A water lily. There is an evolutionary secret staring right at you in this picture. Can't see it? Read on to find out what it is, then come back here and click on the photo as many times as you can to see it in extreme-close-up-o-vision.

A few posts ago, I told you that star anise is interesting because it belongs to a group of plants that split from the rest of the other flowering plants early on, and that for a long time, scientists felt plants like these retained a lot of the features of the first flowers.

Scientists think that long ago, petals, carpels (the girl bits), and stamens (the boy bits) evolved from leaves. In other words, the leaves were the raw material upon which evolution acted to create a specialized cluster of sexual structures we now call flowers. By this reasoning, a flower is essentially a bunch of colored, modified leaves that the plant has packed together with its gonads at the end of a stem (a pedicel (ped’-i-sell)) for the purposes of luring insects to move pollen from flower to flower, i.e., reproduction. So yes, when you stick your nose in to inhale the perfume of a delicate flower, you are essentially shoving your sniffing nose – doggy-greeting style — into the flowers’ unmentionables.

The 3% of plants that are basal angiosperms (the group in which star anise fits) seem to have a lot of the characteristics we’d expect in first flowers. Their flower parts are usually physically separate and little changed from each other,  like magnolias or star anise or the water lily above – as if each one evolved from an individual leaf. This is not true of highly derived (changed a lot) flowers like orchids,

or this crazy pitcher plant, Nepenthes northiana, with the digital camo in the back of the pitcher and a convoluted and unified structure. Although not a flower, the pitcher is, believe it or not, a modified leaf.

Thus petals are essentially colored leaves, and the stamens of many of these groups, particularly water lilies, are essentially petals/leaves with pollen-making chambers on the ends. Some seem to defy classification as either petal or stamen. Click on the picture at the top of the page and keep clicking on it to magnify it. Look carefully at the stamens at the very edge of the bunch — they are more like purple petals with pollen making slits half way down them than true stamens.

In this photo, notice the transitional stamens toward the outside of the center – they also look like a cross between a petal and a stamen, although in this case, the pollen-making chambers (anthers) are at the tip of the petal rather than halfway down.

For a while, some scientists felt the first flowers looked very much like magnolias, hence an early term for the basal angiosperms, magnoliids. But that view is changing. Showy magnolias were probably a very early specialization.

Scientists have compared plant DNA the same way they compare flower and plant body parts and have concluded the living flower lineage that split the earliest from the rest of the living flowering plants is the diminutive (and threatened) Amborella, pictured here.

Very closely related to Amborella at the base of the tree are the water lily family, Nymphaceae (nymf-a’-see-ay), and the Austrobaileyales, the group that includes star anise (see the tree here). Plants in these groups often possess characteristics of both the two major flowering plant groups that comprise the other 97% of plants, the monocots (grasses, grains, lillies, orchids, etc.) and the eudicots (roses, apples, poppies, maples, etc.), giving scientists more confidence that they inhabit a special place at the base of the flowering plant tree.

Now scientists believe the first flower was likely to have been small, green, simple, and inconspicuous – not unlike Amborella. Nova did a special on one Chinese aquatic fossil candidate for “the world’s oldest flower” in 2007 (see a great short slide show on it here). Though it’s interesting that water lilies, also at the base of the tree (look for Nymphaeales), are also aquatic, the status of the fossil — Archaefructus, or “ancient fruit” — as “oldest flower” has been challenged. There have been other “most ancient flowers” (Bevhalstia pebja) in the past and will surely be new contenders in the future.

So, four weeks and three posts later, it may finally be becoming clear why star anise is such a surprising plant! In addition to the gorgeous and pungent whorled fruits you can use to flavor stir fry pork or decoupage your 70’s hippie bus, it is a member of one of the most ancient flowering plant lineages on Earth and could save you from one of the planet’s newest viruses.

Sitting in the spice rack of many an Asian home, and a very few American homes, is the unusual looking fruit of an ordinary-looking plant with an unexpected use. Here is that plant:

Delicious or deadly? Both -- depending on your perspective. Image by Shu Suehiro, licensed under the Creative Commons Attribution 3.0 Unported License. Click for link.

And here is its fruit:

Science? Art? My favorite intersection. The shiny objects are the seeds. Image by Bryan Arthur, distributed under the under the Creative Commons Attribution ShareAlike 3.0 License. Click image for link.

The plant is star anise, Illicium verum.

If you know it at all, it is as a spice. As its name implies, its flavor is licorice-y, and indeed the plant makes the same flavoring chemical found in true anise, fennel, and licorice: anethole. It can be used on its own in Asian cooking, but is more commonly known for its inclusion in Chinese five spice powder and Japanese seven spice powder. If you’ve never tried one of these blends, do yourself a favor take some for a spin.*

And now for the use you probably didn’t know about: star anise is the raw ingredient used to make oseltamivir, more familiarly known as Tamiflu. The actual raw ingredient is shikimic acid, and many plants, including the North American Sweetgum (with the beautiful genus name Liquidambar) also make it. But star anise is particularly good at making it. The yields are high.

It seems odd to think of a modern drug depending on a botanical source, but tamiflu is seemingly still very much in that category. In 2005, shortages in Chinese star anise production caused a shortage of Tamiflu.

Nonetheless, it takes some fairly heavy organic chemistry gymnastics to get from shikimic acid to oseltamivir. The wikipedia entry notes, in rather understated language,

Some of the steps in the synthesis require careful handling and relatively mild reaction conditions, as they involve the use of potentially explosive azide chemistry.

Hooo-kay. Having taken organic chemistry, I really do believe that organic chemists earn every penny of their six-figure incomes. You’ll also easily realize, if you compare the structures of shikimic acid and oseltamivir, that the Chinese health minister’s suggestion that people in China cook their pork with star anise to ward off influenza is absolute rubbish. They look totally different. And if it takes a 10-step process involving “potentially explosive azide chemistry” to get to oseltamivir from shikemic acid, it ain’t gonna happen in my stomach. Nor can you get swine flu from pork (duh). Still, pork + star anise could well = tasty.

Star anise’s price still rises and falls with flu outbreaks, even though 99.6% of last year’s seasonal flu was resistant to Tamiflu (a sobering and staggering rise from only 12% the year before) and the same thing could easily happen to pandemic H1N1 flu. Still, so far only 39 of 10,000 pandemic H1N1 flu samples tested positive for resistance to Tamiflu in October. And doctors still turn to Tamiflu to fight this flu. Just a few weeks ago, the U.S. Government decided to release the last of its children’s Tamiflu stockpile due to this flu’s disproportionate ability to kill the young — even, disturbingly, some who were apparently otherwise completely healthy prior to infection.

But it’s hard to believe with hundreds of thousands of doses of Tamiflu flowing into all regions of the U.S. that the drug will last long against the virus. Between this and newly developing E. coli-based shikimic acid production techniques, star anise’s run as a flu-fighter will probably be short lived.

Next time: The Curious Taxonomy of Star Anise

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*Chefs are cooking with five-spice powder more and more as they experiment with traditional ingredients in new cuisines. I often make crispy tofu-ginger fritters with five-spice powder, and I also recently found a recipe in Cooking Light for pumpkin pie with five-spice powder. I bet it’d also be good as a replacement for cinammon in snickerdoodles, since cinnamon is one of the ingredients (in my commercial “Asian Gourmet” blend they are, “cinnamon, anise, fennel, ginger, clove, and licorice root”. I note with amusement that makes six.)