Chapter 30

Some More Alkaloids Having Diverse

Skeletal Patterns

30.1 Introduction

Alkaloids are structurally most diversified natural products. They offer simple (e.g.,
in Chaps. 16–22) to very complex structural patterns (e.g., in Chaps. 27 and 28).
Their biological activities claim a special attention for drug discovery (Chap. 33).
Some representative members of a few different classes of alkaloids have been
included and discussed in Chaps. 15–29. To illustrate further structural diversifica-
tions several examples of alkaloids (Fig. 30.1) not included in earlier Chapters are
cited in this chapter with references. The stereostructures of these alkaloids have
been settled in the usual way by suitable combinations of the following: degrada-
tion, spectral analysis, synthesis, chemical correlations, applications of some rules
(e.g., Prelog’s rule, Bredt’s rule, etc.), and occasionally by ORD studies and X-ray
crystallography. A plethora of alkaloids with diversified structural patterns belong-
ing to different classes appearing in the literature during 1960s [1] and till 1988 [2]
have been compiled with some leading references concerning their isolation/struc-
ture/stereochemistry/synthesis. Quite a number of review articles on the uses of
heterocycles in the synthesis of alkaloids have collectively appeared in an edited
book in 2011 [3]. They display wide structural variations of alkaloids.

S.K. Talapatra and B. Talapatra, Chemistry of Plant Natural Products, 915

DOI 10.1007/978-3-642-45410-3_30, © Springer-Verlag Berlin Heidelberg 2015
916 30 Some More Alkaloids Having Diverse Skeletal Patterns

18
HO
O Ph OH
H N H HO
15
H Me OH
O HO HO H
O O H N N O
H AcO N
O H H O
N
Senecionine (+)-Lupanine Crepidine Celgosivir
(Quinolizidine alkaloid) (Indolizidine alkaloid)
(Brachyglottis repasda) (Dendrobium crepidatum, (Leguminosae plants)
(Pyrrolizidine alkaloid) (various Lupinus species, Orchidaceae) [9-11] [12]
(various Senecio species, Leguminosae) [7,8 ]
Asteraceae), and Leguminosae,
Boraginaceae, Orchidaceae,
Scrophulariaceae etc. plants
[4-6]
OH OMe
OMe MeO
H MeO H O Ph
H H O
N H
H N O
OH N O OH OH
H HO N H
O H OH H
H O MeO MeO OMe O H
R O O OMe
OH
O OAc
H OAc Tylophorine (+)-Aconitine (–)-Atisine
OH (pyrroloisoquinoline alkaloid)
OH (Diterpene alkaloid)
(Diterpene alkaloid)
R = H, Protoveratrine A (Tylophora asthmatica, (Delphinium accumulata,
(Aconitum nepelles,
R = OH, Protoveratrine B other Tylophora species, Ranunculaceae), Aconitum heterophyllum,
(Solanum alkaloids) [13,14 ] Cynanchum vincetoxicum, various other Aconitum Ranunculaceae) [21-23]
Veratrum album, V. viride, Asclepiadaceae), species [19-21]
highly oxygenated alkaloid, (Ficus septica,
medicinally used against Moraceae) [15-18]
hypertension
CO2Me
CO2Me
N Me N Me O
O HO
Me O
Ph NH
Ph O NH HO
O MeO
H
MeO2C O
O CO2Me Me N Ph
Ph
N Me O HO
O O
(+)-Crotonosine Sparsiflorine
a-Truxilline b -Truxilline (Proaporphine alkaloid) (Croton sparsiflorus,
(Croton linearis, Euphorbiaceae) [28]
(Erythroxylum coca, Erythroxylaceae) [24,25,26 ]
Euphorbiaceae) [27]
(Cycloaddition products of cinnamoyl
ester of methylecgonine, Chapter, 19)

H H MeO
MeO MeO OMe
OH MeO N
MeO N R HO N O
H H
H H N
OMe O
H
(+)-Haemanthamine H
O OMe
OH (Haemanthus puniceus, HN
R = H, Stepharine Stepholidine Amaryllidaceae),
R = Me, Pronuciferine (Stephania glabra [29], OMe
daffodils (Narcissus
[29] Menispermaceae) ( )-Emetine (Tetrahydro-
pseudonarcissus), [30]
isoquinoline alkaloid)
(Alangium larmarckii,
Alangeaceae) [31,32]
MeO
11 NMe
O HO MeO
10 OMe
O O H NMe
N MeN O
O 8
OMe H
N H
O
MeO OMe O
O OMe
a H
Erythraline OH
MeN
Crystamidineb (=8-Oxo- OMe (+)-Tetrandrine
OMe
10,11-dehydroerythraline) Berberine (Cocculus sarmentosa,
(a Erythrina indica,
(+)-(R,R)-(Isochondrodendrine)
(various Berberis species, Cyclea barbata,
b E. crystagalli, Berberidaceae) [36] (Chondrodendron tomentosum and Menispermaceae)
other Chondrodendron Species, [40-42]
Leguminosae) [33-35] prevalent in the Menispermaceae,
Annonaceae, Umbelliferae plants
[37-39]

Fig. 30.1 (continued)

30.1 Introduction 917

HO2C
O OMe O NMe
H
N Me
N MeHN O
O NMe
N O N O
Me HO N H
Me NH
Acronycine (+)-Febrifugine Physostigmine (Eserine) (+)-Lysergic acid
(Acronychia baueri (Bauerella (roots and leaves of Chinese drug
baueri), Melicope leptococca, Dichroa febrifuga, Hydrangea Main alkaloid from calabar beans (Basic fragment derived
Rutaceae) [43,44] species, Hydrangeaceae) [45-49] (Physostigma venenosum, from Ergot alkaloids),
Legeominosae) [50,51] metabolite of the fungus
Claviceps purpurea
[52-54]

HO N R2 O
H R1
O O N Me
N Me O
O N Me O
HN Ph N
O Me H O O
O Me
O NMe N O
H Me
Spectabiline Affininine, R1
= CH2OH, =H R2 Protopine
(Argemone bocconia,
(Lemonia spectabilis, Affinisine, R1 = H, R2 = CH2OH
Rutaceae) [58,59] Meconopsis, chelidonium,
NH (Peschiera affinis) [60] species and various
Ergotamine Papaveraceae plants) [61]
Ergot (Claviceps purpurea)
[55-57]
H N
N H H
N
O MeO N
N H N
H H N H
H H
HO N
MeO2C MeO2C OH H
CO2Me
(-)-Ajmalicine (+) Yohimbine (+)-Vincamine (-)-Ibogaine
(Rauwolfia serpentina and (Rauwolfia, Vinca, Alchorea (Vinca minor, Vinca major, (Tabernanthe iboga,
other Apocynaceae plants, species, Apocynaceae) Apocynaceae) Apocynaceae)
Apocynaceae) [62-64] [65-67] [68,69] [70-72]

H
CO2Me N
N
H R N
N H
N H H
H N H
20' N CO2Me
MeO H N
19' H (+)-Akuammicine
14 MeO Ac
MeO2C (Alstonia scholaris,
H
(-)-Aspidospermine Vinca Species,
HN (Aspidosperma quebracho-blanco Picralima nitida,
and other Aspidosperma species, P. kleineana , locally
Apocynaceae, [77-80] known as akuamma)
N N
N [81-83]
H
Me
MeO2C N N
1R O
= Me, Condoduramine MeO2C
(Condopharyngia durissima, O O
Serpentinine
Gabunia odoratissima, (Rauwolfia serpentina and N R N
O
other Rauwolfia species, H O R O O
Apocynaceae) H C
R = H, Gabunine Apocynaceae) [76] R = Et, Haplocine O Et

[73-75] R = Me, Haplocidine R = H, Cimicine

(Haplophyton cimicidum, R = OMe,
Apocynaceae) [84,85] Cimicidine
H. cimicidum [86,87]

Fig. 30.1 (continued)

918 30 Some More Alkaloids Having Diverse Skeletal Patterns

Me
N OH
H
H R H
O N
H O H Me
HO N H S
N
N S S
OH H R
H N O N
H O
N H H Me O
Me O
HO H
N (+)-Gelsemine
(+)-Ajmaline Me R = OH, (+)-Himalayamine
(Gelsemium
(Rauwolfia serpentina & Toxiferine-I (Meconopsis villosa, Papareraceae) semipervirens,
other Rauwolfia Species, (Calabash curare alkaloid) R = H, (+)-Limogine
G. elegans,
Apocynaceae) (Strychnos toxifera, (Corydalis claviculata,
Loganiaceae) [95, 96]
[88-90] S. froessi, Strychnaceae) Fumaricaceae) [94]
[91-93]

R
OMe
MeN O NR2
O O H
H
Me H
N
N H
O 14 OR1 R4 O
N N
O 15
H H R3
18
Me R R1 R2 R3 R4
R1O OR2 HO H
Tiliacorinine H Me Me H H
Tiliamosine OMe Me H H H
Ochotensine R1 = H; R2 = Me
(+)-Palustrine [101-103] Tiliacosine
Ochotensimine R1 = R2 = Me (Equisetum palustre, .
OMe Me Me OH H
(Corydalis sibirica, C. ochotensis Equisetaceae), N-Methyltiliarine H H Me H Me
Fumariaceae), and other contains a 13- An exhaustive review [104] on bisbenzylisoquinoline alkaloids
Corydalis species [97-100] -membered ring. was extended afterwards by two more reviews [105, 106 ].

Fig. 30.1 Several alkaloids of diverse skeletal patterns (other than those included in earlier chapters)

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