The Geography of Phytochemical Races

230 5 Wide Disjunctions
Table 5.2 Acetophenone and naphthalene derivatives from Adelanthus decipiens (after Rycroft
et al., 1998b)
Compound No. b Source of plant materiala Sc1 Sc2 Sc3 Wal Ire Co1 Co2 Ecu
Acetophenone
2-Hydroxy-4,
6-dimethoxy
2-Hydroxy-3,4,
[434] – – – – – – 0.11c –
6-trimethoxy
2-Hydroxy-3,4,5,
[435] 0.2 0.1 0.03 – – 3.5 0.03 0.4
6-tetramethoxy
2-Hydroxy-2,3,4,
[436] 2.9 0.6 0.4 – 0.09 – – 0.7
6-tetramethoxy [437] 2.0 0.01 – – 0.02 – – –
Pentamethoxy
Naphthalene
[438] 0.1 0.03 0.01 – – – – 2.0
1,2,3-Trimethoxy [439] 0.1 0.01 0.01 – – 0.15 0.10 0.4
1,2,4-Trimethoxy [440] 0.1 0.01 0.005 – – 7.6 – –
1,2,3,4-Tetramethoxy
1,2-Dimethoxy-3,
[441] 0.1 0.01 0.02 – – 0.07 0.07 0.1
4-methylenedioxy
1,4-Dimethoxy-2,
[442] 12.0 1.7 1.1 0.10 0.25 1.4 0.09 2.2
3-methylenedioxy [443] 3.3 0.5 0.3 0.07 0.15 0.3 0.04 0.3
a Si1, Sc2, and Sc3 = Scotland; Wal = Wales; Ire = Ireland; Co1 and Co2 = Colombia; Ecu = Ecuador.
b Structures appear in Fig. 5.6.
c Concentrations expressed in mM, determined from NMR spectra.
(e.g., Isle of Mull) and on the island of Terceira in the Azores. The Scottish plants
lacked sporophytes, whereas the plants in the Azores, likely growing under more
favorable conditions, bore sporophytes and were abundant.
Rycroft et al. (1999) identifi ed the major components of plants from six locations
in western Scotland and four from the Azores using nuclear magnetic resonance
(NMR) fi ngerprinting and GC-MS. The terpene β-phellandrene [129], which
may be responsible for the aroma of material crushed in the fi eld, was detected
in all specimens. The major components, which appear in Fig. 5.6, were shown
to be methyl everninate [444], the four methyl orcellinate derivatives [445–448],
the two 9,10-dihydrophenanthrene derivatives [449] and [450], the newly described
phthalide “killarniensolide” [451], and the bibenzyl [453]. Methyl everninate was
the major compound in all 10 specimens; other compounds were more varied in
their occurrence. Killarniensolide was not isolated as such but was detected when
extracts were acetylated yielding, among other compounds, [452]. The presence of
the bibenzyl compound [453] in more than trace amounts in P. killarniensis raises
the possibility that it represents contamination from P. spinulosa with which it was
growing at the one site.
Two compounds, although present in material from both Scotland and the Azores,
were present in signifi cantly different amounts in the two. Compound [448], methyl
2-methyl-3,4-methylenedioxy-6-hydroxybenzoate, was present in the six Scottish
specimens to the level of 22, 13, 14, 10, 12, and 10%, as compared to 2, 2, 3, and 2%
for the specimens from the Azores. Similarly with regard to compound [447], the