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)

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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)

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Bisaboleno

Mentol

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2.2 Biosíntesis y ocurrencia

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Tiamina pirofosfato

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11

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Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.

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Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England. 14

Cytidine triphosphate

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Medicinal Natural Products. Paul M Dewick, 2002. John Wiley & Sons, Ltd. England.

Monoterpenes (C10)

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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)

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Medicinal Natural Products. Paul M Dewick. 2002. John Wiley & Sons, Ltd. England.

Tipo:

Mentano Pinano Canfano Fencano Isocanfano Carano Thujano

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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+

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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.

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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

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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

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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

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Iridoids (C10)

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34

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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.

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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

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Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.

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Terpenes. Eberhard Breitmaier. 2006. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.

Oils from cloves (Syzygium aromaticum; Myrtaceae) and cinnamon (Cinnamomum

zeylanicum; Lauraceae)

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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

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50

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Sugiera la formación de los cationes siguientes:

carotyl cation

cadinyl cation

E-humulyl cation

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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

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(-)-zingiberene

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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

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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

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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.

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Medicinal Natural Products. Paul M. Dewick, 2002. John Wiley & Sons, Ltd. England. 67

taxadiene

verticillene

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