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Pf"'t s.: c SJť"',;~é

Published on September 30, 1997by Organizing Committee of the 41st Symposium on

the Chemistry of Terpenes, Essential Oils, and AromaticsProfessor Tetsuo Ho

Faculty of Ag~iculture, Iwate UniversityMorioka 020, Japan

-~ .

1 I 09A 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<*iť ~ •Szukukálek Attila *

1 . ~~

A CI / '\ .:f 7 00 ~ Mentha IOngifolia (J) fz: 18k ~ ~ ~ B ;;$: I=:: j2i 'J, '*'~!I=:: ci:: 'J :fI!i ;IHC:: ~ ~'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 ? ~'iiJ IB=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$10F.lmI:rE mJ (J) 'b (J) ~ ~ n L." -t (J):fI!i;m l;iB;;$: (i~ !HI*-) I=:: --C7.k ~ ~ ~ M I=:: ci:: 'J i~ t: ft, GC, GC-MS ( Column : Supereowax60m x O.25mm, Film thiekness : 0.25 Ji. m , Oven temp. : 80°C "-' 210°C, 3°C /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. é:~ ~ W t. t: (Fig.1) .

3. M. longifolía 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) fi T- ~ ~ < 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 ~ Pí ~ *~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. longifolía 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: (í) 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;iM. 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 Szukukálek 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 Komárno, Slovakia, near River

Donau, was investigated from a chemotaxonomical point of view. The oi! obtained at

flowering stage Oct. 1994, .was exarníneo 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 onAmericanZ(1978), Kokkinii's on Greek:l)(1988) and ozqůven's on Turkish M. longifolia'1J(1995) .

. ,

-.26-

· ,

J,

(\)o

f--l

oo

2'r-------1 2 .2 9 6~-------1 4_.4_:3 '7

~==4-~.::z....l,.....C:l---4_6 . 1OB

P=~-------5 5.52 1

~=-'7B.4_:3B

~o. RT COMPONENT AREA%1 5.694 a -PINENE 0.352 5. 870 2. 5-DIMETHYLTETRAHYDROFURAN * O. 093 6. 318 HEXANAL 0.024 6.886 ,B -PINENE O. 485 7. 013 SABINENE 0.256 7. 571 MYRCENE 0.377 8.579 LIMONENE 0.778 8.858 CE)-2-HEXENAL 0.029 8. 959 1.8-CINEOLE 0.72

10 9. 184 ·(Z) -OC IMENE O. 69I

11 .9.669 CE)-OCIMENE O. 11t BUTYL ISOVALERATE

12 10.815 ISOAMYL ISOVALERATE 0.-0313 10. 992 TERPINOLENE 0.0614 12.296 3-0CTYL ACETATE O. 1515 14.437 3-0CTANOL Q. 2416 16. 855 HEXYL ISOVALERATE O. 0617 18. 305 (MENTHONEJ ({6. 7718 . 18. 697 CZ)-3-HEXENYL ISOVALERATE I Q.55

J.9 19.247 (J SOMENTHONE.) (4.10)20 20. 307 ,B-BOURBONENE + CAMPHOR 0.2221 21. 091 SHC ** O. 0522 21. 648 SABINENE HYDRATE. CIS- 0.02

22. 200 MENTHYL ACETATE O. 0223 22. 850 SHC ** 0.0724 23. 330 ,B -ELEMENE 0.2025 23. 504 NEO-MENTHOL O. 1026 24. 024 (j} -CARYOPHYLLENE ) O. 6527 24. 181 4-TERPINEOL O. 0428 25. 330 MYRTENAL 0.0529 25. 469 O. 0530 26. 024 PHENYLACETALDEHYDE O. 1531 26. 322 :; MENTHOL O. 1732 27.435 PULEGONE O. 1033 27. 572 HUMULENE O. 0334 28. 326 SHC ** 0.05:J5, 28. 832 a -TERP 1NEOL O. 1636 29.450 ~ERMACRENE D) i(4.9737 30. 113 PIPERITONE O. 1238 30. 357 DECANOL 2. 1139 30. 565 SHC ** 0.5840 31. 651 6 -CAD INENE O. 1541 I 31. 782 O. 0442 31. 939 SHC ** O. 0643 34. 169 DIOSPHENOL O. 0844 36.409 GERANYLACETONE 0.0345 39.102 BHT 0.0646 39. 287 CIS-JASMONE O. 1247 40. 730 0.04

I 48 42. 188 O. 1549 42. 592 CARYOPHYLLENE OXIDE O. 1050 45. 710 2.4-DODECADIENAL * O. 1451 46. 108 OCTANOIC ACID 0.4052 48. 040 O. 0453 48. 380 ~. 10. 14-TRIMETHYL-2-PENTADECANONE 0.0454 49. 081 SPATHULENOL O. 1455 51. 153 THYMOL O. 0956 51. 696 O. 0857 55. 521 DECANOIC ACID O. 3658 58. 235 FARNESOL O. 04

59 59. 164 DIHYDROACTINIDIOLIDE I 0.0461 72. 801 I 0.09

TOTAL 1100.00

* TENTATIVE** SESQUITERPENE

'-