2.1 Clasificación 2.2 Biosíntesis y ocurrencia 2.3 ... y p… · 2.1. Clasificación Medicinal...

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


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.

-H+ H2O, -H+

22


25

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.


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

Sesquiterpenes (C15)



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


43


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

zeylanicum; Lauraceae)

44

Antimigraine agent in feverfew (Tanacetum parthenium)


(+)-artemisic acid

sataleno

curcumeno48

ChamigraneThujopsaneWiddraneCuparane

49

Sugiera la formación de los cationes siguientes:

carotyl cation

cadinyl cation

E-humulyl cation

52


Matricaria chamomilla; Compositae/Asteraceae

54

(-)-zingiberene

55


Matricaria chamomilla; Compositae/Asteraceae

57

Ópticamente activo



Artemisinin is an important antimalarial component in Artemisia annua, a Chinese herbal

drug. 60

Trichothecenes


Diterpenes (C20)


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


66

taxadiene

verticillene


2.1 Clasificación 2.2 Biosíntesis y ocurrencia 2.3 ... y p… · 2.1. Clasificación Medicinal...

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