Trivial, systematic and semisystematic names of natural brassinosteroids

 

Trivial name(s)a

Systematic name(s)b

Semisystematic namec

Numberd

Classificatione

Referencef

Brassinolide

(22R,23R)-2a,3a,22,23-Tetrahydroxy-6,7-seco-5a-campestano-6,7-lactone

Brassinostanolactone

(Brassinolide)

BR1

Bl

Grove et al., 1979

28-Homobrassinolide

(22R,23R)-2a,3a,22,23-Tetrahydroxy-6,7-seco-5a-stigmastano-6,7-lactone

28-Homobrassinostanolactone

(28-Homobrassinolide)

BR17

HBl

Ikekawa et al., 1984

Dolicholide

(22R,23R)-2a,3a,22,23-Tetrahydroxy-6,7-seco-24-methylene-5a-cholestano-6,7-lactone

Brassinost-24(28)-enolactone

[24(28)-Didehydrobrassinolide]

BR3

BDl

Yokota et al., 1982b

28-Homodolicholide (Homodolicholide)

(22R,23R,24E)-2a,3a,22,23-Tetrahydroxy-6,7-seco-24-ethylidene-5a-cholestano-6,7-lactone

(24E)-28-Homobrassinost-24(28)-enolactone

[(24E)-28-Homo-24(28)-didehydrobrassinolide]

BR10

HBDl

Yokota et al., 1983a

28-Norbrassinolide

(22R,23R)-2a,3a,22,23-Tetrahydroxy-6,7-seco-5a-cholestano-6,7-lactone

28-Norbrassinostanolactone

(28-Norbrassinolide)

BR14

NBl

Abe et al., 1983

24-Epibrassinolide

(22R,23R)-2a,3a,22,23-Tetrahydroxy-6,7-seco-5a-ergostano-6,7-lactone

24-Epibrassinostanolactone

(24-Epibrassinolide)

BR27

Ebl

Ikekawa et al., 1988

3-Epibrassinolide

(22R,23R)-2a,3b,22,23-Tetrahydroxy-6,7-seco-5a-campestano-6,7-lactone

3-Epibrassinostanolactone

(3-Epibrassinolide)

BR51

Bl3b

Konstantinova et al., 2001

2-Deoxybrassinolide

(22R,23R)-3a,22,23-Trihydroxy-6,7-seco-5a-campestano-6,7-lactone

2-Deoxybrassinostanolactone

(2-Deoxybrassinolide)

BR43

HBl2d

Schmidt et al., 1995b

Castasterone (Brassinone; Brassinosterone)

(22R,23R)-2a,3a,22,23-Tetrahydroxy-5a-campestan-6-one

Brassinostanone

(Brassinone)

BR2

Bk

Yokota et al., 1982a

28-Homocastasterone [Homobrassinosterone; (24S)-24-Ethylbrassinosterone; 24-Ethylbrassinone]

(22R,23R)-2a,3a,22,23-Tetrahydroxy-5a-stigmastan-6-one

28-Homobrassinostanone

(28-Homobrassinone)

BR12

HBk

Abe et al., 1983

Dolichosterone

(22R,23R)-2a,3a,22,23-Tetrahydroxy-24-methylene-5a-cholestan-6-one

Brassinost-24(28)-enone

[24(28)-Didehydrobrassinone]

BR4

BDk

Baba et al., 1983

28-Homodolichosterone (Homodolichosterone)

(22R,23R,24E)-2a,3a,22,23-Tetrahydroxy-24-ethylidene-5a-cholestan-6-one

(24E)-28-Homobrassinost-24(28)-enone

[(24E)-28-Homo-24(28)-didehydrobrassinone]

BR11

HBDk

Baba et al., 1983

28-Norcastasterone (28-Norbrassinosterone; Brassinone)

(22R,23R)-2a,3a,22,23-Tetrahydroxy-5a-cholestan-6-one

28-Norbrassinostanone

(28-Norbrassinone)

BR15

NBk

Abe et al., 1983

24-Epicastasterone (24-Epibrassinosterone)

(22R,23R)-2a,3a,22,23-Tetrahydroxy-5a-ergostan-6-one

24-Epibrassinostanone

(24-Epibrassinone)

BR9

Ebk

Yokota et al., 1987a

25-Methylcastasterone

(22R,23R)-2a,3a,22,23-Tetrahydroxy-25-methyl-5a-campestan-6-one

25-Methylbrassinostanone

(25-Methylbrassinone)

BR33

25HBk

Taylor et al., 1993

25-Methyldolichosterone

(22R,23R)-2a,3a,22,23-Tetrahydroxy-25-methyl-24-methylene-5a-cholestan-6-one

25-Methylbrassinost-24(28)-enone

[25-Methyl-24(28)-didehydrobrassinone]

BR16

25HBDk

Kim et al., 1987

2-Epicastasterone

(22R,23R)-2b,3a,22,23-Tetrahydroxy-5a-campestan-6-one

2-Epibrassinostanone

(2-Epibrassinone)

BR20

Bk2b

Takahashi et al., 1987

2-Epi-25-methyldolichosterone

(22R,23R)-2b,3a,22,23-Tetrahydroxy-25-methyl-24-methylene-5a-cholestan-6-one

2-Epi-25-methylbrassinost-24(28)-enone

[2-Epi-25-methyl-24(28)-didehydrobrassinone]

BR24

25HBDk2b

Takahashi et al., 1987

3-Epicastasterone

(22R,23R)-2a,3b,22,23-Tetrahydroxy-5a-campestan-6-one

3-Epibrassinostanone

(3-Epibrassinone)

BR21

Bk3b

Takahashi et al., 1987

3,24-Diepicastasterone

(22R,23R)-2a,3b,22,23-Tetrahydroxy-5a-ergostan-6-one

3,24-Diepibrassinostanone

(3,24-Diepibrassinone)

BR23

Ebk3b

Takahashi et al., 1987

2,3-Diepicastasterone

(22R,23R)-2b,3b,22,23-Tetrahydroxy-5a-campestan-6-one

2,3-Diepibrassinostanone

(2,3-Diepibrassinone)

BR22

Bk2b3b

Takahashi et al., 1987

2,3-Diepi-25-methyldolichosterone

(22R,23R)-2b,3b,22,23-Tetrahydroxy-25-methyl-24-methylene-5a-cholestan-6-one

2,3-Diepi-25-methylbrassinost-24(28)-enone

[2,3-Diepi-25-methyl-24(28)-didehydrobrassinone]

BR25

25HBk2b3b

Takahashi et al., 1987

1b-Hydroxycastasterone

(22R,23R)-1b,2a,3a,22,23-Pentahydroxy-5a-campestan-6-one

1b-Hydroxybrassinostanone

(1b-Hydroxybrassinone)

BR28

1b-hydroxyBk

Kim, 1988 (Kim, 1991)

1a-Hydroxy-3-epicastasterone (3-Epi-1a-hydroxycastasterone)

(22R,23R)-1a,2a,3b,22,23-Pentahydroxy-5a-campestan-6-one

1a-Hydroxy-3-epibrassinostanone

(1a-Hydroxy-3-epibrassinone)

BR29

1a-hydroxyBk3b

Kim, 1988 (Kim, 1991)

Typhasterol (Typhasterone; 2-Deoxybrassinosterone)

(22R,23R)-3a,22,23-Trihydroxy-5a-campestan-6-one

2-Deoxybrassinostanone

(2-Deoxybrassinone)

BR7

Bk2d

Schneider et al., 1983

28-Homotyphasterol

(22R,23R)-3a,22,23-Trihydroxy-5a-stigmastan-6-one

2-Deoxy-28-homobrassinostanone

(2-Deoxy-28-homobrassinone)

BR37

HBk2d

Abe et al., 1995

2-Deoxy-25-methyldolichosterone

(22R,23R)-3a,22,23-Trihydroxy-25-methyl-24-methylene-5a-cholestan-6-one

2-Deoxy-25-methylbrassinost-24(28)-enone

[2-Deoxy-25-methyl-24(28)-didehydrobrassinone]

BR18

25HBDk2d

Yokota and Takahashi, 1987

28-Nortyphasterol

(22R,23R)-3a,,22,23-Trihydroxy-5a-cholestan-6-one

2-Deoxy-28-norbrassinostanone

(2-Deoxy-28-norbrassinone)

BR49

NBk2d

Fujioka et al., 2000b

Teasterone (Theasterone; 3-Epi-2-deoxybrassinosterone)

(22R,23R)-3b,22,23-Trihydroxy-5a-campestan-6-one

3-Epi-2-deoxybrassinostanone

(3-Epi-2-deoxybrassinone)

BR8

Bk2d3b

Abe et al., 1984

28-Homoteasterone

(22R,23R)-3b,22,23-Trihydroxy-5a-stigmastan-6-one

3-Epi-2-deoxy-28-homobrassinostanone

(3-Epi-2-deoxy-28-homobrassinone)

BR34

HBk2d3b

Schmidt et al., 1993

3-Epi-2-deoxy-25-methyldolichosterone

(22R,23R)-3b,22,23-Trihydroxy-25-methyl-24-methylene-5a-cholestan-6-one

3-Epi-2-deoxy-25-methylbrassinost-24(28)-enone

[3-Epi-2-deoxy-25-methyl-24(28)-didehydrobrassinone]

BR19

25HBDk2d3b

Yokota and Takahashi, 1987

3-Dehydroteasterone

(22R,23R)-22,23-Dihydroxy-5a-campestan-3,6-dione

3(3-O)-Didehydro-2-deoxybrassinostanone

[3(3-O)-Didehydro-2-deoxybrassinone]

BR36

Bk2d3k

Abe et al., 1994

Yokota et al., 1994

Secasterone

(22R,23R)-22,23-Dihydroxy-2b,3b-epoxy-5a-campestan-6-one

2,3-Diepi-2,3-anhydrobrassinostanone

(2,3-Diepi-2,3-anhydrobrassinone)

BR38

Bk2,3epoxy

Schmidt et al., 1995a

24-Episecasterone

(22R,23R)-22,23-Dihydroxy-2b,3b-epoxy-5a-ergostan-6-one

2,3,24-Triepi-2,3-anhydrobrassinostanone

(2,3,24-Triepi-2,3-anhydrobrassinone)

BR46

EBk2,3epoxy

Friebe et al., 1999

2,3-Diepisecasterone

(22R,23R)-22,23-Dihydroxy-2a,3a-epoxy-5a-campestan-6-one

2,3-Anhydrobrassinostanone

(2,3-Anhydrobrassinone)

BR52

EBk2,3epoxy2a3a

Antonchick et al., 2003

Secasterol

(22R,23R)-22,23-Dihydroxy-5a-campest-2-en-6-one

2,3-Didehydro-2,3-dideoxybrassinostanone

(2,3-Didehydro-2,3-dideoxybrassinone)

BR53

D2-Bk2d3d

Antonchick et al., 2003

6a-Hydroxycastasterone

(22R,23R)-2a,3a,6a,22,23-Pentahydroxy-5a-campestane

6a-Brassinostanol

(6a-Brassinol)

BR47

B6a-hydroxy

Fujioka et al., 2000a

6-Deoxocastasterone (6-Deoxobrassinosterone; 6-Deoxodihydrocastasterone)

(22R,23R)-2a,3a,22,23-Tetrahydroxy-5a-campestane

Brassinostane

(Brassinane)

BR5

Bd

Yokota et al., 1983b

6-Deoxodolichosterone (6-Deoxodihydrodolichosterone)

(22R,23R)-2a,3a,22,23-Tetrahydroxy-24-methylene-5a-cholestane

Brassinost-24(28)-ene

[24(28)-Didehydrobrassinane]

BR6

BDd

Yokota et al., 1983b

6-Deoxo-28-homodolichosterone (6-Deoxodihydrohomodolichosterone; 6-Deoxohomodolichosterone)

(22R,23R,24E)-2a,3a,22,23-Tetrahydroxy-24-ethylidene-5a-cholestane

(24E)-28-Homobrassinost-24(28)-ene

[(24E)-28-Homo-24(28)-didehydrobrassinane]

BR13

HBDd

Yokota et al., 1987b

6-Deoxo-28-norcastasterone

(22R,23R)-2a,3a,22,23-Tetrahydroxy-5a-cholestane

28-Norbrassinostane

(28-Norbrassinane)

BR41

NBd

Spengler et al., 1995

6-Deoxo-24-epicastasterone

(22R,23R)-2a,3a,22,23-Tetrahydroxy-5a-ergostane

24-Epibrassinostane

(24-Epibrassinane)

BR42

Ebd

Spengler et al., 1995

6-Deoxo-25-methyldolichosterone (6-Deoxodihydro-25-methyldolichosterone)

(22R,23R)-2a,3a,22,23-Tetrahydroxy-25-methyl-24-methylene-5a-cholestane

25-Methylbrassinost-24(28)-ene

[25-Methyl-24(28)-dehydrobrassinane]

BR31

25HBDd

Kim, 1988 (Kim, 1991)

3-Epi-6-deoxocastasterone (3-Epi-6-deoxodihydrocastasterone)

(22R,23R)-2a,3b,22,23-Tetrahydroxy-5a-campestane

3-Epibrassinostane

(3-Epibrassinane)

BR30

Bd3b

Kim, 1988 (Kim, 1991)

6-Deoxotyphasterol

(22R,23R)-3a,22,23-Trihydroxy-5a-campestane

2-Deoxybrassinostane

(2-Deoxybrassinane)

BR39

Bd2d

Griffiths et al., 1995

6-Deoxo-28-nortyphasterol

(22R,23R)-3a,22,23-Trihydroxy-5a-cholestane

2-Deoxy-28-norbrassinostane

(2-Deoxy-28-norbrassinane)

BR50

NBd2d

Yokota et al., 2001

6-Deoxoteasterone

(22R,23R)-3b,22,23-Trihydroxy-5a-campestane

3-Epi-2-deoxybrassinostane

(3-Epi-2-deoxybrassinane)

BR45

Bd2d3b

Fujioka et al., 1998

3-Dehydro-6-deoxoteasterone

(22R,23R)-22,23-Dihydroxy-5a-campestan-3-one

3(3-O)-Didehydro-2-deoxybrassinostane

[3(3-O)-Didehydro-2-deoxybrassinane]

BR40

B2d3k

Griffiths et al., 1995

Teasterone-3-laurate

(22R,23R)-22,23-Dihydroxy-6-oxo-5a-campestan-3b-yl dodecanoate or (22R,23R)-3b-dodecanoyl-22,23-dihydroxy-5a-campestan-6-one

3-Epi-2-deoxybrassinostanone 3-laurate

(3-Epi-2-deoxybrassinone 3-laurate)

BR44

Bk2d3b laurate

Asakawa et al., 1996

Teasterone-3-myristate

(22R,23R)-22,23-Dihydroxy-6-oxo-5a-campestan-3b-yl tetradecanoate or (22R,23R)-3b-tetradecanoyl-22,23-dihydroxy-5a-campestan-6-one

3-Epi-2-deoxybrassinostanone 3-myristate

(3-Epi-2-deoxybrassinone 3-myristate)

BR35

Bk2d3b myristate

Asakawa et al., 1994

23-O-b-D-Glucopyranosyl-25-methyldolichosterone

(22R,23R)-23-O-b-D-Glucopyranosyloxy-2a,3a,22-trihydroxy-25-methyl-24-methylene-5a-cholestan-6-one

23-O-b-D-Glucopyranosyl-25-methylbrassinost-24(28)-enone

[23-O-b-D-Glucopyranosyl-25-methyl-24(28)-didehydrobrassinone]

BR26

23-gly-25HBDk

Yokota et al., 1987c

23-O-b-D-Glucopyranosyl-2-epi-25-methyldolichosterone

(22R,23R)-23-O-b-D-Glucopyranosyloxy-2b,3a,22-trihydroxy-25-methyl-24-methylene-5a-cholestan-6-one

23-O-b-D-Glucopyranosyl-2-epi-25-methylbrassinost-24(28)-enone

[23-O-b-D-Glucopyranosyl-2-epi-25-methyl-24(28)-didehydrobrassinone]

BR32

23-gly-25HBDk2b

Kim, 1988 (Kim, 1991)

3-O-b-D-Glucopyranosylteasterone

(22R,23R)-3-O-b-D-Glucopyranosyloxy-22,23-dihydroxy-5a-campestan-6-one

3-O-b-D-Glucopyranosyl-3-epi-2-deoxybrassinostanone

(3-O-b-D-Glucopyranosyl-3-epi-2-deoxybrassinone)

BR48

3-gly-Bk2d3b

Soeno et al., 2000

 

a Currently accepted trivial names: synonyms already reported in parenthesis or brackets; b According to International Union of Pure and Applied Chemistry and International Union of Biochemistry and Molecular Biology, IUPAC-IUB Joint Commission on Biochemical Nomenclature, The nomenclature of steroids, Pure and Applied Chemistry 61: 1783-1822, 1989; c proposed by M. A. T. Zullo & L. Kohout, Semisystematic nomenclature of brassinosteroids, Plant Growth Regulation 42(1): 15-28, 2004; d BR1-BR16 according to N. B. Mandava (1988), Plant growth-promoting brassinosteroids, Annual Review of Plant Physiology and Plant Molecular Biology 39: 23-52, the remaining proposed by Zullo & Kohout (2004); e according to the rules proposed by V. A. Khripach, V. N. Zhabinskii & A. E. De Groot (1999), Brassinosteroids (BS) in nature, in V. A. Khripach, V. N. Zhabinskii & A. E. De Groot, Brassinosteroids: a new class of plant hormones, Academic Press, San Diego, Chapter 2, pages 7-23; f First report of isolation or detection.

 

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