Sapientrione, a Tricarbonylated Nor-triterpene with a New Carbon Skeleton from the Roots of <i>Sapium glandulosum</i> (Euphorbiaceae)

Lira, Nikole D. T.; Silva, Anauara L.; Martorano, Lucas H.; Silva, Carlos V. A.; Freitas, Maria E. G.; Rodrigues-Junior, Valnês S.; Santos Jr., Fernando M. dos; Abreu, Lucas S.; Agra, Maria F.; Braz-Filho, Raimundo; Silva, Marcelo S.; Tavares, Josean F.

doi:10.21577/0103-5053.20250177

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Full Paper • J. Braz. Chem. Soc. 37 • 2026 • https://doi.org/10.21577/0103-5053.20250177 linkcopy

Sapientrione, a Tricarbonylated Nor-triterpene with a New Carbon Skeleton from the Roots of Sapium glandulosum (Euphorbiaceae)

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Abstract

The Euphorbiaceae family is well recognized for its chemical diversity, particularly in terpenoid metabolites, while species of the genus Sapium are traditionally used in folk medicine but remain scarcely explored chemically. The phytochemical investigation of the roots of Sapium glandulosum afforded sapientrione (1), a nor-triterpene with an unprecedented carbon skeleton, featuring a seven membered ring fused to C-26. The compound was purified by chromatographic techniques and its structure was fully elucidated by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy associated with high-resolution electrospray ionization-mass spectrometry (HRESIMS) and supported by infrared and UV data. A plausible biosynthetic pathway from the multifloryl cation is proposed. Preliminary assays indicated moderate antimycobacterial activity without cytotoxicity. The discovery of sapientrione expands the structural diversity of triterpenoids and reinforces the phytochemical potential of Sapium species as a source of novel natural products.

Keywords:
Sapium glandulosum; Euphorbiaceae; antimycobacterial activity; Mycobacterium tuberculosis; cytotoxicity

	HSQC		HMBC		COSY
	δ_C	δ_Ha	² J _CH	³ J _CH	1Hx1H
1	206.8	-	2H-2	H-5; H-9; 3H-25	-
2	52.4	Ha 3.43 (d; 17.0 Hz) Hb 3.54 (d; 17.0 Hz)	-	-
3	209.7	-	2H-2	3H-23; 3H-24	-
4	48.2	-	3H-23; 3H-24; H-5	H-2	-
5	49.8	1.67 (dd; 12.3 and 2.6 Hz)	-	3H-23; 3H-24; 3H-25; H-7a
6	22.5	Ha 1.76 (dqui; 12.3 and 2.6 Hz) Hb 1.65 (d; 2.6 Hz)	H-5; 2H-7	-
7	36.5	Ha 2.45 (dt; 14.8 and 3.5 Hz) Hb 2.10 (m)	2H-6	H-26	H-26
8	144.2	-	H-7b; H-9	2H-6; H-11a	-
9	47.6	2.64 (d; 8.8 Hz)	H-11b	2H-12; H-26; 2H-7; 3H-25	H-26; H-11b
10	54.7	-	H-5; H-9; 3H-25	2H-2; 2H-6; H-11a	-
11	28.7	Ha 1.75 (m) Hb 1.51 (m)	H-9; H-12a	-	H-9
12	37.5	Ha 2.15 (m) Hb 1.51 (m)	H-11b	H-9; H-18; 3H-27
13	43.4	-	2H-12; H-18; 3H-27	2H-11; 2H-19;	-
14	160.7	-	H-15; H-26	2H-12; H-18; 3H-27	-
15	125.7	5.76 (d; 1.4 Hz)	-	H-26	H-26
16	200.5	-	H-17	H-18; 2H-22	-
17	42.3	2.71 (m)	H-18; 2H-22	H-15	H-18
18	44.9	1.84 (dt; 13.2 and 3.9 Hz)	H-17	H-22a; 3H-27	H-17
19	37.2	Ha 1.43 (m) Hb 1.01 (s)	H-18	H-17; 3H-29; 3H-30
20	30.7	-	3H-29; 3H-30	H-18; 2H-22	-
21	34.6	Ha 1.29 (m) Hb 1.33 (m)	2H-22	3H-29; 3H-30; H-17
22	21.4	Ha 2.27 (dq; 13.6 and 3.3 Hz) Hb 1.32 (m)	H-17	H-18
23	28.3	1.15 (s)	-	H-5; 3H-24	-
24	21.8	1.13 (s)	-	H-5; 3H-23	-
25	12.6	1.00 (s)	-	H-5; H-9	-
26	126.1	6.04 (m)	-	2H-7; H-9; H-15	H-9; H-15; H-7b
27	28.4	1.01 (s)	-	2H-12; H-18	-
29	24.6	0.85 (s)	-	3H-30	-
30	33.5	0.81 (s)	-	3H-29	-

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[TFN1] ^a
Multiplicity and coupling constant (J, Hz), in parenthesis.

[TFN2] ¹
H chemical shifts (δ_H) and coupling constants (J) obtained from the

[TFN3] ¹
H 1D NMR spectrum. Assignments deduced from heteronuclear single quantum correlation (HSQC), heteronuclear multiple bond correlation (HMBC) and correlation spectroscopy (COSY) spectra.