Abstract
Four new monoterpenes, (1R*,2S*)-1,2-dihydroxy-p-menth-4(8)-en-3-one (1), (4S*)-4-hydroxy-p-mentha-1,8-dien-3-one (2), (4S*)-4-methoxy-p-mentha-1,8-dien-3-one (3), and (3R*,4R*,6S*)-3-acetoxy-6-hydroxy-p-mentha-1,8-diene (4) together with four known compounds have been isolated from the aerial parts of Mentha microphylla. The structures were determined using spectroscopic methods particularly high resolution 1H-, 13C-NMR as well as 2D 1H-1H COSY, HMQC and HMBC analysis.
References
-
1
Villaseñor I M, Echegoyen D E, Angelada J S.
A new antimutagen from Mentha cordifolia Opiz.
Mutat Res.
2002;
515
141-6
-
2
Szöllösi R, Varga I S.
Total antioxidant power in some species of Labiatae (adaptation of FRAP method).
Acta Biologica Szegediensis.
2002;
46
125-7
-
3
Yamasaki K, Nakano M, Kawahata T, Mori H, Otake T, Ueba N. et al .
Anti-HIV-1 activity of herbs in Labiatae.
Biol Pharm Bull.
1998;
21
829-33
-
4
Iscan G, Kurkcuoglu M, Husnu Can Baser K H, Demiric F, Kirimer N.
Antimicrobial screening of Mentha piperita essential oils.
J Agric Food Chem.
2002;
50
3943-6
-
5
Mimica-Dukic N, Popovic M, Jakovljevic V, Szabo A, Gasic O.
Pharmacological studies of Mentha longifolia phenolic extract. II. Hepatoprotective activity.
Pharm Biol.
1999;
37
221-4
-
6
Arakawa T, Osawa K.
Pharmacological study and application to food of mint flavour - antibacterial and antiallergic principles.
Arom Res.
2000;
1
20-3
-
7
Inoue T, Sugimoto Y, Masuda H, Kamei C.
Antiallergic effect of flavonoid glycosides obtained from Mentha piperita L.
Biol Pharm Bull.
2002;
25
256-9
-
8
Burbott A J, Hennessey Jr J P, Johnson Jr W C, Loomis W D.
Configuration of piperitone oil of Mentha piperita
.
Phytochemistry.
1983;
22
2972-3
-
9
Bohlmann F, Zeisberg R.
13C-NMR-Spektren von Monoterpenen.
Org Mag Reson.
1975;
7
426-32
-
10
Ohashi M, Inoue S, Sato K.
A synthesis of diosphenols.
Bull Chem Soc Jpn.
1976;
49
2292-3
-
11
Baeckstrom P, Jacobsson U, Koutek B, Norin T.
Photochemical transformations of protonated phenols. A one-step synthesis of umbellulone from thymol.
J Org Chem.
1985;
50
3728-32
-
12
Angell A, Hefendehl F W.
Strukturbestimmung von Diosphenolen.
Phytochemistry.
1972;
11
3359-61
-
13
Garg S N, Agarwal S K.
New monoterpene diols from essential oil of Ferula jaeschkeana
.
Phytochemistry.
1988;
27
936-7
-
14
Garg S N, Misra L N, Agarwal S K.
Essential oil from rhizomes of Ferula Jaeschkeana
.
Phytochemistry.
1989;
28
634-6
-
15 Wehrli B K. In: Progress in the Chemistry of Organic Natural Products. Herz W, Griesebach H, Kirby GW, editors New York; Springer Verlag 1979: pp 26-7
-
16
Park S -H, Kim S -U.
Modified monoterpenes from biotransformation of (-)-isopiperitenone by suspension cell culture of Mentha piperita
.
J Nat Prod.
1998;
61
354-7
-
17
Cantín A, Lull C, Primo J, Miranda M A, Primo-Yúfera E.
Isolation, structural assignment and insecticidal activity of (-)-(1S,2R,3R,4S)-1,2-epoxy-1-methyl-4-(1-methylethyl)-cyclohex-3-yl acetate, a natural product from Minthostachys tomentosa
.
Tetrahedron: Asymmetry.
2001;
12
677-83
-
18
Prasad R S, Dev S.
Chemistry of ayurvedic crude drugs - IV: Guggulu (resin from Commiphora mukul - 4) absolute stereochemistry of mukulol.
Tetrahedron.
1976;
32
1437-41
-
19
Van Dyk M S, Van Rensburg E, Rensburg I P B, Moleleki N.
Biotransformation of monoterpenoid ketones by yeasts and yeast-like fungi.
J Mol Cat B: Enzym.
1998;
5
149-54
Ahmed A. Mahmoud
Present address: Department of Chemistry
College of Science
King Faisal University
P.O. Box 1759
Hofuf 31982
Saudi Arabia
Fax: +20-966-358-6437
Email: amahmoud64@yahoo.com