Environment and gene expression

Rose Genetics Flower Pigments
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There are many cases where gene expression is altered by environmental conditions. Siamese cats, for example, are fully pigmented only on those parts of the body that are significantly cooler than core body temperature. At the opposite extreme, wingless fruitflies have an annoying habit of flying away when their larvae are maintained at a temperature of 75 °F or above.

There are also cases where some condition, possibly temperature, alters the pigment content of roses. I have two reports on the anthocyanin pigments found in garden roses:
Marshall (1976)
http://bulbnrose.x10.mx/Roses/breeding/MarshallArkansana1976.html
Eugster and Märki-Fischer (1981)
http://bulbnrose.x10.mx/Roses/breeding/EugsterPigments1991/EugsterPigments1991.html

According to Marshall, Rosa foetida bicolor contains only cyanin. To the contrary, E & M-F wrote, “The Austrian copper (R. foetida bicolor) contains surprising amounts of peonin, as already mentioned. If its progeny contain anthocyanins—which is not always the case—they always include peonin. An example is ‘Lady Penzance’ (Penzance, 1894), a shrub rose bearing coppery red flowers with a yellow center.”

Marshall reported that ‘Hansa’ contained some peonin, but more cyanin. According to E & M-F, “The richest source of almost pure peonin is the old shrub rose ‘Hansa’ (Schaum and Van Tol, 1905; Fig. 11). Its mauve-red flowers show what can be achieved by high levels of pure peonin!”

Eugster and Märki-Fischer: “Peonin is probably derived from cyanin. Whether the methylation occurs at the level of the cyanidin or only at its glucosides is unknown.”

In the cases I mentioned above, it appears that the enzyme that converts cyanin to peonin is variable in its expression. I can’t say for sure why it produces more peonin around Zurich, Switzerland than Morden, Manitoba.

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I’m sorry Karl, this post was identified by the system as spam and required moderation. I’m not sure why. Perhaps the other moderators with greater experience may be able to provide an answer.

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Hi Karl,

You had me at ‘Hansa’. Haha

I did find this reference to cyanins and peonin being impacted by pH, but that couldn’t be the whole situation or ‘Hansa’ would be acting like hydrangeas.

“The Peonin is an anthocyanin. This pigment is bound to two hexose molecules to attain stability. This is because anthocyanins are unstable compounds and change according to pH. The change in pH brings about the color change in Peony flowers.”

Forgive me if this is already common knowledge. It was new info to me.

Source: https://www.chegg.com/homework-help/peonin-red-pigment-found-petals-peony-flowers-consider-struc-chapter-16-problem-6ctp-solution-9780077354800-exc

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pH can alter color of the pigments, but in the cases that I’m puzzling over, a pigment (peonin) was apparently produced by R. foetida bicolor growing in Switzerland, but not in Canada.

The difference between cyanidin-3-glycoside and peonidin-3-glycoside is a single methyl group, as this image shows.

This pic came from a paper on gene-splicing in Petunias, but it might be the same reaction found in Roses.
Karl

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I forgot I have some other papers on the inheritance of pigments.
de Vries: Flavonoids in rose petals (1974) - Quercitin correlated with Cyanidin, Kaempferol with Pelargonidin.
http://bulbnrose.x10.mx/Roses/breeding/deVriesTable1974.html
de Vries: Rose pigments II (1980)
http://bulbnrose.x10.mx/Roses/breeding/deVriesPigments1980.html

Bohm: Biosynthesis of Anthocyanins (1999)
http://bulbnrose.x10.mx/KKing/RosePigments/BohmAntho1999.html
Geissman: Anthocyanins, Chalcones, Aurones and Flavones (1955) - This one gives some techniques for identifying the pigments.
http://bulbnrose.x10.mx/KKing/RosePigments/GeissmanPigments1955.html

This diagram shows the pathways leading to the three monoglucosides found in garden roses: pelargonidin, cyanidin and peonidin. The orange outlines indicate the steps that might lead to an increase in pelargonidin at the expense of cyanidin and peonidin.

The evidence presented by de Vries (1974) suggests that a form of F3’H limits the conversion of dihydrokaempferol to dihydroquercetin, which leaves more of the precursor for pelargonidin, kaempferol and apigenin.

The two orange boxes indicate further possibilities where substrate specificity might allow DFR and/or 3GT to be more active in the sequence leading to pelargonidin than to cyanidin/peonidin.

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Suntory has been working on genetically modifying these pathways for decades but I haven’t seen much in the way of publications or products. Perhaps someone with access to primary literature can poke around to see if there has been anything new published.

https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1365-313X.2008.03447.x

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Don,
This gene-splicing is all very high tech and interesting, especially when the developers discuss the failures as well as patenting the successes. But they remind me of the people who peeled the colored stickers from Rubik’s cubes, then claimed to have solved the puzzle.

I don’t have the details of the Suntory research, but I suppose it’s about the opposite of what happened in the petunia splicing. In that case, the native DFR did a great job of converting dihydromyricetin to leucodelphinidin, and was about as adept at making leococyanidin from dihyhdroquercetin. But it would not touch dihydrokaempferol, and therefore no pelargonidin was produced. The splicers had to borrow other genes from maize to get the desired orange petunias. I’d have to check, but I’m guessing that the native 3GT also had a problem with substrate specificity.

And that’s an issue that could be explored without borrowing genes from other families. We already have a form of 3GT in roses that is a bit uncertain as to the type of sugar it is supposed to add to the anthocyanidin skeleton. In most garden roses, glucose is involved. But in some asian species sophorose is sometimes substituted, and more rarely rutinose is brought in. These sugars alter the color of the pigment in interesting ways. Sophorose tilts the color towards the orange shades. This adds a distinctive tint to some forms of Rosa moyesii, R. fargesii, and R. rugosa ‘Salmon Pink’.

I don’t know how the rutinosides of cyanidin and peonidin look in roses, but they are responsible for the color of Anthurium amnicola.

http://bulbnrose.x10.mx/KKing/RosePigments/KamemotoAnthurium1996/KamemotoAnthurium1996.html

It would be interesting to see whether this indecisive enzyme would operate on leucopelargonidin. I have no idea what color pelargonidin-3-sophoroside would be, but I’d like to find out.

It is not a simple matter of separating the sophorosides and rutinosides from glucosides, because a single enzyme presumably handles all three versions. But a gene encoding an indecisive enzyme is probably more likely to mutate to a more decisively non-glucose version.

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I have not read the petunia work but yours is a great synopsis. With Suntory it was supposedly vacuolar pH that gave them the mauve rather than blue. They were experimenting with the rosacyanins as well.

It is evident that the technology is not the obstacle. Nobody wants to invest in expensive gambles when the work product will get tied up in regulation purgatory long enough for the patents to expire.

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Don,
Here’s a bit from a Suntors patent.

Novel compound contained in blue rose (delphinidin-based rosacyanin)
US 20120011771 A1
Yuko Fukui, Yoshikazu Tanaka
Suntory Holdings Limited
Since rosacyanins have a cyanidin backbone in a portion of their structure, there the possibility that they are synthesized based on cyanidin, a common precursor with cyanidin or an analog of cyanidin. However, since this remains to be only speculation, what types of substances are actually used as precursors and what types of pathways are used in synthesis have yet to be clearly determined.
On the other hand, delphinidin is synthesized instead of a portion of the cyanidin in roses in which flavonoid 3 2,5 2-hydroxylase gene is expressed as a result of genetic recombination as previously described. If the aforementioned hypothesis regarding the rosacyanin synthesis pathway, namely that rosacyanin is synthesized by using cyanidin as a precursor, is correct, then rosacyanin would not be synthesized in these genetically modified roses in which cyanidin serving as precursor is essentially absent.
When the inventors of the present invention conducted an analysis to obtain findings regarding rosacyanin synthesis using the aforementioned genetically modified roses that hardly contain any cyanidin or have a considerably decreased cyanidin content in comparison with a host as described in Patent Document 1 or Patent Document 2, contrary to expectations, a novel compound was found to be present having a chemical structure that clearly differed from that of rosacyanins inherently possessed by roses. Moreover, this novel compound was clearly determined to be uniquely present in roses in which flavonoid 3 2,5 2-hydroxylase gene was expressed by genetic recombination, thereby leading to completion of the present invention

I would love to know whether pelargonidin could become the basis for a rosacyanin. I won’t even try to guess at the color … if it can be made.

Stoddard (Orangeade as a Parent, 1980) made a cross that might be expected to generate such a thing, but maybe not.
“Colors were remarkably free of bluing (mauve and magenta), factors certainly present among the many pollens used. Yet Angel Face duplicated, even exceeded, itself in one seedling except that the fragrance was absent. Another Angel Face seedling was soft gray with an orange edging, unique in my experience, and lovely but with more than enough faults to outweigh its only merit.”
http://bulbnrose.x10.mx/Roses/breeding/orangeade.html

Maybe the hypothetical pelargonidin-rosacyanin would turn up in the F2, in offspring that expressed more pelargonidin than cyanidin.

BTW, gray with orange edging is odd, but I once had a tropical Hibiscus, ‘Fifth Dimension’, that was sometimes just that color.
https://davesgarden.com/guides/pf/showimage/254208/#b

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I recall Tropicana had a novel pigment or pathway for pelargonidin for a rose though I don’t offhand remember the particulars. Do you have anything on it? I think Eugster mentioned it maybe.

A neighbor of mine grows tropical hibiscusesii in his window. A couple years ago I used the pollen both ways on some of his hardy cultivars and both of those on another neighbor’s Rose of Sharon. Nothing stuck. The Flemming brothers were geniusesii imho.

FWIW hibiscus seeds are among the easiest to extract and germinate.

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If the hibs would set seed. None of the forty types I had down south would there and none of them here will, either. Dangit.

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Once upon a time, almost 30 years ago, I had about 25 glorious hibiscus in my garden. I had plans, but nothing came of them. I was especially fond of ‘Ross Estey’ because the blooms usually lasted 3 days without wilting or fading. I never could get seeds from it … not on my own plant nor on the otehrs I found around the area.

Sam McGredy, after he retired, mentioned that he was doing some experiments crossing hibiscus. I don’t know how far he got.

BTW, some of the “rosa-sinensis” complex hybrids suffer from a sort of cryptic sterility. The original species come from numerous islands that may differ in mineral content. Soil on a coral atoll is bound to differ from that surround a dead volcano or a splinter from a continental mass. The species have evolved to use different trace elements in their reproductive parts. Two species or varieties that cross readily in one garden, may refuse entirely in another because one or the other isn’t getting the trace of whatever it needs to make pollen or ova.

I read about this business while I was living in Florida, but haven’t been able to trace supporting information since then. There is a hibiscus grower-breeder down this way. Maybe it’s a matter of humidity as well as trace elements.

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The diagram I posted above is good as far as it goes. It shows that variations in the structure of three enzymes may be involved in the relative abundance of pelargonidin vs. cyanidin+peonidin.

However, it leaves out other products that are derived from the same precursors. For example, some of the dihydrokaempferol is transformed into apigenin, which may serve as co-pigment in some cases. Similarly, dihydroquercetin is “parent” to luteolin, which is a light yellow pigment that has the odd property of deepening (rather than fading) when exposed to UV.

And more importantly, dihydroquercetin begets quercetin. This can act as co-pigment, or when methylated and/or glycosolated it becomes a yellow pigment. In addition, it serves some interesting and important functions in warding off infections and infestations. Here are some notes:
http://bulbnrose.x10.mx/KKing/Quercetin.html

Changing a color may seem like a trivial thing, but it can disrupt other processes. For instance, Lammerts (1964) reported on the inheritance of pelargonidin in roses. “Another consideration in the breeding of roses with these lovely colors is that this mutation for some unknown reason also is associated with factors for weaker plant growth.”
http://bulbnrose.x10.mx/Roses/breeding/Lammerts/Lammerts_pelargonin.html

This pigment-correlated weakness may be related to the weaknesses in ‘Château de Clos Vougeot’ and its descendant ‘Baby Château’. I have not seen either of these roses, but descriptions, pictures and breeding suggest that pelargonidin may be present in them. Certainly, ‘Baby Château’ provided the brilliant orange and scarlet colors to ‘Käthe Duvigneau’, ‘Floradora’ and ‘Cinnabar’.

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Searched awhile locally (Canada) for the purest expression (look alike, as real seems endangered) of the one color palette of Hawaii’a state flower in “nurseries” … I believe called Hibiscus brackenridgei … to accompany the invasive ginger examples in the house from Hawaii’a - made do with a “box store offering” that does a good job of the pure yellow (no red) … indoors, living room, full sun, 66-70deg F normal temp range, 50 to 65% humidity and A/C in summer - point is the yellow sets seeds as does the pastel red and the red eye yellow that are located beside it.

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Todays bloom, good for a day
IMG_4631 (2).JPG

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I was rereading Eugster & Märki-Fischer (1990) and noticed a possible solution to a minor mystery.
http://bulbnrose.x10.mx/Roses/breeding/EugsterPigments1991/EugsterPigments1991.html

Where did ‘Veilchenblau’ get its color? The answer seems to be that ‘Crimson Rambler’ is colored by peonin as well as cyanin and pelargonin. This is relevant for two reasons: (1) Peonin is produced directly from cyanin, and (2) cyanin “blues” when combined with co-pigments whereas peonin does not (at least, not in roses).

If ‘Crimson Rambler’ is heterozygous for the gene encoding AMT, then about 1 in 4 self-seedlings (on average) should lack peonin, and be free to “blue” as co-pigments combine with cyanin.

Furthermore, if ‘Crimson Rambler’ is also heterozygous for one or more genes affecting the concentration of flavones and/or gallotannins, then there would also be segregation for it/them. In other words, about one-fourth of the offspring should “blue”, but a fraction of those would “blue” as effectively as ‘Veilchenblau’.

Some of the orange-toned Polyanthas would be much improved by the AMT gene that would drain off some of the cyanin that is involved with “bluing”. ‘Golden Salmon’, for example, would look much better with a bit of clear peonin-red rather than the cyanin+co-pigment purple.

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I speculated above about the possibility of a rosacyanin based on pelargonidin. No need to speculate. In fact, I already have a link to a paper that mentions one.
5-carboxypyranopelargonidin 3-glucoside (36) has been isolated from extracts of strawberries (Andersen et al., 2004).
http://bulbnrose.x10.mx/KKing/RosePigments/AndersonRosacyanin2008/AndersonRosacyanin2008.html

Does one already exist in roses? One place to look is at ‘Margo Koster’. It has a vaguely orange-tinted base color (rosacyanin?) with a light-sensitive orange overlay of callistephin (pelargonidin 3-O-glucoside).

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Don,
I had to do some searching, and quickly learned that ‘Tropicana’ is also the name of a variety of leaf lettuce, as well as the citrus-based beverage. Pelargonidin in all of them.

Eugster and Märki-Fischer (1991) did mention ‘Tropicana’ under its European name:
“With pelargonin one also always finds some of the 3-glucoside (callistephin, 63; see Fig. 7). The 5-glucoside 64 is very rare; it occurs, for instance, in ‘Super Star’ (Tantau, 1960).”
http://bulbnrose.x10.mx/Roses/breeding/EugsterPigments1991/EugsterPigments1991.html

I have read elsewhere (Ogata, et al., 2005) that the 5-glucoside is unstable.

Nature 435, 757-758 (9 June 2005)
Plant biochemistry: Anthocyanin biosynthesis in roses
Jun Ogata, Yoshiaki Kanno, Yoshio Itoh, Hidehito Tsugawa & Masahiko Suzuki
Anthocyanin is the principal pigment in flowers, conferring intense red-to-blue cyanic colours on petals and helping to attract pollinators. Its biosynthesis involves glycosylation steps that are important for the stability of the pigment and for its aqueous solubility in vacuoles. Here we describe anthocyanin biosynthesis in roses (Rosa hybrida), which is unlike the pathway used in other flowers in that it relies on a single enzyme to achieve glycosylation at two different positions on the precursor molecule. Phylogenetic analysis also indicates that this previously unknown glucosyltransferase enzyme may be unique to roses, with glycosylation having apparently evolved into a single stabilizing step in other plants.

Figure 1. A previously undiscovered rose anthocyanidin glucosyltransferase and its phylogeny. a,
Comparison of the reaction pathways of anthocyanin glycosylation in the rose and in other plants:
the rose glucosyltransferase RhGT1 catalyses two reactions instead of one.
3-GT, glucosyltransferase specific for the hydroxyl group at position 3 on the anthocyanidin molecule.

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I was studying the structure of rosacyanins, and it occurred to me that Stoddard’s (1980) gray and orange seedling might have gained its ground color from a pelargonidin-based rosacyanin. The orange margin would be callistephin [pelargonidin-3-monoglucoside], corresponding to the ruby border of ‘Angel Face’, which is chrysanthemin [cyanidin-3-monoglucoside].

Orange border on gray may not thrill everyone, but imagine these colors combined with a good dose of yellow. Now we have an orange border on tan/brown, which may be of greater interest.

And if we go full-on chameleon, we could have gray or tan, soon changing to orange with gray or tan reverse.

The reverse bicolors have not been as well developed as our other possibilities. Take a peak at ‘Rev F Page-Roberts’, and imagine it as tan with orange reverse. Or even gray with orange reverse.
http://bulbnrose.x10.mx/Roses/Rose_Pictures/R/RevFPage-Roberts.html