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Fig. 2 in Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Fig. 2. Lead compound, ku-76 and its SAR.

Fig. 1 in Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Fig. 1. Examples of non-selective gravitropism inhibitors.

Fig. 7 in Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Fig. 7. Synthesis of configurationally fixed analogues 5.

Fig. 11 in Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Fig. 11. (continued).

Fig. 19 in Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Fig. 19. Retrosynthetic scheme for glucosinolate synthesis.

Fig. 9 in Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Fig. 9. Illustrative examples of trivial names of glucosinolates. MYR, myrosinase.

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Data from: Metabolomic and transcriptomic data on major metabolic/biosynthetic pathways in workers and soldiers of the termite Prorhinotermes simplex (Isoptera: Rhinotermitidae) and chemical synthesis of intermediates of defensive (E)-nitropentadec-1-ene biosynthesis

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Fig. 13 in Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Fig. 13. Inhibitory activity tests of gravitropic bending and elongation for o-styrylbenzoic acid analogues 5 and NPA (0.05–5 μM). Data for gravitropic bending and elongation represent the mean ± SD. Asterisk indicates statistically significant differences between treatments and controls at p <0.05 (Dunnett's test, n = 7).

Fig. 9 in Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Fig. 9. Inhibitory activity tests of gravitropic bending (left) and elongation (right) for naphthyl analogues (a) ku-76, (b) 1a and (c) 1b. 1a completely inhibited elongation at 5 and 50 μM. Data for gravitropic bending and elongation represent mean ± SD. Asterisk indicates statistically significant differences between treatments and controls at p <0.05 (Dunnett's test, n = 7).

Fig. 18 in Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Fig. 18. Some proposed glucosinolates (GSLs) in need of more evidence. (A) Two GSLs suggested from MS to be isomers of [3], but without general NMR evidence or published MS/MS evidence for the position of the acetyl groups at the rhamnose residue, as opposed to the glucose residue or another isomer. (B) 2-Hydroxy-8-(methylsulfinyl)octyl GSL suggested from MS/MS evidence but without NMR evidence.

Fig. 13 in Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Fig. 13. The usefulness of the COSY spectrum for establishing connectivity, and an example of NMR of an intact glucosinolate (GSL). (A) The 1H NMR spectrum of 3-(hydroxymethyl)methylpentyl GSL (141) in D2O. A major impurity of acetate from the ion exchange isolation is seen. (B) The corresponding COSY spectrum. Signals along the diagonal correspond to the 1D spectrum. Whenever protons are found at the same or neighboring carbons, a "cross peak" can be seen with the x-coordinate of the one signal and the y-coordinate of the other. Original data by the authors (CEO and NA, Sections 6.1 and 6.2).

Fig. 6 in Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Fig. 6. Biosynthesis of six Met-derived glucosinolates (GSLs) in Arabidopsis thaliana starting with chain elongation (8 enzymatic steps for increasing the number of C atoms with two), followed by core GSL biosynthesis leading to the parent dihomoMet derived GSL 84, 4-(methylsulfanyl)butyl GSL. Further sequential secondary modifications of the parent GSL, via 4-(methylsulfinyl)butyl GSL (64) and but-3-enyl GSL (12) ends with 2-hydroxybut-3-enyl GSL (mixture of two stereoisomers, 24R and 24S, in this species) (Sønderby et al., 2010a). A different route leads from 64 to the alcohol [26] and the benzoyl ester 5 (Lee et al., 2012).

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Fig. 5 in Design and chemical synthesis of root gravitropism inhibitors: Bridged analogues of ku-76 have more potent activity

Fig. 5. Configurationally fixed (stilbene type) analogues.

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Fig. 8 in Glucosinolate structural diversity, identification, chemical synthesis and metabolism in plants

Fig. 8. Examples of the diversity of glucosinolate breakdown products. MYR, myrosinase.