California Lomatiums Part III.# Composition of the Hydrodistilled Oils from Two Varieties of Lomatium dissectum. Isolation of a New Hydrocarbon

Journal of Essential Oil Research: JEOR, Sep/Oct 2004 by Bairamian, Sona, Beauchamp, Philip S, Descalzo, Josette T, Dev, Barbara C, Et al

Abstract

The oils of Lomatium dissectum var. dissectum and L. dissectum var. multifidum were analyzed by GC and GC/ MS. [beta]-Phellandrene/limonene (25.3%), [beta]-caryophyllene (10.8%), palmitic acid (6.6%), (E)-[beta]-ocimene (5.4%), linolenic acid (4.7%); palmitic acid (15.3%), octanol (9.0%), octyl acetate (5.3%), [beta]-caryophyllene (4.1%), linolenic acid (4.8%); myrcene (19.0%), 4-methylpentyl 2-methylbutyrate (13.9%), limonene (5.8%), [alpha]-bisabolol (5.1%), cuparene (5.0%), 4-methylhexyl 2-methylbutyrate (4.2%) constituted the major components of the respective hydrodistilled oils from the fruits, uppers (stems and leaves) and roots of L. dissectum var. dissectum. The corresponding oils from L. dissectum var. multifidum showed, palmitic acid (12.1%), palmitoleic acid (8.9%); decyl acetate (7.6%), linolenic acid (7.4%), linoleic acid (6.9%); (Z)-S-hexenol (18.5%), palmitic acid (8.6%), myrcene (6.0%), decyl acetate (4.9%), longifolene (4.2%); and myrcene (23.1%), longifolene (20.4%), limonene (6.0%), palmitoleic acid (5.1%) as the major components. The root oils of both varieties contained nearly 4% of a new hydrocarbon, (E)-2-methyl-3-octen-5-yne.

Introduction

In earlier reports, we had described the composition of the hydrodistilled oils obtained from L. califomicum and L. torreyi belongingto the Apiaceae family (1,2). (Z)-Ligustilide and related phthalides were reported to be the major components of the oils from the fruits as well as the uppers of the two species. The reported muscle relaxant property of (Z)-ligustilide was implicated as a possible chemical component in the water extracts of the roots of L. californicum to be responsible for the paralyzing effect on snakes. This property and the medicinal value of this genus to the natives have prompted a continuation of the study of the hydrodistilled oils from Lomatiums native to California.

Two varieties of L. dissectum, L. dissectum var. dissectum and L. dissectum var. multifidum, grow extensively in the Pacific Northwest extending into the interior of southern California. They can be found from the sea level to elevations over 7,500 ft, mostly on dry rocky slopes, meadows and talus (3). Variously known in English as 'toza root,' 'cough root,' 'chocolate tips," and 'Indian balsam," both have been widely used by the earlier natives for their medicinal and food values (3,4). The natives of the Columbia Plateau near the tributary streams running to the Columbia River from the eastern flanks of the Cascade Mountains, used L. dissectum to harvest fish. The effect on the fish was likened to them getting drunk or being knocked out; but not killed. One group boiled the roots and the water was then poured into the stream or pool to elicit this effect. The harvested fish were strung on a willow twig for transport back to camp where they were cooked and eaten (3).

A preliminary report of the composition of the hydrodistilled oils from L. dissectum var. multifidum was made earlier (5). The present report provides a detailed comparison of the compositions of the hydrodistilled oils from the two varieties of Lomatium dissectum.

Experimental

Plant material: Lomatium dissectum var. dissectum and L. dissectum var. multifidum were collected in the month of June in their mature fruiting stage. Lomatium dissectum var. dissectum was collected in the vicinity of the bridge over Van Duzen River in the Six Rivers National Forest, on light duty road 511 and about 8 mi from its junction with Highway 36. GPS location: N 40� 22.530', W 123� 30.216', elevation 2,442 ft. Lomatium dissectum var. multifidum was collected along the steep banks of the East Fork of Mount Home Creek in the San Bernardino National Forest, between 18.4 and 18.5 mi markers on Highway 38 about 300 yd from Mountain Home Creek trailhead near the first slightly flat area below to the left of trail. GPS location: N 34�07.662'; W 116� 58.798'; elevation 5414 ft. Plant identification was confirmed by Steven Boyd, curator, Rancho Santa Ana Botanic Gardens, Claremont, CA, where herbarium samples have been deposited.

Isolation of oils: The plants from each location were shaken free of loose dirt and dead organic material. They were washed with deionized water and separated into (i) fruits, (ii) stems and leaves (uppers), and (iii) roots. Each part was patted dry with paper towels, weighed and separately blended in a food blender with added water. Each was hydrodistilled and the distillates saturated with NaCl. Extraction with CH^sub 2^Cl^sub 2^ followed by drying the extracts with anhydrous Na^sub 9^SO^sub 4^, rotovaping the CH^sub 2^Cl^sub 2^ at 35�-40�C and at aspirator pressure followed by further drying for 15 min at ~10 torr resulted in the respective oils. The plant materials and their respective oil data are summarized in Table I.

Isolation of L. dissectum var. dissectum root oil components: A 2.78 g portion of the root oil was applied to 50 g silica gel column packed as a slurry in hexane. The column was eluted with 100mL each of 100:0, 98:2, 96:4, 90:10, 80:20, 60:40, 50:50, 40:60, 20:80 and 0:100 mixtures of hexane: Et^sub 2^O. Fifty-two fractions, approximately 15 mL each, were collected and analyzed by TLC. The developed plates were visualized under UV followed by I2 vapors. Starting with fraction #5, eveiy fifth fraction was analyzed by GC and GC/ MS. GC analysis was also done of one fraction on each side of the fifth fraction whose GC/MS indicated the presence of either the M[Theta] 122 enyne component or the fragments at m/z 85,103 for the methylbutyrates. Fractions of similar chemical contents were combined for further purification.