2.1 clasificación 2.2 biosíntesis y ocurrencia 2.3 ... y p… · 2.1. clasificación medicinal...
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Maestría en Ciencias: Productos Naturales y
Alimentos
Química de Productos Naturales
2. Terpenoides
2.1 Clasificación
2.2 Biosíntesis y ocurrencia
2.3 Aislamiento y técnicas de separación
2.4 Elucidación estructural
2.5 Mono-, sesqui-, di-, triterpenoides
2.6 Carotenoides
R-carvona(caraway) (menta)
S-carvona
2.1. Clasificación
Medicinal Natural Products. Paul
M Dewick, 2002. John Wiley &
Sons, Ltd. England.
2
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
Parent hydrocarbons of terpenes (isoprenoids)
3
Medicinal Natural Products. Paul M Dewick, 2002 John Wiley & Sons, Ltd. England. 4
Scheme of the biogenesis of mono- and sesquiterpenes
Terpenes. Eberhard Breitmaier. 2006.
WILEY-VCH Verlag GmbH & Co. KGaA,
Weinheim, Germany.
5
Medicinal Natural Products. Paul M Dewick, 2002 John Wiley & Sons, Ltd. England. 6
2-metilbuta-1,3-dieno
(isopreno)
R-carvona(caraway) (menta)
S-carvona
2-metilbuta-1,3-dieno
(isopreno)
7
Bisaboleno
Mentol
8
2.2 Biosíntesis y ocurrencia
9
Tiamina pirofosfato
10
11
12
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
13
Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England. 14
Cytidine triphosphate
15
Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England.
Monoterpenes (C10)
16
geranial (E-citral) citronelal β-mirceno neral (Z-citral)
(aceite de limón) (aceite de citronela) (lúpulo) (aceite de limón)
citronelol geraniol linalool nerol
(aceite de rosa) (aceite de geranio) (aceite de cilantro) (aceite de rosa)
17
Medicinal Natural Products. Paul M Dewick. 2002. John Wiley & Sons, Ltd. England.
Tipo:
Mentano Pinano Canfano Fencano Isocanfano Carano Thujano
19
Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England. 20
Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England. 21
Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England.
-H+ H2O, -H+
22
23
Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England. 24
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
25
26
Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England. 27
Irregular monoterpenes
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Compositae/Asteraceae
28
29 Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Pyrethrins
30
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 31
alcohol Artemisia
alcohol Yomogi
alcohol Santolina
Biogenesis of natural products. Kumar, B.; Kumar Chopra, H. 2005. Alpha Science International Ltd.
Middlesex, UK.
Ormenis multicaulis Matricaria recutica Chamaemelum mixtum
32
Iridoids (C10)
33
34
35
Sesquiterpenes (C15)
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 36
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 37
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 38
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
39
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. 40
matricin
santonina
de Kraker, J.-W.; Franssen, M. C. R.; Dalm, M. C. F.; de Groot, A. Bouwmeester, H. J. Plant Physiology,
2001, 125, 1930–1940.
(-)--cariofileno
41
42
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
43
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
Oils from cloves (Syzygium aromaticum; Myrtaceae) and cinnamon (Cinnamomum
zeylanicum; Lauraceae)
44
Antimigraine agent in feverfew (Tanacetum parthenium)
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 45
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 46
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 47
(+)-artemisic acid
sataleno
curcumeno48
ChamigraneThujopsaneWiddraneCuparane
49
50
51
Sugiera la formación de los cationes siguientes:
carotyl cation
cadinyl cation
E-humulyl cation
52
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 53
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Matricaria chamomilla; Compositae/Asteraceae
54
(-)-zingiberene
55
56 Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Matricaria chamomilla; Compositae/Asteraceae
57
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 58
Ópticamente activo
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 59
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Artemisinin is an important antimalarial component in Artemisia annua, a Chinese herbal
drug. 60
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 61
Trichothecenes
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 62
Diterpenes (C20)
63 Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England.
Clorofila a
64
65
R1 R2
Me Me alfa-tocoferol
Me H beta-tocoferol
H Me gamma-tocoferol
H H delta-tocoferol
The (3R,7R,11R)-enantiomer of phytane has been found in meteorites, oil slate, other sediments and, last but
not least, in human liver. Oil slate additionally contains (-)-(3R,7R,11R)-phytanoic acid which has also been
isolated from butter. 1,3(20)-Phytadiene is one among many constituents of tobacco Nicotiana tabacum
(Solanaceae); (E)-1,3-phytadiene and its (Z)-isomer are found in zooplankton. Chlorophyll in the chloroplasts of
plant cells exemplifies an ester of (+)-(2E,7R,11R)-2-phyten-1-ol usually referred to as phytol. 2,6,10,14-
Phytatetraene-1,19-diol, better known as plaunotol, is the chief constituent of the leaves of the Thai medicinal
plant Croton sublyratus (Euphorbiaceae) used as "plau noi" or "kelnac" as an antiulcerative
Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
66
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 67
taxadiene
verticillene
Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 68
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