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Essential Oil of Slovakian Mentha longifolia Huds.

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Attila Szkukalek
Attila Szkukalek

The essential oil of Mentha longifolia from Slovakia was analyzed by GC-MS. The main components were identified as menthone (75.7%), isomenthone (4.0%), piperitone (2.0%), ¦Â-caryophyllene (2.6%) and germacrene-D (4.9%). Previous studies on M. longifolia from different regions found varying primary components, indicating the Slovakian strain has a distinct chemical profile compared to other populations studied. The oil composition supports using chemistry to distinguish M. longifolia chemotypes.

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¡¤, , " ~'l JJ1/L" r;j ~ ~1/!!e-~tJ(A 11r'~~ ~ /-6 rrt/vvn o I 5'~{)Vd~?¨¦__I cf! C?m 'V..-b'uL F _-;fc /;l.J<YJJ Ut[ -- r 4V~ (p'/L S'kvn-!i;.",- /,,~~ f-l'" I ,,/tet ioil! -A-' f/l=?diZ,i trn Cbt 10 M , ) Cf q 7 (}il:~.; a:?,-_t~fv;'(). ,lvIlY'! l o--?a. I jl~l):p~. ~) 4/hn-/< /J,1,~11.--1 J!')Gd/I')'IA ~d -/!-j, _~t-{ ?--.VJ€-.-7~i/.r'-~¡¤ {Jl-i-{1 0-m-r' cf..e;C l7V7L_4..,. 1 .c:Jl-e.~ r-r-;rt~, +': 4; ~fl¨¦&~ c/i!;/1z,tC2t.e? /)(? CLv~ A-er ~(J~ld'fX-. J ~2L rVI- SUCWUl,fc? <;d s-?-e M,..-e ~ (' It#k~ CttM UA>; 7' rt44~~l' , Pf"'t s.:c SJ?"',;~¨¦ Published on September 30, 1997 by Organizing Committee of the 41st Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics Professor Tetsuo Ho Faculty of Ag~iculture, Iwate University Morioka 020, Japan
-~ . 1 I 09 A CI J' .:f 7 ~ Mentha longifolia Huds. (J) ~ ;IH P.lt51 (i~ T~I*-J;t m !i: ~, Charles Univ. ~ *) O 1! ~ iW ~ ? ;~ 7.1<*i? ~ ? Szukuk¨¢lek Attila * 1 . ~~ A CI / ' .:f 7 00 ~ Mentha IOngifolia (J) fz: 18k ~ ~ ~ B ;;$: I=::j2i 'J, '*'~!I=:: ci:: 'J :fI!i ;IH C:: ~ ~'1fT t. t: C::t: 0, itt. *~D 6 ;f1. --C ~ .Q longiforia (J):fI!i;1H C::Ia: ~ ts. tj, ~ P.lt~' tJ{ menthone -C, lY.> (: t;i t A .:f- T jv .'" / *~11::; 7.1<~ ~ -a Iv C' ~ t: , ';::(J) i 'Y :h ta: Chemotaxonomy (J) ~ tili tJ) 6 !J!1~ tJ{ ffl t;: ;f1. .Q (J) C' tJ. 'F r=:: -t (Ji) *~~~~" .Q . 2. H~M~(J)~nc::~m ~ ~T ? ~'iiJIB=F (J) :::J ? j[... .J tili IR r=:: 'f !i: "9 .Q longifolia ~ ~ (J) jfi < (J):tt ~ PJf ~ :l" (S.Attila) (J) ~ ~~ ImI~ I=::~ M i.. ~tff t. t: . 1994$10F.lmI:rE mJ (J) 'b (J) ~ ~ n L." -t (J):fI!i;m l;i B;;$: (i~ !HI*-) I=::--C7.k ~ ~ ~ M I=:: ci:: 'J i~ t: ft, GC, GC-MS ( Column : Supereowax 60m x O.25mm, Film thiekness : 0.25 Ji. m , Oven temp. : 80¡ãC "-' 210¡ãC, 3¡ãC /min., EI-MS: 70eV) I:::: --C ~ 1fT ~ tt: , -t (J) *5 ~, :fI!i;1H ~ P.lt~ l;i menthone (75.7%) C', -t (J) I~ tJ) I:::: isomenthone (4.0%), piperitone (2.0%), B-earyophyllene (2.6%), germaerene-D (4.9%) tJ. ¨¦: ~ ~ W t. t: (Fig.1) . 3. M. longifol¨ªa oil (J) Chemotaxonomieal ts: ~ ~ 1.10 jt --C t: (J) fi Ia: Ji- W ff~ ~ tJ{ ~ :tJ tj ~ "9 ~ (J) C', tJ) ':J --C ~t!!ES 6 Ia: 1m =€ ~ viridis C:: ~ =€ ~ O) longifolia ~ Ht it --c, lb. < spicata C:: L., t: 11 tJ{ ci:: ~ (J) C' Ia: tJ. ~ tJ) C::m ~ L., t: i: C:: tJ{ dr;.Q. ;::;f1. Ia:, 1m =€ ~ O) fiT- ~ ~ < c::, L.,It L.,It ~ =€ (J) @I"* tJq:e !~ '9 .Q tz. l'/) C'dr;.Q. 1962~, ;ji ~ 6 O) ~ T~I O) 'f !i: fi O) ~' 1fT*5 ~ 1 ), Lawrenee 2) , Kokkinii3 ) (J) ~ 15- ~ 'b C::I=:: , M. longifolia O) ft ~ P¨ª ~ *~91J ~c "9 .Q C::;j:, O) ci:: oj tJ. P.lt~' *I=:: tJ..Q ; CD piperitenone oxide, ? piperitone oxide, ? earvone, @ dihydroearvone, ? linalool, ? germaerene-D, (J) 3-oetanol, 3-oetanone. *t: , m J-. j[... :::J ~ M. longifol¨ªa I::::':J ~ --C (a) 1,8-eineole(47.6%), (b) pulegone(42.1 %), (e) piperitone (38.4%), 1,8-eineole (19.4%), menthone (1.3%) (J) 3 *~~tJ' 6 *tJ{ M. bzguven I::::d::-:)--C~ 15- ~ h l l .Q 4). *~.z: (¨ª) iili I::::ff :g t;i :@ -:) 't: ~ M. iongifolia O) J!i ~ fltJ) G, trans-sabinene hydrate 5), 1,2-epoxy-neomenthyl aeetate, rose-oxide 6 ) ~ -t ;f1. --f ;f1. ~ PX~ C::"9 .Q 'f !i: fi 'b ~ 15- ~ ;f1. --C ~ .Q . ;;$: ~ 15- O) A CI r; .:f 7 ~ M. longifolia (J) PX51 *ta: m I-- j[... :::J (J) (e) (J) ~ ;IH ~ I::::jfi ~ tJ{ , t: O) *C:: tt t1 ~ --C menthone C:: piperitone (J) ~ ~ ~ tJ{ ~ ts: tj, z; (J) J 'Y tJ t;i M. longiforia (J) ~JT~ ~ PX~ *c ~ jt 6 h .Q .
II 10 Fig.1 Gas chomatogram of Slovakian M. longifolia Oil :>CMX 1) S.Shimizu and N.lkeda; Bull. Agric. Chem. Japan 26, 84 (1962) S.Shimizu and N.lkeda; Perfum. Essent. Oil Record 52, 708 (1961) 2) B.W.Lawrence; Ph.D. Thesis Rijkusuniversiteit, Groningen (1978) 3) S.Kokkinii and V.P.Papageorgou; Planta Medica 54, 59 (1988) 4) M.bzgOevn et a/.; Annual Con. of Med. Plant Res., Hall (Germany) Sept.(1995) 5) D.Karasawa and S.Shimizu; Agric. Biol. Chem. 42, 433 (1978) 6) D.Karasawa, S.Shimizu, S.Shatar and et a/.; J. Essent. Oil Res. 7, 255 (1995) Essential Oil of Slovakian Mentha longifolia Huds.. Den'ei Karasawa, Sumio Shtmizu and Szukuk¨¢lek Attila* Dept. of Biosciense and Biotechnology Shinshu Univ. and Dept. of Pharm. Charles Univ. Czech*. The essential oi! of a wild M. longifolia strain from Kom¨¢rno, Slovakia, near River Donau, was investigated from a chemotaxonomical point of view. The oi! obtained at flowering stage Oct. 1994, .was exarn¨ªneo by _GC-MS to identify more than thirty constituents. The principal substances have been confirmed as follows; menthone(75.7%), isomenthone (4.0%), piperitone (2.0%), B-caryophyllene (2.6%) and germacrene-D (4.9%). A survery of the following previous studies on M. longifolia indicates that Slovakian M. longifolia seems a new chemical strain; our results on European1)(1962), Lawrence's on American Z (1978), Kokkinii's on Greek:l)(1988) and ozq?ven's on Turkish M. longifolia'1J(1995) . . , -.26-
¡¤ , J, () o f--l o o 2 'r-------1 2 .2 9 6 ~-------1 4_.4_:3 '7 ~==4-~.::z....l,.....C:l---4_6 . 1 OB P=~-------5 5.52 1 ~=-'7B.4_:3B
~o. RT COMPONENT AREA% 1 5.694 a -PINENE 0.35 2 5.870 2.5-DIMETHYLTETRAHYDROFURAN * O. 09 3 6.318 HEXANAL 0.02 4 6.886 ,B -PINENE O. 48 5 7. 013 SABINENE 0.25 6 7. 571 MYRCENE 0.37 7 8.579 LIMONENE 0.77 8 8.858 CE)-2-HEXENAL 0.02 9 8.959 1.8-CINEOLE 0.72 10 9. 184 ¡¤(Z) -OC IMENE O. 69 I 11 .9.669 CE)-OCIMENE O. 11 t BUTYL ISOVALERATE 12 10.815 ISOAMYL ISOVALERATE 0.-03 13 10.992 TERPINOLENE 0.06 14 12.296 3-0CTYL ACETATE O. 15 15 14.437 3-0CTANOL Q. 24 16 16.855 HEXYL ISOVALERATE O.06 17 18.305 (MENTHONEJ ({6.77 18 . 18. 697 CZ)-3-HEXENYL ISOVALERATE I Q.55 J.9 19.247 (J SOMENTHONE.) (4.10) 20 20. 307 ,B-BOURBONENE + CAMPHOR 0.22 21 21. 091 SHC ** O.05 22 21. 648 SABINENE HYDRATE. CIS- 0.02 22. 200 MENTHYL ACETATE O. 02 23 22. 850 SHC ** 0.07 24 23. 330 ,B -ELEMENE 0.20 25 23. 504 NEO-MENTHOL O. 10 26 24. 024 (j} -CARYOPHYLLENE ) O. 65 27 24. 181 4-TERPINEOL O. 04 28 25. 330 MYRTENAL 0.05 29 25. 469 O.05 30 26. 024 PHENYLACETALDEHYDE O. 15 31 26. 322 :; MENTHOL O. 17 32 27.435 PULEGONE O. 10 33 27. 572 HUMULENE O.03 34 28. 326 SHC ** 0.05 :J5, 28. 832 a -TERP 1NEOL O. 16 36 29.450 ~ERMACRENE D) i(4.97 37 30. 113 PIPERITONE O. 12 38 30. 357 DECANOL 2. 11 39 30. 565 SHC ** 0.58 40 31. 651 6 -CAD INENE O. 15 41 I 31. 782 O.04 42 31. 939 SHC ** O.06 43 34. 169 DIOSPHENOL O.08 44 36.409 GERANYLACETONE 0.03 45 39.102 BHT 0.06 46 39. 287 CIS-JASMONE O. 12 47 40. 730 0.04 I 48 42. 188 O. 15 49 42. 592 CARYOPHYLLENE OXIDE O. 10 50 45. 710 2.4-DODECADIENAL * O. 14 51 46. 108 OCTANOIC ACID 0.40 52 48. 040 O.04 53 48. 380 ~. 10. 14-TRIMETHYL-2-PENTADECANONE 0.04 54 49. 081 SPATHULENOL O. 14 55 51. 153 THYMOL O.09 56 51. 696 O.08 57 55. 521 DECANOIC ACID O.36 58 58. 235 FARNESOL O.04 59 59. 164 DIHYDROACTINIDIOLIDE I 0.04 61 72. 801 I 0.09 TOTAL 1100.00 * TENTATIVE ** SESQUITERPENE '-

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Essential Oil of Slovakian Mentha longifolia Huds.

  • 1. ¡¤, , " ~'l JJ1/L" r;j ~ ~1/!!e-~tJ(A 11r'~~ ~ /-6 rrt/vvn o I 5'~{)Vd~?¨¦__I cf! C?m 'V..-b'uL F _-;fc /;l.J<YJJ Ut[ -- r 4V~ (p'/L S'kvn-!i;.",- /,,~~ f-l'" I ,,/tet ioil! -A-' f/l=?diZ,i trn Cbt 10 M , ) Cf q 7 (}il:~.; a:?,-_t~fv;'(). ,lvIlY'! l o--?a. I jl~l):p~. ~) 4/hn-/< /J,1,~11.--1 J!')Gd/I')'IA ~d -/!-j, _~t-{ ?--.VJ€-.-7~i/.r'-~¡¤ {Jl-i-{1 0-m-r' cf..e;C l7V7L_4..,. 1 .c:Jl-e.~ r-r-;rt~, +': 4; ~fl¨¦&~ c/i!;/1z,tC2t.e? /)(? CLv~ A-er ~(J~ld'fX-. J ~2L rVI- SUCWUl,fc? <;d s-?-e M,..-e ~ (' It#k~ CttM UA>; 7' rt44~~l' , Pf"'t s.:c SJ?"',;~¨¦ Published on September 30, 1997 by Organizing Committee of the 41st Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics Professor Tetsuo Ho Faculty of Ag~iculture, Iwate University Morioka 020, Japan
  • 2. -~ . 1 I 09 A CI J' .:f 7 ~ Mentha longifolia Huds. (J) ~ ;IH P.lt51 (i~ T~I*-J;t m !i: ~, Charles Univ. ~ *) O 1! ~ iW ~ ? ;~ 7.1<*i? ~ ? Szukuk¨¢lek Attila * 1 . ~~ A CI / ' .:f 7 00 ~ Mentha IOngifolia (J) fz: 18k ~ ~ ~ B ;;$: I=::j2i 'J, '*'~!I=:: ci:: 'J :fI!i ;IH C:: ~ ~'1fT t. t: C::t: 0, itt. *~D 6 ;f1. --C ~ .Q longiforia (J):fI!i;1H C::Ia: ~ ts. tj, ~ P.lt~' tJ{ menthone -C, lY.> (: t;i t A .:f- T jv .'" / *~11::; 7.1<~ ~ -a Iv C' ~ t: , ';::(J) i 'Y :h ta: Chemotaxonomy (J) ~ tili tJ) 6 !J!1~ tJ{ ffl t;: ;f1. .Q (J) C' tJ. 'F r=:: -t (Ji) *~~~~" .Q . 2. H~M~(J)~nc::~m ~ ~T ? ~'iiJIB=F (J) :::J ? j[... .J tili IR r=:: 'f !i: "9 .Q longifolia ~ ~ (J) jfi < (J):tt ~ PJf ~ :l" (S.Attila) (J) ~ ~~ ImI~ I=::~ M i.. ~tff t. t: . 1994$10F.lmI:rE mJ (J) 'b (J) ~ ~ n L." -t (J):fI!i;m l;i B;;$: (i~ !HI*-) I=::--C7.k ~ ~ ~ M I=:: ci:: 'J i~ t: ft, GC, GC-MS ( Column : Supereowax 60m x O.25mm, Film thiekness : 0.25 Ji. m , Oven temp. : 80¡ãC "-' 210¡ãC, 3¡ãC /min., EI-MS: 70eV) I:::: --C ~ 1fT ~ tt: , -t (J) *5 ~, :fI!i;1H ~ P.lt~ l;i menthone (75.7%) C', -t (J) I~ tJ) I:::: isomenthone (4.0%), piperitone (2.0%), B-earyophyllene (2.6%), germaerene-D (4.9%) tJ. ¨¦: ~ ~ W t. t: (Fig.1) . 3. M. longifol¨ªa oil (J) Chemotaxonomieal ts: ~ ~ 1.10 jt --C t: (J) fi Ia: Ji- W ff~ ~ tJ{ ~ :tJ tj ~ "9 ~ (J) C', tJ) ':J --C ~t!!ES 6 Ia: 1m =€ ~ viridis C:: ~ =€ ~ O) longifolia ~ Ht it --c, lb. < spicata C:: L., t: 11 tJ{ ci:: ~ (J) C' Ia: tJ. ~ tJ) C::m ~ L., t: i: C:: tJ{ dr;.Q. ;::;f1. Ia:, 1m =€ ~ O) fiT- ~ ~ < c::, L.,It L.,It ~ =€ (J) @I"* tJq:e !~ '9 .Q tz. l'/) C'dr;.Q. 1962~, ;ji ~ 6 O) ~ T~I O) 'f !i: fi O) ~' 1fT*5 ~ 1 ), Lawrenee 2) , Kokkinii3 ) (J) ~ 15- ~ 'b C::I=:: , M. longifolia O) ft ~ P¨ª ~ *~91J ~c "9 .Q C::;j:, O) ci:: oj tJ. P.lt~' *I=:: tJ..Q ; CD piperitenone oxide, ? piperitone oxide, ? earvone, @ dihydroearvone, ? linalool, ? germaerene-D, (J) 3-oetanol, 3-oetanone. *t: , m J-. j[... :::J ~ M. longifol¨ªa I::::':J ~ --C (a) 1,8-eineole(47.6%), (b) pulegone(42.1 %), (e) piperitone (38.4%), 1,8-eineole (19.4%), menthone (1.3%) (J) 3 *~~tJ' 6 *tJ{ M. bzguven I::::d::-:)--C~ 15- ~ h l l .Q 4). *~.z: (¨ª) iili I::::ff :g t;i :@ -:) 't: ~ M. iongifolia O) J!i ~ fltJ) G, trans-sabinene hydrate 5), 1,2-epoxy-neomenthyl aeetate, rose-oxide 6 ) ~ -t ;f1. --f ;f1. ~ PX~ C::"9 .Q 'f !i: fi 'b ~ 15- ~ ;f1. --C ~ .Q . ;;$: ~ 15- O) A CI r; .:f 7 ~ M. longifolia (J) PX51 *ta: m I-- j[... :::J (J) (e) (J) ~ ;IH ~ I::::jfi ~ tJ{ , t: O) *C:: tt t1 ~ --C menthone C:: piperitone (J) ~ ~ ~ tJ{ ~ ts: tj, z; (J) J 'Y tJ t;i M. longiforia (J) ~JT~ ~ PX~ *c ~ jt 6 h .Q .
  • 3. II 10 Fig.1 Gas chomatogram of Slovakian M. longifolia Oil :>CMX 1) S.Shimizu and N.lkeda; Bull. Agric. Chem. Japan 26, 84 (1962) S.Shimizu and N.lkeda; Perfum. Essent. Oil Record 52, 708 (1961) 2) B.W.Lawrence; Ph.D. Thesis Rijkusuniversiteit, Groningen (1978) 3) S.Kokkinii and V.P.Papageorgou; Planta Medica 54, 59 (1988) 4) M.bzgOevn et a/.; Annual Con. of Med. Plant Res., Hall (Germany) Sept.(1995) 5) D.Karasawa and S.Shimizu; Agric. Biol. Chem. 42, 433 (1978) 6) D.Karasawa, S.Shimizu, S.Shatar and et a/.; J. Essent. Oil Res. 7, 255 (1995) Essential Oil of Slovakian Mentha longifolia Huds.. Den'ei Karasawa, Sumio Shtmizu and Szukuk¨¢lek Attila* Dept. of Biosciense and Biotechnology Shinshu Univ. and Dept. of Pharm. Charles Univ. Czech*. The essential oi! of a wild M. longifolia strain from Kom¨¢rno, Slovakia, near River Donau, was investigated from a chemotaxonomical point of view. The oi! obtained at flowering stage Oct. 1994, .was exarn¨ªneo by _GC-MS to identify more than thirty constituents. The principal substances have been confirmed as follows; menthone(75.7%), isomenthone (4.0%), piperitone (2.0%), B-caryophyllene (2.6%) and germacrene-D (4.9%). A survery of the following previous studies on M. longifolia indicates that Slovakian M. longifolia seems a new chemical strain; our results on European1)(1962), Lawrence's on American Z (1978), Kokkinii's on Greek:l)(1988) and ozq?ven's on Turkish M. longifolia'1J(1995) . . , -.26-
  • 4. ¡¤ , J, () o f--l o o 2 'r-------1 2 .2 9 6 ~-------1 4_.4_:3 '7 ~==4-~.::z....l,.....C:l---4_6 . 1 OB P=~-------5 5.52 1 ~=-'7B.4_:3B
  • 5. ~o. RT COMPONENT AREA% 1 5.694 a -PINENE 0.35 2 5.870 2.5-DIMETHYLTETRAHYDROFURAN * O. 09 3 6.318 HEXANAL 0.02 4 6.886 ,B -PINENE O. 48 5 7. 013 SABINENE 0.25 6 7. 571 MYRCENE 0.37 7 8.579 LIMONENE 0.77 8 8.858 CE)-2-HEXENAL 0.02 9 8.959 1.8-CINEOLE 0.72 10 9. 184 ¡¤(Z) -OC IMENE O. 69 I 11 .9.669 CE)-OCIMENE O. 11 t BUTYL ISOVALERATE 12 10.815 ISOAMYL ISOVALERATE 0.-03 13 10.992 TERPINOLENE 0.06 14 12.296 3-0CTYL ACETATE O. 15 15 14.437 3-0CTANOL Q. 24 16 16.855 HEXYL ISOVALERATE O.06 17 18.305 (MENTHONEJ ({6.77 18 . 18. 697 CZ)-3-HEXENYL ISOVALERATE I Q.55 J.9 19.247 (J SOMENTHONE.) (4.10) 20 20. 307 ,B-BOURBONENE + CAMPHOR 0.22 21 21. 091 SHC ** O.05 22 21. 648 SABINENE HYDRATE. CIS- 0.02 22. 200 MENTHYL ACETATE O. 02 23 22. 850 SHC ** 0.07 24 23. 330 ,B -ELEMENE 0.20 25 23. 504 NEO-MENTHOL O. 10 26 24. 024 (j} -CARYOPHYLLENE ) O. 65 27 24. 181 4-TERPINEOL O. 04 28 25. 330 MYRTENAL 0.05 29 25. 469 O.05 30 26. 024 PHENYLACETALDEHYDE O. 15 31 26. 322 :; MENTHOL O. 17 32 27.435 PULEGONE O. 10 33 27. 572 HUMULENE O.03 34 28. 326 SHC ** 0.05 :J5, 28. 832 a -TERP 1NEOL O. 16 36 29.450 ~ERMACRENE D) i(4.97 37 30. 113 PIPERITONE O. 12 38 30. 357 DECANOL 2. 11 39 30. 565 SHC ** 0.58 40 31. 651 6 -CAD INENE O. 15 41 I 31. 782 O.04 42 31. 939 SHC ** O.06 43 34. 169 DIOSPHENOL O.08 44 36.409 GERANYLACETONE 0.03 45 39.102 BHT 0.06 46 39. 287 CIS-JASMONE O. 12 47 40. 730 0.04 I 48 42. 188 O. 15 49 42. 592 CARYOPHYLLENE OXIDE O. 10 50 45. 710 2.4-DODECADIENAL * O. 14 51 46. 108 OCTANOIC ACID 0.40 52 48. 040 O.04 53 48. 380 ~. 10. 14-TRIMETHYL-2-PENTADECANONE 0.04 54 49. 081 SPATHULENOL O. 14 55 51. 153 THYMOL O.09 56 51. 696 O.08 57 55. 521 DECANOIC ACID O.36 58 58. 235 FARNESOL O.04 59 59. 164 DIHYDROACTINIDIOLIDE I 0.04 61 72. 801 I 0.09 TOTAL 1100.00 * TENTATIVE ** SESQUITERPENE '-