rats. Journal of Agricultural and Food Chemistry, 24, 377–380.
43.
WatabeT, HiratsukaA, IsobeM, OzawaN. (1980) Metabolism of d-limonene by hepatic microsomes to nonmutagenic epoxides toward Salmonella typhimurium.Biochemical Pharmacology, 29, 1068–1071.
44.
WatabeT, HiratsukaA, OzawaN, IsobeM. (1981) A comparative study on the metabolism of d-limonene and 4-vinylcyclohex-1 ene by hepatic microsomes. Xenobiotica, 11, 333–344.
45.
MiyazawaM, WadaT, KameokaH. (1996) Biotransformation of a-terpinene in common cutworm larvae (Spodoptera litura Fabricius). J. Journal of Agricultural and Food Chemistry, 44, 2889–2893.
46.
AbrahamWR, StumpfB, KieslishK. (1986) Microbial transformation of terpenoids with 1-p-menthene skeleton. Applied Biochemistry and Biotechnology, 24, 24–30.
47.
MiyazawaM, WadaT. (2000) Biotransformation of γ-terpinene and (-)-α-phellandrene by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 48, 2893–2895.
48.
PierceHDJr, ComJE, OehlschlagerAC, BordenJH. (1987) Monoterpene metabolism in female mountain pine beetles, Dendroctonus ponderosae Hopkins, attacking ponderosa pine. Journal of Chemical Ecology, 13, 1455–1480.
49.
MiyazawaM, OhsawaM. (2002) Biotransformation of α-terpineol by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 50, 4916–4918.
50.
SugaT, AokiT, HirataT, Ym SookLee, NishimuraO, UtsumiM. (1980) Biotransformation of foreign substrates with callus tissues. Transformation of terpineols with tobacco suspension cells. Chemistry Letters, 229–230.
51.
MadyasthaKM, SriratsarV. (1985) Biotransformation of α-terpineol in rat: Its effects on the liver microsomal cytochrome P-450 system. Bulletin of Environmental Contamination and Toxicology, 15, 165–170.
52.
Draczynska-LusiakB, SiewinskiA. (1989) Enantioselectivity of the metabolism of some monoterpenic components of coniferous tree resin by Armillariella mellea (honey fungus). Journal of Basic Microbiology, 29, 269–275.
53.
MiyazawaM, KumagaeS, KameokaH. (1999) Biotransformation of (+)- and (-)-menthol by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 47, 3938–3940.
54.
SugaT, HamadaH, HirataT, IzumiS. (1987) Stereoselectivity in oxidative and reductive transformations of p-menthane derivatives with the cultured cells of Nicotiana tabacum.Chemistry Letters, 5, 903–906.
55.
FuruyaT, OriharaY, MiyatakeH. (1989) Biotransformation of (-)-menthol by Eucalyptus perriniana cultured cells. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry, 10, 1711–1719.
56.
AsakawaY, TakahashiH, ToyotaM, NomaY. (1991) Biotransformation of monoterpenoids, (+)-and (-)-menthols, terpinolene and carvotanacetone by Aspergillus species. Phytochemistry, 30, 3981–3987.
57.
MadyasthaKM, SrivatsanV. (1988) Studies on the metabolism of l-menthol in rats. Drug Metabolism and Disposition, 16, 765–772.
58.
MiyazawaM, KumagaeS, KameokaH. (2001) Biotransformation of (R)- and (S)-terpinen-4-ol by the larvae of common cutworm (Spodoptera litura). Journal of Agricultural and Food Chemistry, 49, 4312–4314.
59.
Wolf-RainarA, StumpfB, KieslishK. (1986) Microbial transformations of N-(4-chlorphenyl)benzoisothiazolone. AppliedMicrobiology and Biotechnology, 24, 24–30.
60.
MiyazawaM, MiyamotoY. (2004) Biotransformation of (1R)-(+)- and (1S)-(-)-camphor by the larvae of common cutworm (Spodoptera litura). Journal of Molecular Catalysis B: Enzymatic, 27, 83–89.
61.
TuckerAO, MaciarelloMJ. (1990) Essential oils of cultivars of Dalmatian sage (Salvia officinalis L.). Journal of Essential Oil Research, 2, 139–144.
62.
CroteauR, FeltonM, KarpF, KjonaasR. (1981) Relationship of camphor biosynthesis to leaf development in sage (Salvia officinalis). Plant Physiology, 67, 820–824.
63.
HarborneJB, BaxterH.Phytochemical Dictionary, A Handbook of Bioactive Compounds from Plants. Taylor and Francis, London, UK.1993.
64.
AsahinaY, IshidateM. (1928) Camphorol. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen, 61, 533–536.
65.
LeibmanKC, OrtizE. (1973) Mammalian metabolism of terpenoids. I. Reduction and hydroxylation of camphor and related compounds. Drug Metabolism and Disposition: the Biological Fate of Chemicals, 1, 543–551.
66.
RobertsonJS, HussainM. (1969) Metabolism of camphors and related compounds. Biochemical Journal, 113, 57–65.
BradshawWH, ConradHE, CoreyEJ, GunsalusIC, LednicerD. (1959) Microbiological degradation of (+)-camphor. Journal of the American Chemical Society, 81, 5507–5560.
69.
MiyazawaM, MiyamotoY. (2004) Biotransformation of (1R)-(+)- and (1S)-(-)-camphor by the larvae of common cutworm (Spodoptera litura). Journal of Molecular Catalysis B: Enzymatic, 32, 83–89.
70.
ChapmanPJ, MeermanG, GunsalusIC. (1965) The microbiological transformation of fenchone. Biochemical and Biophysical Research Communications, 20, 104–108.
71.
PfrunderB, TammC. (1969) Reactions with microorganisms. XVIII. Microbiological conversion of bicyclic monoterpenes by Absidia orchidis. 2. Hydroxylation of fenchone and isofenchone. Helvetica Chimica Acta, 52, 1643–1654.
72.
OriharaY, FuruyaT. (1994) Biotransformation of (+)- and (-)-fenchone by cultured cells of Eucalyptus perriniana.Phytochemistry, 36, 55–59.
73.
MiyazawaM, YamamotoK, NomaY, KameokaH. (1990) Bioconversion of (+)-fenchone to 4-endo-hydroxfenchone by Aspergillus niger.Chemistry Express, 5, 407–410.
74.
MiyazawaM., KameokaH. (1988) Biotransformation and bioavailability of (+)-fenchone to hydroxyfenchone in rabbits. Chemistry Express, 3, 503–506.
75.
MiyazawaM, MiyamotoY. (2004) Biotransformation of (+)-(1R,2S)-fenchol by the larvae of common cutworm (Spodoptera litura). Tetrahedron, 60, 3091–3096.