Paspalic acid

[silenziox]

1. What is the formula of Paspalic acid?
2. SWIM is interested only of paspalic acid, not
   lysergic acid or LSA's. Does every strain of C. Paspalum
   produce Paspalic Acid? SWIM made a search and there was
   one post where other bee claimed that there is 3
   different strains (white, brown and violet if SWIM
   reckoned correctly) where the violet was the only strain
   which produced lsa's, but there weren't any info wether
   every strain produced paspalic acid.

[sean1234]

Post 402353

(Bubbleplate: "The Formulas and techniques I listed above", Tryptamine Chemistry) heres the article he is talking about. the question wasnt answered. I find it very strange that the color differences only appear in liquid culture and not agar. . .

[silenziox]

SWIM remembered also that he had seen photos of 2 strains
of C. paspali, both on agar plates. The other strain looked
white and fluffy, centered on the agar-plate like those round cotton swabs used for removing make-up and the other
one was brown, grainy looking stuff, all over the agar plate like vomit.  

[silenziox]

Digging up the dirt at google, I found out this link:

http://groups.google.fi/groups?q=6-Methyl-8&hl=fi&lr=&ie=UTF-8&oe=UTF-8&selm=1233594%40com.com&rnum=4

   28 OF 29  CA 
AN   66:53178  CA
TI   Role of chanoclavines in the biosynthesis of ergot alkaloids
AU   Fehr, Th.; Acklin, Werner; Arigoni, Duilio
CS   Eidg. Tech. Hochsch., Zurich, Switz.
SO   Chem. Commun. (1966), (21), 801-2
     CODEN: CCOMA8
DT   Journal
LA   English
CC   8 (Microbial Biochemistry)
AB   [7558-42-1] SODIUM DL-MEVALONATE-2-14C WAS FED TO SURFACE CULTURES
     OF CLAVICEPS STRAIN OF PENNISETUM TYPHOIDEUM, AND THE ALKALOID
     MIXTURE FORMED WAS ISOLATED AND RIGOROUSLY PURIFIED THE TOTAL
     RADIOACTIVITY INCORPORATED WAS ABOUT 10.  SMALL RADIOACTIVE SAMPLES
     OF [2390-99-0] CHANOCLAVINE I, [1150-44-3] ISOCHANOCLAVINE I, AND
     [1466-08-6] CHANOCLAVINE II 0.01, 0.02, AND 0.025 RESPECTIVE
     INCORPORATION AND LARGE AMOUNTS OF LABELED [548-42-5] AGROCLAVINE
     5.5 INCORPORATION AND [548-43-6] ELYMOCLAVINE 3.5 WERE FOUND.
     DEGRADATION OF THE LABELED AGROCLAVINE AND ELYMOCLAVINE SHOWED THAT
     IN BOTH CASES C-17 HAD 90 AND C-7 ABOUT 7 OF THE TOTAL ACTIVITY.
     DEGRADATIONS OF CHANOCLAVINE I, ISOCHANOCLAVINE I, AND CHANOCLAVINE
     II SHOWED THAT 90 OF THE ACTIVITY WAS LOCATED AT THE C-METHYL GROUP
     AND ABOUT 7 AT THE HYDROXYMETHYL GROUP.  LABELED ELYMOCLAVINE WAS
     CONVERTED TO CHANOCLAVINE I WITH 90 OF THE LABEL CONFINED TO THE
     HYDROXYMETHYL GROUP.  WHEN LABELED CHANOCLAVINE I WAS GIVEN TO
     CLAVICEPS PASPALI, 2 OF THE RADIOACTIVITY WAS INCORPORATED INTO
     [5516-88-1] 6-METHYL-8 9-ERGOLEN-8-CARBOXYLIC ACID SIMILARLY,
     FEEDING CHANOCLAVINE I TO SURFACE CULTURES OF PENNISETUM GAVE 7-10
     OF LABELED AGROCLAVINE WHICH, UPON DEGRADATION, HAD 96.4 OF THE
     ACTIVITY AT C-7 AND 6.4 AT C-17.  CHANOCLAVINE I HAS A TRANS
     RELATION OF THE LABELED ATOM AND THE OLEFINIC PROTON.  THE
     CONVERSION OF CHANOCLAVINE I INTO AGROCLAVINE IS ACCOMPANIED AT SOME
     STAGE BY A TRANS-CIS ISOMERIZATION OF THE DOUBLE BOND HOWEVER,
     EXPERIMENTS UNDER SIMILAR CONDITIONS WITH HYDROXYMETHYL-LABELED
     ISOCHANOCLAVINE I PREPARED BY THE UV ISOMERIZATION OF LABELED
     CHANOCLAVINE I FAILED TO REVEAL ANY SIGNIFICANT INCORPORATION INTO
     THE ALKALOIDS OF BOTH PENNISETUM AND CLAVICEPS.
ST   CLAVICEPS ERGOT ALKALOIDS; ERGOT ALKALOIDS CLAVICEPS; ALKALOIDS
     ***ERGOT***     ***CLAVICEPS***  ; CHANOCLAVINES CLAVICEPS;
     PENNISETUM ALKALOIDS
IT   Ergot
        (chanoclavine formation by)
IT   Alkaloids, biological studies
        (ergot, formation of, by Claviceps)
IT   Isochanoclavine I
        (prepn. of)
IT   548-42-5   548-43-6   1150-44-3   1466-08-6   5516-88-1
        (formation of, by Claviceps)
IT   2390-99-0
        (structure of, formation of by Claviceps)
  
   29 OF 29  CA 
AN   66:8854  CA
TI   Biosynthesis of ergot alkaloids.  Incorporation of chanoclavine-I in
     ergoline derivatives
AU   Groeger, Detlef; Erge, D.; Floss, Heinz G.
CS   Inst. Biochem. Pflanzen, Deut. Akad. Wiss., Halle Saale, Ger.
SO   Z. Naturforsch., B:  Anorg. Chem., Org. Chem., Biochem., Biophys.,
     Biol. (1966), 21(9), 827-32
     CODEN: ZENBAX
DT   Journal
LA   German
CC   7 (Plant Biochemistry)
AB   CLAVICEPS PASPALI CULTURED WITH TRITIUM LABELED [73-22-3]
     L-TRYPTOPHAN INCORPORATED 30 OF THE RADIOACTIVITY INTO [2390-99-0]
     CHANOCLAVINE I.  CLAVICEPS PASPALI FURTHER METABOLIZED UP TO 40 OF
     THE ACTIVITY OF CHANOCLAVINE I TO THE ERGOLINE DERIVATIVES
     [548-43-6] ELYMOCLAVINE, [548-42-5] AGROCLAVINE, AND [82-58-6]
     LYSERGIC ACID.  NO CONVERSION OF ELYMOCLAVINE OR AGROCLAVINE INTO
     CHANOCLAVINE I COULD BE DEMONSTRATED.  THE REACTION SEQUENCE
     L-TRYPTOPHAN TO CHANOCLAVINE I TO AGROCLAVINE TO ELYMOCLAVINE TO
     LYSERGIC ACID WAS ESTABLISHED.
ST   CLAVICEPS ERGOT ALKALOIDS; ALKALOIDS   ***ERGOT***
     ***CLAVICEPS***  ; ERGOT ALKALOIDS CLAVICEPS; CHANOCLAVINE
     CLAVICEPS; CLAVICEPS ERGOT ALKALOIDS; ERGOT ALKALOIDS CLAVICEPS;
     ALKALOIDS   ***ERGOT***     ***CLAVICEPS***  ; CHANOCLAVINE
     CLAVICEPS
IT   Ergot
        (formation of ergoline derivs. by Claviceps paspali)
IT   73-22-3, biological studies
        (chanoclavine-I formation from, by ergot)
IT   2390-99-0
        (ergoline deriv. formation from, by ergot)
IT   478-94-4
        (formation from chanoclavine)
IT   548-42-5   548-43-6   14466-03-6
        (formation from chanoclavine I by ergot)

The question still remains; how to produce only
paspalic acid and does every strain of C. paspali produce it.