Unique chemistry associated with diversification in a tightly coupled cycad-thrips obligate pollination mutualism Author Terry, L. Irene * & School of Biological Sciences, University of Utah, 257 S 1400 E, Salt Lake City, UT, 84112, USA Author Moore, Chris J. Author Roemer, Robert B. Author Brookes, Dean R. Author Walter, Gimme H. text Phytochemistry 2021 112715 2021-06-30 186 1 19 http://dx.doi.org/10.1016/j.phytochem.2021.112715 journal article 264171 10.1016/j.phytochem.2021.112715 fced7782-3e4a-48dc-8070-835350576f0d 1873-3700 8258649

Table 1 The chemical compounds found on pollen and ovulate (receptive and non-receptive) cones of Macrozamia miquelii (n is given for the total number of volatile samples and the number taken at midday as indicated ) . For each compound is given: its Kovat’ s retention index (RI), and its average % contribution to total emissions, the number of samples in which it was detected (N), and measurements of emission rate ( ng min 1 ) within each cone type. In the average and minimum emission rate columns are the rates of all cone samples and, within parentheses, the rate for midday samples alone, if it changed. All maximum rates are from midday samples alone .

Compound a	CAS #	RI, column		Cone type, number of cones, n = total number of volatile samples (number of midday samples) b
				Pollen, 10 cones, n = 38 (18)					Receptive ovulate, 14 cones, n = 19 (15)					Non-receptive ovulate, 9 cones, n = 11 (9) c
				Avg.	N	ng min 1, all (midday only)			Avg.	N	ng min 1, all (midday only)			Avg.	N	ng min 1, all
		Nonpolar	polar	%		Avg.	min	max	%		Avg.	min	max	%		Avg.	min-
																	max
Aliphatics
2-methylbut-3-en-2-ol (MBO)*	115-18-4	592	1027	25.08	31	1165	13 (88)	6382	15.07	8	317 (353)	10.0	1125	nd	1 pre	tr	nd-tr
						(1632)
3-methybut-2-en-1-ol (prenyl	556-82-1	799	1338	0.38	36	14 (18)	0.45	66	0.47	9	8	0.18	21	nd	nd	nd	nd
alcohol)*
octanal *	124-13-0	1004	1306	0.12	6	1	0.50	1	0.24	7	1	0.50	1	0.46	5 pre	1	0.5–1
nonanal *	124-19-6	1108	1410	0.22	19	3	0.27	6	0.94	13	3	0.54	8	2.44	9	3	0.4–5.0
decanal	112-31-2	1208	1515	0.42	6	2	0.90	3	0.95	5	2 (3)	1.52	4	1.24	4 pre	2	1.2–3
prenyl acetate *	1191-16-8	925	1271	4.21	37	283 (436)	5 (34)	2275	5.19	13	84 (102)	0.41	508	9.26	1 pre	4	4
prenyl butyrate *	71820-56-9	1103	1411	0.06	11	2 (3)	1.20	6	0.24	4	3 (5)	1.04	7	nd	nd	nd	nd
prenyl crotonate *	211429-69-	1161	1563	16.97	38	744 (1137)	1.35	2683	29.44	19	232 (386)	2(19)	1121	nd	3 post	tr	nd-tr
5
6-methyl-5-hepten-2-one*	110-93-0	988	1355	0.12	6	1	0.49	1	0.19	7	1	0.29	2	0.27	5 pre	0.3	0.3–0.5
Benzenoids
methyl benzoate *	93-58-3	1103	1636	0.08	5	1 (2)	1.00	3	nd	nd	nd	nd	nd	nd	nd	nd	nd
methyl salicylate *	119-36-8	1202	1796	0.13	23	9 (11)	0.53	66	0.04	4	0.3	0.03	1	nd	nd	nd	nd
cumic alcohol isomer	536-60-7	1259	2015	0.84	36	9	2.00	24	2.07	13	6	0.04	11	7.97	6	10	1.6–16
cumic alcohol isomer	536-60-7	1271	2029	0.76	36	9	2 (2.6)	27	1.81	14	5	0.13	10	7.51	6	10	1.6–14
4-ethylbenzaldehyde *	4748-78-1	1171	1725	0.81	25	15 (18)	0.10	40	1.45	14	6	0.58	13	4.19	5 pre	7	4.7–7
3-ethylbenzaldehyde	34246-54-3	1186	1756	0.26	10	2	1.10	4	0.54	11	1	0.19	3	1.56	5 pre	2	1.7–3
cinnmaldehyde *	104-55-2	1187	NA	0.14	6	1	1.00	1	0.26	6	1	0.26	1	0.50	5 pre	1	0.7–1
3-ethylacetophenone	22699-70-3	1282	1842	1.38	38	14 (16)	1.29	62	3.61	16	11	0.05	28	17.71	8	14	2.0–22
4-ethylacetophenone	937-30-4	1305	1852	1.00	38	12 (15)	1.3 (2.3)	77	3.20	14	10	0.03	19	11.78	8	11	1.6–19
Monoterpenes
bornylene	464-17-5	908	NA	0.25	26	71	13.61	165	tr	3	tr	tr	tr	nd	nd	nd	nd
α- pinene *	80-56-8	938	1011	23.32	34	5134	0.93	21,514	9.76	19	830	0.85	11,821	38.01	10	35	1.2–155
						(7313)					(1124)
α- fenchene	471-84-1	951	1047	0.31	15	73 (97)	3 (10)	214	0.33	2	78	5.71	150	nd	nd	nd	nd
camphene *	79-92-5	951	1056	0.56	18	128 (147)	17.91	346	0.25	2	63	0.51	126	nd	nd	nd	nd
sabinene *	3387-41-5	977	1116	0.17	17	47 (64)	2.20	256	0.12	5	20	0.02	90	1.75	1 pre	3	3
β- pinene *	127-91-3	982	1100	0.79	27	211 (270)	0.14	1236	0.21	13	28 (40)	0.15	323	0.27	6	3	0.3–8
β- myrcene *	123-35-3	993	1174	6.63	38	624 (910)	1.6 (35)	4778	12.64	19	196 (247)	2.18	1748	24.90	9	37	0.9–73
α- phellandrene	99-83-2	1008	1170	0.35	25	37 (48)	2.10	191	1.10	11	11 (15)	1.06	53	2.63	5 pre	4	3.5–5
Δ-3-carene *	13466-78-9	1015	1148	0.17	19	50 (54)	0.36	256	0.08	4	11	1.05	37	nd	nd	nd	nd
α- terpinene *	99-86-5	1022	1190	19.63	30	4692	1.70	29,979	7.13	14	668 (849)	0.57	7504	0.84	4	1	0.9–2
						(5588)
p-cymene *	99-87-6	1031	1285	3.10	32	788 (907)	0.82	5100	1.69	13	162 (232)	2.26	1979	1.93	10	2	0.7–5
limonene *	138-86-3	1035	1210	2.36	33	576 (731)	0.87	3836	1.55	14	81 (125)	0.95	912	2.24	8	3	0.4–13
β- phellandrene	555-10-2	1035	1221	0.91	18	233 (256)	0.32	1423	0.22	4	12	1.07	25	nd	nd	nd	nd
1,8-cineole	470-82-6	1035	1221	0.06	1	1	0.84	1	0.31	1	12	11.69	12	4.02	2 pre	5	3.3–7
(Z)-β- ocimene *	3338-55-4	1041	1250	0.20	34	23 (29)	0.4 (2.8)	169	0.12	11	3	0.42	18	nd	nd	nd	nd
(E)-β- ocimene *	3779-61-1	1052	1268	0.10	31	10 (14)	0.36	105	0.24	12	8 (10)	0.28	36	0.16	1	0.2	0.2
γ- terpinene *	99-85-5	1065	1259	0.60	22	159 (195)	1.75	784	0.40	12	24 (31)	0.40	236	1.21	2 pre	2	1.4–2
terpinolene *	586-62-9	1096	1298	0.35	22	95 (116)	0.89	413	0.18	6	33 (40)	0.08	179	nd	nd	nd	nd
allo ocimene *	7216-56-0	1134	1390	0.06	11	7 (10)	0.00	25	0.07	5	3	0.29	8	nd	nd	nd	nd