California Lomatiums, Part IV(a): Composition of the Essential Oils of Lomatium rigidum (M.E. Jones) Jepson. Structures of Two New Funebrene Epimers and a Tridecatriene

Journal of Essential Oil Research: JEOR, Nov/Dec 2004 by Beauchamp, Philip S, Descalzo, Josette T, Dev, Barbara C, Dev, Vasu, Et al

Analysis of oils from collections (ii) and (iii): The GC profiles of the oils from the fruits and stems and leaves of collections (ii) and (iii) matched very closely with the fruits and stems and leaves oils from collection (i). The root oils also had similar GC profiles; however, with two quite noticeable exceptions. First, the root oil from collections (ii) and (iii) showed 26% of a component (RI 1291) which was not detected in the oil from collection (i). Second, the percent composition of I, which was 48.2% in collection (i), was only 3.3% in collections (ii) and (iii). This component with RI1291 was isolated from the corresponding root oil by liquid chromatography. Its structure (Z,Z,Z)-3,6,9-tridecatriene IV was established from its NMR data (Table IV). The all (Z)-configuration for IV derives its analogy from the excellent agreement of its allylic carbon chemical shifts with those of linolenic acid (21). At present, we are unable to provide an explanation for the observed variation in the composition of the root oils of the same species. Further work will need to be undertaken to study this variation.

It is interesting to note that the content of the related phthalide derivatives like (Z)-ligustilide in the oils of this Lomatium species is rather insignificant when compared to L. californicum and L. torreyi (2,3). Currently, work is in progress to study the variation in the occurrence of (Z)-Iigustilide and/ or other phthalide derivatives in the other species of this genus.

Acknowledgements

The authors wish to thank the Camille and Henry Dreyfus Foundation for a Senior Scientist Mentor Initiative Grant for Undergraduate Research to V. Dev. Thanks to Lawrence M. Blakely, professor emeritus, botany department, California State Polytechnic University, Pomona, and Ruth M. Blakely for assisting with plant collection. Thanks to Floyd Howell, chemistry department, California State Polytechnic University, Pomona, for the maintenance of instruments, and to Richard J. Raffel, Los Angeles Police Department Forensics Laboratoi~y,for determining optical rotations. Last but not least, our thanks to Kathleen Nelson, forest botanist, Inyo National Forest, for permits to collect the plant material.

References

1. S.S. Strike, Ethnobotany of California Indians, Volume 2. Aboriginal uses of California's indigenous plants. Koeltz Scientific Books USA/ Germany (1994).

2. P.S. Beauchamp, AT. Bottini, V. Dev, A.B. Melkani, and J. Timbrook, Analysis of the Essential oils from Lomatium californicum (Nutt.) Math, and Const. In: Food Flavors, Ingredients and Composition. Edit., G. Charalambous, p. 605-610. ElsevierSci. Publ. B. V.,Amsterdam (1993).

3. A. Bedrossian, P.S. Beauchamp, V. Dev, S. Kwan, E. Munevar-Mendoza, and E.K. Okoreeh, Composition of the Essential oils of Lomatium torreyi. J. Essent. oil Res., 10, 473-477 (1998).

4. S.C. Bairamian, P.S. Beauchamp, J.T. Descalzo, B.C. Dev, V. Dev, S. Frost and CamV. Nguyen, California Lomatiums Part III. Composition of the Hydrodistilled oils From Two Varieties of Lomatium dissectum. Isolation of a New Hydrocarbon. J. Essent. oil Res., 16,461 -468 (2004).