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(12) Patent Application Publication (10) Pub. No.: US 2004/0058818A1 Li (43) Pub US 200400.5881.8A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0058818A1 Li (43) Pub. Date: Mar. 25, 2004 (54) SYSTEM FOR INCREASING THE (60) Provisional application No. 60/161,460, filed on Oct. PRODUCTION OF CAMPTOTHECIN FROM 25, 1999. PLANTS Publication Classification (76) Inventor: Shiyou Li, Nacogdoches, TX (US) (51) Int. Cl." ........................... A01N 25/00; AO1B 79/02 Correspondence Address: (52) U.S. Cl. ..................................... 504/116.1; 47/58.1 R Alan R. Thiele (57) ABSTRACT JENKENS & GILCHRIST The present invention provides a System for increasing the 3200 Fountain Place production of indole and quinoline alkaloids, particularly 1445 ROSS Avenue camptothecins and related compounds, in plants, based upon Dallas, TX 75202-2799 (US) management of plant hormones. This invention includes a System and a method for accelerating the growth of young (21) Appl. No.: 10/670,930 tissues, inducing the production of camptothecins-bearing glandular trichomes, maximizing the harvest of glandular (22) Filed: Sep. 25, 2003 trichomes, and preserving and treating the glandular tri chomes for maximum camptothecins yield. The present Related U.S. Application Data invention is useful for any plant matters containing alka loids, regardless of the plant matters genetic origin, natural (63) Continuation of application No. 09/696,042, filed on or cultivated variety, and natural or cultivated growing Oct. 25, 2000. conditions. Patent Application Publication Mar. 25, 2004 Sheet 1 of 37 US 2004/0058818A1 1 R=R=H, R=OH 10 2 R=R=OH, R=H 3 R=OCH R=H.R=OH 4 R=H, R=R=OH 5 R=H, R=OCH R=OH 6 R=R=R=H 7 R=R=H, R=O(CH2)CH 8 R=OCH R=H, R=O(CH2)CH Diagrams of the chemical structures of major natural camptothecin and its analogs in Camptotheca acuminata: camptothecin (1), 10-hydroxycamptothecin (2), 10 methoxycamptothecin (3), 11-hydroxycamptothecin (4), 11 methoxycamptothecin (5), 20-deoxycamptothecin (6), 20 hexanoylcamptothecin (7), 20-hexanoyl-10 methoxycamptothecin (8), 22-hydroxyacuminatine (9), 19 hydroxymappicine (10), 19-O-methylangustoline (11), and vincoside-lactam (12). Fig. 1. Patent Application Publication Mar. 25, 2004 Sheet 2 of 37 US 2004/0058818A1 Intermediate Tissue Leaf Definition 1-4 week old CPT% (fw) 0.02.2450- 0.00135 Stem Definition = 2 year old CPT % (fw) 0.00795 - 0.00036 Stem Wood Definition = 2 year old CPT % (fw) 0.00309 - 0.00007 0.00566 0.00027 Note: Shiyou Li, et al. unpublished. CPT distribution in different tissues of Camptotheca acuminata (Seed source: SFA 94-03; leaf, stem, and root materials were collected in May, wood and bark samples were collected in August and fruit samples were collected in June, August, and October, respectively) (mean + S.d.) (on the basis of fresh weight). Fig. 2 Patent Application Publication Mar. 25, 2004 Sheet 3 of 37 US 2004/0058818A1 a. Top Scanning electron micrograph of surface view of lower leaf epidermis of Camptotheca Lowreyana Katie' Scale Bar = 100 um. b. Bottom) Scanning electron micrograph of mature glandular trichome (GT) on lower leaf surface of Camptotheca Lowreyana Katie'. Scale Bar - 5um. Fig. 3 Patent Application Publication Mar. 25, 2004 Sheet 4 of 37 US 2004/0058818A1 Average Average Average Glandular Young Leaves Old Leaves Species/Variety Glandular trichome Density CPT Concentration CPT Concentration trichome length trichome width (um) (% s.d.) (% + s.d.) un cauma 34.87 - 3.92 13.64 - 1.97 46.80 E 5.26 0.05822 - 0.01654 0.016 07 at 0.00204 yunnanensis 35.20 - 2.70 13.72 it 1.27 27.10 - 1.40 0.05443 - 0.01499 0.1308 - 0.002.7 Yalal 46.49 4.5 10.94 - 1.42 81.50 - 6.50 0.084.23 - 0.01541 0.020210,0321 lowreyana 42.46 - 3.34 14.64 - 1.68 65.50 E 10.41 0.10641 - 0.01612 0.0274 - 0.00167 "Katie' 56.32 it 6.72 4.02 - 1.87 69.20 - 14.45 0.12284 + 0.01089 0.02632 + 0.00278 "Hicksii' Note: Shiyou Li, et al. unpublished. Glandular trichome size and density on lower leaf surfaces and CPT concentration in leaves of Camptotheca (on the basis of fresh weight.) Fig. 4 Patent Application Publication Mar. 25, 2004 Sheet 5 of 37 US 2004/0058818A1 COOH COOH N NH 2 -------ee-ee-o-o-o-o-o-wo- Cu?N tryptophanH (Trp) Route A H Indoleacetic acid (IAA) tryptamine N NH 21 O-glucose N - O CHOC StrictOsidine Camptothecin (CPT) Diagram of two biosynthetic pathways showing tryptophan (TRP) as a biosynthetic precursor for both indoleacetic acid (Route A for stimulating growth) and camptothecin (Route B for inhibiting growth). Fig. 5 Patent Application Publication Mar. 25, 2004 Sheet 6 of 37 US 2004/0058818A1 W. Photograph of C 2 tothec 2 l O W e 22. "Katie Fig. 6 Patent Application Publication Mar. 25, 2004 Sheet 7 of 37 US 2004/0058818A1 Drawing of a Camptotheca leaf after leaf-tip pinching. Fig. 7 Patent Application Publication Mar. 25, 2004 Sheet 8 of 37 US 2004/0058818A1 control before pruning second pruning third pruning fourth pruning first harvest 1. Drawing of a Camptotheca Seedling T-pruning treatments and control. Fig. 8 Patent Application Publication Mar. 25, 2004 Sheet 9 of 37 US 2004/0058818A1 Drawing of the leaf-tip pinching technique as applied in Camptotheca. Fig. 9 Patent Application Publication Mar. 25, 2004 Sheet 10 of 37 US 2004/0058818 A1 Patent Application Publication Mar. 25, 2004 Sheet 11 of 37 US 2004/0058818A1 quºu?e3.J.L.Quoqo?I Patent Application Publication Mar. 25, 2004 Sheet 12 of 37 US 2004/0058818A1 Treatment I Treatment II Control (cm) (30 cm) (40 cm) Before treatment (March 25, 1997) 52.61 - 544 52.15 3.57 50.72 - 6.12 After treatment (March 25, 1997) 52.61 - 5.44 30.00 - 0.00 40.00 - 0.00 Net Growth (March 25-July 12, 1997) 40.10+ 8.86 a 39.599.73 a 32.93 - 7.82 b Net Growth (July 12-Sept. 13, 1997) 19.52 - 11.39 a 31.87+ 8.41 b 32.00 - 9.52 b Mean height growth of plants with different T-pruning treatments (mean + s.d.) (means with the same letter are not significantly different at O=0.05). Fig. 12 Patent Application Publication Mar. 25, 2004 Sheet 13 of 37 US 2004/0058818A1 Treatment I Treatment II Control (30 cm) (40 cm) Before treatment (March 25, 1997) 1.03 + 0.17 1.04 - 0.27 1.03 - 0.17 After treatment (March 25, 1997) 1.03 + 0.17 1.00 0.00 OO at 0.00 July 12, 1997 10.143.06 a 10.21 it 3.60 10.04 - 3.16 Sept. 13, 1997 - - 10.56 - 3.34 a 17.00 - 5.82 b 16.33 - 5.21 b Mean branch number of plants with different T-pruning treatments (mean -- s.d.) (means with the same letter are not significantly different at o=0.05). Fig. 13 Patent Application Publication Mar. 25, 2004 Sheet 14 of 37 US 2004/0058818A1 Camptotheca acuminata Monthly Biomass Production of intact Young Tissues -Control - T-Pruning ea 92 t d S s E 9. March April May June July Aug Sept Oct Nov Month Graph of the monthly biomass production of intact young tissues with and without T-pruning Fig. 14 Patent Application Publication Mar. 25, 2004 Sheet 15 of 37 US 2004/0058818A1 Treatment I Treatment II Control (30 cm) (40 cm) CPT Content (%) 1.0164 - 0.00141 a 0.0351 - 0.0020 b .0437 - 0.0037 c Effects of T-pruning treatments on CPT contents (%) of intact young tissues of Camptotheca acuminata (mean E s.d.) (means with the same letter are not significantly different at or=0.05) (samples were collected on June 20, 1998) (fresh weight). Fig. 15 Patent Application Publication Mar. 25, 2004 Sheet 16 of 37 US 2004/0058818A1 Camptotheca acuminata Effect of Pinching on CPT Concentration Whole Plant SS O ho d () O U) H al d 3 4. 5 Days after Pinching Graph of the effect of pinching on CPT concentration in the whole plant of Camptotheca acuminata. Fig. 16a Patent Application Publication Mar. 25, 2004 Sheet 17 of 37 US 2004/0058818A1 Camptotheca acuminata Effect of Pinching on CPT Concentration intact Young Tissues a S. 9. wd t ed C O 9 H U 3 4. 5 Days after Pinching Graph of the effect of pinching on CPT concentration in intact young tissues of Camptotheca acuminata. Fig. 16b Patent Application Publication Mar. 25, 2004 Sheet 18 of 37 US 2004/0058818 A1 Camptotheca acuminata Effect of Pinching on CPT Yield Whole Plant G E. O o d He f 9 3 4 5 Days after Pinching Graph of the effect of pinching on CPT yield on the whole plant in Camptotheca acuminata. Fig.16c Patent Application Publication Mar. 25, 2004 Sheet 19 of 37 US 2004/0058818A1 Camptotheca acuminata Effect of Pinching on CPT Yield Intact Young Tissues S 9. 9. () und U wd S s O) O ha O 5 9. g X H al C) 3 4. 5 Days after Pinching Graph of the effect of pinching on CPT yield on intact young tissues in Camptotheca acuminata. Fig.16d Patent Application Publication Mar. 25, 2004 Sheet 20 of 37 US 2004/0058818A1 Camptotheca acuminata CPT induction by Pinching TYoung Leaves Relatively Young Leaves SS o t s d C C D o O Days after Treatment Graph of CPT induction by pinching in young leaves and relatively young leaves of Camptotheca acuminata.
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