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October 9, 2010 6:40 AM
Explore references by research topic: "conessidine" initiated, resulting in 2 candidates
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25 references were found containing the concept "conessidine".
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Answer set 8 created with 25 answers from CAPLUS
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1. Wrightia tomentosa, a substitute for Holarrhena antidysenterica
By Jayaswal, S. B.
From Indian Journal of Pharmacy (1977), 39(2), 37-9. Language: English, Database: CAPLUS
Alkaloids were isolated from the medicinal plant W. tomentosa and identified as conkurchine, conessine, conessidine, holarrhine, and
kurchine.
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Copyright © 2010 American Chemical Society (ACS). All Rights Reserved.
2. Amoebicidal activity of steroidal alkaloids of Wrightia tomentosa in vitro
By Jayaswal, S. B.
From Indian Journal of Pharmacy (1976), 38(4), 112-13. Language: English, Database: CAPLUS
When 5 W. tomentosa alkaloids were tested in vitro against Entamoeba histolytica, conessine (I) [546-06-5] was the most amoebicidal
agent whereas holarrhine [61089-72-3] was the least active. Conessidine [6877-20-9], conkurchine [3792-62-9], and kurchicine [1400-
17-5] occupied intermediate positions.
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3. Steroidal alkaloids. CLVII. Alkaloids from the bark of Holarrhena febrifuga (Apocynaceae)
By Dadoun, Henri; Cave, Andre; Goutarel, Robert
From Annales Pharmaceutiques Francaises (1973), 31(3), 237-47. Language: French, Database: CAPLUS
The bark of H febrifuga of East African origin contained 2.4% steroidal alkaloids, principally holafebrine and connessine. The following 8
steroidal alkaloids were also isolated: conessimine, isoconessimine, connarrhimine, conessidine, conkurchine (all having a conan-5-
ene skeleton), holaminol, holarrhimine, and holaphylline (having the 3-aminopregn-5-ene skeleton with various functional groups at C-
18 and C-20).
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4. Steroidal alkaloids. CL. Synthesis of conessidine, 3β-methylamino-N-demethylcona-5,18(N)-diene, from paravallarine.
Synthesis of N3-methylholarrhimine and of its 20R-epimer
By Einhorn, Jacques; Monneret, Claude; Khuong, Huu qui
From Bulletin de la Societe Chimique de France (1973), (1)(Pt. 2), 301-3. Language: French, Database: CAPLUS
N3-Methylholarrhimine (20S-I) and its (20R)-epimer were prepd. by acetylating 3β-(methylamino)pregn-5-ene-18,20-diol-20-one
ethylene ketal to give II. The ketal group was removed from II, the keto group converted to its oxime, and treated with Na, followed by
EtNH2-Li to give I. (20S)-I was cyclized with CrO3 to conessidine.
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5. Steroidal alkaloids. CXXXII. Alkaloids of Holarrhena crassifolia leaves
By Einhorn, Jacques; Monneret, Claude; Khuong-Huu-Qui
From Phytochemistry (Elsevier) (1972), 11(2), 769-77. Language: French, Database: CAPLUS
Leaves of H. crassifolia from Laos and Cambodia were rich in alkaloids of the conkurchine type. This discovery is an argument for
maintaining the species H. crassifolia, which was confused with H. curtisii, an apocynaceous species from Malaysia which contains
alkaloids of a different type. The structure of a new alkaloid, N-formyl-conkurchine is described and the reactivity of its functional groups
outlined.
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6. Fragmentation of steroidal diamines in the mass spectrometer
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By Longevialle, P.
Edited by Ogata, Koreichi
From Recent Develop. Mass Spectrosc., Proc. Int. Conf. Mass Spectrosc. (1970), 1266-72. Language: English, Database: CAPLUS
The mass spectral fragmentation of steroidal diamines involve the ionization of a neutral N group followed by an intramol. H
rearrangement to the charged N to give a new radical which then undergoes fragmentation. The generality of this mechanism is
discussed.
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7. Steroidal alkaloids. CII. Fragmentation of steroidal diamines and their derivatives in mass spectrometry
By Longevialle, Pierre; Diatta, Luc
From Organic Mass Spectrometry (1970), 3(6), 803-16. Language: French, Database: CAPLUS
The mass spectra of steroidal mols. bearing two N-contg. functions in remote positions show a new type of fragmentation initiated by an
interaction of these two functions. The phenomenon is described in the case of diamines and derivs. (imines, amides).
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8. Kurchi bark (Holarrhena antidysenterica cortex), a drug of great therapeutic potential
By Gjerstad, Gunnar; Modak, Arvind
From Quarterly Journal of Crude Drug Research (1968), 8(1), 1141-51. Language: English, Database: CAPLUS
Review of a common Indian drug with special attention to the chemistry. The bark contains O-free alkaloids (conessine, conimine, etc.)
, conkurchine-group alkaloids (including conessidine), and O-contg. alkaloids in leaves (kurchiphyllamine and kurchiphylline) and bark
(holarrhenine, holafrine, holarrhetine).
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9. Steroids. XC. Steroid alkaloids. 34. Ozonolysis and methylation of concurchine qnd its derivatives
By Qui, Khuong-Huu; Mink, Truong-Ho; Labler, L.; Goutarel, R.; Sorm, F.
From Collection of Czechoslovak Chemical Communications (1965), 30(4), 1016-23. Language: English, Database: CAPLUS
cf. CA 62, 4092g, 10477e. Concurchine (I) (irehline) has been shown to be 3β-amino-N-demethylcona-5,18(N)-diene, and not 3β-
amino-N-demethylcona-5,17(20)-diene (Tschesche and Roy, CA 51, 2827c). Methylation of I gave trimethylconcurchine (II), identical
with conessine, and dimethylconcurchine (III). Both bases II and III were also prepd. by methylation of conessidine (IV). II was
obtained by methylation of conessimine (V) and III, III from 20α-acetamido-18-acetoxy-3β-dimethylamino-5-pregnene (VI) by way of 20
α-acetamido-3β-dimethylamino-5-pregnen-18-ol (VII) and 20α-amino-3β-dimethylamino-5-pregnen-18-ol (VIII). I (200 mg.) heated with
5 ml. 85% HCO2H and 8 ml. 38% HCHO 4 hrs. at 100°, the mixt. dild. with ice, the base liberated by NH3, and extd. with Et2O gave,
after chromatography on SiO2, 181 mg. II, m. 126-6.5° (Me2CO), and 19 mg. III, m. 159-60° (Me2CO). Similarly, 83 g. IV gave II and III,
and V and III gave II. Treatment of 865 mg. VI in 10 ml. MeOH with 33 ml. N KOH in MeOH at room temp. gave 823 mg. VII, m. 247-50°
(MeOH-Me2CO), [α]21D -42° (all in CHCl3). This (582 mg.) refluxed 2 hrs. with 70 ml. EtOH and 70 ml. 2N H2SO4, the EtOH evapd.,
the residue heated 1 hr. at 80°, treated with aq. NH3, and extd. with CHCl3 gave 546 mg. VIII, m. 195.5-7.5° (CH2Cl2-Et2O), [α]21D -
15°. Treatment of 50 mg. VIII in 1 ml. AcOH with 30 mg. CrO3 in 5 drops H2O, the mixt. dild. with 4 ml. AcOH and 5 drops H2O,
allowed to stand 24 hrs., then treated with ice, aq. NH3, and extd. with Et2O gave 45 mg. III, [α]21D -60°, -48° (EtOH). Ozonolysis of I
was not conclusive for its structure.
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10. Steroid alkaloids. XXVII. Preparation of conkurchine and conessidine from holarrhimine
By Qui, Khuong-Huu; Labler, Ludwik; Minh, Truong-Ho; Goutarel, Robert
From Bulletin de la Societe Chimique de France (1964), (7), 1564-6. Language: Unavailable, Database: CAPLUS
Conkurchine (I) and conessidine (II) were prepd. by the CrO3 oxidn. of holarrhimine (III) and the 3N-Me deriv. (IV) of III, resp.,
confirming the structures elucidated for I and II (cf. preceding part). III (100 mg.) in 5 cc. AcOH treated overnight with 40 mg. CrO3 in
0.5 cc. H2O gave 85 mg. I, m. 151° (Et2O and sublimed at 150°/0.02 mm.), [α]D -52° (c 0.75, CHCl3), -47° (c 0.75, abs. EtOH). I (30
mg.) and 2 cc. Ac2O heated 4 hrs. on a water bath, and the crude product refluxed 1 hr. with abs. EtOH yielded 3β-acetamido-18ξ-
ethoxy-N-demethyl-N-acetyl-5-conanene, m. 260°, [α]D 0°(c 1, CHCl3). I (20 mg.) in 1 cc. MeOH treated with 1 drop 0-HOC6H4CHO
gave the salicylal deriv., m. 247° (MeOH), [α]D 14° (c 0.7, CHCl3). IV (50 mg.) in 1 cc. AcOH treated dropwise with 30 mg. CrO3 in 0.2
cc. H2O, dild. with 0.2 cc. H2O and 2 cc. AcOH, stirred to soln., and kept 13 hrs., the run repeated with 50 mg. IV, and the combined
runs worked up together yielded 97 mg. II, m. 124-5° (sublimed at 115-20°/0.2 mm.) (Me2CO), [α]D -64° (CHCl3). The infrared
spectrum of II is recorded.
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11. Steroid alkaloids. XXVI. Conarrhimine and alkaloids of the conkurchine group. Structures of conkurchine and conessidine
. Identity of conkurchine and irehline
By Janot, Maurice Marie; Jarreau, Francois Xavier; Minh, Truong-Ho; Qui, Khuong-Huu; Goutarel, Robert
From Bulletin de la Societe Chimique de France (1964), (7), 1555-63. Language: Unavailable, Database: CAPLUS
cf. CA 60, 13296h; 61, 5717e. The structures Ia (R = H) (I) and Ia (R = Me) (II) were established for conkurchine and conessidine,
resp., correcting the previous assignments by Tschesche and Roy (CA 51, 2827c). The partial syntheses of conarrhimine (III), 3Beta;-
amino-N-demethyl-5,20(N)-conadienine (IV), and the 3β-MeNH analog (V) of IV were given. IV and V differed from I and II, resp. I was
identical with irehline. N-Acetylconamine (2.26 g.) in 200 cc. dry C6H6 refluxed 1 hr. with 2.3 g. BrCN, treated with an addnl. 2.3 g.
BrCN, and refluxed 2 hrs. yielded 2.31 g. 3β-acetylamino-N-demethyl-N-cyano-5-conanene (VI), m. 229-30° (EtOH and sublimed at 190
°/0.01 mm.), [α]D 31° (c 1, CHCl3). VI (1.5 g.) refluxed 24 hrs. under N with 17 g. KOH, 30 g. H2O, and 120 cc. MeOH yielded 400 mg.
3β-acetylamino-N-demethyl-5-conanene, m. 251-2° (Me2CO and sublimed at 220°/0.01 mm.), [α]D -57° (c 1.5, CHCl3). VI (1.5 g.) in
105 cc. MeOH refluxed 48 hrs. with 30 g. KOH in 33 cc. H2O under N, and the crude product (1.2 g.) treated in EtOH with HCl yielded
1.14 g. III.2HCl, m. >300°, [α]D -28° (c 1, MeOH); III m. 135-6° (sublimed at 110-20°/0.01 mm.), [α]D -26° (c 2.5, CHCl3). III (1.7 g.) in
20 cc. MeOH treated 1 hr. with 0.6 cc. o-HOC6H4CHO gave 2.1 g. salicylal deriv. (VII), m. 195° (MeOH), [α]D 45° (c 1.3, CHCl3). VII
(500 mg.) in 50 cc. CH2Cl2 treated with 1 g. Na2SO4 and gradually with 120 mg. N-chlorosuccinimide and stirred 1 hr., and the product
refluxed under N with 500 mg. Na in 50 cc. abs. MeOH yielded 450 mg. 3β-salicylalamino analog (VIII) of IV, m. 208° (C6H6-hexane), [
α]D 46° (c 1.3, CHCl3). VIII (400 mg.) and 90 cc. 3N HCl heated on a water bath yielded 250 mg. IV; IV.2HCl m. >300° (abs. EtOH-
Me2CO), [α]D -9° (c 1, MeOH). IV (400 mg.) in 15 cc. MeOH treated 1 hr. with 0.15 cc. BzH gave the 3-benzalamino analog, m. 180°
(Me2CO), [α]D 10° (c 1, CHCl3). IV (130 mg.) gave similarly VIII. 3β-Acetylamino-N-demethyl-5-conanene (600 mg.) in 50 cc. CH2Cl2
treated 1 hr. with 1 g. Na2SO4 and 1 g. N-chlorosuccinimide, and the product refluxed 1 hr. with 600 mg. Na in 60 cc. abs. MeOH
yielded 180 mg. 3β-AcNH analog (IX) of IV, m. 263° (Me2CO and sublimed at 220°/0.01 mm.), [α]D -30° (c 0.8, CHCl3). N-
Acetylisoconessimine (5 g.), m. 134°, in 150 cc. dry C6H6 added dropwise to 10 g. BrCN in 300 cc. dry C6H6 under N with stirring and
refluxed 4 hrs. gave 5.25 g. 3β-acetylmethylamino-N-demethyl-N-cyano-5-conanene (X), m. 255° (Me2CO), [α]D 37° (c 2, CHCl3). X
(2.97 g.) treated at 120° under N with 23 g. K in 45 cc. H2O and 180 cc. MeOH during 20 hrs. yielded 2.78 g. 3β-acetylmethylamino-N-
demethyl-5-conanene (XI), m. 193-4°, [α]D -25° (c 1, CHCl3). XI (660 mg.) in 50 cc. CH2Cl2 stirred 1.5 hrs. with 1 g. Na2SO4 and 310
mg. N-chlorosuccinimide, and the product refluxed under N with 600 mg. Na in 60 cc. abs. MeOH gave 650 mg. 3β-AcMeN analog (XII)
of IV, m. 223-4° (Me2CO), [α]D -29° (c 0.8, CHCl3). XII (105 mg.) in 2 cc. EtOH heated 4 hrs. under pressure with 500 mg. NaOH
pellets, 1 cc. H2O, and 2 cc. EtOH yielded 90 mg. V, m. 157° (Me2CO), [α]D -26° (c 1, CHCl3). Irehdiamines A and B removed from the
ext. of the leaves of Funtumia elastica, the residual crude base (24.76 g.) treated 0.5 hr. with 10 cc. C5H5N and 50 cc. Ac2O on a water
bath, and the crude product (20.15 g.) chromatographed on 600 g. Al2O3 gave 2.3 g. di-Ac deriv. (XIII) of I.H2O, m. 194° (95% EtOH), [
α]D -5° (c 0.9, CHCl3). XIII (54 mg.) in 4 cc. MeOH heated 2 hrs. on a water bath with 3 cc. 2N H2SO4 yielded 48 mg. 3β-acetylamino-
N-demethyl-5,18(N)-conadienine (XIV), m. 248° (Me2CO), [α]D -56° (c 0.9, CHCl3). XIII (30 mg.) sublimed at 150°/0.02 mm. gave 25
mg. XIV. XIII (100 mg.) in 7 cc. 95% EtOH, and 1 g. NaOH in 2.5 cc. H2O heated 3 hrs. at 200° in an autoclave, and the crude product
(70 mg.) sublimed at 150°/0.02 mm. yielded I, m. 150° (dry Et2O), [α]D -51° (c 1, CHCl3). XIV (46 mg.) and 2 cc. Ac2O heated 4 hrs. on
a water bath, and the crude product refluxed with abs. EtOH gave 3β-acetylamino-18ξ-ethoxy-N-acetyl-N-demethyl-5-conanene, m. 263
° (Me2CO), [α]D ± 2° (c 1, CHCl3). I (30 mg.) in 2 cc. Me2CO refluxed 10 min. yielded the 3β-Me2C:N analog (conkurchinine) of I, m.
164° (Me2CO and sublimed at 150°/0.02 mm.), [α]D -58° (c 1, CHCl3), -44° (c 1, abs. EtOH). I (80 mg.) and 3 drops BzH in 0.5 cc.
MeOH yielded 57 mg. 3β-PhCH:N analog of I, m. 210° (MeOH), [α]D -12° (c 1, CHCl3). I (50 mg.) in 1 cc. MeOH and 0.1 cc. o-
HOC6H4CHO gave similarly the 3β-(o-HOC6H4CH:N) analog of I, m. 245° (MeOH), [α]D 15° (c 1, CHCl3). XIV (100 mg.) in 5 cc. 1:1
CH2Cl2-C6H6 treated with 30 cc. 5% aq. NaOH and 0.2 cc. BzCl gave 106 mg. 3β-acetylamino-20α-benzoylamino-5-pregnen-18-al
(XV), m. 262° (Me2CO), [α]D 20° (c 1, 1:1 C5H5NMeOH). XV (52 mg.) in 8 cc. MeOH stirred 2 hrs. with 300 mg. KBH4 gave 40 mg.
18-ol analog (XVI), m. 180° resolidifying and remelting at 238° (Me2CO). XVI (190 mg.) in 15 cc. MeOH heated 3 hrs. in an autoclave at
200° with 2 g. NaOH in 5 cc. H2O yielded 130 mg. holarrhimine, m. 184° (Et2O), [α]D -12° (c 1, CHCl3). XIV (75 mg.) in 5 cc. AcOH
hydrogenated 5 hrs. over 50 mg. PtO2 yielded 3β-acetylamino-N-demethyl-5α-conanine (XVII), m. 253° (Me2CO), [α]D 16° (c 0.9,
CHCl3). XVII (30 mg.), 1 cc. HCO2H, and 1 cc. CH2O refluxed 3.5 hrs. yielded 27 mg. 3β-acetylamino-5α-conanine (mallouphyllamine)
, m. 219° (Me2CO and sublimed at 200°/0.02 mm.), [α]D 38° (CHCl3). XIV (48 mg.) in 5 cc. 95% EtOH treated 4 hrs. with 100 mg.
NaBH4 gave 40 mg. 3β-acetylamino-N-demethyl-5-conanene (XVIII), m. 250° (Me2CO), [α]D -53° (c 0.9, CHCl3). XVIII (45 mg.), 1 cc.
HCO2H, and 1 cc. aq. CH2O heated 4 hrs. on a water bath yielded 42 mg. 3β-acetylamino-5-conanene, m. 214° (Me2CO and sublimed
at 200°/0.02 mm.), [α]D -13° (c 1, CHCl3). I (43 mg.) gave similarly conessine, m. 124° (Me2CO and sublimed at 120°/0.02 mm.), [α]D
23° (c 1, abs. EtOH). The infrared spectrum of I is recorded.
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12. Steroidal alkaloids. Identity of conkurchine and irehline
By Janot, Maurice Marie; Jarreau, Francois Xavier; Truong-Ho, Minh; Khuong-Huu, Qui; Goutarel, Robert
From Compt. Rend. (1964), 258(7), 2089-91. Language: Unavailable, Database: CAPLUS
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Conkurchine (I) was found to be identical with irehline (II) and established as III (R = H); conessidine was shown to be III (R = Me) (IV)
. V (R = H) (VI) and V (R = Me) (VII), isomeric with I and IV, resp., were synthesized. N-Acetylconamine was demethylated by the von
Braun method via 3β-acetamido-N-cyano-N-demethyl-5-conanene, m. 229-30°, [α]D 31deg; (CHCl3), to 3β-acetamido-N-demethyl-5-
conanene, m. 251-2°, [α]D -57° (CHCl3), which hydrolyzed with KOH-MeOH yielded the 3β-NH2 analog (conarrhimine), m. 135-6°, [α]
D -26° (CHCl3). Salicylideneconarrhimine, m. 195°, [α]D 45° (CHCl3), treated with N-chlorosuccinimide yielded 3β-salicylidenamino-N-
chloro-N-demethyl-5-conanene, which refluxed with NaOMe-MeOH gave 3β-salicylidenamino-N-demethyl-5,20(N)-conadiene; this
hydrolyzed with 3N HCl yielded VI.2HCl, m. >300°, [α]D -9.5° (MeOH); the benzylidene deriv. of VI m. 180°, [α]D 10° (CHCl3). N-
Acetylisoconessimine was demethylated to 3β-acetylmethylamino-N-demethyl-5-conanene, m. 193-4°, [α]D -25° (CHCl3), which
dehydrogenated via the intermediate chloramine yielded 3β-acetylmethylamino-N-demethyl-5,20(N)-conadiene, m. 223-4deg;, [α]D -29°
(CHCl3); this sapond. with 4N alc. NaOH gave VII, m. 157°, [α]D -26° (CHCl3) [conessidine m. 123°, [α]D -63.5° (CHCl3)]. The m.p.
and [α]D values were detd. for the following compds.: I, 152-3°, -51.9°; II, 150-1°, -51°; benzylidene deriv. of I, 206°, -12°; benzylidene
deriv. of II, 210°, -12°; salicylidene deriv. of I, 245°, 15.6°; salicylidene deriv. of II, 244°, 15°; di-Ac deriv. hydrate of I, 183°, --; di-Ac
deriv. hydrate of II, 194°, -5°; di-Ac deriv. ethanolate of I, 263°, --; di-Ac deriv. ethanolate of II, 263°, 0. These values indicate the
identity of I and II. Holarrhimine oxidized with CrO3 in AcOH yielded III (R = H), identical with I and II.
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13. Separation of kurchi alkaloids by paper chromatography
By Shanker, Jai; Basu, N. K.
From Proceedings of the Rajasthan Academy of Sciences (1961), 8(No. 1-2), 88-93. Language: Unavailable, Database: CAPLUS
The alkaloids of the bark of Holarrhena antidysenterica are sepd. into fractions sol. in ligroine, Et2O, and CHCl3 by successive extn.
The ligroine fraction is sepd. into conessine, conessidine, conkurchine, and an unidentified alkaloid (Rf 0.18) when chromatographed
on Whatman No. 1 paper strips buffered at pH 7, with CHCl3:AmOH:EtOH:H2O (7:8:3:2) solvent. The Et2O-sol. fraction is sepd. into
the same known alkaloids and 2 unidentified alkaloids (Rf 0.24 and 0.31). The fraction sol. in CHCl3 is sepd. into conessidine and 7
unidentified alkaloids by using paper strips buffered at pH 6 and the same solvent system.
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14. Kurchi alkaloids. III. New bases from kurchi bark
By Tschesche, Rudolf; Wiensz, Klaus
From Chemische Berichte (1958), 91, 1504-11. Language: Unavailable, Database: CAPLUS
cf. C.A. 51, 2827c. The isolation of 5 new alkaloids from kurchi bark is described. Crude alkaloids (81 g.) in 100 cc. MeOH were mixed
with 200 g. Al2O3, the mixt. dried in vacuo at 50° and added to a column of 2.5 kg. Al2O3, and the column chromatographed
successively with C6H6, C6H6-CHCl3, CHCl3, CHCl3-MeOH, MeOH, and 5% aq. AcOH; 1000-cc. fractions were collected. Fractions
29-31 (9:1 C6H6-CHCl3) evapd., the residue dissolved in 30 cc. hot Me2CO, the insol. portion extd. with Me2CO in a Soxhlet app., and
the Me2CO ext. evapd. gave kurchamine (I), leaflets, m. 110-14°, which treated with dil. HClO4 and recrystd. from H2O gave I.H ClO4
which was reconverted to 450 mg. I, m. 115-17°, Rf 0.65 (4:1:5 BuOH-AcOH-H2O), [α15D -16 ± 2° (c 0.767, CHCl3), [α19D -15 ± 2° (c
0.900, 96% EtOH); I.HClO4, m. above 335°; I.H I, m. 275-6°; picrate, m. 194-5°; salicylidene deriv., red crystals, m. 133-5°. I (70 mg.)
refluxed 1 hr. with 0.8 cc. HCO2H and 3.2 cc. aq. CH2O, treated with an addnl. 0.4 cc. HCO2H and 2 cc. aq. CH2O, refluxed again 1
hr., concd. to 1 cc., basified with 20% aq. NaOH, and extd. with Et2O, and the crude residue from the ext. recrystd. at -15° from Me2CO
gave kurchessine (di-Me deriv. of I) (II), m. 132-3°, Rf 0.60, [α]22D -36 ± 1° (c 1.112, CHCl3), [α]22D -17 ± 2 (c 1.050, MeOH);
II.HClO4, decomp. 277-9° with previous sintering; picrate, m. 228-30°. The residue from fractions 71-89 (2:3 C6H6-CHCl3) recrystd.
from 50 cc. Me2CO and then 20 cc. boiling EtOH gave tetramethylholarrhimine (III), m. 218-22°; N-Bz deriv., m. 175°, which gave in the
usual manner 30 mg. III, m. 227-9°, [α]21D -35 ± 2° (c 1.009, CHCl3), Rf 0.52. The fractions 103-17 (98:2 CHCl3-MeOH) yielded about
3 g. holarrhimine (IV) sulfate, m. 33-5°, which gave IV, m. 184°, [α]20D -15 ± 3° (c 0.500, CHCl3); picrate, m. 109-11°; salicylidene
deriv., m. 247-9°; benzylidene deriv., m. 183°. The mother liquors from III allowed to stand with 3% HCl deposited 60 mg. (3)-N-
methylholarrhimine-2HCl (V.2HCl) m. above 360°, [α]20D -28 ± 2° (c 1.275, MeOH); free V, Rf 0.66; V picrate, m. 133-5°. Crude
alkaloid (340 g.) from 20 kg. bark of Holarrhena antidysenterica (kurchi bark) in 1300 cc. 96% EtOH treated with stirring and refluxing
with 80 cc. 80% H3PO4 and 320 cc. abs. EtOH, the supernatant decanted, the residue washed with a little EtOH, shaken 1 hr. with
1000 cc. H2O, and filtered, the filtrate basified with NaOH and extd. with CHCl3, the ext. re.ovrddot.extd. with 5% HCl, the aq. acidic
ext. basified and extd. with CHCl3, the CHCl3 ext. evapd., the residue dissolved in 100 cc. EtOH, the soln. fractionally pptd. in the usual
manner with H3PO4, the ppt. (103 g.) obtained with 100 cc. alc. H3PO4 shaken with 1000 cc. H2O, the undissolved phosphates (25 g.)
dissolved in 200 cc. 2N HCl, the soln. filtered, basified with aq. NaOH, and extd. with CHCl3, the ext. shaken with 3% HClO4, the aq.
acidic phase basified with NaOH, and the ppt. purified through the sulfate gave 3.2 g. IV; the mother liquor from the phosphate ppt.
treated with 30 cc. alc. H3PO4, the pptd. brownish phosphates (57.5 g.) treated with 500 cc. H2O, the undissolved residue (15 g.)
decompd. in the usual manner, the resulting base (9.2 g.) dissolved in 50 cc. Me2CO, the soln. treated with 3 cc. ο-HOC6H4CHO, the
pptd. salicylidene deriv. (6.87 g.) recrystd. from 500 cc. dioxane to give 1.73 g. product, m. 262°, the material dissolved in 50 cc. 2N HCl
with heating during 1 hr., cooled, basified, and extd. with 800 cc. Et2O, and the ext. dried, concd., and allowed to stand yielded 0.6 g.
(20)-N-methylholarrhimine (VI), m. 163-4° (Me2CO-Et2O), Rf 0.56, [α]22D -19° (c 1.200, CHCl3), -17° (c 0.933, 96% EtOH); VI.HCl, m.
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293-4°; picrate, m. 98-9°. The various kurchi alkaloids chromatographed on buffer-zone paper by the method of Schmall, et al. (C.A. 50,
17332h), were immobilized at the following pH values: conessidine 4.8, trimethylconcurchine 5.6, conessine 5.9, holarrhenine 7.0, IV
7.2, II 5.7, III 6.3, V 7.0, VI 7.2, I 7.2.
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15. Kurchi alkaloids. II. The constitution of conessidine
By Tschesche, Rudolf; Roy, Akhil Chandra
cf. C.A. 50, 1042g. Conessidine (I), C22H34N2, has been isolated from the kurchi bark. Treating 31 mg. I in 1 cc. H2O and 1 drop
AcOH with 30 mg. KI in 1 cc. H2O gives I.HI.H2O, small rods, m. 223-5° [free base has [α]D18 -49 ± 2° (c 1, EtOH)]; on hydrogenation
in AcOH with PtO2, I absorbs 2 mol H. I (108 mg.) in 5 cc. MeOH is added to 100 mg. reduced PtO2 in 10 cc. MeOH and shaken 4 h. in
a H atm., causing the absorption of 2.5 cc. H; the filtered soln. is evapd. and the residue hydrogenated in the same way, causing the
absorption of another 2.8 cc. H. The isolation and hydrogenation are repeated another 3 times, causing a total absorption of 6.5 cc. H
(75% of the theor. amt.). From the final MeOH filtrate 20 mg. dihydroconessidine (conimine) (II), needlelike crystals, m. 133-5.5°, [α]
D18 -27 ± 2° (EtOH), crystallizes. Refluxing 100 mg. II 1 h. with 1.1 cc. 40% HCHO and 1 cc. HCO2H gives conessine (III), m. 123-7°, [
α]D18 21 ± 2° (EtOH). Shaking 32 mg. I with 48 mg. p-MeC6H4SO2Cl in 3 cc. C5H5N, keeping the soln. overnight, and evapg. the
mixt. in vacuo give I ditosylate-H2O, fine rods, m. 225-7°. When 6.5 mg. I and 6.2 mg. conkurchine (IV) are mixed each with 2.4 mg. o-
H2NC6H4CHO, 2 cc. MeOH, and 1 equiv. HCl-MeOH, made up to 5 cc., and kept 24 h. no color is formed; however, when 5 cc. H2O is
added an orange-yellow color soon develops because of the formation of a dihydroquinazolinium deriv. similar to that of 1-pyrroline (cf.
Sch.ovrddot.op.hivin.f and Oechler, C.A. 30, 59967). Refluxing 100 mg. I 1 h. with 3 cc. 40% HCHO and 0.8 cc. HCO2H, adding
another 2 cc. HCHO and 0.4 cc. HCO2H, and refluxing another hr. give 30 mg. dimethylconessidine, plates, m. 125-7°, [α]D18 12 ± 3°
(CHCl3). Treating 35.4 mg. trimethylconkurchine (V) in 1 cc. dil. AcOH with 100 mg. KI in a little H2O gives V.2HI, needles, m. 328-30°
(decompn.). Methylation of IV with HCHO in HCO2H gives V, m. 124-6°. Extg. 10kg. kurchi bark as described earlier, chromatographing
80 g. alkaloid ext. over 2500 g. Al2O3, and eluting with C6H6 give 4 g. III; elution with C6H6-CHCl3 (9:1) gives V mixed with other
alkaloids. Fractions 39-45 (350 mg.), recrystd. from Me2CO, give V. Ozonization of 70 mg. V or I in 20 cc. dry CHCl3 at -80° until a
deep blue color is formed, evapg. the soln. at 0° in vacuo to dryness, treating the residue in 5 cc. MeOH with 1 g. NaBH4 at 0°, keeping
it overnight, refluxing the reduced material 8 h. with 2N NaOH in 50 cc. MeOH, evapg. in vacuo, adding 5 cc. sirupy H3PO4, and distg.
off the AcOH in a N arm. give 85% of the theor. amt. of AcOH. Extg. 2 g. of the MeOH eluate obtained in the earlier investigation in 100
cc. CHCl3 with 1 l. 1% HClO4, concg. the acid ext. in vacuo, making it alk. with NH4OH, extg. with CHCl3, evapg. the CHCl3, taking up
the residue (800 mg.) in 500 cc. H2O, and adding 15 cc. concd. HCl give 240 mg. conamine-HCl (VI) [free base, m. 97.5-101.5°, [α]
D18 -21° (CHCl3)]. From the mother liquors of VI, another alkaloid, probably holarrhimine (VII) or one of its derivs., is isolated; on
methylation with HCHO and HCO2H it yields tetramethylholarrhimine, m. 224-7°. The results show that IV has a double bond capable
of being readily hydrogenated between C atoms 17 and 20 which supports the structure of ring E in the formula suggested by Haworth,
et al. (C.A. 48, 6452f), for VII.
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16. Chromatographic separation of kurchi alkaloids (Holarrhena antidysenterica)
By Tschesche, Rudolf; Petersen, Rudolf
cf. Bertho, C.A. 34, 111.6. Powdered kurchi bark (2 kg.) was stirred 8 days with 3 l. Et2O, 3 l. EtOH, 2 l. CHCl3, and 800 ml. aq. NH3
(optimum), concd. to 800 ml. and extd. into 3% HCl. The acid soln. upon basifying with NH3 and re.ovrddot.extn. with CHCl3 gave 22 g.
of crude alkaloid (I). I in C6H6 was passed through Al2O3 and eluted with 2 l. C6H6 (II), 1.2 l. C6H6/Et2O (1:1)(III), 1 l. C6H6/CHCl3
(1:1) (IV), 2 l. CHCl3 (V), 1.5 l. CHCl3 (2% MeOH) (VI) and 1.2 l. MeOH with 70% recovery. The alkaloid fractions III-VI were extd. from
the solvents with 1% HClO4, basified, re.ovrddot.extd. with CHCl3, evapd. to dryness, reconstituted in 3% HCl, divided into fifths and
NH3 added to pH 5.4-5.6, 6.0-6.4, 6.8-7.2, 7.8-8.2, and 8.6-9.3. The 6.0-8.2 fractions were extd. with CHCl3, evapd. to dryness,
redissolved in MeOH and the alkaloid HCl salt pptd. with 20-30 fold Me2CO. Thus II-IV gave at pH 6.0-6.4 condessine, at pH 6.8-7.2
conessine, and at 7.8-8.2 conessimine. V and VI at pH 8.6-9.3 gave a mixt. of a new alkaloid holarrhessimine (VII), C22H36N2O, 0.18
g., m. 160-4° (pptd. from the sulfate with NH3), [α]D18 -30 ± 3° (c 0.775, CHCl3; c 0.6547, EtOH) [hydrobromide, m. 293-4°; picrate, m.
250-5° (decompn.); methiodide, m. 279-80°], and conimine, sepd. by pptg. VII from an alc. H2SO4 soln. at pH 5 by addn. of H2O. A
technique for paper chromatography of alkaloids is described.
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17. Isotope techniques in biochemistry
By Radin, Norman S.
From Nucleonics (1948), 2(No. 1;No. 2), 50-6;33-45. Language: Unavailable, Database: CAPLUS
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A review
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18. Isotope techniques in biochemistry
By Radin, Norman S.
From Nucleonics (1947), 1(No. 1;No. 2;No. 4), 24-33;48-59;51-9. Language: Unavailable, Database: CAPLUS
A review
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19. Early effect of x-rays on ovaries of normal and adrenalectomized rats
By Ickowicz, M.
From Proceedings of the Society for Experimental Biology and Medicine (1947), 66, 646-9. Language: Unavailable, Database: CAPLUS
The pycnotic lesions of the cells in the granular layer of the ovarian follicles of rats usually seen 4 hrs. after x-ray irradiation are
prevented by previous adrenalectomy.
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20. Enzyme studies on human blood. I. Proteolytic activity associated with a fraction of plasma
By Shinowara, Geo. Y.
From Proceedings of the Society for Experimental Biology and Medicine (1947), 66, 456-60. Language: Unavailable, Database: CAPLUS
The action on casein of whole dried plasma and its primary fractions sepd. by low-temp. EtOH pptn. was investigated. No kinase was
added and there was no previous treatment with CHCl3 or other activator. Fraction I had a high degree of proteolytic activity. The
enzyme is inactivated at 80° and is most active near pH 7.
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21. Kurchi alkaloids. VI. Further methods for recognition of the kurchi bases
By Bertho, Alfred; Schonberger, Walter; Kaltenborn, Ludwig
From Justus Liebigs Annalen der Chemie (1947), 558, 62-70. Language: Unavailable, Database: CAPLUS
Conessine (I) and 10% EtOH-H3PO4 give the compd. C24H40N22H3PO4.3H2O (II), m. 230°, decomp. 237°. Concurchine (III) gives
the phosphate (IV), C21H32N2. 2/3H3PO4.1/3H2O, m. 282° (decompn.); conessidine (V) yields a phosphate (VI), C21H32N2.2
/3H3PO4.2/3H2O, m. 266° (decompn.). The crude alkaloid ext. E 4 (cf. C.A. 34, 111.6) (200 g.) in 800 cc. EtOH, refluxed 30 min. with
300 g. 20% EtOH-H3PO4, gives a ppt. of the neutral phosphates (IV and VI), slightly sol. in EtOH; the filtrate on cooling gives II; the
total yield is 147-8 g. The total ppt., treated with 1 l. cold H2O, gives 44 g. insol. ppt.; the ie-cold filtrate, treated with NaOH, gives 68-70
g. crude I, which, extd. with 40-60° petr. ether, gives 40 g. I (m. 126°); therefore the crude ext. contains at least 20% I. The mixt. of IV
and VI in dil. HCl, neutralized with NaOH and the free bases extd. with ether and sepd. as the salicylidene compds., yields about 10% V
and 16-17% III; these values agree with earlier results (Part III) and thus the pptn. of III and V as phosphates is practically quant. The
crude ext. E 3 yields from the neutral fraction 1-2% of a compd., C22H18O, m. 166.5°, whose soln. shows a violet-blue fluorescence in
the light of a quartz lamp; it does not react with CH2N2. The mother liquors from the pptn. of I oxalate, freed of (CO2H)2 with NaOH,
the bases freed of III by o-HOC6H4CHO, the brown residue (230 g.) in 1.5 l. 2 N AcOH freed of o-HOC6H4CHO with ether, the
liberated bases extd. with CHCl3, the residue (179 g.) shaken with 2.5 l. 40-60° petr. ether, the ext. treated 6 hrs. with moist CO2, and
the pptd. carbonate (m. 91°) in dil. AcOH treated with NaOH, give 1.5 g. of the base, C23H34N2, m. 129.5° (di-HI salt, with 2 mols.
H2O, decomp. 174°; diperchlorate, with 2.5 mols. H2O, m. 283°; methiodide, with 1 mol. H2O, m. 263°; mono-Ac deriv. m.254°); this
base differs from those reported by Siddiqui and Pillay (C.A. 27, 1886). The presence of a side-chain Me2N group in I (which is
indicated by the formation of Me3N by the Hofmann degradation of conessine bis-(methylammonium hydroxide)) is shown by heating 2
g. I in 10 cc. concd. HCl 6 hrs. at 250-5°; the Me2NH was identified as the H2PtCl6 salt; the resulting base, C22H33N, was isolated as
the amorphous yellow methiodide (with 0.5 mol. H2O), m. 266° (decompn.), and the cryst. metho-perchlorate, m. 202-3°. The
previously reported dihydro-conessine, m. 97.5°, on further reduction over Pt oxide at 17.5° gives the compd. m. 105°, [α]19 38.5° (2%
in abs. EtOH), reported by Sp.ovrddot.ath (C.A. 24, 2463). The dihydroconessine bis(methylammonium hydroxide) on distn. yields
apoconessine, whose sulfate (C23H35N.0.5H2SO4) m. 146° and nitrate m. 171°.
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22. Kurchi alkaloids. III. The active principal alkaloid conkurchine
By Bertho, Alfred
From Justus Liebigs Annalen der Chemie (1944), 555, 214-40. Language: Unavailable, Database: CAPLUS
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cf. C.A. 34, 111.6. Conkurchine (I) forms a carbonate, C21H22N2.0.5H2CO3, m. 149-50° (decompn.), on passing CO2 into an ether
soln. contg. some H2O; it is completely decompd. by hot H2O but can be recrystd. from 1:1 EtOH-H2O. I and KN3 in 2 N AcOH yield
the azide, C21H32N2.HN3.0.25H2O, m. 204.5° (decompn.). The di-HI salt of I m. 278° (decompn.). I (1 g.) and 10 g. MeI in 20 cc. abs.
EtOH, boiled 3 hrs., the soln. evapd. to dryness, taken up in H2O, and made alk. with NH4OH, give a small quantity of a base
(salicylidene deriv., light yellow, m. 123-4° (decompn.)) and, from the aq. soln., 1.21 g. dimethylconkurchine-2MeI (II), m. 277°
(decompn.). When the reaction is carried out in MeOH, 0.5 g. I yields 0.13 g. II and 0.23 g. of a salicylidene compd., C30H42N2O2,
light yellow, m. 159.5° (decompn.). I (1 g.) and 1 g. acetoin in 30 cc. EtOH, refluxed 3 hrs., give 0.13 g. of the condensation product,
C46H68N4, m. 256-7°; with very dil. HNO3 it gives the nitrate of I. Me2C(OH)CHO gives an isomer, m. 247°. MeCH:CHCH2CHO gives
a small quantity of a product m. 172°. I and o-HOC6H4CHO in Me2CO give the salicylidene compd. (III), m. 244.5-5°, [α]D16.5 15.60°
(2% in CHCl3); in aq. EtOH it gives a deep violet FeCl3 reaction; 100 parts of a satd. soln. in Me2CO at 17.5° contains 0.182 part of III.
A 1% soln. of I in Me2CO (50 g.) and 0.2 g. o-HOC6H4CHO, allowed to stand 2 days at 15°, give 94.9% III. Benzylidene deriv. of I, m.
205.5-6°, [α]D20 -12.38° (2% in CHCl3); methiodide, m. 245.5°; m-nitrobenzylidene deriv., pale yellow, m. 201-2°, [α]D21 -7.05° (2% in
CHCl3); anisylidene deriv., m. 193-4.5°, [α]D19 3.1° (2% in CHCl3). III is suitable for the isolation of I from alkaloid mixts. I may be
regenerated from III by heating 4.1 g. with 50 cc. 2 N HCl on the water bath for 1 hr. (yield, 2.65 g.; theory, 3 g.); the I thus prepd. is
very pure; it m. 152.5-3°, [α]D -51.9°. III with HNO3 gives a practically quant. yield of the nitrate of I. The crude base II (Part II) from the
mother liquors of the 1st oxalate pptn., on extn. with ether and then with CHCl3, gives a mixt. of I and its dihydrate (IV), m. 302-3°
(decompn.), [α]D -34.87° (1.5% in EtOH), from which IV is sepd. by soln. in dil. HCl, pptn. with NaOH, and extn. with 1 l. ether; I can be
removed from the aq. soln. as III; the mother liquor from III gives conessidine dihydrate, m. 291-2° (decompn.); this was described as
an amorphous compd. in Part II. IV with very dil. HNO3 yields the nitrate of I; concd. HCl and IV give I. The H2O in IV is not removed by
heating at 150° in a high vacuum for 1 day or at 110° for 4 days. IV is not formed from I by crystn. from aq. MeOH. IV yields 75% of the
salicylidene deriv. (dihydrate), light yellow, m. 205.5° (decompn.); with warm dil. HCl it yields I; the H2O is not lost on drying for 4 days
at 110° in a high vacuum. In some cases IV and o-HOC6H4CHO yield a salicylidene deriv. with 1 mol. H2O, m. 182-3° (decompn.); it
does not react with MeI; when boiled with EtOH, there results an EtOH compd., m. 263°. Dibenzoylconkurchine seps. with 1.25 mols.
H2O, the hydrate m. 267°; it is not changed by boiling EtOH. I in abs. MeOH over Pt oxide yields a dihydro deriv. which with HCHO and
HCO2H at 120-30° gives 51.7% of conessine (V). Further reduction of V in abs. MeOH over Pt oxide yields the dihydro deriv. (VI), m.
97.5°, [α]D19 37.3° (2% in abs. EtOH); dimethiodide, m. 303-4° (decompn.), [α]D21 23.5° (H2O); dimethoperchlorate, does not m. up to
345°, [α]D21 28.9° (MeOH); the dimethoperchlorate of V has [α]D23 2.9° (MeOH). VI was prepd. also by catalytic reduction of I for 75
hrs. and methylation of the resulting product (mixt. of dihydro and tetrahydro derivs.).
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23. Pharmacological tests on the extract and alkaloids of Holarrhena antidysenterica
By Bertho, Alfred
From Archiv fuer Experimentelle Pathologie und Pharmakologie (1944), 203, 41-6. Language: Unavailable, Database: CAPLUS
In this plant conessine is the chief alkaloid but small amts. of conessidine, conkurchine, kurchicine and holarrhenine are also present.
In very high dilns. these alkaloids, like emetine, kill paramecia, colpidia and daphnia.
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24. Alkaloids of Holarrhena antidysenterica. II. Two further new alkaloids from the bark and the seeds of Indian Holarrhena
and their constitutional relationship to conessine
By Siddiqui, Salimuzzaman
From Journal of the Indian Chemical Society (1934), 11, 283-91. Language: Unavailable, Database: CAPLUS
cf. C. A. 27, 1886. A mash of 20 kg. of seeds of Holarrhena antidysenterica in a mixt. of 9 parts of alc. and 1 part of concd. NH4OH was
heated to boiling for 30 min. and cooled to 40°. The mixt. was well stirred and 10% alc. KOH was added. The percolate was extd. after
1 week and 6 further percolations with 5% alc. KOH were made. After acidification with AcOH, and concn. in vacuo the residue was
extd. with light petroleum ether and the oil-free residue was made strongly alk. with NaOH and extd. with Et2O and CHCl3. These exts.
contained 130 g. of alkaloids. The more strongly basic disecondary base conimine (I) was pptd. as a carbonate on passing CO2
through a moist AcOEt soln. of the secondary bases while conessimine (II) and isoconessimine (III) remained in soln. and were sepd.
by fractional crystn. from EtOAc. The main portion of III, however, was isolated from the fraction of tertiary bases from the final mother
liquors of conessine H oxalate by fractionally pptg. the bases from the aq. soln. of the cryst. HBr salt with NH4OH and NaOH. Working
on this basis, 40 g. of conessine (IV), m. 123-4°, and 2.5 g. of III, m. 92°, were obtained from the noncarbonate-forming fraction, while I,
m. 134°, and 2 g. of III, m. 80-90°, were obtained from the carbonate-forming fraction, after sepg. from the latter the insol. sulfates
which yielded 3 g. of holarrhimine (V), m. 183° (C. A. 27, 1886). Working up 30 kg. of the freshly dried bark yielded 120 g. of IV and 2 g.
of III from the noncarbonate fraction, together with 15 g. of II, 10 g. of III and 3 g. of I from the carbonate fraction. The sulfate group
yielded 30 g. of V, traces of holarrhine and 15 g. of a cryst. residual alkaloid, m. 150-73°, from the mother liquors of V. III, C23H38N2,
m. 92° (cor.), [α]D28 30.0°, contains 2 N-Me groups and 1 active H, and is characterized by the following salts: HCl salt, B.2HCl, m. 335
°; chloroplatinate, m. 285° (decompn.); HI salt, m. 316° (readily sol. in cold H2O); picrate, m. 198-200° (decompn.); and HBr salt, m.
344° (decompn.). I, C22H36N2, crystallizes from concd. solns. in Et2O, petroleum ether, AcOEt or Me2CO in clusters of needles, m.
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130° (cor.), [α]D28-30°, and contains 2 active H atoms and only 1 N-Me group. It forms a HCl salt, B.2HCl, m. 318-20° (decompn.);
chloroplatinate, m. 296-8° (decompn.); picrate, m. 140-1°; and HI salt, m. 293°. The Ac and Bz derivs, of II, C25H40N2O (HCl salt, m.
278-80°; chloroplatinate (B.HCl)23PtCl4, m. 254-6° (decompn.)), and C30H12N2O, m. 121°, were prepd. as addnl. proofs of its
secondary character as already indicated by its formation of a nitroso deriv. Failure of attempts to methylate II to a ditertiary base with
MeI in various solvents led to refluxing the base with HCO2H and HCHO at 100° and the production of IV, m. 126°, [α]D28 27.6°. IV
was similarly produced from I and III and from the mixt. of petroleum-sol. bases left after the sepn. of IV. The nomenclature of the
secondary bases is intended to mark their relationship to conessine and is based on the assumption that the difference between
conessimine and isoconessimine depends on whether the active H is attached to the one or the other of the 2 basic N atoms, and that
in conimine 1 active H is attached to each of the 2 N atoms. In view of the no. of their C atoms and N-Me groups, as well as their m. p.
and optically activity, I and III are considered to be quite distinct from conessidine and conkurchiue (C. 4. 27, 3715) recently isolated
from the kurchi bark. A table of the properties of the alkaloids isolated from the bark and seeds of H. antidysenterica is given.
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25. Kurchi alkaloids. I. Some new bases from Holarrhena antidysenterica
By Bertho, Alfred; von Schuckmann, Gustav; Schonberger, Walter
From Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1933), 66B, 786-90. Language: Unavailable, Database: CAPLUS
Eight Holarrhena alkaloids have been described (cf. Siddiqui and Pillay, C. A. 27, 1886, and earlier investigators), although it is doubtful
that they are all chem. individuals. From a concd. crude ext. of kurchi bark the authors have now isolated in pure form from the
petroleum ether-sol. portion of the bases 3 new alkaloids, conessidine, C21H32N2 (I), conkurchine, C20H32N2 (II) and curchenine,
C21H32N2O2 (III), in addn. to conessine (IV) (the chief product), kurchinine and other bases which have not yet been thoroughly
characterized. I, recrystd. 8 times from acetone, m. 123°, depresses the m. p. of IV about 30°, [α]D21 -52.2° (CHCl3), contains 1 N-Me
group; di-HI salt, begins to become discolored about 200°, m. 259° (decompn.); diperchlorate, m. 243° (decompn.). II, m. 153°, [α]D21 -
67.4° (96% alc.), weathers on standing and then gives too low values for H and N, contains no N-Me group, mol. wt. in benzene 296.6;
methiodide, amorphous hygroscopic powder, becomes discolored 220°, m. 274°; sulfate, m. 342°; oxalate, decomps. 325°; Ac deriv.,
m. 233°. III, m. 335-6°, [α]D21 -92.0° (in 2 N HCl), contains no O- or N-Me group; sulfate, needles with 1 EtOH, [α]D -78.3° (water).
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