antitermitic activity of lonchocarpus castilloi

8/4/2019 Antitermitic Activity of Lonchocarpus Castilloi

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Journal of Chemical Ecology, Vol. 21, No. 4, 1995

A N T I T E R M I T IC A C T I V I T Y O F Lonchocarpus castilloiF L A V O N O I D S A N D H E A R T W O O D E X T R A C T S

R . R E Y E S - C H I L P A , * 'l N . V I V E R O S - R O D R I G U E Z , zF. GOME Z-GA RIBA Y, 2 and D. ALA VEZ -SO LAN O2

t nstituto de Ecologia A. C.Apartado Postal 63Xalapa, Veracruz, 91000, M~xico71nstituto de Quhnica, Universidad National Aut6noma de MFxicoCiudad UniversitariaCoyoacdn, 04510 MFxico, D.F.

( R e c e i v e d S e p t e m b e r 2 3 , 1 9 94 ; a c c e p t e d D e c e m b e r 3 0 , 1 9 94 )

A b s t r a c t - - T h e h e a r tw o o d o f t h e tr o p ic a l t re e Lonchocarpus castilloi S t a n d l e y( L e g u m i n o s a e ) i s h i g h l y r e s i s t a n t t o a t t a c k b y t h e d r y w o o d t e r m i t e s Crypto-termes brevis ( W a l k e r ) ; n e v e r t h e l e s s s u c c e s s i v e e x t r a c t i o n w i t h h e x a n e , d i -e t h y l e t h e r , a c e t o n e , m e t h a n o l , a n d w a t e r r e d u c e d i t s r e s i s t a n c e t o th e s e o r g a -n i s m s . A n t i te r m i t i c p r o p e r t i e s o f t h e e x t r a c ts w e r e b i o a s s a y e d u s i n g i m p r e g -n a t e d f i l te r p a p e r d i s k s . A l t h o u g h t h e f i v e e x t r a c t s r e d u c e d b o t h f e e d i n g a n ds u r v i v a l o f C. brevis, n o s i g n i f ic a n t d i f fe r e n c e s a m o n g t h e m w e r e d e t e c t e d .C h o i c e f e e d i n g t e s t s s h o w e d t h a t t e r m i t e s a v o i d e d e a t i n g t h e p a p e r t r e a t e dw i t h th e e x t ra c t s . T w o f l a v o n o id c o m p o u n d s i s o la t e d fr o m t h e h e a r t w o o d ,e a s t i l le n D a n d c a s t i ll e n E , i m p r e g n a t e d i n t o f i l te r p a p e r s h o w e d c o n c e n t ra -t i o n - d e p e n d e n t f e e d i n g d e t e r r e n t a c t i v i t y , b u t w e r e n o t t o x i c t o C. brevis.K e y W o r d s - - F e e d i n g d e t e r r e n t s , t e r m i t e s , Cryptotermes brevis, l s o p t e r a ,Lonchocarpus castilloi, L e g u m i n o s a e , h e a r t w o o d , f l a v o n o i d s , a n t i t e rm i t i ca c t i v i t y , c a s t il l e n D , c a s t i l le n E .

I NTRODUCT ION

Lonch ocarpus castilloi S t a n d l e y ( L e g u m i n o s a e ) i s a tr e e in d i g e n o u s t o t h e t ro p -i ca l s u b h u m i d fo r e st i n so u t h e r n M e x i c o , C e n t r al A m e r i c a , a n d n o rt h er n S o u t hA m e r i c a . I t c a n r e a ch 3 0 m i n h e i g h t an d 4 0 c m d i a m e t e r a t b r ea s t h e i g h t( O r te g a -E s c a lo n a et a l . , 1 9 9 1 ). I n M e x i c o it i s k n o w n a s " m a c h i c h e . " L o c a l l y ,*T o w h o m c o r r e s p o n d e n c e s h o u l d b e a d d r e s s e d .

4550098-0331/95/0400-0455507.50/0 1995 Plenum Pub lishingConporation


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456 REYES-CHILPA E T A L ,

t h e t i m b e r is u s e d i n b r i d g e s , h o u s i n g , r u ra l w a g o n s , a n d f o r m a n u f a c t u r i n gv e n e e r , p l y w o o d , s t a v e s , a n d p a r q u e t. I t is a l s o r e c o m m e n d e d f o r r a il r o a d c r o s s -t ie s , s t a k e s , f e n c e p o s t s , a n d p o s t c r o s s - a r m s ( E c h e n i q u e - M a n r i q u e , 1 9 70 ).Lonchocarpus cas t i l lo i h e a r t w o o d h a s b e e n r e p o r t e d t o b e v e r y d u r a b l e i na c c e l e r a t e d f ie l d t e s t s ( B~ i r c e n a s - P a z o s , 1 9 9 5 ) ; i t i s a l so h i g h l y r e s i s t a n t t o s e v -e r al w o o d - r o t ti n g fu n g i ( R e y e s - C h i l p a et a l ., 1 9 87 ) a n d t o th e d r y w o o d t e r m i t eC ~ p t o t e r m e s b r e v i s ( W a l k e r ) ( P 6 r e z - M o r a l e s e t a l . , 1 9 8 4) .

C u r r e n t e v i d e n c e i n d i c a t e s t h a t n a t u r a l r e s i s t a n c e t o fu n g i ( L a k s , 1 9 8 8;D 6 o n e t a l . , 1 9 8 0; H a r t a n d S h r i m p t o n , 1 9 7 9) a n d t e r m i t e s (S c h e f f r a h n , 1 9 9 1;M c D a n i e l , 1 99 2) i s p r i m a r i l y d e t e r m i n e d b y t h e c o n c e n t r a t i o n a n d t y p e o f s e c -o n d a r y c o m p o u n d s f o u n d i n t h e h e a r t w o o d . I n th i s c o n t e x t , it h a s b e e n s h o w nt h a t t h e n a t u r a l d e c a y r e s i s t a n c e o f Lonchocarpus cas t i l lo i h e a r t w o o d i s a l s oc h e m i c a l l y d e t e r m i n e d . E x t r a c t io n o f t h e h e a r t w o o d w i th a s e r i e s o f o r g a n i cs o l v e n t s r e d u c e d i ts d e c a y r e s i s ta n c e ( R e y e s - C h i l p a et a l . , 1 9 8 7 ), a n d t h e e x t r a c t ss h o w e d a n t if u n g a l a c t iv i t y in v it r o ( R e y e s - C h i l p a , 1 9 86 ). C h r o m a t o g r a p h i c s e p -a r a t i o n o f t h e h e x a n e e x t r a c t a f f o r d e d f o u r 2 - m e t h o x y f u r a n a u r o n o l s n a m e dc a s t il le n s A , B , C , a n d D , a s w e l l a s o n e a - h y d r o x y - d i h y d r o - c h a l c o n e , c a s t i ll e nE (G 6 m e z - G a r i b a y e t a l . , 1 9 90 ). T h e s e f l a v o n o i d c o m p o u n d s ( F i g u r e 1 ), i n h ib -i te d th e m y c e l i a l g r o w t h o f th e f u n g u s Lenz i tes t rabea P e t s . e x F t . T h e m o s ta c t iv e c o m p o u n d w a s t h e c a s t i ll e n E , f o l l o w e d b y c a s t il l e n D ( G 6 m e z - G a r i b a ye t a l . , 1990) .

W e n o w h a v e e x a m i n e d t h e e f f e c t o f L. castilloi h e a r t w o o d e x t r a c t s a n d o f

4 I I u , ~ 6 ' s '0 0 M e1 - C as t i l len A : R1 = Rz - H2. - Cast i l len D: R1 + Rz = OCHzO

3. - Cas t i l l en B : R1 = R - H4. - Ca st i l len C : Rt + Rz = OCH zO

o H L O "S , ~ o H ~"

0S .- C a s t i l l e n E

FIG. l . Flav ono ids from Lonchoca rpus castilloi heartwood. C asti l len A (1) , Cas ti l len D(2), Casti l len B (3) , Casti l len C (4) , and Casti l len E (5) .


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ANTITERMIFIC ACTIVITY OF L . c a s t i l l o i 457

castillens D (2) and E (5) on the feeding and survival of C. brevis. We alsoreport the isolation of two additional compounds, pongaglabrone and 4-hydroxy-benzofuran, from the heartwood.

METHODS AND MATERIALS

Lonchocarpus casti l loi was collected at the "Lacandona" tropical rainforest, Chiapas, Mrxico (B~rcenas-Pazos et al. , 1980). Wood samples andvoucher specimens are deposited at the Ecology Institute's Herbarium (Xal) inXalapa, Mexico.

Termite Collection. Cry.ptotermes brevis termites were obtained from oldbeams in Xalapa City. The beams were sawed and stored under controlledconditions (23C, 75% relative humidity) until employment, and bioassays alsowere conducted under these conditions. Beam pieces were split on a paper;termites were taken up with entomological tweezers. Only active pseudergatesabove the third instar were used for bioassays. Selection of active specimenswas done as follows. A group of 40 pseudergates was placed inside a 50-mlbeaker, and that beaker was placed perpendicular to another. The first 30 ter-mites that passed to the second beaker were chosen (Prrez-Morales et al. , 1984).

Wood Block Bioassays. Sapwood and heartwood blocks (2 x 1 z 0.5 cm,smallest dimension being parallel to the fiber) were cut from a board. The blockswere carefully sand-papered, oven dried (105C, 24 hr), and weighed. Heart-wood blocks were successively extracted in a Soxhlet apparatus with hexane,diethyl ether, acetone, methanol, and water. After each extraction step (10 hr),an equal number of blocks were removed. Extractive yields were calculated asthe percentage of oven-dried weight loss (Table 1).

Sapwood and heartwood (extracted and unextracted) blocks were testedagainst C. brevis. Each block was placed in a glass vial with 30 pseudergates.The vials were capped with filter paper. Each treatment was replicated fivetimes. Mortality was recorded periodically, and the wood consumption wasdetermined at the end of the test period (seven weeks) as the percentage of oven-dried weight loss.

Filter Pa pe r Bioassays. Lo nch ocarp us casti l loi heartwood shavings(500 g) were extracted under reflux with the same sequence of solvents describedpreviously. The extracts were concentrated in a rotary evaporator and freeze-dried when the solvent was water. Solutions (2.5% w/v) of each extract wereprepared in order to impregnate filter paper disks. This concentration was chosensince 2% was the mean extractive yield from blocks. Hexane and diethyl etherextracts were dissolved in a mixture of hexane-ethy l acetate 1 : 1 (HE), andacetone and methanol extracts were dissolved with a mixture of acetone-meth-


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45 8 REYES-CHILPA ET AL.

anol 70:30 (AM). Each solution was poured into a Petri dish, and filter paperdisks (Whatman No. 1, diameter = 7 cm) were dipped for 30 sec and then airdried. Impregnated disks were then placed in a hood for 12 hr. Control diskswere treated with the solvent mixtures only.

Two bioassays were run with the impregnated filter paper: (1) For forcefeeding, a disk was placed into a Petri dish and 15 termites were added. (2) Forthe choice test, one disk of each treatment, including the AM control, wassectioned into six equal slices. A slice of each treatment was then fixed to thebottom of a Petri dish (Figure 2) with a bit of "Blue Tac" plaster (Williams,1980) and 15 termites were added. Five replicates per test were run. Mortalitywas recorded periodically. Paper consumption was quantified at the end of thetest (36 days).

Isolation of Compounds. Heartwood shavings (650 g) were extracted atroom temperature with hexane and then with methylene chloride. After concen-tration, the methylene chloride extract was chromatographed over silica gel. Thecompounds were obtained by preparative TLC and identified by ~H NMR, ~3CNMR, IR, UV, and MS.

Castillens D and E were tested using impregnated filter paper and followingthe force-feeding protocol. The solutions tested were 0.025, 0.05, 0.1, and0.15% w/v with acetone as solvent. Control paper disks were treated with thesolvent only.

FIG. 2. Choice test. Feeding of termites on filter paper impregnated with hexane (hx),diethyl ether (et), acetone (ac), methanol (me), or water (ag) extracts of Lonchocarpuscastilloi heartwood. Control disks (c) treated only with a mixture of acetone-methanol(7:3).


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ANTITERMITIC ACTIVITY OF L. castilloi 459

RESULTS

Extracted Wood. Cryptotermes brevis p s e u d e r g a t e s a te o v e r si x t i m e s m o r eo f Lonchocarpus casti l loi f u l ly e x t r a c t e d h e a r t w o o d b l o c k s t h a n o f t h e s o u n dh e a r t w o o d ( T a b l e 1 ). T h e m o s t e f fi c ie n t s o l v e n t t ha t re n d e r e d h e a r t w o o d m o r es u s c e p t i b l e w a s m e t h a n o l a n d t h e n w a t e r . H e a r t w o o d b l o c k s s u c c e s s i v e l ye x t ra c t e d w i t h h e x a n e , d i e t h y l e th e r , a n d a c e t o n e w e r e e a t e n e q u a l l y w h e n c o m -p a r e d w it h s o u n d h e a r t w o o d . T e r m i t e s c o n s u m e d 1 .7 t im e s m o r e o f e x t ra c t e dh e a r t w o o d b l o c k s t h a n s a p w o o d . S a p w o o d s e e m e d a l s o t o b e e a t e n m o r e t ha ns o u n d h e a r t w o o d , b u t th e d if f e r e n c e w a s n o t si g n if i ca n t w h e n e x a m i n e d b yA N O V A ( T a b l e 1 ); n e v e r t h e l e s s , i t w a s s i g n if ic a n t ( P = 0 . 0 0 1 ) b y S t u d e n t ' s tt es t. A t t h e e n d o f t h e t e s t p e r i o d , t e r m i t e s u r v i v a l w a s s i m i l a r a m o n g a l l t r e a t-m e n t s ( T a b l e 1 ) .

Effects of Extracts. A l l t h e h e a r t w o o d e x t r a c t s i n c o r p o r a t e d i n to f il te r p a p e rr e d u c e d b o t h t h e p a p e r c o n s u m p t i o n a n d t h e s u r v i v a l o f t e r m i t e s ( T a b l e 2 ). N os i g n if i c a n t d i f f e r e n c e s a m o n g t h e e x t r a c t s w e r e d e t e c t e d . O n a v e r a g e , t h e r e w a sa f iv e f o ld r e d u c t io n in c o n s u m p t i o n w h e n t h e tr e a t m e n t s w e r e c o m p a r e d w i t ht h e c o n t r o l ; t h e re w a s a l s o a t w o f o l d r e d u c t i o n in t e r m i t e s u r v i v a l . T h e a b o v ed a t a s u g g e s t e d t h a t a l l t h e e x t r a c t s c o n t a i n e d a n t i t e r m i t i c c o m p o u n d s .I n t h e c h o i c e f e e d i n g t es t , p s e u d e r g a t e s c o n s u m e d o n l y th e c o n t ro l a n da v o i d e d a l l t h e f il te r p a p e r s l i c e s t r e a te d w i t h t h e h e a r t w o o d e x t r a c ts ( F i g u r e 2 ).S u r v i v a l in th i s te s t w a s s i m i l a r to t h a t d e p i c t e d f o r c o n t r o l s in th e f o r c e - f e e d i n ge x p e r i m e n t ( s e e T a b l e 2 ) .

Compounds Isolated. T L C o f th e h e x a n e e x t ra c t o f L. castilloi h e a r t w o o ds h o w e d t he p r e s e n c e o f ca s t il le n s A , B , C , D , a n d E a s c o m p a r e d w i t h a u th e n t ic

TABLE 1. FEEDING AND SURVIVAL OF C~_ptotermes brevis PSEUDERGATES ON L.castilloi WO OD AFTER47-DAY EXPOSURE"Extrac tive y ie lds C o n su m p t i o nTreatment (% w/w ) (% w eig ht loss) Survivors

Sapw ood 1.77a 9.0aHeartwood 0.52a 7.8aExtracted heartwoodHexane 2.79 0.61 a 6.0aEthe~ 0.36 0.87a 6.2aAcetone 2.28 0.40a 5.8aMethanol 3.84 2.17b 6.6aW ater ' 0.76 3.16b 11.5a"M eans (N = 5") using 30 termites per replicate. N umb ers followe d by s am e letter are not signifi-cantly different at P > 0.05 (D uncan's NMRT").hN = 4.


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460 REYES-CHILPA ET AL.

T A B L E 2 . F E E D I N G A ND S U R V I V A L O F C~.p to termes brev i s P S EU D E R G A T E S O N P A P E RI M P R EG N A T E D W I TH H E A R T W O O D E X T R A C T S O F L. cast i l lo i A F T E R 3 6 - D A Y E X P O S U R E "

T r e a t m e n t C o n s u m p t i o n ( m g ) S u r v i v o rsC o n t r o l H A 1 3 . 7 a 1 0 . 4 aC o n t r o l A M 1 4. l a 9 . 8 aH e x a n e 1 . 8 b 4 , 4 bE t h e r 3 . 2 b 4 . 4 bA c e t o n e 2 . 6 b 3 . 8 bM e t h a n o l 4 . 5 b 4 . 4 bW a t e r 3 . I b 4 . 2 b

" M e a n s ( N = 5 ) u s in g 1 5 t e r m i t e s p e r r e p l i c a t e . N u m b e r s f o l l o w e d b y s a m e l e t t e r a r e n o t s i g n i f i -c a n t ly d i ff e re n t a t P > 0 , 0 5 ( D u n c a n ' s N M R T ) .

samp le s . T h e me th y len e ch lo r id e ex t r ac t r en d e red ca s t i l l en D (2 5 mg ) , c a s t i l l enE (4 9 m g ) , p o n g a g l a b r o n e ( 6 m g ) , a n d 4 - h y d r o x y - b e n z o f u r a n ( 1 3 m g ) b y c o l -u m n c h o m a t o g r a p h y a n d p r e p a ra t iv e T L C . C a s t il le n s D a n d E w e r e t h e n c ry s -t a l l i z ed , an d th e sp ec t r a l d a t a f ro m th e p u r i f i ed co mp o u n d s ag reed wi th th o sep r e v i o u s l y r e p o r te d ( G 6 m e z - G a r i b a y e t a l ., 1 9 9 0) .

Castillen D. C o l o r l e ss s ol id , m p 1 2 1 C . 13C N M R ( C D C I 3 , 5 0 M H z ) :1 9 7 . 0 [C = 0 ] , 1 6 6 . 5 [C -6 ] , 1 6 2 . 2 [C - l a ] , 1 47 .1 [C -3 ' ] , 1 4 6 . 4 [C -4 ' ] , 1 4 5 . 6[C -o ~ ], 1 2 6 . 4 [C - I ' ] , 1 2 3 . 8 [C -4 ] , 1 1 9 . 7 [C - 6 ' ] , 1 1 5 . 2 [C -3 a ] , 1 1 3 . 3 [C -7 ] ,1 1 0 . 9 [C -5 ' ] , 1 10 .1 [C -2 ] , 1 0 7 . 7 [C -2 ' ] , 1 0 7 . 2 [C -/3 ], 1 0 3 . 7 [C -5 ] , 1 0 0 . 7[ O C H 2 0 ] , 5 2 .5 [ O C H 3 ] , 4 1 . 0 [ A r -C H 2 ] .

Castillen E. C o l o r l e s s s o l id , c r y s t a l l y z e d f r o m d i e th y l e t h e r, m p 7 2 - 7 3 C .13C N M R (C D C I3 , 5 0 M H z) : 2 0 4 . 5 [C = 0 ] , 1 5 9 . 4 [C -4 ' ] , 1 4 4 . 8 [C -o ~ ] , 1 36[C -2 ' ] , 1 3 0 . 8 [C -6 ' ] , 1 2 9 . 4 [C -3 ] , 1 2 8 . 8 [C -5 ] , 1 2 8 . 4 [C -2 ] , 1 2 6 . 9 [C -6 ] , 1 2 5 . 5[C -4 ] , 11 8.1 [ C - l ] , 1 1 2 . 3 [C - I ' ] , 1 1 1 .1 [C -3 ' ] , 1 0 5 .1 [C-/3 ], 1 0 4 . 5 [C -5 ' ] , 7 7 . 8[ C - ~ ' l , 4 2 . 9 [ C - / 3 ' ] .

P o n g a g l a b r o n e ( K h a n n a a nd S e s h a d r i, 1 9 6 3) a n d 4 - h y d r o x y - b e n z o f u r a nwere a l so o b ta in ed a s so l id s an d id en t i f i ed b y th e i r sp ec t r a l d a t a .

Effects of Castillens D and E. C o n s u m p t i o n b y t e rm i t e s o f fi lt er p a p e ri m p r e g n a t e d w i t h c a s ti ll e n D d e c r e a s e d a s th e c o n c e n t r a t i o n o f t hi s c o m p o u n din c rea sed (T ab le 3 ) . T h e h ig h es t co n c en t r a t io n t e s t ed (0 . 1 5 % w/v ) c au sed a 3 . 7 -f o ld r e d u c t io n i n t h e a m o u n t o f p a p e r e a te n a s c o m p a r e d t o th e c o n t r o l . S u r v i v alo f t e rmi t e s w as n o t a f fec t ed b y an y co n cen t r a t io n o f c a s t il l en D t e s ted .

S im i l a r r e su lt s we re o b ta in ed wi th ca s t i ll en E (T ab le 4 ) . I n t h is c a se , t h e0 . 1 5 % t r e a t m e n t c a u s e d a 2 . 6 - f o l d r e d u c t i o n i n p a p e r c o n s u m p t i o n . S u r v i v a l o ft e rmi t e s was n o t a f f ec t ed a t an y co n cen t r a t io n t e s t ed .

S in ce sma l l amo u n t s o f c a s t il l en C , an d a m ix tu re o f c a s t i ll en s A an d B


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ANTITERMITIC ACTIVITY OF L. casti l loi 4 6 1T A B L E 3 . F E E D IN G A N D S U R V I V A L O F C~ptotermes brev i s P S E U D E R G A T E S O N P A P E R

I M P R EG N A T E D W IT H C A S T I L LE N D A F T ER 2 8 - D A Y E X P O S U R E "

T r e a t m e n t C o n s u m p t i o n ( r ag ) S u r v i v o r sC o n t r o l 9 . 4 a 1 4 . 8 a0 . 0 2 5 % 7 . 4 a c 1 3 , 8 a0 . 0 5 0 % 4 . l b c 1 3 . 2 a0 . 1 0 0 % 3 . l b 1 3 . 6 a0 . 1 5 0 % 2 . 5 b 1 4 .4 a

" M e a n s ( N = 5 ) u s i n g 1 5 t e r m i t e s p e r r e p l ic a t e . N u m b e r s f o l l o w e d b y t h e s a m e l e t t er a r e n o ts i g n i f i c a n t l y d i f f e r e n t a t P > 0 . 0 5 ( D u n c a n ' s N M R T ) ,

T A B L E 4 . F E E D IN G A N D S U R V I V A L O F Crypto termes brev i s P S E U D E R G A T E S O N P A P E RI M P R EG N A T E D W I TH C A S T IL L E N E A F TE R 2 8 - D A Y E X P O S U R E "

T r e a t m e n t C o n s u m p t i o n ( r ag ) S u r v i v o r sC o n t r o l 1 4 . 6 a 1 1 . 8 a0 . 0 2 5 % 1 3 . 3 a 1 2 .0 a0 . 0 5 0 % 1 6 . 2 a 1 3 . 2 aO , 1 0 0 % 7 . 0 b 1 0 . 6 a0 . 1 5 0 % 5 . 5 b 1 1 .0 a

" M e a n s ( N = 5 ) u s i n g 1 5 t e r m i t e s p e r r e p l ic a t e . N u m b e r s l b l l o w e d b y s a m e l e tt e r a r e n o t s i g n i fi -c a n t l y d i f f e r e n t a t P > 0 . 0 5 ( D u n c a n ' s N M R T ) ,

w e r e a v a i l a b l e , th e s u b s t a n c e s w e r e a l s o t e s t e d a t t l, e l o w e r c o n c e n t r a t i o n( 0 . 0 2 5 % w / v ) f o l lo w i n g t he f o r c e - f ee d i n g p r o t o c o l. N e i th e r p a p er c o n s u m p t i o nn o r s u r v i v a l o f t e r m i t e s w a s s i g n i fi c a n t l y d i ff e r e n t f r o m c o n t r o l s .

D I S C U S S I O N

T h e h e a r t w o o d o f Lonchocarpus castilloi c o n t a i n s a n t i t e r m i t i c c o m p o u n d sto Cry.ptotermes brevis p s e u d e r g a t e s . T h e s e c o m p o u n d s w e r e e x t r a c t e d w i t h f o u ro r g a n i c s o l v e n t s a n d w a t e r a s i n d i c a t e d b y t h e f o r c e - f e e d i n g t e s t w i t h i m p r e g -na ted fi lt er pa per (Ta bl e 2 ) . A t the co n cen tra t i o n t e s t ed , a l l the ex tra c t s w eree q u a l ly e f f e c t i v e . S i m i la r r e s u lt s h a v e b e e n r e p o r t e d f o r o t h e r t r o p i c a l h a r d w o o d s(C a r te r a n d d e C a m a r g o , 1 9 8 3 ; C a r t e r e t a l . , 1 9 7 5 ) . F e e d i n g - d e t e r r e n t a c t i v i t y ,b u t n o t t o x i c i ty , w a s d e t e c t e d f o r t h e p r e v i o u s l y k n o w n f u n g i s ta c t ic f l a v o n o i d s( G 6 m e z - G a r i b a y e t a l . , 1 9 9 0 ) , t h e c a s t il le n s D a n d E (T a b l e s 3 a n d 4 ) . T h e s e


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4 6 2 R E Y E S - C H I LP A ET A L .

c o m p o u n d s c o u l d b e r e m o v e d b y h e x a n e a n d o t h e r n o n p o l a r s o lv e n t s ; n e v e r -t h e l e ss , r e d u c t i o n o f t h e h e a r t w o o d t e r m i t e r e s i s t a n c e w a s o n l y n o t e d a f t e re x t r a c t i o n w i t h m e t h a n o l a n d w a t e r ( T a b l e 1). T h e a b o v e r e su l ts s u g g e s t s t h ato t h e r c o m p o u n d s c o u l d b e d i re c t ly i n v o l v e d i n L . c a s t i U o i t e r m i t e r e s i s t a n c e o rc o u l d p l a y a s y n e r g i s t i c r o l e .

B e s i d e s c a s t il le n s D a n d E , o t h e r f l a v o n o i d s h a v e b e e n p r e v i o u s l y t e s te da g a i n s t t e r m i t e s ( S c h e f f r a h n , 1 9 9 1 ; S u p r i a n a , 1 9 8 3) . S e v e r a l f l a v o n o i d s w e r ea b l e t o r e p e l l C . b r e v i s a t ta c k w h e n i m p r e g n a t e d i nt o a h ig h l y s u s c e p t i b le w o o d( W o l c o t t, 1 9 53 ). M o s t o f t h e m s h o w e d p o o r a c t i v it y , b u t t a x i fo l i n a n d p o m i f e r i nw e r e c o n s i d e r e d o u t s ta n d i n g . F o r in s ta n c e , t r e a t m e n t w i t h 0 . 0 5 , 0 . 1 0 , o r 0 . 2 %t a x i f o li n s o l u t i o n s f o r 1 0 m i n w a s e n o u g h t o p r o t e c t s u s c e p t i b l e w o o d f o r t w oy e a r s ( W o l c o t t , 1 9 5 3 ). R o t e n o n e , a w e l l - k n o w n in s e c t i c i d a l i s o f l a v o n o i d , w h i c hc a n b e i s o la t e d f r o m t h e ro o t s o f s e v e r a l l e g u m e s p e c i e s , h a s a l s o b e e n f o u n dt o b e t o x i c a n d to d e t e r th e f e e d i n g o f s u b t e r r a n e a n t e r m i t e s C o p t o t e r m e s f o r -m o s a n u s S h i r a k i ( K ~e ~k ov ~i e t a l . , 1 9 8 8 ) . A f z e l i n a l so h a s b e e n r e p o r t e d t o b et o x i c t o H e t e r o t e r m e s i n d i c o l a W a s m a n n ( S u p r ia n a , 1 9 83 ). A t p r e s e n t, h o w e v e r ,f l a v o n o i d s s e e m t o b e m o r e i n v o l v e d i n t h e r e s i st a n c e o f w o o d t o f u n g i t h a n t ot e rm i t e s . A n t i fu n g a l p r o p e rt ie s o f m o n o m e r i c a n d p o l y m e r i c w o o d f l a v o n o i d sa r e d o c u m e n t e d ( D 6 o n e t a l . , 1 9 8 0 ; H a r t a n d H i l l i s , 1 9 7 2) . O n th e o t h e r h a n d ,a n t it e rm i t ic c o m p o u n d s i d en t if ie d f r o m w o o d h a v e b e e n f o u n d t o b e p r e d o m i -n a n t ly t e r p e n o i d s ( f r o m m o n o t e r p e n e s t o t r i t e r p e n e s ) , a l i p h a t ic a c i d s , n a p h t h o -a n d a n th r o q u i n o n e s , s i m p l e q u i n o n e s , s t il b e n e s a n d , n a p h t h o p y r a n s ( S c h e f f ra h n ,1 9 91 ) . T h e r e f o r e , in t h e c a s e o f L . c a s t i l l o i h e a r t w o o d r e s i s t a n c e t o C . b r e v i s ,i t s e e m s p r o b a b l e t h at b e s i d e s t h e f e e d i n g d e t e r r e n t s c a s t i ll e n D a n d E , o t h e ra c t i v e c o m p o u n d s , p r o b a b l y o f a n o n f l a v o n o i d n a t u r e , r e m a i n to b e i d e n ti f ie d .

Acknowledgments--R.R.C. and N .V.R. thank Dr. R aym undo D~ valos Sotelo for his supportwhile carrying on this work.

REFERENCESBARCENAS-PAZOS,G.M . 1995. Caracterizaci6n tecnol6gica de veinte especies m aderables de IaSelva Lacandona. Madera y Bosques (Mexico) I ( 1 :9-38.BARCENAS-PAZOS,G.M ., REJON, R .R ., and ECHENIQUE-MANRIQUE,R. 1980. Especies Maderablesde la Selva Lacandona. La M adera y su Uso en la Construcci6n No. 6. IN IRE B, Xalapa,M 6xico, 18 pp.CARTER, F .L ., and OE CAMARGO,C.R.R . 1983. Testing antitermitic properties of Brazilian woo dsand their extracts. Wood Fib. Sci. 15(4):350-357,CARTER, F.L., BEAL,R .H .. and BULTMAN. .D. 1975. Extraction o f antitermitic substances from23 tropical hardwoods. Wood Sci . 8(1):406-410.Dt~ON, G., CHADENSON, M., and HAUTEVILLE,M. 1980. Influence des extraits naturels du bo is sursa r6sistance a la pourriture. Bois For. Trop. 191:75-90.


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ANTITERMITIC ACTIVITY OF L . c a s t i t l o i 4 6 3

E CH EN IQ U E-M A N RIQ U E. R . 1 9 7 0 . D e s c r i p c i d n , C a r a c t e f f s t i c a s y U s o s d e 25 M a d e r a s T r o p i c a l e sM e x i c a n a s . S e r ie M a d e r a s d e M ~ i co . B i b l i o t e c a d e l C o n s t r u c t o r N o , 5 . C A N A I C , M e x i c o .2 3 7 p p .

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H A R T , J H . , a n d H I L LIS , W . E . 1 9 7 2 . I n h i b i t i o n o f w o o d - r o t t i n g f u n g i b y e l l a g i t a n n i n s i n t h e h e a r t -w o o d o f Quercus albo. Phytopathology 6 2 : 6 2 0 - 6 2 6 .

H A R T , J . H , a n d S H RIM PT ON , D . M . 1 9 7 9 . R o l e o f s ti l b e n e s i n re s i s t a n c e o f w o o d t o d e c a y . Phy-topathologr 6 9 : 1 1 3 8 - 1 1 4 3 .

K HA NN A R . N . , a n d S E S H A Dm , T . R . 1 9 6 3 . P o n g a g l a b r o n e , a n e w c o m p o n e n t o f t h e s e e d o f P o n -gamia glabra i ts c o n s t i t u t i o n a n d s y n t h e s i s . Tetrahedron 1 9 : 2 1 9 - 2 2 5 .

KREC~KOVA, J . , KRE( 'EK, J . . an d HARMATHA, J . 1988 . Fe ed ing de te r r e n t a c t iv i ty o f cer t a in p lan ts u b s t a n c e s a g a i n s t s u b t e r r a n e a n t e r m i t e Copto termes formosanus ( R h i n o t e r m i t i d a e ; I s o p t e r a ) ,i n F . S e h n a l , A . Z a b z a , a n d D . L . D e n l i n g e r , ( e d s. ). E n d o c r i n o l o g i c a l F r o n t ie r s in P h y s i o l o g -i c al I n s e c t E c o l o g y . W r o c l a w T e c h n i c a l U n i v e r s i ty P r e s s, W r o c l a w , p . 1 0 5 - 1 0 7 .

L A K S, P . E . 1 9 88 . W o o d p r e s e r v a t i v e a s tr e e s d o i t . Am . Wood Pres. Assoc. 1 9 8 8 : 1 4 7 - 1 5 5 .M C D A N IE L , C . A . 1 9 9 2 . M a j o r a n t i t e r m i t i c c o m p o n e n t s o f t h e h e a r t w o o d o f s o u t h e r n c a t a l p a . J .

Ch em. Eco L 1 8 ( 3 1 : 3 5 9 - 6 3 9 .ORTEGA-ESCALONA. F. , CASTILLO-MORA LES, 1 . , an d CARMONA-VALDOVINOS, T. 1991. A na to m /a

d e l a m a d e r a d e v e i n t i s e i s e s p e c i e s d e l a S e l v a L a c a n d o n a , C h i a p a s . L a M a d e r a y s u U s o ,V o l . 2 6 . ln s t i tu t o d e E c o l o g i a A . C . - U n i v e r s i d a d A u t 6 n o m a M e t r o p o li t a n a , X a l a p a , M ~ x i c o ,2 0 0 p p .

PI~REz-MORALES, V . . SEGURA-WARNHOLTZ, G . an d BRUNHUBER-MENENDEZ, J .L . 1984 . R es is t en ci an a t ur a l d e 18 e s p e c i e s d e m a d e r a s m e x i c a n a s c o n t ra e l a t a q u e d e t e r m i t a s d e m a d e r a s e c a ,Cryptotermes brevis ( W a l k e r ) , ( K a l o t e r m i t i d a e , I s 6 p t e r a ) . M e m o r i a s d e l C o n g r e s o M e x i c a n od e P a to l o g / a F o r e s t a l, S e p t e m b e r 2 6 - 2 9 , 1 9 84 . D u r a n g o , M 6 x i c o .

R E Y ES -C m L PA , R . 1 9 8 6 . L o s m e t a b o l i t o s s e c u n d a r i o s e n l a r e s i st e n c i a n a t u r a l d e {a m a d e r a a l ap u d r i c i 6 n : N u e v o s f l a v o n o i d e s f u n g i s t~ i ti c o s a i s l a d o s d e l_zmchocarpus castilloi. M S c t h e s i s .I N I R E B , X a l a p a , M 6 x i c o . 9 5 p p .

REYES-CHILPA, R. . PI~REZ-MORALES, V. an d DEL ANGEL-BLANCO, S. 198 7. In f lu en cia de lo s extr ac -t i r o s e n l a r e s i s t e n c i a n a t u r a l d e s e i s m a d e r a s t r o p i c a l e s al h o n g o d e p u d r i c i 6 n m o r e n a Lenz.itestrabea. B i 6 t ic a (M 6 x i c o ) 1 2 ( 1 ) : 7 - 1 3 .

SC HE FFR AH N, R . H 1 99 1. A l l e l o c h e m i c a l r e s is t a n c e o f w o o d t o t e r m i t e s . Sociobiology 1 9 ( 1 ] : 2 5 7 -2 8 1 .

S UP RIA N A. N . 1 9 8 3 . P r e l i m i n a r y t e s t s o n t h e e f f e c t o f n a t u r a l l y o c c u r r i n g c h e m i c a l s o n t e r m i t e s .I R G / W P / 1 1 8 1 . F o u r t e e n th A n n u a l M e e t i n g o f th e I n te r n a ti o n a l R e s e a r c h G r o u p o n W o o dP r e s e r v a t i o n . A u s t r a l i a , M a y 1 9 8 3 . I I p p .

W IL LIA M S, R . M . C . 1 9 8 0 . A v i s i t t o M e x i c o t o a d v i s e o n t h e t e r m i t e r e s e a r c h p r o g r a m e a t I N I R E B( L A C I T E M A I X a l a p a, V e r a c ru z . N o v e m b e r 7 - 2 9 , 1 98 0. R e p or t C V R / 8 1 / 5 . M a n u s c r ip t o fl i m i t e d d i s t r i b u t i o n . C e n t r e f o r O v e r a s e a s P e s t R e s e a r c h , L o n d o n , 1 7 p p .

W O L C O T r, G . N . 1 95 3. S t i l b e n e a n d c o m p a r a b l e m a t e r i a l s f o r d r y w o o d t e r m i t e c o n t r o l . J. Eeon.Entomol. 4 6 ( 2 1 : 3 7 4 - 3 7 5 .

antitermitic activity of lonchocarpus castilloi

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