LUCLARICIN, A NEW LIGNAN FROM <i>PHYLLANTHUS ACUMINATUS</i>

Duarte, Susyanne L. F.; Nascimento, Yuri M.; Madeiro, Sara A. L.; Costa, Vicente C. O.; Agra, Maria F.; Sobral, Marianna V.; Braz-Filho, Raimundo; Carvalho, Mario G.; Carvalho, João E.; Ruiz, Ana L. T. G.; Turri, Larissa S.; Silva, Marcelo S.; Tavares, Josean F.

doi:10.21577/0100-4042.20170266

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Artigo • Quím. Nova 41 (8) • Aug 2018 • https://doi.org/10.21577/0100-4042.20170266 copy

LUCLARICIN, A NEW LIGNAN FROM PHYLLANTHUS ACUMINATUS

Authorship SCIMAGO INSTITUTIONS RANKINGS

The secondary metabolites of the aerial parts of Phyllanthus acuminatus Vahl (Phyllanthaceae) and the biological activity of one of them were characterized in this study. This chemical investigation led to isolation of two lignans, luclaricin (1), a new arylnaphtalene-typelignan, and justicidin B (2). The structures of isolated compounds were determined based on 1D and 2D-NMR, HRESIMS and IR. The cytotoxic activity of justicidin B was assessed against tumor cell lines (MCF-7, U251, NCI-ADR/RES, NCI-H460, OVCAR-3, HT29 and K562) and a non-tumor cell line (HaCat) using sulforhodamine B assay. Justicidin B showed strong cytotoxic activity against the tumor cell lines HT29, K562 and U251 with GI₅₀ values of 2.28, 3.29 and 5.76 mol L^-1, respectively.

Keywords:
lignans; Phyllanthus; cytotoxicity; glioma cells

Position	HMQC		HMBC
Position	δ_C	δ_H(mult, J)	² J _CH	³ J _CH
C(1)	129.5	-	-	H-3
C(2)	127.7	-	-	H-6; H-7
CH(3)	105.4	6.86 (s)	-	-
C(4)	150.1	-	-	H-6; MeO-4
C(5)	150.4	-	-	H-3; MeO-5
CH(6)	106.3	7.11 (s)	-	H-7
CH(7)	126.7	7.68 (s)	-	H-6
C(8)	127.9	-	-	-
CH₂(9)	65.0	5.34 (d, J =12.5)5.31 (d, J =12.5)	-	-
C(1')	131.5	-	H-2'	H-5'
CH(2')	110.4	6.83 (sl)	-	-
C(3')	147.3	-	-	H-5'
C(4')	147.1	-	-	H-6'
CH(5')	108.1	6.85 (d, J =8.0)	-	-
CH(6')	123.4	6.79 (dd, J =8.0 and 2.0)	H-5'	-
C(7')	136.9	-	-	H-3; H-2'
C(8')	128.7	-	-	2H-9; H-7
C(9')	172.3	-	-	-
OCH₂O	101.0	5.99 (d, J= 1.0)5.95 (d, J =1.0)	-	-
(OCOCH₃)	171.0	-	CH₃ (OCOCH₃)	2H-9
(OCOCH₃)	20.7	2.03 (s)	-	-
OCH₃-4	55.6	3.73 (s)	-	-
OCH₃-5	55.8	3.96 (s)	-	-

LINE / TREATMENT	GI₅₀ (mol L^-1)
LINE / TREATMENT	JUSTICIDIN B	DOXORUBICIN
U251 (glioma, CNS)	5.76	0.05
MCF-7 (breast)	7.96	0.06
NCI-ADR/RES (resistantovary)	86.10	>46.00
NCI-H460 (lung)	57.91	0.08
OVCAR-3 (ovary)	184.44	1.16
HT29 (colorectal)	2.28	0.46
K562 (leukemia)	3.29	0.40
HaCat (non-tumor cell line)	10.50	0.15

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