flavonoides de especies de nama

7/26/2019 Flavonoides de Especies de Nama

1/6

Ph Syst. Evol. 151,223-228 (1986)

P lunt SV stemn tits

nnd E uolut inn

9 by Springer-Verlag 1986

S y s t e m a t i c s o f N ama H ydroph y l l a ceae) : F l a v o no i ds a nd

P hy l e t i c P o s i t i o n o f s e c t A ra chno i d ea and sec t Cine rascen t ia

B y

John D. Bacon Nianbai Fang and Tom J. M abry

Received July 10, 1985)

Key Words:

Angiosperms, Hydrophyllaceae, Nama.-Chemotaxonomy,

flavones, 6 -m etho xy flavones, C-glycosyl f lavones.

Abstract: Eigh t f lavonoids, four 6-oxygen ated f lavones, two m ethyl e thers of

luteolin, apigenin 6,8-C-diglucoside and quercetin 3-O-glucoside, were isolated

f r om

Nama lobbii

and

N. rothrockii,

sole members of sects .

Arachnoidea

and

Cinerascentia, respectively. Both taxa d iverge m arked ly f rom o ther na m as in

mor pho logy a nd c h r omosome numbe r a nd the i r p l a c e me n t i n

Nama

has been

quest ioned. T he occu rrence of 6-oxygen ated f lavones in these taxa adds to their

a lready dist inctive nature . Flav ono id evidence argues tha t b oth are m ore c losely

allied to Eriodictyon than e i ther is to Nama.

A s s e c o n d l a r g e s t g e n u s i n t h e Hydrophyllaceae, Nama c o m p r i s e s

a b o u t 5 0 s p e ci es d i s tr i b u t e d p r i m a r i l y in t h e d r i e r a r e a s o f t h e s o u t h -

w e s t e r n U n i t e d S t a t e s a n d n o r t h e r n M e x i c o . S o m e s p e c i e s , n e v e r t h e l e s s ,

o c c u r in m o r e m e s i c h a b i t a t s i n t h e s ie r ra s o f t h e w e s t e r n U n i t e d S t a te s a n d

t h e h i g h l a n d s o f c e n t r a l a n d s o u t h e r n M e x i c o . M o r p h o l o g i c a l l y d i v e rs e ,

s p ec ie s r a n g e i n h a b i t f r o m s m a l l, s h o r t - li v e d a n n u a l s t o r o b u s t , w o o d y

s u b s h r u b s . F o l l o w i n g t h e t r e a t m e n t o f H IT CH CO CK ( 1 9 3 3) , s p e c ie s a r e

s t r u c t u r e d i n t o f i v e s e c t i o n s : s e c t s .

Arachnoidea, Cinerascentia,

Conanthus, Zonolacus, a n d Nama. T h e l a t t e r s e c t i o n is m u c h t h e l a rg e s t

a n d h o u s e s t h e b u l k o f t h e s p e ci es w h i le t h e f o r m e r f o u r s h e l t e r o n l y six

s p e c ie s , w i t h t h r e e o f t h o s e r e s i d e n t i n s e c t. Conanthus. A l t h o u g h e a c h o f

t h e s m a l l e r s e c t i o n s i s p o s s e s s e d o f c l e a r l y u n i q u e f e a t u r e s , t h e s p e c ie s o f

sec t . Arachnoidea a nd se c t . Cinerascentia a r e s o d i s t i n c t i v e t h a t t h e i r

p l a c e m e n t w i t h in t h e b o u n d a r i e s o f Nama h a s b e e n q u e s t i o n e d ( B A c o N

1974, CHANCE & BACON 1984, RAVEN & AXZLROD 1978) .

Nama rothrockii

GR A y, the s ing le spe c ie s o f s e c t .

Chwrascentia,

e x h i b i t s c a p i t a t e i n -

f l o re s c e n c e s a n d c r e n a t e l e a v es , f e a t u r e s f o u n d in n o o t h e r n a m a s : N .

lobbii G R A Y , s o l e m e m b e r o f s e c t. Arachnoidea, e x h i b i t s l o c u l i c i d a l l y a n d

s e p t ic i d a ll y d e h i s c e n t c a p su l e s, w h i l e c a p s u l e s o f o t h e r n a m a s a r e


2/6

224 J .D . BACON & al.:

l o c u l i c i d a l l y d e h i s c e n t o n l y . I n d e e d , N. Iobbi i w a s t r e a t e d a s a n E r i od i c -

t y o n by G RE E N E ( 1885 : p . 202 ) a n d H A L E ( 1906 : p . 265 ) , t he t w o t a x a

e x h i b i t t h e s a m e c a p s u l a r d e h i s c e n c e p a t t e r n , a n d i t i s t h r o u g h N. lobbi i

t h a t t h e n e a r e s t r e l a t i v e o f N a m a t r a d i t i o n a l l y h a s b e e n i d e n t i f i e d a s

E r i o d i c t y o n (H ~T cH C OC K 1 93 3). T h e r e f o r e , p l a c e m e n t o f N. lobbi i as we l l

a s N . r o t h r o c k i i i s c r i ti c a l f o r e s t a b l i s h i n g n o t o n l y g e n e r i c l i m i t s b u t a l s o

r e l a t i o n s h i p s o f N a m a . A s p a r t o f a n o n g o i n g s y s t e m a t i c r ev i s io n o f N a m a

t h e f l a v o n o i d s o f t h e se t w o s p e ci es h a v e b e e n i s o l at e d a n d i d e n ti f ie d . W e

r e p o r t h e r e i n t h e f la v o n o i d s a c c u m u l a t e d b y t h e t w o s p e ci es a n d c o n s i d e r

t h e i r p l a c e m e n t i n l ig h t o f t h e se a n d o t h e r d a t a .

xperimental

Air-dr ied leaf , s tem and f lower mater ia l (300g for N. Iobbi i

[B coN

1701

U.S .A. : Nevada : Douglas Co. ] ; 390g for N. rothrocki i [BAcoN 1 8 1 2 U.S.A.:

Ca l i forn ia : lnyo Co. ] , vouchers to be depos i t ed a t TEX) was ground to a f ine

pow der and ex t rac ted 3 hours wi th d ich lorom ethane : e thy l ace ta te ,

70 :30 v /v , a i r d ry ing be tween ex t rac tions . M ate r ia l was then ex t rac ted 2 24

hours with 85 aqueous methano l . L ike ex t rac t s were com bined , reduced to a

s m a ll vo lum e unde r w a t e r va c uum a nd s ub je c te d t o c o l um n c h r o m a t og r a p hy ove r

Polyc la r (G A F C orp . ) us ing va r ious m ix tures of d i ch lorometha ne , e thy l ace ta te

and me thanol a s so lvents . F lavono ids were moni tore d w i th U V l igh t (366 nm ) as

they were e lu ted f rom colum ns . E lu ted f rac t ions were pur if i ed by fu r the r co lum n

c h r o m a t o g r a p h y o r b y p a p e r c h r o m a t o g r a p h y o n W h a t m a n 3 M M p a p e r u s in g

15 or 40 acet ic ac id or ter t iary b utan ol : glac ia l acet ic ac id : H2 0, 4 : 3 : 1 , v/v ,

as solvents . UV spect ra w ere recorded fol lowing pro cedu res as se t for th in MABRY

& al. (1970). IH N M R spec t ra were recorded for tr ime thyls i ly l e the r de r iva tives of

a ll comp oun ds on a V ar ian E M 390 spec t romete r .

Resul ts

A t o t a l o f e i g h t f l a v o n o i d s , s i x a g l y c o n e s a n d t w o g l y c o s id e s , w e r e

i s o l a t e d F r o m t h e t w o s p e c i e s o f N a m a ( T a b l e 1 ) , I n c l u d e d a m o n g t h e

i so l a te d c o m p o u n d s w e r e t he a g l y c o n e s 6 - m e t h o x y a p i g e n i n ( I) , 6 - m e -

t hoxya p i ge n i n 7 - m e t hy l e t he r ( I I ) , 6 - m e t hoxya p i ge n i n 4 ' - m e t hy l e t he r ( I I I ) ,

l u te o l in Y - m e t h y l e th e r ( I V ) , l u t e o li n 7 , Y - d i m e t h y l e t h e r ( V ) , 6 - m e t h o x y -

l u t e o l i n 4 ' - m e t h y l e t h e r ( V I ) a n d t h e g l y c o s i d e s q u e r c e t i n 3 - O - g l u c o s i d e

( V I I ) a n d a p i g e n i n 6 , 8 - C - d i g l u c o s i d e ( V I I I ) . I n a d d i t i o n t o i s o la t e d

f l a v o n o id s , c r u d e c h r o m a t o g r a m s o f e a c h s p ec ie s e x h i b it e d t r a c e a m o u n t s

o f y e t t o b e i s o l a t e d g l y c o s i d e s ; N. l obb i i e x h i b i t e d t w o f a i n t s p o t s w i t h R f

v a lu e s in k e e p i n g w i th t h o s e o f f la v o n o l 3 - O - m o n o g l y c o s i d e s . N a m a

r o t h r o c k i i e x h i b i t e d a si n g le f a i n t s p o t w i t h R f v a l u e s a p p r o x i m a t i n g t h o s e

o f ( V I I I ) a n d s u g g e s t i n g a C - g l y c o s y l f l a v o n e o r a 3 , 7 - O - g l y c o s i d e .

W h i le t h e f l a v o n o i d p r o f i l e s o f e a c h s p e c ie s a r e c l e ar l y d i ff e r e n t, t h e

a g l y c o n e c o m p o n e n t o f b o t h a r e s im i la r a n d d o m i n a t e d b y 6 - o x y g e n a t ed

f l a v o n e s . I t a p p e a r s t h a t N . r o t h r o c k i i l a c k s t h e a b i l i t y t o m e t h y l a t e

p o s i t io n 7 o f 6 - m e t h o x y a p i g e n i n w h i le N. l obb i i is i n c a p a b le o f m e t h y l a t -


3/6

F l a vono i ds a nd S ys te m a t ic s o f Nama Hydrophyllaceae) 225

Table 1. S t ruc ture o f e luc ida ted f l avon oids of Nama lobbii a n d N. rothrockii

R ~

R

O H O

Flavonoid

Subs t i tu t ion pa t t e rn +

R I R R 3 R 4 R ~ R 6

I 6 -Methoxyapigenin

I I 6 Methoxyapigenin 7-methyl e the r

l l I 6 -M ethoxyapigenin 4 ' -me thyl e the r

IV ~uteo l in 3 ' -me thyl e the r

V Luteol in 7,3 ' -dimethy l e ther

VI 6-Methoxy lu teo l in 4 ' -me thyl e the r

VII Apigenin 6,8-C-diglucoside

VIII Quercetin 3-O-glucoside

H O M e O H H H

H O M e O M e H H

H O M e O H H H

H H O H H O M e

H H O M e H O M e

H O M e O H H O H

H C- g l c O H C- g l c H

O - g lc H O H H O H

+glc = glucose; O M e = O C H 3.

Tab le 2 . D i s t r ibu t ion of f lavonoids in Nama lobbii a n d N. rothrockii

O H

O H

O M e

O H

O H

O M c

O H

O H

T a x o n F l a v o n o i d n u m b e r

I

I1 I I I I V V V I V I I V I I I

N. lobbff + + + + +

N. rothrockii + + + + + +

i ng e i th e r p o s i t i o n 3 ' o r 7 , o r b o t h , o n t h e l u t e o li n s k e l e t o n ( T a b l e 2 ) . T h e

g l y c o s id i c c o m p o n e n t s o f e a c h s p ec i es , in c o n t r a s t , a r e q u i t e d i f f e r e n t .

E v e n a s s u m i n g t h a t t h e u n - i s o l a t e d g l y c o s i d e s o f e a c h a r e i d e n t ic a l a n d t h e

s a m e a s t h o s e i d e n t i f i e d , t h e r e r e m a i n s a r e m a r k a b l e q u a n t i t a t i v e

d i f f e r e n c e i n t h e m a j o r g l y c o s i d e a c c u m u l a t e d ; t h e C - g l y c o s y l f l a v o n e o f

N. lobbii is t h e m a j o r f l a v o n o i d , q u a n t i t a t i v e l y , i n th e t a x o n , w h i l e

q u e r c e t in 3 - O - g l u c o si d e is a m i n o r c o m p o n e n t in N. rothrockii.

D i s c u s s i o n

I n s e g r e g a t i n g N. lobbii a n d N. rothrockii i n t o m o n o t y p i c s e c t i o n s ,

H IT CH CO CK ( 1 9 3 3 ) w a s g i v i n g d u e r e c o g n i t i o n t o t i le s i n g u l a r l y n o t a b l e

1 6 P I. S y s t . E v o l . V o l . 1 5 1 N o . 3 ~ 4


4/6

226 J .D . BACON & al.:

c h a r a c t e r s w h i c h e a c h d i s p l a y s . I n d e e d , G R E E N E

1885)

a n d H A L L ( 1 9 0 6 )

a s c r i b e d e v e n m o r e s i g n if ic a n c e to t h e f e a t u r e s e x h i b i t e d b y N. Iobbii a n d

t r e a t e d t h a t t a x o n a s a n

Eriodic tyon.

HITCnCOCK'S d i s p o s i t i o n o f N .

lobbii

w a s i n f l u e n c e d , a t l e a s t i n p a r t , b y h is d i s p o s i t io n o f a n o t h e r p r o b l e m a t i c a l

t a x o n , Turricula parryii GRAY)M A CB RID E. T h i s t a x o n h a d b e e n s h u f f l e d

b a c k a n d f o r t h b e t w e e n N a m a (GRA Y 1876: 6 21 , PETER 1897: 69, BRANr~

1913: 160) and Eriodic tyon (GR EE NE 1889: 22, HALL 1902: 106) or

r e c o g n iz e d a s t h e m o n o t y p i c Turr icula (MACBR1DE 1917: 42 ). HITCHCOCK

( 1 9 3 3 ) , n o t i n g s i m i l a r i t i e s i n s e e d f e a t u r e s , c o r o l l a f e a t u r e s , h a b i t a n d

c a p s u l a r d e h i s c e n c e o f t h e la t t e r t a x o n a n d

Er iod ic tyon

s p e c ie s , c h o s e t o

r e c o g n i z e i t a s Eriodic tyon parryi i . C o n s i d e r i n g N. lobbii, h e c o n c l u d e d

t h a t , w i th t h e e x c e p t i o n o f c a p s u l a r d e h i s c e n c e , it s c h a r a c t e r s w e r e t h o s e o f

N a m a .

a l t h o u g h d i v e r g e n t e n o u g h t o m e r i t r e c o g n i t i o n a s a m o n o t y p i c

s e c t io n . H e t h e n w e n t o n t o p o i n t o u t t h a t i t w a s t h r o u g h

E. par ry i i (= T .

parryi i ) a n d N. lobbii t h a t t h e t r u e r e la t i o n s h i p s o f Eriodic tyon a n d N a m a

w e r e m a n i f e s t . H o w e v e r , a d d i t i o n a l d a t a f o r t h c o m i n g si n ce 1 93 3 p o r t r a y

t h e r e l a t i o n s h i p b e t w e e n N a m a a n d Er iod ic tyon a s l e s s d i r e c t t ha n

c o n c l u d e d b y H JTCH CO CK a n d s u g g e s t t h a t

N. lobbi i

a n d

N. ro throck i i

a r e

m o r e d i s t a n t f r o m t h e b u l k o f N a m a t h a n h e r e c k o n e d .

CAVE & CONSTANCE (19 42 , 194 4, 194 7, 195 7, 195 9) an d CONSTANCE

( 1 96 3 ) h a v e e x t e n s i v e ly s u r v e y e d t h e

Hydrophy l laceae

f o r c h r o m o s o m e

n u m b e r s a n d a d d i t i o n a l s u r v e y s h a v e b e e n c o n d u c t e d f o r

N a m a BACON

1974, 1984). Al l spec ies o f

EriodicO,on

h a v e b e e n c o u n t e d a n d a ll p o s se s s

n = 14. I n c o n t r a s t , Turricula e x h i b i t s n = 1 3, s u p p o r t i n g i t s t r e a t m e n t as

a m o n o t y p i c g e n u s ; a c c e p t i n g t h i s p l a c e m e n t , a n y d i r e c t l i n k b e t w e e n

N a m a a n d Eriodic tyon, a s e nv i s io ne d by HITC HC OCK, i s s e ve r e d . W i th

a b o u t 9 0 o f t h e s p ec ie s o f N a m a c o u n t e d , t he e m e r g e n t c h r o m o s o m a l

p i c t u r e is t h a t o f a s tr i k i n g l y d i p l o i d t a x o n w i t h n = 7 , w i t h t h e e x c e p t i o n

o f s e c t s . Arachno idea a n d C wrascen t ia; N. Iobbii e xh ib i t s n = 14 , wh i l e N .

ro throck i i

h a s n = 1 7 . A l t h o u g h t h r e e t a x a o f

N a m a

a r e c o n s i s t e n t l y

t e t r a p l o i d , e x c l u d i n g t h e a f o r e m e n t i o n e d s e c t i o n s , a l l h a v e r e a d i l y

i d e n t i f i a b l e r e l a t i v e s w i t h i n N a m a p r o p e r ; n e i t h e r N. ro throck i i n o r N .

Iobbii

c a n b e s o p o s i t i o n e d . A l s o , C HA N CE & B AC ON ( 1 9 8 4 ) h a v e s h o w n

t h a t s e e d f e a t u r e s o f

N. lobbii

a n d

N. ro throck i i

a r e d i s t i n c t i v e w i t h i n

N a m a ; b o t h s p e ci es p r o d u c e m u c h l a r g e r s e ed s w i t h a t h i c k e r s e ed c o a t a n d

b o t h e x h i b i t d i s t i n c t i v e s c u l p t u r i n g p a t t e r n s w h e n c o m p a r e d t o o t h e r

n a m a s . M o r e o v e r , t h e h a b i t o f th e s e t w o s p e ci es is n o t t h a t o f N a m a , f o r

b o t h a r e r h i z o m a t o u s ( B a c o N , p e r s. o b s . , JE PS ON 1 94 3, M u N z & K E C K

1 9 5 9 ) ; o t h e r n a m a s a r e t a p - r o o t e d . I t i s s i g n i f i c a n t i n t h i s r e s p e c t t h a t

Eriodic tyon

i s a r h i z o m a t o u s t a x o n ( M u N z & K E C K 1 95 9).

T h e p r e s en c e o f & o x y g e n a t e d f l a v o n e s in

N. Iobbii

a n d

N. ro throck i i

a d d s f u r t h e r t o t h e u n i q u e n a t u r e o f t h e se t a x a w i t h i n N a m a . A d d i t i o n a l


5/6


6/6

228 J. D. Bacon

a l . :

Flavonoids and Systematics of

N a m a ( H y d r o p h y l l a c e a e )

R e f e r e n c e s

BACOn, J. D., 1984: Chr omosome numbers and tax onom ic notes in the genus

N a m a ( I t y d r o p h y l l a c e a e ) .

II. - Sida 10, 26 9- 27 5.

- 1974: Chromo some numbers and taxo nomic notes in the genus

N a m a

( H y d r o p h y l l a c e a e ) . -

Brit tonia 26, 101 - 105.

BRANt~, A., 1913:

H y d r o p h y l l a c e a e .

In ENC,LI~r~, A., (Ed.): Das Pflanzenreich IV, 25,

1 -210.

CARLQUIST S ECKHAKT, V. M., MICI-IENER, D. C., 1983: Wo od an atomy of

H y d r o p h y l l a c e a e . I . E r i o d i e t y o n . -

Aliso 10, 397-412.

CAVE, M., CONSTANCE,L., 1942: Chromosome numbers in the

H y d r o p h y l l a c e a e . -

Univ. Calif. Publ. Bot. 18, 205-216.

- 1944: Chro mosome numbers in the

H . v d r o p h y l l a c e a e .

II, - Univ, Calif. Publ.

Bot. 18, 293- 298.

- 1947: Chromo som e numbers in the


III. - Univ. Calif. Publ.

B o t . 1 8 4 4 9 -

465.

- 1950: Chromo some numbers in the

l l y c h o p h y l l a c e a e .

IV. - Univ. Calif. Publ.

Bot. 23, 363-382.

- 1959: Chro moso me numbers in the


V. - Univ. Calif. Publ.

Bot. 30, 233-258.

CHA~C~, G. D., B;,cor4, J. D., 1984: Systemat ic implications o f seed coa t

morphology in

N a m a ( H y d r o p h y l l a c e a e ) . -

Amer. J. Bot. 71,829-842.

CONSTANCE, L., 1963: Ch rom os om e number and c lassificat ion in


- Brittonia 15, 273-285.

GRAY, A., 1876: Botany o f California. - In Geologic al Survey of California, I,

l -

628.

GREYiNg, E. L., 1885: Studies in the botany of Cal ifo rni a and par ts adjacent . -

Bull. Calif. Acad. 1,201- 202.

- 1889: New or notewor thy species. VI. - Pittonia 2, t 3 -2 4 .

HALL, H. M., 1902: A botanical survey of San Jacinto Mou ntai ns. - Univ. Calif.

Publ. Bot. 1, 1-140.

- 1906: Studies on Californian plants. II. - Z6e 5, 26 3- 26 6.

HrrcHcocK, C. L., 1933: A taxo nomic study of the genus N a m a . - Amer. J. Bot.

26, 415-430, 518-534.

MABRY, T. J., MARKH,~M, K. R., THOMAS,M. B., 1970: The systematic identification

of flavonoids. - Berlin, Heidelberg, New York : Springer-Verlag.

MACBRIDV., J. F., 1917: Notes on the

I t y d r o p h y l l a c e a e

and a few other North

Americ an spermatophytes. - Contr. Gray Herb. 49, 2 3 - 59.

PETER, A., 1897 :

H y d r o p h y l l a c e a e . -

In ENGLUR, A., PRAN'rt, K., (Eds.):

Natfirliche Pflanzenfamilien IV/3 a, 5 4 - 71.

RAWN, P. H ., AXELROD, D. I., 1978: Origin and rela tionships of the Cali fornia

flora. - Univ. Calif. Publ. Bot. 72, 1 - 134.

Addresses of the authors: Jo~N D. BACON, Department of Biology, The

Universit y of Texas at Arlington , Arlington , TX 76019, U . S . A . - N~^N~A~ FANC

and TOM J. MAI3RY, Dep artment of Botany, The University o f Texas a t Austin,

Austin, TX 78712, U.S.A.

flavonoides de especies de nama

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