Star Anise

Sepulchritude Forum: The Absinthe Forum Archive Thru March 2002: Archive thru January 2002:Star Anise
By Malhomme on Saturday, December 15, 2001 - 02:41 am: Edit

LOL!!!

By Mr_Rabid on Saturday, December 15, 2001 - 12:14 am: Edit

Thank you Don! You made my work-day!

By Chevalier on Friday, December 14, 2001 - 10:23 am: Edit

(Grin!)

By Don_Walsh on Thursday, December 13, 2001 - 02:41 pm: Edit

OK, I have a little anecdote for you.

In the early 80s I attended a conference at Ft Benning GA Infantry Center & School. The conference was about small arms, not CABOs -- chemical agents of biological origin -- but nevertheless there was a fellow from Edgewood Arsenal present, and at some point he came over to have a look at my display of various silenced weapons. And he made some flip remark about umbrella guns -- a reference to the KGB's infamous weapon that Bulgarian wetwork boys used to whack a few defectors in the 70s.

Ah yes, says I, the old ricin pellet trick. And I pronounced the toxin rissin, almost like 'risen'.

Rissin? says he? We call it righ-sin. (Phonetic spelling of ricin.)

So I did a tap dance and sang "Let's call the whole thing off!"

The guy from Edgewood looked at me like I was nuts and wandered off shaking his head.

Some people just take their work too damned seriously. NO sense of humor at all.

By Chevalier on Thursday, December 13, 2001 - 05:57 am: Edit

Tetradototoxin -- and the Fugu fish connection -- is mentioned in Fleming's novel "Doctor No", which follows the novel "From Russia With Love". James Bond survived, thanks to a fortuitously nearby doctor. 007's poisoner, the Russian Rosa Klebb, was eliminated shortly afterward. (Perhaps by "Wild Bill"?)

By Don_Walsh on Thursday, December 13, 2001 - 03:33 am: Edit

Anyway, I prefer saxitoxin.

While the Russians favor ricin.

By Don_Walsh on Thursday, December 13, 2001 - 03:32 am: Edit

I don't recall that it was identified in the film but it was probably mentioned, if not by name at least by source, in YOU ONLY LIVE TWICE (the book) if not FRWL.

Did you know that Fleming, as an aide to the DG of Royal Naval Intelligence in WWII, accompanied his boss to the US? Where is assignment was to choose between William Donovan and J.Edgar Hoover as the person that the Brits would lobby FDR to put in charge of American central intelligence? Fleming chose lawyer and ex-general Donovan, a WWI hero, over file clerk and closet queen Hoover, and the rest is history.

There is a rumor that Fleming whacked out a Japanese agent while in NY.

Later he was Reuters bureau chief in Moscow.

We bureau chiefs stick together.

By Chevalier on Wednesday, December 12, 2001 - 08:59 am: Edit

Ah, yes -- tetradototoxin. It nearly snuffed out 007. ("From Russia with Love")

By Don_Walsh on Wednesday, December 12, 2001 - 04:01 am: Edit

I found a lot of Japanese refs in searching on Google for illicium anisatum, illicum anisatum, Japanese star anise, etc., one at a time. Most had no English abstract and were in Japanese. Sigh.

You can bet that the Japanese are interested in a Japanese species with toxic properties. Lots of poisonous flora and fauna are of great interest to the pharmaceutical giants, as they often have therapeutic or research value. The most famous Japanese one is tetradototoxin, from fugu (puffer fish) -- which may also be one of the key ingredients in zombie dust (a la The Serpent and the Rainbow.)

A final anecdote: even the Thais, who use quite a bit of star anise in certain dishes, which I happen to love, like pig's knuckles in star anise sauce over rice, say that star anise is a 'warming' herb and you shouldn't eat too much of it. The Thai name of the herb is buay gaek. The pork dish is called kao khao moo. It's delicious.

But I have never heard of a fatality or even illness in Thailand from eating star anise. However, I will start asking herbal pharmacists and doctors etc. If the star anise supply is sometimes tainted with its toxic lookalike cousin from Japan, Thailand would be hit sooner than Europe.

PS I have never noticed any 'secondary effects' from my wife's pig's knuckle rice soup except for my waistline.

By Petermarc on Wednesday, December 12, 2001 - 03:10 am: Edit

i heard one time the anus being refered to as the 'brown star-fish'...shall we draw parallels?

By Artemis on Wednesday, December 12, 2001 - 02:55 am: Edit

Don, thanks for the welcome; it's good to be back.

Now this is a fascinating thread.

A longgg time ago I was searching for absinthe information, and I found some info about a scientist who had proved, at least to his own satisfaction, that certain compounds associated with the anise plants were fully capable of causing all the negative physiological effects attributed to absinthe and then some.
FWIW, the researcher was Japanese; that much I remember. I never mentioned it here because I was never able to find it again.

Star anise pods are such beautiful things, so alien-looking. I sent one to an artist friend and he agreed. But picture the Pontarlier distillers, having to worry that unscrupulous vendors had sneaked anisatum pods in amongst the verum - easier to scrap badiane than worry about sorting it out, even if they perceived a difference between the two species, which I doubt.

By Don_Walsh on Tuesday, December 11, 2001 - 09:03 pm: Edit

The definitive reference is THE ESSENTIAL OILS, unfortunately this book costs about $700 US +/- $100, so this is a library trip rather than something likely to be on the reference shelf here soon (money going for equipment instead.)

I.verum oil vs I.anisatum oil:

Anethole is out front in both (80-90%).

I.verum has also anisaldehyde and methylchavicol

I.anisatum has safrol (safrole) and eugenol instead.

The GCs would have same main peak (anethole) but very different minor peaks.

These toxic sesquiterpenes, such as anisatin, would show up much later in a GC run if at all, and if one discontinued the analysis when the volatile stuff had come over -- wouldn't see them at all. Hell, they might thermally decompose on the column. HPLC might be a better technique, not as fast and convenient though.

The two oils have very different refractive indices.

Yes, I.verum gives up a lot more oil per ton than does P.anisum, and that is precisely why so much star anise gets used in pastis and Spanish anise, even though the Spanish have the best P.anisum, it's said. I have not tried to buy the oils (why should I? I distill from the herbs) but this is well known.

By Mr_Carfax on Tuesday, December 11, 2001 - 08:35 pm: Edit

Just some additional background information from a very reputable source involved in the essential oil manufacturing industry which demonstrates that misidentification of species runs a close second to deliberate adulteration.


"What happens in the essential oil world is that Pimpinella oil gets adulterated with Illicium oil.

The BP allows both, but Pimpinella oil is so expensive that even if it has this botanical name it is most often faked up. You can see from the GC trace in the BP that Pimpinella oil has gamma himachalene which is not in the Star Anise. Low levels of this are a marker. I have not seen a true sample of the Illicium verum oil but I guess that it would be similar to the I. anisatum oil. Also I hear that as the fruits become short the Chinese distil leaves and twigs. It is all very hard to know what actually happens, especially since the oil is mainly sold on anethole levels anyway."

By Petermarc on Tuesday, December 11, 2001 - 04:25 pm: Edit

i was told that some doctors in france tell heart patients that it is ok to drink a small amount of whiskey, but to forget pastis altogether...the plot thickens...

By Chevalier on Tuesday, December 11, 2001 - 03:15 pm: Edit

Or Belladonna. (The poison, not the character from "The Hobbit".)

By Admin on Tuesday, December 11, 2001 - 03:09 pm: Edit

'maladiane' ...

that's my new goth name.

By Mr_Carfax on Tuesday, December 11, 2001 - 02:59 pm: Edit

I'm trying to find out more information on what sort of products were implicated in the original warning from the FSA.

The notice I received from the pharmaceutical industry body in the UK stated that some of the adverse events were associated with infused products.

I am suspecting it is some form of herbal medicine preparation because both the FSA and MCA are involved- if it was only a food, only the FSA would be interested. But because some herbal medicines are regulated as foods in some EU countries, this may explain why the MCA are now in on the act.

By Don_Walsh on Tuesday, December 11, 2001 - 02:05 pm: Edit

Maybe a little reality check is in irder.

I.verum is a common culinary spice.

No one anywhere is proposing its ban, right?

I.anisatum is, supposedly, banned for human consumption. Therefore, the toxic principles, whatever they are, appear to be confined to that distinct species.

The scientific and especially the alternative-medicine, counterculture and homeopathic literature is something of a shambles when it comes to distinguishing categorically between I.verum H. and I.anisatum, the farther back you go the worse it gets, but recent lit. is also suspect because of reliance on old sources.

The practical problem is one of occasional, old as well as contemporary, accidental admixtures of the two star fruit, sometimes resulting in clinical incidents.

Most of the cases I have read about involved children chewing Japanese star anise fruit, or people drinking tea infused from 'star anise' (the report didn't say which species).

I did not read of any recently reported incidents involving ANY star anise containing alcoholic beverage -- absinthe, pastis, whatever.

So, perhaps it is not time to be alarmed.

Maybe it is time for further study and thought.

We have long speculated that some unknown compound in absinthe, not thujone, might have the real psychoactive (if any) or alleged toxic effect (maybe not the same thing, or substance). I am not meaning to suggest that anisatin is the answer, but these complex, high sterospecific sesquiterpenes which are hard to isolate, purify, seperate and characterize, are good suspects.

By Don_Walsh on Tuesday, December 11, 2001 - 01:39 pm: Edit

(-)-anisatin, a sesquiterpene, and a potent antagonist of GABA is supposed to be present in star anise -- whether I.verum, or I.anisatum, or both I can't tell.

It is reasonable to assume that anisatin would potentiate the effects of the mild GABA antagonist, a-thujone. If so this could explain the alleged convulsive effects of absinthe on some people in the Belle-Epoque just as handily as heavy metal poisons.

However, the sesquiterpene, being of much higher molecular weight, would be even more selectively removed from the distillation of a macerated steep liquor than is thujone.

So, I am speculating, a properly made absinthe will be free of anisatin, while a macerated undistilled absinthe may or may not be, depending on variables such as:

-- is anisatin present in the steam-distilled oil?
-- is anisatin present in the expressed oil?
-- is anisatin really present in I.verum fruit as well as the fruit of I.anisatum aka I.religiosum?

Or is anisatin only found in I.verum when the harvested fruit (stars) or the oil was produced from a mixture of I.verum with I.anisatum due to careless cultivation and poor quality control in the harvest?

The implications are staggering. Pastis (and for that matter some Thai food) could be just as hazardous (if this is all true) as I.anisatum-tainted absinthe, old or new.

Ted dislikes star anise. Wow, he has great instincts.

By Don_Walsh on Tuesday, December 11, 2001 - 06:56 am: Edit

http://www.herbmed.org/herbs/Illicium.htm

Searching for I.verum (Hooker) and/or I.anisatum or I.religiosum is complicated by the two variant spellings Illicum and Illicium, as well as the general babel and pandemonium discussed below.

Hooker is the chap who figured out that Chinese star and Japanese star are indeed distinct species. Thank you Mr Hooker. I wish herb vendors could do as well.

There's a lot of scientific lit. discussing convulsants and GABA inhibitors/antagonists (!) in I. species. Often mentioned is anisatin, but I can't find this in Merck. Anisatin is described as equally potent an antagonist of GABA as picrotoxin. Ouch. Derivatives of anisatin are also focused on.

There's also some lit. discussing allergies to star anise oil and its constituents in 1-2% of the population.

Unfortunately a lot of this material is in Japanese and the refs indicate no abstract.

Finally, I suggest to petermarc that we consider submitting 'naughtiane' and 'evilane' to the IUPAC Nomenclature committee, where I have some small influence, as alternatives to badiane.

By Petermarc on Tuesday, December 11, 2001 - 06:33 am: Edit

of course, my theory falls all to hell when applied to the french language, where it would have to be renamed 'maladiane'...

By Petermarc on Tuesday, December 11, 2001 - 06:23 am: Edit

'badiane' has 'bad' as the first three letters...
other examples:
'badger'=mean animal or bothering people
'badminton'=stupid racket game
'badge'=usually shown when you don't want to see it

it's all quite logical...

By Don_Walsh on Tuesday, December 11, 2001 - 06:12 am: Edit

Artemis! Long time no hear. Welcome back!

By Artemis on Tuesday, December 11, 2001 - 02:56 am: Edit

"I think the most significant thing we have discovered here from an absinthe-centric point of view, is that we have hit upon for first time as far as I know, the reason why in some places badiane was/is considered no good"

Good work, Don. It's certainly the first explanation I've heard that's anywhere near logical. I agree that Illicium Verum has its place in absinthe. It's when it's overused, or used to cover up faults/lackings that it gets nasty.

By Don_Walsh on Monday, December 10, 2001 - 10:12 pm: Edit

Scratch the 'prior to a certain point.' I just did a Google search in illicum anisatum and got three pages, a lot of which were essential oils or herb vendoes, or aromatherapy vendors, and many of them do not distinguish between I.anisatum and I.verum; they either falsely identify Japanese star anise as I.verum or vice versa. This not 1880, this is 2001 about to be 2002 and they are selling oil of Japanese star anise as a cure for flatulence. Someone is gonna die of farting.

Here's a good Spanish page, that is selling oil of I.verum, and includes a warning not to confuse I.verum with I.anisatum or I.religiosum. It also says that the best way to tell the fruit apart is that Japanese star anise does not hane the anise scent. (Other sources say is smells of cloves). This ref talks of 'shikitoxins' present in the Japanese star and that is why it is banned for human consumption.

www.cedrosa.com.mx/info%5CS280.htm

The Japanese star is more shrivelled and has barbed tips on the points.

Even the old sources do say that accidental mixing (due to careless harvesting no doubt) of the two, is an occasional problem.

They also say that the Chinese and Japanese use I.anisatum to kill rats, and other pests; and also use it as a fish kill, and eat the fish despite the method of catch!

I think the most significant thing we have discovered here from an absinthe-centric point of view, is that we have hit upon for first time as far as I know, the reason why in some places badiane was/is considered no good (Pontarlier vs the Jura). It was the confusion between the two species, which at one time were thought to be one and the same. Illicum verum means TRUE Illicum, to distinguish it, probably, from Japanese Star, and I bet this term dates to no earlier than the discovery of the fact that these are distinct species. (Which discovery is described and dated in one of the refs I gave.)

Also note that the Spanish refer to 'badiana' simply the Iberian of Fr. badiane. I have not seen mention here before of the Spanish form of the word. Well, it's just the Pyrenees and a few 12-toed basques in between. Don't both nations wish the mountains were higher?

By Mr_Carfax on Monday, December 10, 2001 - 09:47 pm: Edit

"I think that prior to a certain point, these two species were being mistaken for one another, and therefore, if you take these old sources at face value, you would conclude that star anise (I.verum) oil or fruit, is toxic, when it is not. "

Funny you say this Don, I just looked in a copy of Clarkes "A Dictionary of Practical Materia Medica" (1921) which still has some popularity amongst herbal medicine practitioners and the entry for Chinese Star Anise is Illicium Anisatum.

There is no entry for Illicium verum.

By Don_Walsh on Monday, December 10, 2001 - 09:30 pm: Edit

Shikimic acid comes from the same source (I.anisatum, aka I.religiosum) but, is not related otherwise. It's a major natural precursor of phenylalanine, tyrisine and trytophan (and thus most plant alkaloids).

There is no listing for sikimin or shikimin.

Interestingly, Eyckmann (in 1881) claimed to find the same toxic principle in I.verum.

It is totally unclear whether sikimin, if it exists, is present in the pods, but is or is not present in the oil, when extracted by steam distillation, or by expression (squeezing) or by maceration.

Likewise, some of the old references I just cited, claim that safrole is present in I.verum oil.

It is not.

I think that prior to a certain point, these two species were being mistaken for one another, and therefore, if you take these old sources at face value, you would conclude that star anise (I.verum) oil or fruit, is toxic, when it is not.

However it is prudent to assume that the I.anisatum or I.religiosum IS toxic, whether such toxicity is acute from sikimin (if it exists) or whether the risk is carcenogenicity (unproven but suspected) of safrole.

Believe me, analytical chemistry and seperation technology today is FAR from that of 1880, and if there is a genuine toxic principle in Japanese star anise, it will be well understood, identified, and documented. There is no need to rely on 19th century sources.

By Don_Walsh on Monday, December 10, 2001 - 09:15 pm: Edit

It certainly helps to read a little deeper. I.anisatum is also called I.religiosum, and is/was cultivated around Buddhist temples in China and Japan. The Japanese name is sikimi or shikimi, and that is origin of the name of the alleged toxic principle, sikimin.

See:

http://www.ibiblio.org/herbmed/eclectic/kings/illicium.html

Also:

http://www.meridianinstitute.com/echerb/Files/classics/culbre1/culb-i.html

Instructions are given for telling this from I.verum.

Now, the related substance shikimuc acid I have heard of, so let me go back to my Merck and dig.

By Don_Walsh on Monday, December 10, 2001 - 09:00 pm: Edit

Merck Index shows no mention of any 'sikimin'

I will check the Web.

By Don_Walsh on Monday, December 10, 2001 - 08:56 pm: Edit

1880? (Cough)

I will look up sikimin, but, my late 20th century (1996, 5 year old) Merck Index does not mention any such stuff, and does describe this as a pharmaceutical agent. NO mention of toxicility.

By Bob_Chong on Monday, December 10, 2001 - 08:40 pm: Edit

"Eykmann found in the seeds a crystalline, poisonous, non-glucosidal, non-alkaloidal body, sikimin, soluble in hot water, alcohol, and chloroform. For an account of the analysis, see Amer. Jour. Pharm., 1881, p. 407. The volatile oil (oil of star-anise, from Japanese fruit), according to Schimmel & Co., contains safrol, and has a density of 0.984 to 0.994 at 15° C. (59° F.). The fruit is described above. It is highly poisonous, and attention was drawn to this fruit through cases of poisoning which occurred in the Netherlands, in 1880, as also in Japan, their native country. Fatalities in children have resulted from the ingestion of the seeds, the toxic symptoms being vomiting, convulsions resembling those of epilepsy, with frothing at the mouth, loss of consciousness, dilated pupils, and the face excessively cyanotic."

From http://www.ibiblio.org/herbmed/eclectic/kings/illicium.html

Which, when added to Don's post and viewed in light of other infamous 19th C. "research" that still informs public policy, should be taken with a grain of salt, naturally.

BC

By Don_Walsh on Monday, December 10, 2001 - 08:36 pm: Edit

Illicum anisatum contains: mostly anethole (same as I.,verum, fennel, and regular anise. But unlike those three it also contains small amounts of eugenol (which is harmless, clove oil, tootheache remedy) and safrole.

Safrole (main component of sassafras oil) is on the suspect list as a substance 'which may be reasonably expected to be a carcinogen'. It is not a proven human carcinogen.

We have discussed safrole on this forum before.

The upshot was, much ado about nothing.

Oil of Japanese Star Anise is listed in Merck as a carminative and expectorant under 'Therapeutic Uses". It is not described as toxic, unlike thujone or wormwood oil for example. Or absinthe.

So my guess is, ho-hum.

It's just our overly protective public servants being eternally vigilant. Snore.

By Don_Walsh on Monday, December 10, 2001 - 08:13 pm: Edit

Is Japanese star anise grown anywhere but Japan?

What is the toxic principle in I.anisatum that is not present in I.verum?

I.verum is a very important culinary spice in Thailand. There is nothing wrong with it. The use of it in absinthe in the proper proportions and when appropriate is just fine.

I will look into the Japanese variant.

By Zman7 on Monday, December 10, 2001 - 07:17 pm: Edit

Yes, I remember that Chinese Star Anise is "Illicium Verum" and not "Illicium Anisatum."

By Zman7 on Monday, December 10, 2001 - 07:10 pm: Edit

Yet another reason to avoid, at all costs, badiane.

By Mr_Carfax on Monday, December 10, 2001 - 06:29 pm: Edit

A friendly community message for homebrewers...

I expect most would use Pimpinella anisum, but there has been a warning issued by the UK Food Standards Agency regarding the use of Chinese Star Anise (Illicium verum).

The FSA and Medicines Control Agency are investigating reports of adverse neurological reactions in adults and children following consumption of products containing Chinese Star Anise in 3 other european states.

It appears it may be possible that some suppliers of Chinese Star Anise are in fact supplying Japanese Star Anise (Illicium anisatum) which is regarded as poisonous- however they are still trying to establish if this is what has actually happened or whether it solely involves the products implicated.

In the meantime they have put out a general warning for purchasers of bulk herb to ensure they are not receiving Japanese Star Anise.

May your neurological reactions be only those that are desired.....

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