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Phytochemistry of Camptotheca Decaisne

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Phytochemistry of Camptotheca Decaisne Send Orders for Reprints to [email protected] Pharmaceutical Crops, 2014, 5, (Suppl 2: M9) 163-172 163 Open Access Phytochemistry of Camptotheca Decaisne Shiyou Li* and Ping Wang National Center for Pharmaceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen F. Austin State University, Nacogdoches, TX 75962, USA Abstract: To date, chemical investigations of the genus Camptotheca have been primarily focused on C. acuminata. Total 78 compounds have been isolated from the species, including alkaloids (1-28), ellagic acids (29-40), flavonoids (41-46), sterols (47-48), terpenes (49-55), tannins (56-71), polyphenols and fatty acids (65-72), iridoid (73), lignan (74), polyols (75 and 76), amide (77), and sacchardide (78). The contents of camptothecin (CPT, 1), the major active alkaloid varies significantly with Camptotheca species and varieties, tissue and tree age and seasonal changes. Among all taxa of Camp- totheca, C. acuminata var. acuminata has the lowest CPT contents (0.2249-0.3162% in young leaves, and 0.0392- 0.0572% in older leaves). C. lowreyana “Hicksii” has the highest CPT contents in both young and old leaves, approxi- mately 1.5-2 folds higher than those in C. acuminata var. acuminata. Young leaves and mature fruits have high CPT con- tents than other tissues in Camptotheca. In young tissues of C. acuminata var. acuminata, the lowest CPT levels were found in March and April (0.074% and 0.081%, respectively) and highest in June (0.265%). Keywords: Alkaloids, Camptotheca, Camptothecin variations, Camptothecins (CPTs), Ellagic acids, Flavonoids, sterols, Terpenes. CHEMICAL CONSTITUENTS The oxygenated positions may be present either as hydroxyl and methoxy groups or occasionally ester or glucose The report of chemical constituents of Camptotheca has (Table 1). So far 10 quinoline camptothecinoids (3, 5-13) been restricted to C. acuminata. To date, 78 compounds have have been reported by scientists in the United States, been isolated from C. acuminata, including alkaloids (1-28), China, and Japan. 10-hydroxy-20-deoxycamptothecin (3) ellagic acids (29-40), flavonoids (41-46), sterols (47-48), was isolated by Lin and coworkers in 1989 from the fruit terpenes (49-55), tannins (56-71), polyphenols and fatty ac- of C. acuminata and possessed a strong cytotoxicity against ids (65-72), iridoid (73), lignan (74), polyols (75 and 76), P388 leukemia cell [6]. Two new camptothecinoids amide (77), and sacchardide (78) (Fig. 1 and Table 1). 10-methoxy-20-O-acetylcamptothecin (5) and 20--D- glucopyranosyl 18-hydroxycamptothecin (13), together 10- Alkaloids methoxycamptothecin (4), 18-hydroxycamptothecin (8), Camptothecin (CPT, 1), a pyrrolo[3,4-b]-quinoline 20-O-acetylcamptothecin (10) and 20-deoxycamptothecin alkaloid, was first identified from the stem wood of C. acu- (12) were isolated from root bark and leaf of C. acuminata minata in 1966 by Dr. Monroe E. Wall and Dr. Mansukh C. by Zhang et al. in 2004 [2]. Hsu et al. in 1977 [3], and Wani of Research Triangle Institute in systematic screening Lin et al., in 1978, 1979 and 1982 [7-9] isolated 11- of natural products for anticancer drugs [1]. In 1969, Dr. hydroxycamptothecin (6), 11-methoxycamptothecin (7), Wani and Dr. Wall had also first isolated two minor and re- respectively, together with 10-methoxycamptothecin (4) lated components 10-hydroxycamptothecin (10-HCPT, 2) and 20-deoxycamptothecin (12) from the fruit of C. acumi- and 10-methoxycamptothecin (4) by further fractionation of nata. 18-hydroxycamptothecin (8) was also found from the the stem wood of C. acuminata. Compounds 1 and 2 were fruit of C. acuminata [10]. Two minor camptothecinoids also found to occur in other plant parts, including leave [2], 20-hexanoylcamptothecin (9), 20-hexanoyl-10-methoxyca- stem bark [2], fruit [2, 3], and root [2, 4]. Since then C. acu- mptothecin (11) with one known compound 12 were identi- minata is considered to be a rich plant source of the potent fied from stem bark of C. acuminata in 1979 [11]. Com- camptothecinoids. This class is characterized by a penta- pound 20-deoxycamptothecin (12) was reported as a minor cyclic ring structure embodying pyrrolo[3,4-b]-quinoline camptothecinoid from the fruit of C. acuminata [12]. 20- moiety (rings A, B and C), conjugated pyridone moiety (ring formylbenz [6,7] indolizino[1,2-b]quinoline-11 (13H)-one D) and a chiral centre within a six membered -hydroxy lac- (14), 22-hydroxyacuminatine (15), and 19-hydroxyma- tone (ring E) [5]. This planar pentacyclic ring structure is ppicine (18) are three minor quinoline alkaloids isolated thought to be one of the most important factors in inhibition from the root of C. acuminata [2] and the fruit of C. acu- of DNA topoisomerase I. Oxygenation is also usually ob- minata [13]. served at C-10 and C-11 and often at C-18 and C-20. Five minor indole alkaloids were reported, including an- gustoline (16) from the stem and the fruit of C. acuminata *Address correspondence to this author at the National Center for Pharma- [15, 16], 19-O-methylangustoline (17) from the fruit of C. ceutical Crops, Arthur Temple College of Forestry and Agriculture, Stephen acuminata [17], camptacumotine (19), camptacumanine F. Austin State University, Nacogdoches, TX 75962, USA; Tel: 936-468-2071; Fax: 936-468-7058; E-mail: [email protected] (20), and naucleficine (21) isolated from the fruit of 2210-2906/14 2014 Bentham Open 164 Pharmaceutical Crops, 2014, Volume 5 Li and Wang R1 A B C N O R N 2 D E R3 O R 4 O 1 R1 = H, R2 = H, R3 = CH3, R4 = OH N O N O N N N O N O 2 R1 = OH, R2 = H, R3 = CH3, R4 = OH N N H 3 R1 = OH, R2 = H, R3 = CH3, R4 = H H O CH3 4 R1 = OCH3, R2 = H, R3 = CH3, R4 = OH N O 5 R1 = OCH3, R2 = H, R3 = CH3, R4 = OAc R OH OR 6 R1 = H, R2 = OH, R3 = CH3, R4 = OH OH CH3 7 R = H, R = OCH , R = CH , R = OH 16 R=H 1 2 3 3 3 4 14 R=CHO 18 19 17 R=CH 8 R1 = H, R2 = H, R3 = CH2OH, R4 = OH 15 R=CH2OH 3 9 R1 = H, R2 = H, R3 = CH3, R4 = OCO(CH2)4CH3 10 R1 = H, R2 = H, R3 = CH3, R4 = OAc 11 R1 = OCH3, R2 = H, R3 = CH3, R4 = OCO(CH2)4CH3 12 R1 = H, R2 = H, R3 = CH3, R4 = H 13 R1 = H, R2 = H, R3 = CH2OH, R4 =-D-glucopyranosyl NH N O N O N O N O N H COOH N N N N H H O H H H H H OCH3 O O O H3C O OHC O O O O OH OH 20 21 O OH O OH OH OH HO OH OH O HO OH HO 22 23 24 N O N H H H O O N CH3 N O O OH O N N OH H CH2OH COOH OH HO OH 27 28 25 26 O 29 R1=H, R2=CH3, R3=H, R4=OH O O R 4 30 R1=H, R2=CH3, R3=-D-glucopyranosyl, R4=H O 31 R1=H, R2=CH3, R3=CH3, R4=OCH3 OR3 32 R1=H, R2=CH3, R3=CH3, R4=OH R1 33 R =OCH , R =CH , R =CH , R =OCH O OR2 1 3 2 3 3 3 4 3 O 34 R1=H, R2=H, R3=H, R4=H 35 R1=H, R2=CH3, R3=H, R4=H O 36 R1=H, R2=CH3, R3=CH3, R4=H R1O O R5 37 R1=CH3, R2=CH3, R3=CH3, R4=H, R5=H 38 R1=CH3, R2=CH3, R3=CH3, R4=-D-glucopyranosyl, R5=H R2O OR4 39 R1=CH3, R2=H, R3=H, R4=CH3, R5=H 40 R =CH , R =CH , R =CH , R =CH , R =OCH O OR3 1 3 2 3 3 3 4 3 5 3 O R2 OH 41 R1=H, R2=OH 42 R1=-D-galactopyranosyl, R2=OH HO O 43 R1=-D-glucopyranosyl, R2=OH RO 44 R1=-D-galactopyranosyl, R2=H OR1 47 R=H 45 R1=-D-glucopyranosyl, R2=H OH O 48 R=-D-glucopyranosyl 46 R1=H, R2=H Fig. (1) contd…. Phytochemistry of Camptotheca Decaisne Pharmaceutical Crops, 2014, Volume 5 165 COOH COOH R3 HO R1 HO HO R2 49 R1=H, R2=-OH, R3=COOCH3 52 53 50 R1=H, R2=-OH, R3=CH3 51 R1=OH, R2=-OH, R3=COOH O OH O OH O O OH 54 55 OH OH HO OH HO O OH HO HO OH HO O HO OH O O O O O HO O OH OH HO O OH OH O HO HO OH OH O O O O O H O HO C O C C O C HO OH H OH OH OH O CHO O O OH O O OH HO O O HO CHO OH OH HO HO OH O O CHOH O O CHO O HO O O CHOC C HO O OH OH HOHO O OH OH 56 HO HO OH OH OH HO 57 OH HO OH OH O HO HO HO HO O CHOO OH HO O O CHO O O OH O O O O O O OH HO HO HO O O OH HO CHO OH HO HO OH O OH O CHOH O C OC O OH HO OH HO OH OH OH H O OH O OH O OH OH 58 59 OH HO OH OH OH HO OH OH OH HO OH O O HO O O O HO OH O OH HO C O HO HO O OH O O CHO O HO O OH O CH CH O C O O O HO OH O O HO OH OH OH OH 61 60 O OH OH O HO O OH OH OH O OH HO O OH OH HO O OH OH O OH O O HO O OH HO O OH O O O OH O HO OH HO OH O OH 62 63 Fig.
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